18 Women, 39 Dates, 1 Wild Ride: A Guide to Attraction on the Internet
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:
- Your written profile
- Your photos
- 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:
- Confidence
- 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:
- 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.
- 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:
- They’re not going to beat down your door to go on a date with you.
- To be successful, you must play the numbers game and message a lot of women.
- 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