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18 Women, 39 Dates, 1 Wild Ride: A Guide to Attraction on the Internet

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If you ask me, Okcupid is one of the greatest websites ever created. In the last four months, I’ve been on 39 dates (one every three days!) with 18 different women, and all of them have been excellent in one way or another.

Even better, I’ve learned so much about myself—what my values are, what I’m really looking for in a partner, and the different hats I wear for different people in my life.

If you’re honest with yourself, you’ll see that you act a little differently around different people—you put on different masks—depending on the environment you’re in and who’s around you.

The ways that different people affect me is pretty interesting, and it’s been fun to see how certain personalities will bring out different parts of my character.

Learning which of those parts I like and which I don’t has been helpful in learning to choose a woman who compliments me and brings out the parts of myself that I want to display more of.

But to have this kind of learning experience, first you must meet a lot of people and spend time with them.

Funny side note: It took me so damn long to write this that I had to change the statistics three times to reflect new numbers.

Debunking Myth #1: Internet dating is hard/doesn’t work/other lame excuses

Another thing I’ve learned in the last few months is that my experience with online dating is atypical. Most men I’ve talked to hate online dating (or dating in general) because they’ve had poor experiences with it—no one approaches them, women don’t respond to their messages, dates go poorly, etc.

The one exception I know of is my good friend, J.D. Roth, who also experienced a lot of success when he tried his hand at online dating (and is now in a committed relationship). We’ve shared countless hours now trading stories about our experiences, and I’ve learned a lot from his journey.

But these are not good statistics!

A message of hope: I have another good friend who is now married and just had a child with a wonderful woman he met online, but only after enduring quite the slog of bad dates and general “I hate online dating” sentiments. He stuck it out, and I bet he’s glad he did!

It does not have to be this way. If you’re willing to accept reality as it is and adjust your mindset, you can have a fantastic experience. It’s true!

I think the world would be a better place if more men embraced online dating, became good at it, and connected with more incredible women that help them learn about who they are.

So, today, that’s my goal—to teach men how to get better at getting a date on the Internet.

My apologies to the ladies—this one isn’t for you. But I’m hoping you’ll benefit indirectly from more confident men you find worthy of your attention.

Let’s get started.

Tl;dr—Your Mindset is The Only Thing That Matters

When I dove back into the dating scene a few months ago—keep in mind the last time I went on a date with a stranger was nearly 7 years ago (7 years!)—I was excitedly telling a friend about a first date I’d just come back from.

He listened, and he seemed happy for me, but there was hesitation in his voice. I asked him, “Mark, I know you don’t care about my dating life, but can you at least get a little excited for me?”

We both laughed and he apologized, but then he told me the reason he wasn’t excited was because he couldn’t see it happening for himself. It wasn’t a story he could place himself in.

He told me about the time he put up a profile on Okcupid and had a poor experience—no girls ever sent him messages, very few replied to the ones he sent, and the few dates he went on were mostly duds. He didn’t meet anyone who was interesting enough to see again, or the ones who were weren’t interested in him.

That’s when I had a very big realization. Mark and I were looking at the same set of circumstances with a completely different mindset.

I said, “Mark, that’s the same experience I’m having! Ladies rarely send me messages out of the blue, the number of replies I get are far fewer than the ones I send, and I rarely see a girl again after our first date. But I’m having an amazing time!”

The truth is, I’ve had far more failures than successes with this new online dating experience, but I don’t really spend much time thinking about the failures. Instead, I focus on the successes and what I learn from them.

About success: Defining what success is for yourself in a situation like this would be a good idea. You must learn to manage your expectations expertly to have a good experience.

This is the perfect opportunity to include the far-too-often-used-but-very-true quote from Michael Jordan:

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

To have a good experience with dating, online or otherwise, you have to embrace this perspective.

Think about it in practical terms. The vast majority of relationships fail. Most of them long before they get anywhere significant. This is a mandatory part of the process for finding the one that will not fail.

With each date I go on that doesn’t go further, I get one step closer to understanding exactly what I want, and I get to hang out with a genuinely cool person in the process, even if she isn’t the one for me.

If you can look at the dating game through this lens, you’ll probably be a much happier and less jaded person.

Oh, and by the way: happy and unjaded are what most women would call “attractive qualities.” So, consider that for a moment.

Before you even get started with your dating life, work on your mindset. It really is the most important part of the entire picture.

Debunking Myth #2: A Brief Introduction to Your Competition (aka The Craigslist Penis Effect)

Years ago in college, long before I knew it existed as a documented phenomenon, I accidentally discovered—quite literally I’m afraid to admit—what is known as the “Craigslist Penis Effect.”

One reason so many guys are afraid of Internet dating is because they fear all the competition. They’re afraid there’s no way they can beat out all the men clamoring for attention and get a date. Just read this article from a successful but jaded ex-employee of a popular dating site to see how much fear of competition and “low quality women” there is.

Let me assure you, if you’re capable of even reading through this article, then you can have your pick of women, all thanks to the Craigslist Penis Effect.

Let me explain.

I was a sophomore in college, and I had just gotten my first campus job as a resident assistant. One night, while talking to a few co-workers, they confessed they’d found a post in Craiglist’s Casual Encounters (where adults troll for casual sex and prostitutes probably make a lot of money) posted by our boss, let’s call him Johan.

Casual Encounters was a brand new discovery to me—I’d never heard of it before.   Exploring the facets of such a seedy underbelly of the Internet was funny and exciting.

In a failed attempt to mess with our boss, a few friends and I created a fake posting as a woman looking for casual sex in hopes that Johan would respond and we could have a laugh about it.

Well, we never did get a response from Johan, but what we did get, to our utter amazement, was an inbox full of penis pictures. I couldn’t believe it. Hundreds and hundreds of one-line emails:

Hi, I’m ____________. Check out my ****!

[Insert gratuitous photo here].

I was disgusted, but also amazed at what had happened.

Weeks later, a new friend I’d made on campus confessed to me that he’d created his own Casual Encounters post in the hopes of attracting some women, but hadn’t had any luck.

A light bulb went off in my head. I realized, “Wow, men and women really do think differently.” This was a big discovery for 19-year-old Tyler. Sure, I’d always known it, but I’d never seen it so clearly before.

This is when I decided to run a little experiment.

One weekend, finding myself without any homework to finish and nothing particularly entertaining to do, I created two identical advertisements in Casual Encounters—one for “men seeking women” and one for “women seeking men.”

The ads were nothing special, nothing racy. I used the same copy for both, and simply described a very average but fictional character.

At the end of the woman’s ad, I added a note: “Please do not send any nude pictures.”

By the end of the weekend, I could not believe the results of my little experiment. Once again, hundreds of emails from men responding to the woman’s ad. And, despite the clear request in the ad, my inbox was filled with penises. I couldn’t delete them fast enough!

And, on the other hand, not one single response to the man’s ad. Well, not from a woman anyway. Apparently gay men have a hard time following directions as well.

What’s the moral of the story? It’s that not only does the average man have no idea how to approach a woman, but can’t even follow simple, explicit instructions.

This is good for you!

It means all of that competition you think you’re up against is really not competition at all. It’s just noise. Noise that makes you look even better when you show up in a nice girl’s message inbox.

If you can form a full sentence and don’t show your **** off to strangers, you have a better than good shot at landing some dates.

And if you still don’t believe me, spend a few minutes reading through the incredibly awful messages that women on Okcupid get every…single…day.

Online Dating: It Really is a Numbers Game (But Not the Kind You Think)

“You’re kind of a player.”

A very good friend said this to me, and it was pretty shocking. A “player” is not a word I’ve ever associated myself with, and certainly not one I’ve ever heard anyone use to describe me.

When I think of a player, I picture some slick dude who preys on women, leading them on to get sex while he scouts out other opportunities. But that’s not me. I mean, I’m just a guy—like any other—looking for a fun and authentic lady to share my life with.

If I’m being honest, my ultimate goal is to get married and have a kid. In the mean time, I’m meeting lots of really interesting people—never leading them on or being dishonest. That doesn’t say “player” to me.

But what it does say is that—here in America—we have some very strange and unhelpful cultural views when it comes to successful dating.

What I’m about to say next will make perfect sense to some readers, and it will make others very angry and uncomfortable:

Successful dating (especially online dating) is all about the numbers. It’s about approaching, meeting, and getting to know as many women as you can so that you really get to know exactly what you do and do not want from a relationship.

Here in the U.S. we sell each other the fantasy that the way to find your “true love” is to randomly bump into them, fall in love, and never look back.

Don’t bother getting to know yourself. Don’t bother learning about how relationships work by trying a number of them. Just wait for that one opportunity where you accidentally run into the girl of your dreams, and the rest is history.

