6 Major Pitfalls for Guys to Avoid When Online Dating

They say you learn more from failing at something than from succeeding. If that’s the case, I’ve learned quite a bit about the online dating world over the years. Still, you’ve only really learned from your failures if you can adjust your actions to achieve some success, so a 100% failure rate doesn’t make you an expert so much as an idiot who refuses to take a hint. To that end, I’ve also had some successmore as time went on, in fact. So while I’m obviously not claiming that I’m the greatest online dating expert of all time, I can confidently say I have learned some useful and important truths when it comes to making it work.

Even though I wouldn’t win any dick-measuring contests about how many girls I’ve gone out with from dating websites, I think I have some legitimate insights into what works and what doesn’t work because I had to put a lot of effort, trial and error into figuring it out. And while none of this is an exact science—you just can’t predict what any one person is going to respond to—the following bits of advice are things that I’ve come to realize are particularly important in having online dating success.


Pitfall #1: Self-Deprecation

A friend of mine once told me about a joke he leads off with when talking to girls online. It was genuinely funny, but it was about his (lack of) height. You might think it seems pretty cool of you to show a woman that you can laugh at yourself and that your perceived shortcomings (no pun intended) don’t bother you. The problem is, when you immediately mention your "flaws," no matter how much good humor you put behind them, you usually come off as insecure.

The first thing it does is call immediate attention to a characteristic that, at least in your mind, could be a deal-breaker. But she already knows your vital stats from looking at your profile (which should be completely filled out, more on that below), and if she was on the fence about dating you in the first place, bringing up potentially irreconcilable differences right off the bat won't help your cause. You're trying to give her reasons to say YES, not to say NO.

I boiled it down to one qualifier for my friend: how many dates have you gotten when you used this opening line? It turns out he often got a positive response from people who thought it was a funny and honest thing to say, but when it came to going on actual dates with said women, the answer was none. This is probably because anything resembling insecurity is an instantly unattractive feature.

I used to be the king of self-deprecation, but at some point it actually makes people uncomfortable. Most folks are willing to accept you for who you are, and if your physical peculiarities are a problem for a potential date, you don’t want to go out with them in the first place. You'll never change their mind by specifically pointing them out. Here's a scientific chart to help you understand:


Pitfall #2: Proving What a Great Guy You Are

You know the phrase “nice guys finish last?” It’s complete bullshit. Girls actually do like nice guys, they just don’t like when you’re a complete pansy. There’s a big difference. I’ll be writing a lot more about that in a future post, but it's not the main point here. 

One of the big pitfalls that “nice” guys fall into is trying to prove how great a guy they are so they can stand out in a crowd of assholes. There is a crowd of assholes out there, but trying to qualify yourself, much like Point #1 above, winds up working against you. There’s a very important thing to keep in mind when dating online, or really dating in general: if you are a great person, she will figure it out. You don’t have to try and prove it all the time by saying/doing the most sensitive thing you can think of at any given moment.

The more “sensitive” you try to be, the less appealing you wind up actually being. Trying too hard at anything is a turnoff, but trying too hard to be nice is a subconscious turnoff that can still elicit a seemingly positive response ("That's so sweet!"), making it extra-confusing. A woman can appreciate anyone being a nice person, but what you don’t realize is that she’s thinking you’re sweet like a puppy dog, not sweet like a man she’s attracted to. While you're later wondering where it all went wrong, the sad truth you may never understand is that you’ve tried way too hard.

Bottom line: most women you date aren’t complete idiots. They can tell if you’re a good person or not. Let them figure it out on their own instead of trying to prove it and putting yourself immediately in the “subservient friend box.” You should still be nice, but they don’t want you to wait hand and foot on them unless your goal is to become their personal butler.


Pitfall #3: Assuming She’ll "Get" You

This is where things get a little tricky. While you don’t want to deliberately try to qualify how great a person you are, you also can’t make any assumptions that your good intentions will automatically translate into good vibes on her end. If you say something incredibly offensive but mean well, she’ll still be offended. And as mentioned in Pitfall #1, If you say something super self-deprecating and assume she’ll understand that you’re not insecure, there’s about a 95% chance that you’re wrong (see scientific chart above). Believe me when I say that sarcasm tends not to translate well online, so you have to be very careful and specific with how you word things.