But then look at the divorce rate in the west (50% at the time of this writing), and it shouldn’t be so hard to see that the fairy tale doesn’t work well in reality.

That’s not to say the fairy tale scenario doesn’t happen. Quite the opposite—it happens all the time. Everyone knows at least a few couples with great meeting stories.

The problem is this: If you don’t do the work to get to know yourself and what types of people compliment you well in a relationship, then you won’t be prepared to make good judgments when you find yourself in that situation.

So, the moral of the story is that to find yourself in a good relationship, you probably need to find yourself in a few less-than-ideal ones (that you quickly excuse yourself from) beforehand.

And remember this:

When you call a guy a “player” (or a girl a “slut”) because they date a lot, you’re doing the whole world a great disservice by making people feel shame or guilt about trying to find a good partner. It’s bad for everyone. Just don’t do it.

Besides, if you want to get even one date online, you’re going to need to get in touch with a lot of women because it takes a lot of messages to get a date. Do not expect to send one message and get one date. It simply does not work that way.

A Few Very Important Rules About Attracting High Quality Women

Different online dating services use different methods to match people up and let them evaluate you (and you to evaluate them), but the backbone of basically any service are these three pieces:

  1. Your written profile
  2. Your photos
  3. Some type of proprietary matching system/algorithm

A classic mistake that men seem to make over and over is to focus exclusively on finding great pictures of themselves and ignoring the quality of their written profile.

When you think about it, the reason men make this mistake so often is because we’re very visual creatures—we value the looks of the women we date more than women value ours.

It would be wildly inaccurate to say women don’t care about looks. Physical attraction has to be there to get a date, but women, in general, are far more forgiving when it comes to the looks department. That is, if you display that you have an interesting and unique character, and you don’t send up any red flags (more on this in a moment).

So yes, you hideous ogre, even you can get a date if you’re at least a bit interesting, comfortable with yourself, and you take the time to write a decent profile.

Confidence and Humor are Your Best Allies (Also, confidence and humor)

We’re all different, and I can’t even pretend to know what every woman is looking for in a man, but in my escapades so far, there seem to be two characteristics that women, universally appreciate and are attracted to:

  1. Confidence
  2. Humor

So, these two qualities should be the backbone of your written profile. Don’t be so damn serious! Women (everyone, really) likes to laugh, so bring out your funny side when you’re putting yours together. Loosen up and throw a joke in once in a while.

Of course, this should happen naturally; you can’t force it. Have you ever been around someone who was trying so hard to be funny that it made you feel sorry for him? Don’t be that guy!

If you really are not a funny person, you have two options:

  1. Learn to be funny. Take an improv class. Practice playing jokes on your friends. Do something that gets you actively practicing humor every day. Then, update your profile as you get better and better at it. Learning just enough humor to capture a woman’s attention is really not that much work, and it’s worth the effort.
  2. Embrace that you’re a stick in the mud. Don’t even try to be funny. If you’re confident with your own personality, it’ll come across, and women like confident men. Make no mistake, this will limit the number of women who’ll be interested in you, but if you’re truly confident in your humorless personality… you won’t care!

Important note on humor: Unless you’re supremely funny, do not attempt self-deprecation. It won’t come across as humorous. Instead, you’ll sound like you hate yourself. Unattractive!

Everyone Sucks at Talking About Themselves. Here’s How to Suck Less

Remember, if you want to attract a woman and get a date, especially online, you have to understand how they think and how they make decisions. It’s different from how you do, so start doing your homework!

The primary difference between how men and women communicate is that men deal primarily in facts—who, what, where, and when. We pride ourselves on being able to communicate essential information in as few words as possible. Efficiency!

This is fine if you’re talking to another man, but when you’re writing your online dating profile, you’re not talking to your drinking buddies! You’re trying to appeal to a woman—someone who cares just as much about the facts, but is just as interested in the details of your story.

When a woman reads your profile, she’s going to care much less about facts like what you do for a living, the hobbies you have, and what kind of music you like, than she is about the why behind it all.

Let me illustrate.

Bad example:

I’m Tyler. I’m a writer, I like to climb mountains, and Elliott Smith is my favorite musician.

Good example:

I write for a living, and I love my job because I get paid to spread ideas that are important to me. If I’m not writing, I’m out climbing mountains; I rarely feel more alive than I do when I’m alone in the wilderness. It’s a way for me to get to know myself better.

 And I love all kinds of music, but Elliott Smith is my favorite musician because I can get lost in his melodies and the lyrics are some the smartest I’ve heard.

The second example is longer, but also better when it comes to telling a woman about who you really are.

A word of warning: It’s important to learn to speak the “feminine language” a bit, but don’t over-do it. What you want is to strike a balance between communicating critical details in a way that a woman will enjoy reading without throwing out your masculine qualities.

For Best Results, Watch Lots of Soap Operas

Remember, just as much as you’re not on an online dating site to talk to your drinking buddies, she’s not there to read something that reminds her of chatting with her girlfriends.

When it comes to presenting yourself online, a bit of mystery is your friend!

Your profile should not be an autobiography; a life story is not necessary—and not helpful, either—to get a date online.

Have you ever read a book where the end of each chapter leaves you unexplainably excited to read the next one? Or a TV show that ends each episode with some type of cliffhanger?

A perfect example of this is the soap opera story format. If you’re a man, it’s likely you’ve never even seen a soap opera before or, if you have, you got so bored you turned it off after ten minutes and vowed to never watch one again.

I don’t blame you—they aren’t made for us. They’re made for women, and women love them!

Do yourself a favor and watch an episode of a daytime soap opera sometime. The formula is quite simple and dangerously effective:

Step 1: Build up an elaborate and compelling story over the course of an hour.

Step 2: End the episode just before the climax, leaving you with no resolution.

Step 3: Make the next episode about something else entirely, and don’t address the original story again for many more episodes, if ever at all!

This format is incredibly frustrating to men—we want to know what happens, and we want to know now! It’s also frustrating to women, except they love it, and can’t get enough. This is how a soap opera series can go for 72 years (Not even joking!) and create lifetime watchers and evangelists.

Your profile should work like a soap opera; give just enough details about yourself in a way that builds up to one big mystery by the end, and then do not resolve it!

If you want to capture a woman’s attention, make yourself a mystery to her that she has to figure out. Women have incredible imaginations. If you make them do the work to figure you out, they’ll fill out the story with details that are attractive to them. If you simply give them the whole story up front, you run the risk of coming across as boring, and you’ll lose their attention quickly.

Phrases That Should NEVER Appear in Your Dating Profile

When you’re trying to attract women online, you have fewer tools to do so than you would in person. Non-verbal communication does most of the heavy lifting. When a girl is reading your profile, she’s getting none of it.

Basically, anything you say about yourself can and will be interpreted differently depending on who’s reading. No surprise there, really, but the question becomes:

What do you do about it?

The truth, I believe, is you really don’t have to do much. We know that women prefer a confident man, so your job, essentially, is to show her that you are one. Succeeding at that has more to do with staying away from certain “red flags” than it does with explaining away how awesome you are (confident men don’t need to explain that they’re awesome).

Here are a few key phrases that men seem to use over and over in their online dating profiles despite the fact they make women want to vomit:

1. “I’m looking for someone to complete me” (or any variation of this).

This does not say, “I’m strong and confident.” Instead, it says, “I can’t be whole without someone else around me.” It screams neediness, and it’s unattractive—to both men and women! Instead, you want to convey that you’re happy with your life as it is, and that you don’t need anyone else, but you’d like to share yourself with someone.

2. “I’m missing love in my life.

Never say this. Ever. Talk about putting pressure on someone. If you met a woman at the grocery store and struck up a conversation with her, would you tell her this? Of course not! So don’t do it here. What this says is, “I put the responsibility for my happiness on other people’s’ shoulders. I’m needy and unhappy, and I want you to fix this for me.” Not so attractive, right?

Love is something that grows over time. Never say anything that makes a woman feel like the two of you have to fall in love right away or it won’t work out. Don’t put that pressure on someone.

3. “I’m a nice guy.

This is one of those “If you have to tell me you are, you probably aren’t” statements. Strong and confident guys (not to be confused with arrogant) are also nice, but they don’t need to tell anyone because it’s not important.

What “I’m a nice guy” actually communicates is that you probably aren’t nice on the inside at all. You’re probably quite angry and frustrated because you’re a people pleaser who does nice things to get something in return instead of just to be a good person, and you’re actually passive aggressive.

How’s that for an interpretation?

4. “I live for the weekends” (or anything else that says “I hate my job”). 

You probably think everyone hates their job and this is just your duty as a man, but hey, you’re optimistic!

When a woman reads this, what she really hears is, “I’m generally grumpy and don’t have much energy for life. I hope you’ll plan lots of things for us to do on the weekends because it’s the only time I have enough energy to pretend I’m happy.”

If you truly hate your job, this is something you need to fix before you even try to start dating.

5. “I want a good woman.”

Talk about putting pressure on a girl and coming off with a bad attitude! Of course you want a “good woman.” Everyone does, dummy! But when you say that, you come across as jaded and untrusting—you put people at arm’s length before you even know them.

It also says you make judgments about a woman’s character without considering how you contribute to a relationship. “This girl wasn’t right for me, therefore she’s a ‘bad’ woman!” Come on…

Do not utter any of these red flags in your profile unless your goal is to be endlessly frustrated.

The Photo Conundrum: Quality or Quantity?

If you have the right personality, women are far more forgiving in the looks department than men are. Whether or not that’s fair or right is a discussion for another time, but it is a reality. Luckily, it’s a reality that works to your advantage.

Still, you do need to post enough good pictures of yourself to give a girl the reassurance the person she’s going to meet is truly attractive to her. People in general are extremely skeptical of any kind of image posted online—evidenced by the classic meme of calling “Photoshop!” anytime you see a picture that looks too good/crazy/unusual to be true.

So, the answer to the quality or quantity question is “both.” It should be balanced.

Everyone knows you’re trying to show off the best photos of yourself (quality), so there needs to be enough of them that give the same vibe to convince a girl that she’s not being duped into meeting someone 10 years older and 50 pounds heavier (quantity).

The Photo Flops of Online Dating Dunces

What makes a “quality” photo when you’re trying to get a date online? A number of things, really—a good composition of you at the right angle with the right lighting that’s authentic and conveys your best features. But this is another aspect of online dating where you can do just fine by avoiding a few serious mistakes and not worry about getting everything perfect.

Here are few things to avoid.

1. It’s not a beauty pageant.

Actually, it kind of is, but do not doctor photos. One of the worst things you can do is try to make yourself seem “too perfect.” People are incredibly skeptical about photographs these days—and rightly so.

If your profile is filled with professional glamour shots (why you have these in the first place is beyond me, but just in case…), you’re going to set off a lot of B.S. radars when women look at your pictures. They want to see the real you, so give them a variety of pictures, but make them casual. If it’s professionally posed, leave it out.

2. Keep it recent.

Again, women want to know who you are now, not who you were five years ago.

Yes, you might get more first dates if you post old pictures of yourself with a smaller forehead and waistline, but let’s keep the end goal in mind here—a second date. You won’t be getting many of those using a bait and switch strategy like that. Remember the role of confidence here. A confident man is okay with who he is right now. Don’t be the guy pining for the glory days.

3. Include a good face shot and a good body shot.

Both a head shot and a body shot are mandatory for being honest about who you are. Remember—humans fill in holes in a story with their own details from their imagination. This can play to your favor with your personality, but not with your appearance.

I’m not joking when I say how skeptical people are about photos on dating sites. If all you share are a few pictures of your face, women are going to assume the worst all takes place below the neckline. And if all your pictures are body shots with your face removed…well… you have bigger problems that aren’t going to be solved here today!

4. Go easy on the camping/outdoors/sports photos.

Guys love to show off their hobbies—skiing, fishing, camping, rock climbing, etc. It’s okay to toss a few photos like this in to show people you get out and you’re active, but the problem with these pictures—especially if you don’t have others—is that they’re very low on useful information for a potential date.

Hats, sunglasses, and helmets hide your face. Snowsuits make you look like a giant marshmallow man. You’re probably in some weird position that makes it hard to see what you really look like. Feel free to use these photos to tell a story about yourself, but don’t rely on them to show ladies what you actually look like.

5. Avoid pictures with friends.

There are two reasons why this is a no-no. First, it’s incredibly annoying to go through a series of photos and have to play “Where’s Waldo” with your potential date. If a girl can’t even tell who you are in your photos, you’re not going to get a second look.

Secondly, it does not help your cause to post pictures of yourself with people who are more attractive than you. This seems like common sense, but guys (girls are huge offenders, too) love to post pictures of themselves with their buddies. You can get away with this if it’s just one or two photos, but if all your shots are you with other people, and you’re less attractive than them, the spotlight isn’t really on you, is it?

Try to avoid getting messages that say, “Hey, I think your friend is cute!”

6. Never post photos of you with other women.

We’ll file this under the “Duh” category, but it’s another thing men consistently do that gets them nowhere in the online dating world.

Assuming she gives you the benefit of the doubt that you’re not posting pictures of you with your many girlfriend, there are only two ways that a woman will interpret a picture of you with a female friend. If she’s more attractive than her, she’ll look like competition—not something ladies are typically into before they even know you. Or, if she’s less attractive than her, she’ll see you as less attractive, too.

There’s just no good outcome here. Avoid!

As a bonus, here’s something you should do: Always play up your best feature.

If you have great hair, take lots of shots of you and your glorious locks blowing in the wind. If you’re really fit, get some form fitting clothes, and take some good full-body shots. I have really blue eyes. Women notice them a lot. So, I try to play them up as much as possible when I take a picture of myself.

Warning: You may have a great body, but there is a very small percentage of women who are interested in seeing it bare as their first introduction to you. If you’re trying to get laid and nothing else, feel free to take as many vain, shirtless mirror shots as you like.

But know that while many women will find you attractive, they’ll also reject you when you put yourself on display like that. To show off a good body, just don’t dress like a slob; get some clothes that fit you nicely.

The Sad (But Also Liberating) Statistics Behind Messaging Girls Online

There are only three things you really know about sending messages to girls when you’re trying to get a date online:

  1. They’re not going to beat down your door to go on a date with you.
  2. To be successful, you must play the numbers game and message a lot of women.
  3. It doesn’t really matter what you say as long as you don’t come off as a total doorknob.

Let’s take a quick look at each of these. We’ll tackle the first two together.

The #1 Reason Most Guys Have a Bad Experience With Online Dating

Why do most guys I meet say they hate online dating and that it “doesn’t work?” To be blunt, it’s because they don’t try hard enough.

They think just because they took ten minutes to write a self-summary (often no more than a list of demands for a woman with little to offer back) and throw up a few pictures of themselves from a recent camping trip that the Internet will magically provide a never-ending line of women to beat down their door.

Not going to happen!

Let me share a little potentially embarrassing personal data to illustrate this point.

After four months of having an active profile on Okcupid, I have received exactly 15 unsolicited messages from girls. That’s less than once a week! Of those 15, only 5 had any substance to them. The rest were lame “Hi there. The end.” kind of messages.

In that same four months, I’ve sent a first message (follow-up replies omitted from this count) to 88 different girls. 23 messages received some type of reply, and only 12 ended in an actual face-to-face date.

If you do the math on that, only 14% of the messages I’ve sent—a meager statistic—have resulted in a date. And I’m a good-looking, interesting guy. Okcupid even says so:

But that’s not the point! The point is that in four months, I’ve been on 39 dates with 18 different, interesting women and learned so much about myself in the process.

Your results will vary, but there’s no need to have a bleak outlook. Success heavily favors the persistent. Try to remember that there are 7 billion people on this planet, and that the majority of them are interested in meeting someone they like and are attracted to.

At the end of the day, your “real” odds are actually quite good!

End note: Keep in mind that my numbers could likely have been higher. There were times when I would take weeks at a time off from messaging girls at all, and times when I decided not to reply to a woman who had replied to me. So, there’s no reason you couldn’t do much, much better.

Winning Tactics for Messaging A Girl Online

Moving to point #3 from above. Just like approaching a girl in real life, it really does not matter what you say as long as you avoid being a complete doorknob on your first impression.

With a few caveats, you can say pretty much anything you want as long as you say it with confidence and leave her feeling good about the interaction.

Here are a few rules to follow if you’d like to avoid being avoided:

1. Learn how to spell. 

If you’re not good at spelling, make sure you run your message through some kind of spell checker before you send it.

And for the love of Pete, don’t use shorthand/slang. “Wat up, gurl” is about as attractive to a confident woman as a 13-year-old in baggy pants and sideways ball cap.

2. Keep it casual. 

To have any luck, you need to know the right way to communicate with different people in different settings.

So many guys who are great at what they do in their professional lives have a hard time talking to women because they try to talk the same way they would to business colleague. A first message to a new girl should be fun and light-hearted while still communicating important information about who you are. Leave your TPS reports with bullet points and analysis at the office.