The idea of this isn’t to contradict Pitfall #2, it’s to reinforce the idea that you can’t make any assumptions about how you’re coming across to someone when you’re acting one way but hoping they’re feeling another. So think before you speak/type. She will read many things more than just the words you write, so don’t assume the “real you” will automatically shine through the text in her inbox. Let your real personality show, and do it carefully. Then accept that sometimes—most of the time, actually—it won't perfectly connect. Here's another super-scientific chart for your benefit:


Pitfall #4: Waiting Too Long to Ask For the Date

When you hit it off with someone while chatting online, it can be tempting to keep the conversation going for a while, get to know each other better and connect on a deeper level before meeting in person. But the real connections happen face to face, and she is almost definitely chatting with people other than you no matter what “vibe” you get. Online dating has one goal and one goal only: to get a real, honest-to-god, in-person date with someone. 

Your OKCupid messages are not a time for a heart to heart. If she is responding to you, that’s a sign that she’s at least slightly interested in meeting up. You shouldn’t send her more than three messages before you ask her out. There were times when I felt confident enough to ask for the date in the second message, and I know some people even ask in the first message (I've rarely done that, but if you word it the right way I could see this working). 

So keep your messages personalized (mention something you saw in her profile that you have in common) and reasonably short (too long and it’s both intimidating and inconvenient for her to read), then look for signals she’s actually interested. If she’s responding with very short answers and neither asking you questions back nor attempting to facilitate more conversation, move on. She’s not interested and is just being nice.

Of course, once you meet her in person it’s a whole other conversation game. But with online dating, that meet-up is the one and only goal. If you set up a real date from an online interaction, that’s a win. (Side note: try to keep it as safe a proposition as possible, like coffee in the afternoon or drinks in the evening in a public place.)


Pitfall #5: Caring About Anything After Pressing Send

So you found someone that you really connected with, someone whose profile spoke to you, where you repeatedly shouted “YES” to yourself with each successive talking point, someone whose pictures show the sum of every physical desire you’ve ever wanted. Congratulations! Send her a message, then immediately forget she even exists.

Online dating is a numbers game, plain and simple. This is particularly true for guys, who are typically the ones sending the most messages. There are about a million reasons someone might not respond to you, and almost none of them have anything to do with you as a person. For most normal guys, the majority of women out there will only be mildly interested or not interested at all. Online dating is great for exposing you to people you never would have met otherwise, but it also allows us to be unusually picky, scrutinizing a profile for the slightest incompatibility then writing the whole thing off. Unless you look like Brad Pitt or write the most poetic messages ever to exist on the Match.com servers, you will not get responses from the vast majority of women you contact, and that’s OK. Send it and forget it. Move on to whomever’s next. Hearing back is a bonus.

Speaking of the numbers game, you should be sending as many messages as humanly possible. You should be on your dating site of choice daily if you can. Just like in real life, the best way to increase your chance of success is to be rejected the maximum number of times. Not that I've been rejected about 20 million times in my life. Not like that at all.


Pitfall #6: Not Having a Woman Read Your Profile

Remember how I said your profile is going to be scrutinized by every woman you message? Why not have a woman who knows you scrutinize it before you even start sending messages in the first place? There’s no way to guarantee every person will like what they see, but no one understands the immediate turn-offs many women have like a woman does. Have a close female friend take an honest look over your profile and give you feedback. You don’t have to take all her advice, but you are sure to learn about ways you may be repelling potential dates that you never even realized.

While you’re at it, make sure you fill out a complete enough profile so visitors get a feel for who you are (without writing a novel), and include many pictures of yourself, including recent full-body photos so they can get a real idea of how you look. You may be able to hide some things online, but you can’t lie about your appearance in real life. You might as well not waste your time going out with someone who wouldn’t have been interested in the first place if they knew what you really looked like. Oh, and update your profile regularly. Even if it’s a small change, this helps get your profile back in the rotation and in front of more lady-eyes.


While this list is obviously not exhaustive, I do think it hits on several of the more important things to avoid when online dating for us fellas other than obvious stuff like "don't be a creepy f#$%er." One handy point to note is that many of these tips can—and should—carry over into dating in person as well, although obviously that’s a very different situation with a whole new set of things to look out for. But as I mentioned before, the single purpose of doing this online thing is to get a date with someone in person, so you should be doing everything you can to make that happen.

So good luck and godspeed—a sea of eligible profiles awaits you...