3. Don’t write too much.

This is a psychological thing. Think about the emails sitting in your inbox right now that have been there the longest. Most likely, they’re the ones that are endless paragraphs and require you to do a lot of thinking to reply because you want to write just as much to not come off as rude.

So, they just sit there.

The same applies to online dating. If a girl who gets a dozen messages a day gets a novel from you, you’re probably not getting a reply. She, like anyone else, just doesn’t have the time or capacity to dedicate that much effort to someone she doesn’t even know, and she doesn’t want to appear rude by sending back a short reply.

4. Don’t write too little, either.

Like above, if you start your message with “Wat up gurl?,” you’re not going to get many replies. If you end your message with that, too, you’re not getting any replies.

Put some effort into it you lazy SOB!

5. NEVER use a form letter.

Women are incredibly talented at sniffing out authenticity in men. When I say that online dating is a “numbers game,” some guys take that to mean they should create a generic message and send it to as many women as possible. This is a very bad strategy.

A form letter, by design, communicates important things about you without communicating that you understand anything about her.

And you don’t. You didn’t read her profile; you just copy/pasted some generic garbage and hoped for the best. In any other part of the Internet, this is called SPAM. Scratch that. It’s called SPAM here, too.

6. Don’t ask for a date in the first message. 

This is one of those counter-intuitive things. Men are overly logical about this and think because we’re all on a dating site, the objective of any interaction is clear: to go on a date. So why waste time talking when we could get to the goal faster?

You’re right, these ladies are here with the same goal. They want to go on a date. Probably with you, even. But if they feel pressured in any way from the beginning, you’re toast. They don’t know you yet, and they have lots of options, so it’s going to take a little more finesse.

A Few Messaging Rules that Have Worked Well for Me

On the other hand, here are some tactics I’ve noticed work well for me:

1. Open with a joke. 

Don’t try to be formal when you start a conversation with someone on an online dating site; it feels stiff and boring.

When researchers ask women what they find most attractive in a man, the top two answers are always confidence and humor. Opening your message with a joke displays both. It shows that you’re a fun person and, if you’re actually funny, it’ll catch her attention. Also, the fact you open right up with something funny says you’re confident in your ability to strike up a conversation.

You don’t need permission to be funny and interesting, you just do it.

2. Play off of her profile.

This goes back to not using a form letter. Take a minute to read a girl’s profile before you message her; it’ll give you some material to actually create a unique message from, and she’ll know you didn’t just copy/paste some lame script and hit “send” hoping for the best.

Do you have some common interests? Did she say something you can make a joke from? Does she have a funny picture you can mention?

If you struggle to find anything interesting in her profile, that’s a sign, too! Maybe you don’t have enough in common, and you shouldn’t be wasting your time trying to force something that isn’t there. This will improve the number of replies you get.

3. Build some type of excitement/mystery.

One of my favorite things to do when I write a message to a girl on Okcupid is to find something interesting in her profile that I can relate back to my life. This gives me the opportunity to say something like:

“Oh, and I have a funny/interesting/weird story about [insert shared interest/experience here]. I’ll have to share it with you some time.”

This works extremely well, and I almost always get a reply if I can work that into a message. It works because everyone loves to hear unusual stories or learn something strange about things that are important to them. It doesn’t mean you’re going to fall in love, get married, and have babies, but it’s a great opener because few people can resist following up on a temptation like that.

4. Always end with a P.S.

This is actually just an old copywriting trick, but it works just as well in a message to a potential date as it does anywhere else.

Regardless what else you write, a P.S. message always gets read. Lots of people even skip to the end of a letter just to read the P.S. first. We’re conditioned to look for important information in a message, and we know that the P.S. is usually a good place to find it.

So, I always end a first message with a P.S., and I try to make it a question so it not only gets read, but has a high chance of being responded to.

5. Wait until the second message to ask for a date.

It’s good to be straightforward, but I’ve never had any luck asking for a date on a first message. My success rate goes way up if I wait until at least the second or, more often, the third.

When you think about it, this makes perfect sense. If you approached a girl on the street, you wouldn’t just walk up to her and ask her for her phone number or a date right off the bat. No, you’d find something to open with, get to know her a little, and then ask for a date after you’d had a bit of conversation.

This is what the first few messages between you and a girl on a dating site does—it sets the stage. Through a series of messages, you’re setting the tone and making her comfortable with the idea of talking to you the same way you would in a 2-3 minute conversation with a stranger. It takes longer, and it looks different, but it’s essentially the same thing. Build up a little rapport first, let her respond to you a time or two, and then ask for a date.

6. Do not play “message pong.”

Messaging girls online is equal parts art and science. It’s important to set the stage with a few messages before setting a date, but you also don’t want to let things go too long without asking for a date.

This is for both psychological reasons and practical ones. First, remember that women are getting lots of messages from different guys every single day. If you exchange message after message without ever asking for a date, she’s going to get bored and move on. Endless online chatter can totally kill attraction.

Remember that your biggest asset at the beginning of a relationship like this is your mystery. You want to give her enough information to show her you’re worth pursuing, but you don’t want to give it all away. If you exchange life stories before you ever even meet in person, the first date—the place where true chemistry either happens or it doesn’t is probably going to be a big flop.

Exchange a few messages, ask for a date, and then back off until you meet in person.

The Final Word: Go Forth Young Man; the World is Your Oyster

Dating online needn’t be nearly as tedious as so many jaded men would lead you to believe. By remembering a few simple rules—mainly that you ought to consider the psychology behind how a woman chooses a man and that the same rules apply online that do in real life—you can actually have a lot of fun and success.

And perhaps the most important rule of your dating experience, online or otherwise, can be summed up with this:

Aim first to have fun, accept reality for what it is rather than complain or wish it were different, and go into every encounter with no expectations.

When you keep unrealistic expectations at bay, everything is easier. All pressure is removed, and you’re free to be yourself. Those are conditions that any real relationship needs to turn into something substantial.

So go forth, fellas, and enjoy your dates.

And to any ladies that are still reading this, feel free to point your clueless guy friends here.

A Challenge (and a Valuable Prize) for Men Who Walk the Walk

This is extra-credit for the guys who read this today and actually put it to use.

For the next week, I’m running a challenge. I’m going to give away a 6-month membership to Okcupid’s A-List (the premium version with extra features).

UPDATE 10/04/12: The contest is now closed. Thanks to the few participants that really worked for their entry. The Internet appreciates you! The winner will be contacted today by email.

Image by: Cali4beach

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What smart people are saying about this...

  1. Ann says:

    Tyler, What a great post! I am a woman and am howling with laughter. I think from now on I will only date men who have read and internalized what you wrote. :-)
    Good luck on your search.

  2. Are you familiar with the pickup artist (PUA) community? I just published a book about them. (And actually tonight I did a Reddit AMA with a batch of PUAs.) I’m curious because a lot of what you say here reflects some semi-standard PUA advice, but there are a couple places where it’s different, and you don’t seem to use any jargon.

    • Oh, and for people who aren’t familiar with pickup artists, they’re a subculture of guys who trade tips on how to seduce and manipulate women.

    • I’m vaguely familiar with it, but don’t really pay any attention to who they are or what they’re up to.

      And yes, I try to remain jargon free! In this case, I guess I just don’t know any of it…

      Also, I’m not sure what tone you were trying to imply with the “seduce and manipulate” comment, but every dating encounter has manipulation built into it by default. It’s part of the human courting experience.

      It isn’t wrong to “manipulate”—it’s what you’re supposed to do (men and women alike), but it’s wrong to misrepresent or lie about yourself or your intentions.

      • I completely agree! It’s a question that I thought about a lot and in a great deal of detail … in my book :)

        (Okay enough shameless self-promotion from me … I was just struck by the similarities here!)

  3. Iris says:

    I hope this means that less women will be fantasising about Christian Grey and actually meeting ‘real’ guys that are confident and humorous!

    P.S. Insightful and entertaining article Tyler, except whatever happened to meeting girls the old fashioned way? :)

    • Hey Iris. I don’t think anyone will stop fantasizing (men OR women), but hopefully this will help some guys take the first step to actually getting a date.

      And nothing happened to “the old fashioned” way; this is just another avenue.

  4. Betsy Talbot says:

    As a veteran of online dating (back in the Internet Stone Age of 2001), I can relate to a lot of this. While we had fewer dick pics back then because some people were still on dialup, there was plenty of dickish behavior (from both women and men, to be sure).

    I’m sharing what you’ve written for my single male friends who get a little frustrated at the thought of dating again after age 30 or 40. But I will add one quick tip that will also help you communicate better with women: stop calling them girls unless they are under 12. :)

    Good luck with the rest of your dating adventures!

  5. Joy says:


    So far the women have commented :) Perhaps we (I know I am!) are so appreciative that you chose to share this, in the hopes we have now have zero sex photos and more concrete communication. I once asked a guy, does that really work? and he said, sometimes–that’s why I do it. Really??? Wow. So, thank you for your wonderful, much-needed, reflection of your experiences!

    • Oh, wow. I would love to actually meet a guy who admits to using that strategy and hear his honest “tell all.”

      And yes, I see this has been mostly popular with women so far. Hopefully it’s because the men are out doing the challenge to report back on!

  6. kdivasilver says:

    combatwombat007?! Great screen name… I’m into the online dating scene too–it beats bars, I can screen, and I have met (and even had relationships) with some very fine men. I am selective though–I’ve found that going out with just anyone isn’t a good use of time or energy! This is a good guide–I’m going to send it to a friend who is on OKC but keeps on ending up with, well, wombats…

  7. D says:

    I think at its heart this is good advice for anyone, even if it was geared toward men. I think most people want to meet someone who is funny, happy, and not jaded. Most people don’t want to feel pressured.

    I will disagree with your soap opera bit- I like to argue that “man” shows like The Walking Dead or Star Trek are also soap operas with different packaging. :)

  8. This post certainly did not disappoint, Tyler! I’m somewhat of an online dating veteran. I can say that I 100% agree with many of your tips based on experience, and others that I haven’t used I’m sure will be helpful.

    I met my now-ex girlfriend on Match.com in 2008 and we dated for over 2 years. Since our breakup a few months ago, I’ve been hesitant to get back into dating.

    But your point about not expecting too much and to just have fun with it has made me rethink that there’s no good reason to not get out there again.

    • Finally, a response from a guy! Yep, it’s all about managing expectations.

      Get back in the game, sir. And if you want a free 6-month subscription to Okcupid, you know what to do…

  9. Leslie says:

    This post is right on target. I was in a 8-year relationship that ended abruptly, and I was “thrown” into the dating world once again. I joined OkC a few months after the break-up and I was appalled by all the responses I was receiving (and still receive!) so I was turned off by the whole online dating scene. I stopped logging in after a while. Now I’m trying to keep an open mind and am giving it another shot. I’m going to increase my response rate ;)
    P.S. Happy dating and good luck!

    • Leslie, are you a man or a woman (I can’t tell just by your name, and you don’t have a gravatar photo).

      If you’re a woman, though, the experience is *totally* different.

  10. John says:

    Tyler, great post! Very thorough! I tried online dating in the past and had some good and bad experiences. I found all your advice to be dead-on. I really liked the PS suggestion. I learned that from a female friend of mine. Also, not playing the messaging game. We have to assert our intention and ask for the date.

  11. TLC says:

    Oh, so very true! I decided this summer to try my luck on plentyoffish.com. If I ever try online dating again, I’m going to link to this blog post for men who may want to contact me!

    After two months of sheer frustration, I finally gave up and took down my profile. I spent too much time wading my way through emails from people who lived 100+ miles or more from me, when my profile clearly stated that I was not interested in a long-distance relationship. When I pointed this out to one man who emailed me, he emailed back and called me a bitch. Nice!

    Your point about outdoors photos should be shouted from the mountaintops. No, I don’t care if a man likes hunting/fishing/camping. However, I don’t. And I really don’t want to see the photos of the dead fish you’ve caught. Or even better: the carcass of the deer or elk you’ve just shot. I have no problem with hunting, but seeing the butchered results of your outing doesn’t do a whole lot for me.

    I finally pulled my profile because I had only two dates and wasn’t meeting people, which was my main goal. And because I was spending so much time writing “Sorry, we’re not a match” emails. I felt like all I had accomplished was creating a bunch of admin work for myself.

    However, since you’ve had such good luck on Okcupid, I’ll at least check it out. Thanks for the great blog!

    • I laughed out loud reading this. I just had the same conversation with a girl I met the other day—guys filling their profiles full of pictures of themselves drinking beer in the woods and posing with dead animals.

      I totally get why guys do this, and I think that many women are attracted to a manly man like that, but they don’t really want to see the gory details…

      Also, Plenty of Fish is awful. I went on one date via that site and gave up. Okcupid has been better by an order of magnitude.

  12. Ky says:

    Although I’m happily married, I can see how your ideas of confidence/ humor, choosing somebody who brings out your best qualities, and learning to communicate in a way that’ll attract quality dates is applicable to online dating, as well as real life. Thats how I got Margie (except it wasn’t in an online dating situation, it was in a college class). Very valuable information in any dating venue.

  13. Hi Tyler, that echoes my experience pretty exactly. Is your offer only open for exchanges initiated by the guy? I’m happy to point you to my profile, which I think is decently good.

  14. Glad to hear you’re having a good time, Anthony.

    For this challenge, yes, it would need to be a situation where *you* initiated contact. If a woman contacted you first, there’s not much work involved in getting a date, now, is there? ;)

  15. Meg says:

    Wonderful Article.

    I met my husband online 3 years ago tomorrow (old anniversary’s get voided after the “I Do’s,” right?)

    Before we met and married we both did tons of online dating. And we actually online date now, as well, because it works for us.

    Honesty and Sincerity really can’t be emphasised emphasised enough. A shame they are practised so little, and the discourteous and bizarre so frequently. My favourite opener to date: “I think u might be the perfect woman to finally penetrate me anally.”

    I wasn’t sure how to take that… It’s really more of a second date level statement.

    You’re spot on about self proclaimed “Nice guys.”

    It often reads something like: “I’m nice – so you OWE me your time and attention.”

    Positively twitch inducing.

    To all you gentlemen and ladies out there: happy messaging and good luck!

    CombatWombat007 is a stellar username!

    P.S. http://www.annalsofonlinedating.com also has excellent horrific examples of messages.

  16. Josh says:

    I used to go on OKQ a lot, and for me it was a waste of time. I messaged many many women, tried many different angles, studied dating sites, pickup guys, etc. with no luck.

    But I had much more success with my g/f I met personally at church with whom I’m very serious now. Don’t know if the church thing made quite a difference. But I’ve had much better results meeting with people who I’ve met face-to-face, especially after working on myself to be more confident and social. I’m just glad I don’t have to mess with OKQ anymore. Yeah!

    • Well, I’m sorry to hear you had bad luck with OKC, but that’s great that you found someone another way!

      What exactly did you have the most trouble with? Getting responses to messages? Getting girls to agree to a date? Getting past a first date? Where did the chain break?

  17. Karen says:

    Great post, Tyler! I actually have had good experiences with plentyoffish. Your advice is completely correct – honestly, just avoiding “whassup” as your first message puts a guy in about the top 10% of the messages I got. Related advice: if “whassup” didn’t work the first time, sending her the same message every week is also unlikely to work.

  18. Hi Tyler, so after first bemoaning that of course you had to do this contest /after/ the best Quiver matches I’ve been getting have been in the mid-70s … and two women messaged me … nevertheless I managed to find a good 86% match. Not bad!

    Here was my initial message:

    Hey, so according to what you rated as “important” in your questions, you really want someone smart, honest, and funny …

    Hmm. Well, I have to say, one of my favorite jokes is:

    The bartender says, “Hey, no lawbreaking allowed in here!”
    A guy walks into a bar faster than the speed of light.

    I remember when I first understood Vizzini’s mind game with the Man in Black. Really understood it. Before that point I thought The Princess Bride was great. After that, I thought it was the best movie ever.

    Note: she referenced The Princess Bride as a particular favorite of hers.

    She responded back almost immediately, I wrote back, she responded, I asked her out, she said she’s busy that day, I proposed another time and told another joke.

    It’ll happen, I’m confident of it. I’ll post back if she turns me down.

  19. Matt R says:

    Hey Tyler,

    I’m glad you wrote a post about online dating. I would state that persistence is an important element in online dating.

    The only variable I tend to find that reduces the success based on many stories from other men and my own experience is age.

    If you’re doing cool things and in your mid 20s and beyond, I think it’s the easiest and fastest way to get a date.

    The younger folks I’ve talked to (under 24) tend to have less success. Older women dismiss them and younger girls in their younger 20s are more fickle. These are generalizations of course but I wanted to share an alternative view from somebody younger.

  20. James H. says:

    Long-time OkCupid success story here. From finding my first girlfriend there years ago to starting a new relationship just last month, I can testify to how much it helps an introvert like me find love.

    In fact, this point prompted me to overcome long-standing resistance and made me the one to initiate the “what do you expect of this relationship?” question. We confirmed it as open, too, so that puts me back on the dating scene. Thanks!

  21. Stef says:

    Brilliant. Simply brilliant. I need to share this article with the world, and especially with all of my friends who are online dating. Thank you for finally saying what guys (and some girls, honestly) need to hear.

    I recently received an initial email on OKC in which I was referred to as “My Little Avocado” …what? So guys: don’t do that. Or say things like “Hi ur cute lol”…

    Good luck to everyone out there–it’s not easy. But I’m enjoying it (even the bad dates make for great stories over beers with friends later.)

  22. [...] that article no longer needs to be written as we just came across an excellent post from Tyler Tervooren which sums up our guide better than we could have. Tyler’s a 26 year old [...]

  23. Izzy says:

    I’m blown away. This is hands down the most honest and informative post I have ever read about online dating.

    The times have changed. I think we have reached a point where the tides are turning and online dating is shifting more and more to the norm. Personally, it just seems logical to me. Why should we limit our opportunities to genuinely connect with someone because of geographical constraints? We shouldn’t!

    Online dating eliminates this (to a degree). Of course we still want to live close to that special someone but it eliminates the whole “perfect time, perfect place” concept that so many people try to run with.

    I’m going to share this post with every single person who has a pulse :). Except maybe my parents, I don’t think they need it.

  24. Nancy says:

    Tyler, this is a really interesting read. I have to say, I just deactivated my OKC account a few weeks ago because not only was the signal-to-noise ratio really awful, a former friend–someone I’d explicitly told to stay away from me–found me there and sent me a message to see if I wanted to “catch up.”

    That’s the primary problem I see with dating sites: too many guys go by the photo and can’t be bothered to read–or they decide that the woman doesn’t really mean what she’s said (see above!) and go ahead and violate her requests anyway. Way to show how much respect you have for me right from the get-go. And way NOT to get a response from me.

    I never got photos of the sort you describe, but I did get plenty of messages from guys who couldn’t be bothered to read my “no photo, no response” policy. Or who would email using textspeak despite the fact that I said I’m an editor and a writer (dude, do NOT make me work that hard to read your idiotic message–and I guarantee that if you write it that way, it’s idiotic). The ones from Argentina, Indonesia, etc. were also an eyeroll. And the Tumblr site you posted includes stuff I definitely saw. I often wasn’t sure if I should feel contempt or pity for the guys who sent me that crap. (And that’s before I even get to what I called the “form letters”–the stuff that at best showed no signs of having read my profile, and at worst was crap writing that made it blatantly obvious that they hadn’t. Good lord, do you really think I’m that stupid?)

    I don’t know why it’s so hard for guys to take this stuff at least a little seriously. I don’t think we have to be downright formal, but if I say I won’t contact anyone without a photo, get a damn photo if you’re actually interested. It’s 2012–this is not hard. If I say I’m not interested in a long-distance relationship, look at a map before you reply. A little basic respect and show of interest will go a whole lot further with me than the cleverest of lines.

    And PS: if you find a profile of someone you know, for the love of god, DO NOT REPLY. It’s awkward at best, and the one I got, given the circumstances, was downright creepy and only reinforced my decision to stay away from the guy. You’re not doing yourself any favors there.

  25. Hopefully Online says:

    Really good work. Its a compilation of really good points. The ones that inspires people.

    – Don’t you think its subjective ?
    eg: I tried to follow all the steps you had mentioned to the best of my understanding. Followed by a genuine, “Hi .. Followed by curious/bit funny question about profile. Followed by a quick compliment if I find any”

    All I get back is thanks. Or not even that. And If even one conversation is not up to the mark, OVER . NO more REPLIES. Like they don’t even give a damn about it . Personally I would be take with “sorry I am not interested” over no replies.

    —- Bottom Line —–
    1) Most women have no clue about why they use OKC or what they are looking for.
    eg. “looking for” — Short/long term dating
    Q&A ” Are you ready to meet someone from OKC” — Totally hesitant
    Come on man , where is the logic?

    2) This is the few things that needs REAL PATIENCE. Duh, ! I thought engineering problems were tough. If you are out in the real world, you can get more numbers and dates in 1 hour than what you can get in 10 hours on OKC!

    —- Conclusion —

    Dude, you are like the GOD of ONLINE Dating! :)

    • You’re not looking at this with the right mindset. From how you describe it, it sounds like you’re actually kind of combative and frustrated, and that’s no way to start any kind of relationship.

      So first, calm down. :) Now…

      1. I’m not joking when I say that you have to send a *lot* of messages to end up on one date.

      2. Don’t compliment a woman the very first time you message her. You don’t know her well enough for your compliment to mean anything to her, and *every* guy is complimenting her thinking that it will win her favor. If you want her attention, do something different from everyone.

      3. What a woman wants from OKC is not your concern. Your concern is to get a date so that you can get to know her in person and decide if there’s something worth pursuing. If you don’t like the logic of being on OKC and being hesitant to meet someone, filter those people out! Don’t message them.

      4. Yes, patience is a virtue. Work on channeling more of it every day.

  26. James H. says:

    Hey Tyler. For the contest, I have date-getting message exchange that predates this post. It has turned into a second date after I applied more of your advice, so that must count!

    The exchange:

    [Profile-relevant] high-five! Also, do you read the blog of [Another profile-relevant site and blog URL]?

    High five back at you!

    I haven’t read it but i will drunkenly check it out.

    How are you?

    Not drunkenly, **** autocorrect. I meant definitely*

    You have my permission to peruse it sans sobriety.

    As for me, I continue to ride the creative high of Camp NaNoWriMo success. Less than 20,000 words to go and only halfway through the month.

    Her: :)

    Wow, that’s pretty impressive!

    And exhausting. I can’t overstate how much I recommend attempting NaNoWriMo, though. Do any writing of your own in between schoolwork?

    No. I keep wanting to start a blog- even if it is for my eyes only. The thing is that with school I never have time to do anything like that. Another thing I want to get back to doing is photography, but it’s yet another thing I do not have much time for if I want to do well in school, spend time with the people I love, and still manage to get SOME sleep. Haha. :P

    By the way, I wanted to let you know that I truly enjoyed reading your profile. I found it actually much more intriguing than the majority and loved the wit. :]

    Thanks. I consider it a small sampling of the full package. Do you have time to coffee-grab during an upcoming weekend?

    Sure :] I’m fairly sure we could work something out for this weekend. It’s still only the first week of school and I don’t have too much going on right now. What do you think?

    Sounds good to me. I propose [specific time and place].

    That sounds good to me, I think :]

    [Subsequent clarification of relationship expectations, some limited exchange of hobby notes, avoided too much chatter before actually meeting.]

    • James H. says:

      Some highlights:

      * My very first words referenced something emotionally evocative (a political position) and emphasized my agreement with it. I then followed up with a value-add (the blog reference) that I genuinely enjoy sharing for its own sake.

      * I demonstrated a sincere passion (for NaNoWriMo), as realized through though enough self-motivated (i.e. not dating-driven) work to qualify for a field report on this very site.

      * We see explicit validation of Tyler’s recommendation to include both mystery and humor in dating profiles.

      * I waited a few messages for the date invite. I *also* went out and made the request instead of hovering around the topic, which demonstrated confidence. Having a specific time and place only reinforced that.

      Do you see any additional take-aways from this case study?

    • Nice job, James. And thanks for posting the messages!

  27. Jeffrey says:

    Success! Just set up a date for Thursday night.

    Here’s my original message, which I modeled off your recommendations, and it seemed to go over quite well!


    I love the reverse reverse concert invite tactic. Has that actually worked yet? I’m standing by, waiting to update my profile if it’s a “yes.”

    Do you work for a nonprofit? I just finished working at one on the East Coast before moving out here, and it was definitely an interesting experience.

    - Jeffrey

    p.s. – I want to say not being able to frown is a good thing, but maybe it makes life hard?

    Perhaps it’s a little hard to tell, but I did comment on a couple interesting things from her profile to make a little joke in the first paragraph and then fill out my message with the “p.s.”

    Thanks for the encouragement to make this happen! I feel like a champion whether I win the challenge or not!

  28. One thing I like about online dating is my ability to leverage some badass photos of me taken while traveling. At the very minimum, I like to use my online dating profile(s) as a way to generate more female visitors to my website. In the end online dating just doesn’t seem like the most efficient use of my time when it comes to meeting women.

    I will admit I do have a much better alternative though: As an artist, I’m able to setup an artist booth in and around college campuses. This allows me to interact with as many as 18 different women in a day.

  29. David says:

    Hey Tyler,

    I’ve got a question. I totally agree to all your points and think it’s great that you have shared your lessons and experience. But some things about women in dating website really amazes me.

    1)I do understand women get a lot of weird messages (pity them). But what makes them not reply to even honest straight forward simple messages ?
    Do you agree with me that not all the messages that we send out can be brilliant, witty and catch the women’s attention in the first few sentences ?
    Why don’t they even bother to reply back with a simple “I am not interested” ?
    sometimes, it so happens that I do not get any replies after 2 or 3 messages.

    2) When you say send a lot of messages what does ***LOT*** stand for in absolute numbers? 100,? 1000? or even more than that?

    3)I do agree that patience is very important in here. But, if the only chance of getting a date in here is to be 100% witty and be able to really catch the attention in first few sentences, don’t you think that makes the game bit harder ?

    • David, you seem frustrated. I understand that, but holding onto that will not help you.

      1. You answer in the first part the exact question you ask in the second. It can be *very* draining for a woman to have to, essentially, manage a whole other inbox. And this one is filled with even more spam than usual. If the signal to noise ratio gets too low, even good messages get skipped because they’re tired o reading *anything.*

      Add that to the fact that there are a number of different reasons why someone might not write back to you, and you have a recipe that requires a lot of input on your part!

      If you’ve started a conversation with a woman, it can *still* go dead. This is normal, and you shouldn’t worry about it. Sometimes the attraction just isn’t there.

      Also, if you don’t get a response to your first message, *never* send another. They’re not interested and it won’t work. Simply move on.

      2. Well, in my case (and highlighted in the article), I sent 88 messages that resulted in 14 dates. That doesn’t mean you’ll have the same experience, but you asked for numbers, so there are some numbers.

      3. Yes, of course it makes the game harder. It also makes it more fun. Are you afraid of a challenge, David? :)

      • David says:

        Hi Tyler,

        Thanks for the reply. Your reply is very reassuring. I do agree its a challenge . I like challenges. But the question is what type of challenge? Solving a puzzle kind of challenge? or Winning the national lottery challenge ? ;)

        I have been on OKC for 2 months. Sent more than 200 messages and ended up with just 1 date and we just became friends :D (Well it was kind of my mistake that I didn’t make my intentions clear in the first place before the date, and the girl was no where near to what she looked in the pictures :D)

        Anyways, I do have to admit the fact that the response is a little bit higher these days, after following your guidelines.

        I am still hopeful. Not too hopeful though. You are right, it is just a different experience. But you should never count on it too much.


        • David, women learn early on that responding, even with a simple “I am not interested”, can cause longer conversations. Think about having a telemarketer on the line. What happens when you say “no”? They keep talking. They ask why. They ignore your “no”. It’s not easy being a girl on a dating site; as the great Day[9] says, it’s like having to constantly throw kittens into lava.

          On OkCupid it will tell you when someone visits your profile. Use that as your measure of a response. I find that often women will visit my profile if I do a good job of the opener, even if they don’t respond back. And if they don’t respond, no worries, you know the answer. Claim victory! She took a look! Awesome! Get enough looks and you’ll get a date.

          Always remember that success with women depends on three things:

          1) Your skill in communication, messaging, being confident, etc.
          2) Your physical desirability
          3) Your actual suitability to her
          4) Her emotional state at the time

          Based on this, keep in mind that no matter how skillful you are, you’re likely to strike out a lot due to 3 and 4. So work on your skills, but keep in mind it’s not going to replace numbers.

          Also, keep in mind that if women were less choosy, the good ones would get snapped up by loser guys. Be glad that women are choosy. Don’t hate the game; many other men are worse at it than you are. So work on your looks, work on your skills, work on being an interesting person, and work on being happy single.

  30. michelle says:

    Tyler, thank you thank you for writing this. I spent years (off and on) on OkCupid and other sites, and you are dead on right in everything in this post. I met my now boyfriend on OKCupid, and guess what, he followed all this advice. Dudes, we don’t care what you look like shirtless or if you advertise your oral sex skills – just come across like a thoughtful, engaging human being who’s actually read our profile, and we’ll go out with you! Easy peasy. Not to say that women’s online dating habits don’t need tweaking too…my boyfriend has some doozy horror stories…

  31. David says:

    Well said ANTHONY MILLS,

    I almost always get a visit from a girl whom I write to. Didn’t know it was a measure of success haha. ;) But I was feeling a bit down since most of them never replied after visiting. ! Or it was mostly a dead end message :). I am working on all the things that you had mentioned. I hope I get a date soon enough.
    I guess we are all WARRIORS :D (the good ones) .
    I ain’t gonna give up!


  32. Mika says:


    I’ve never heard of the Craigslist Penis Effect and it really got me snickering like an idiot in front of my laptop in a coffee shop.

    Clay and I actually met online using Match.com His email actually made me want to meet him–his email really stood out from the others (similar to what you wrote above).

    I remember getting a lot of awful emails that I would just role my eyes and delete. I remember one specific email from a man who said something along the lines of: “You have a wonderful smile. I’ve got a house in _____. Want to meet up some time?” Clay teases me about this all the time.. I mean, seriously wtf..!

    Great post,Tyler. All the points you made is something I wished more men knew about online dating.

  33. This post barely scratches the surface of online dating. If you want to take it to another level, I highly recommend reading Blackdragon’s Blog: http://blackdragonblog.wordpress.com

  34. It’s not that online dating is lame and dates usually go well 9 That means ending up in the sack) but the quality of girls online is either very low or you’re dating a hopeless romantic or a girl with a backpack full of old drama/bad relationships.

    There’s a reason these girls are dating online. If they were approached by guys in real life enough they would’t be there.

  35. Jess says:

    Ouch! Mr. Skywalker, I must agree and disagree with you. A woman is apt to try different venues of meeting people when the type or quality of people she meets through her normal, daily routine are insufficient. This has nothing to do with quantity. Also, if her life is busy or she lives in a small, secluded town, then the chances of her meeting someone is less than the average woman. It is true, however, that people tend to carry baggage since they would rather jump into a new relationship rather than process the end of their last one. Loved the article and even though it was geared towards men, well, a number of points could also be used by women!

    • James H. says:

      Agreed, Jess. For that matter, rates of divorce and marital dissatisfaction remind us that plenty of people also make *premature* relationship commitments.

    • I stand by my opinion. If a woman is attractive and has happy feminine (not feministic) vibe then there are tons of guys willing to approach her. They won’t be all “brad Pitt” type of guys though but this is exactly what the average looking woman expects even when she has seen better days in the mirror herself.
      Girls/women who look like a 6 still want to date a 9 preferably with a nice house,a nice car and a promising career. You see the problem there?

      You can say it’s not all about the outside but initially it is. Guys saying otherwise are nice guy liars looking for a pity f*ck.

      • Jess says:

        I agree and then don’t… ha! :) You are completely entitled to your opinion, but I hope you don’t believe all women are like that. No matter how attractive, happy, and feminine a woman might be, she simply cannot attract what isn’t there. If she has no lake, she must find another way to catch her fish! Also, I’m pretty average looking, and I don’t look for Brad Pitt. Guys are visual, it is expected that looks be important to them initially.

  36. @Jess,

    Are you trying to say that there are no suitable men in the place you live? You either live in a very small town with only married men or your standards are too high. Which one is it?

  37. Jess says:

    I wouldn’t know if there are any suitable men here. I only moved here 2 weeks ago. The town has about 500 people in it. I’m not looking to date but I’m sure I have high standards since I value things like morals and ethics :) Click on my name if you insist on being personal.

  38. Excellent article. I’ve always been a hater of online dating and preferred to just go out and meet people. May have to try it sometime.

    One thing I disagree with. I remember reading a study that men look more attractive in photos with female friends ie. social proof. You can tweet me if you want me to hunt down the article :)

  39. Steve Ward says:

    I have a few rules about women several are covered in the post. One of the rules i have about women is you have to earn the right (it dont have be huge could be you done x for me enough times you get to see skin.)

    Seem to work well, then again that not all i do and women seem to enjoy the challenge, although they will never tell me lol.

  40. Tiffany says:

    On behalf of all women, thank you! Someone needed to write this. :)

  41. I love how the world is one big orgy now! Hooray internet dating!

  42. Cija Black says:

    Absolutely awesome article on the topic of men and internet dating. I wish more people had your attitude about it. They act like dating sites are a gumball machine and are shocked and disappointed when they slap up a profile, sit back and wonder why the love of their life hasn’t shown up. Relationships and finding the right fit for your life take more effort then that. I also really applaud the framing of even the failed dates as learning experiences. You are completely right that if men and women for that matter took your approach to profiles and communication they would have a better chance at finding what they want online. I am retweeting and sharing the beejeezus out of this. :)

  43. Michael says:

    I started reading your site because of the name, awesome. But then i stumbled across this post, awesome. But didn’t read it for a very long time as i thought it was long – poor mistake it was half the size i expected because it’d had so many comments. Lesson learned, pay more attention!

  44. AMS says:

    Well, I just came across this post because it was actually referenced in a profile I read on OKQ. I agree with just about everything you say here and I just want to share a bit from my own experiences.

    I’ve been doing the online dating thing for a long time and I’ve had mixed results over the years depending on the approaches that I took and the site I was on. In fact I often thought about starting my own site as a primer to online dating but not an actual dating site and I own the domain cupidsdead.com, I’m not plugging it, there is nothing there, no point in going to it.

    One thing to keep in mind is the site you are on is VERY important to how seriously someone is invested in the process. The two sites I have flipped flopped back and forth between are Match.com and OKQ. But I’ve honestly checked them all out. Like I said at one point I wanted to start my site and part I wanted to provide was a profile on each, the demographic data, success rates, site usage, new users vs stale users, etc.. I’ve put a LOT of thought into this whole thing. I also thought it would be a good way to write off my online dating as “research”.

    As far as my own experiences go, they have varied greatly over the years and one thing I can tell you from mine is that LOOKS do matter. I know this because I’ve been on both ends of the spectrum. I used to work in fitness and was a personal trainer and in those days, I was much leaner, much more chiseled, more defined, had a tan, vascular, etc… I had a much, much, much higher success rate than I do today. Don’t get me wrong, I’m still a good-looking guy, but I’m not what I used to be. To point out another thing, I’m balding so I shave my head with a razor blade. It isn’t a look that is preferred by vast majority of women, especially women in their late 20’s early 30’s. As women get older I think they realize hair is more of a “nice to have” than a “must have”. How do I know this? Because believe it or not, I’ve actually gotten email responses that said, “If you only had hair” or “How would you feel about growing your hair out” or “I’m not into bald dudes”…

    I usually don’t have a problem getting responses to emails that I send that are fairly short but have some substance and include a bit of humor in them. I also try to find tidbits in their profiles I can reference in the emails. But it is a numbers game. I just got through explaining this to my brother who is having a miserable time on match.com and I told him it’s because he doesn’t put enough effort into it. But it really does come down to sales and marketing and you really need to blanket your target demographic if you expect to get a decent return on your efforts.

    There is nothing worse however than a lame profile that says “I like to work hard, play hard, travel as much as I can and I’m training for a marathon or a 5k or 10k” – Well ladies (most of the audience here is ladies judging by the responses posted) EVERY WOMAN says this on their profiles and it doesn’t really give a guy much to work with. If you want a nicely tailored witty email, at least give the guys some material to work with and let them know some important things about you that are unique and that you may have in common with them. Unless all you really want is a guy who likes to travel, runs marathons and likes to work hard and play hard. Well then enjoy reading your one line emails.

    Back to the whole sales and marketing aspect, there are a great deal of women who are skeptical about online dating overall. Keep this in mind because it’s the woman’s number 1 objection that any guy will have to overcome in order to get to the date. If anyone has ever worked in sales, marketing or user experience, part of what your job is getting people past this objection. I’ve worked in sales and marketing and I currently work in user experience design and I’ve been trying to incorporate what is called “emotional design” into the projects I work on. In a nutshell, this is one avenue websites and applications use to help get passed user objections. The number one objection being skepticism.

    Ok, now to try and tie this all together, the main difference that I see between match.com and OKQ is the level of commitment a person is willing to make to the process. Why is this? Well if they are on match.com they are paying a membership fee and if they are OKQ they are doing it for free. MOST of the time the person who is paying the membership fee is more invested in the process than the person who is doing it for free. What does this mean? It means a lot less “cock-shots” for the ladies and a higher conversion rate for guys provided you get a response to your initial email.

    Women generally take more than a few emails before they are willing to meet up or give you their number. This however varies between the two different sites.

    Women on Match.com are LESS skeptical than women on OKQ, again, probably because if you pay for something you take it a bit more seriously. This to me translates into follow up emails, I usually don’t have a problem getting a response to my first email on OKQ however if you ask for “the sale” too soon in the process you will drive a skeptical woman away. If you hesitate and play email tag too long, you will drive the skeptical woman away. Sometimes however, women just bail out in the middle of the process, never to be heard from again.

    Could it be something I said? Maybe. Could it be she wasn’t interested or I didn’t move at her pace, Sure. However it could also be that she got completely turned off by the whole process from the 50,000 other emails she is getting that have “cock-shots” in them and are nothing but a waste of time. Or maybe she got back together with her ex that she just broke up with and she was only on OKQ to make herself feel better or waste some time. On Match.com I rarely have a woman bail in the middle of “the process” and as I get older I am often finding I don’t move fast enough for them and they are asking me to meet or give me their phone numbers before I ask them. I mixed on this, on one hand, yes it’s better to meet sooner rather than later so you don’t waste a ton of time but on other hand, sometimes it feels more like desperation.

    Issues I’ve seen with women on OKQ and have not seen on Match.com –
    Women will open profiles out of spite for an ex.
    Women will open profiles to bolster their confidence because they just got out of a relationship but really aren’t ready to date yet.
    Women will open profiles “because my friends put me up to it”, to these ladies, I say close your profiles or own up to the fact that you really wanted to do it. If you can’t be honest with yourself, who can you be honest with?
    Women will have profiles open for them by their friends.
    The whole Catfishing thing and people just looking to fill a void.

    These are all reasons to stay away from these women, they are insecure, they are not ready to move on from an ex, they are emotionally unavailable, they are overly skeptical about the process and only doing it because their friends are making them or they are just looking to fill a void and have no real intent on starting a relationship.

    My number one pet peeve that happens on OKQ that doesn’t happen on Match.com though is;

    Women who use it not as a dating site but as a site to find friends.

    I read a profile the other day and I tried to go back and find it so I could quote it directly but I couldn’t. This woman was adamant about the fact that she was only looking for friends, that people need to stop trying to hang out with her in hopes of there ever becoming more and waiting for an opportune moment. No offense, but if you are looking to meet guys on a dating website, these guys are going to want to be more than just friends, they are hoping that after hanging out with them a bit, you will see what a catch they are and want to date. I personally don’t even bother with profiles like these because I’m not looking for friends. I’m looking to date and to meet someone I really could spend my life with. Ladies, if you are looking for friends and only friends, use meetup.com, there are plenty of different meetup groups that you can use to find friends with similar interests you won’t waste anyone’s time and you won’t have to deal with the “wolves in sheep’s clothing”.

    My last relationship started on match.com and lasted 10 months. My longest relationship from a dating site was 3 years.

    In closing, guys need to remember when writing their profiles or writing their emails to include humor. I will quote Marilyn Monroe here – “If you can make a girl laugh, you can make her do anything”

    Unfortunately I need to clarify this for some individuals, it should say “Anything within reason”…

    For anyone not having success on OKQ, I would give the alternative a try before you write off online dating all together.

    And No, I’m in no way affiliated with Match.com other than the fact that I use it.

  45. Cija Black says:

    Hello AMS you have clearly given a lot of thought to this whole process as well as considerable research time. I would love to get your feedback on a book I just wrote on this topic. Please contact me at my website if you are interest and thank you writing such a well thought out post.


    dude you realize 39 dates with an average of $50 a date which is barely half a dinner and a drink where i live. 39 times $50 is like $2000 man. So you spent 2,000 dollars and had alot of fun with a 19 lame chicks. And not one of them became a long term relationship? SOUNDS TO ME LIKE A WASTE OF MONEY. but i guess we aren’t all 1%ers’ DOUCHE


    well i don’t have enough time or money to drop 2k on dating WHACK chicks so i play a little message pong to find out if they are even worth meeting. Then i do some skyping too to make sure she is cool. Than i meet up. But your way works too if YOUR HELLA RICH PLAYBOY TRAVELLER NO JOB BALLER ASS SPOON IN THE MOUTH DOUCHE BAG.

  48. Wait, $50 per date!? Most dates I go out on are first dates, coffee dates. I pay for my drink, she pays for hers. Five dollars is an expensive first date for me.

    And if the women you’re going out with are lame, you’re doing it wrong. Internet dating allows you to prequalify like crazy, and OkCupid in particular. Looking through all the questions, you can go on first dates with only the promising ones. Plus, you have a conversation first through messages and/or the phone. Most women never get past that.


    Yeah no more dinner or drank with chicks that suck. Coffee is a better idea i agree.


    Just be careful there are alot of chicks that fund their lifestyle on these online dating sites. Literally eating out for free for years.

  51. I do not even know how I ended up here, but I thought this post was great.

    I do not know who you are but certainly you are going to a
    famous blogger if you aren’t already ;) Cheers!

  52. Katherine says:

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Founded with love by Tyler Tervooren

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