Top 5 Mistakes Men Make In Dating

The key to learning any new skill is to deconstruct it. You want to break the skill – whether it’s playing guitar, learning a new language or even dating – into its core components.

It’s entirely too easy to get distracted by side issues; the would-be martial artist wants to skip straight past the basics to where he learns how to break boards and beat people up, the cooking newbie obsesses about the perfect knife or whether he needs a food processor or a sous-vide appliance while he still hasn’t mastered basic prep.

In dating, we are often distracted – focusing on the perfect approach and opening line or how to get a one-night stand, for example – when our time is better spent learning the central concepts. After all, you need to learn to crawl before you run.

One of the keys to deconstructing a skill is to find and focus on the areas that cause people to stumble and fail. After all, it doesn’t do any good to spend your time learning bad habits that you will only have to unlearn later on.

But sometimes those sticking points aren’t where you think they are.

Worth noting (since somebody will bring it up in the comments) is that the mistakes that hold you back aren’t about technique (leaning in when talking to people, too much physical contact) or planning (forgetting to check logistics). The biggest mistakes are the ones in your head. Before you even approach someone or sit down at your first date, these are the problems that make dating so much more difficult than it needs to be.


5. Stop Overthinking Things

One of the perils of being a geek is that we live in our own heads. We’re clever and we know it… and this is often a problem. You see, when you’re clever and you know it, you’re more likely to actually make things more complicated then they truly are.

We tend to assume that things are always more than they seem whether it’s an SAT question – “That comparison of cow is to goat as BLANK is to BLANK can’t just be because they’re land mammals… maybe it’s because they’re both domesticated and give milk… what else gives milk that we domesticated? Camels? Sheep?”  – to dating.

We have a hard time assuming that perhaps the most obvious answer is the right answer because we grew up believing that the obvious answer was a trap of some kind.  Clearly it’s too obvious, therefore there has to be something we’re not seeing…

This is never more clear than when you see someone playing “Does she like me or not?” They start reading the tea leaves, examining a woman’s behavior as though it were the Zapruder film, looking for tiny clues that would give us insight into what she really means when she says she’s busy that weekend.

This causes many people no end of anxiety, especially those who are worried about being creepy by accident. They become so  caught up in trying to find even the most minute sign of discomfort that they end up being unable to relax and actually interact with her.

Same with knowing when and how to approach someone. The only real approach invitation one needs is a genuine smile, but many guys treat approaching a woman as though they were trying to make a carrier landing – look for hair flipping, the look-away-look back AND the head nod, now call the ball….

This can cause problems even on dates: what did it mean when she declined another drink? She paused a few seconds longer when she was talking about her hobbies… is she wishing she were somewhere else? With someone else? She keeps bringing up her ex – does she mean that she wishes were more like her ex? 

I’ve gotten letters from people who have asked women out on dates – dates that women said yes to – and want me to dissect everything she said or did because there has to be more to it than she thinks they’re fun and wants to go on a date with them.

As a general rule of thumb, people say what they mean. They’re not trying to hide their real feelings and you don’t have to be a master poker-player to find their tells. Unless they’re trying to usurp the throne of Westeros, people aren’t cloaking their true intentions in subterfuge and guile.

Yes, there are assholes out there. There can be times when social conditioning – especially on the part of women – means that they will try to be sparing of somebody’s feelings. But the vast majority of the time, the correct answer is the obvious answer.

4. Stop Playing Games

This is one of my pet-peeves: people who think that the keys to dating are complicated mind-games and arbitrary rules. I split the blame between the pick-up industry (for men) and old-fashioned cultural bullshit like The Rules (for women) for perpetuating the idea that dating is more complicated than whether or not you like someone else and want to pursue a relationship with them.

The PUA industry, for example, gives the idea that women are hypergamous status-seekers who have pre-rejected men; men have to jump through hoops in order to prove that they are worth dating… and even then, women are always looking for reasons to trade in their current boyfriend for a newer, shinier model. Through social proof, compliance ladders, mind games, strategic negging[1] to establish your status above hers, you can convince a woman that you’re not only the new shiny model but she should be seeking yourapproval.


Instead of treating her like a person and getting to know her.

Some schools within the industry take it to a darker, more psychotic place where men should be manipulative as possible, the better to keep her constantly insecure in the relationship and unsure of her standing; after all, if she’s never sure if she’s done something wrong, she’ll be that much more eager to please you. Keep her off-balance and you’ve got your own love slave.

Then there are other cultural ideas like the three days rule (popularized by Swingers): the idea that you shouldn’t call a girl for three days after you got her number for fear of appearing too eager.

The Rules plays its own counterpoint to the misogyny that’s all too present in PUA society; it deals in slut-shaming bullshit and old-fashioned ideals with rules like “Never call first and rarely return his calls”, “don’t see him more than once or twice a week” or “no sex before exclusivity”. After all, to be too accessible or to be willing to own your sexuality means that men won’t respect you, missy.

All of these games and arbitrary rules take getting to know someone and finding out whether you’d be interested in a relationship with them – whether sexual or romantic (or both!) – and turn it into a campaign of manipulativeness and dishonesty. It means that not only are you entering into this interaction in bad faith – after all, you’re not presenting your true self – but that you’re so insecure that you can’t allow yourself to be honest or vulnerable. Moreover, it implies that you see relationships as inherently antagonistic, where only the better games-player “wins”.

Small wonder you’re having dating problems if this is your attitude.

The best thing you can do when you’re interested in someone is to be your best, most authentic self, not what you think you need to be.

3. Take Responsibility

This is something I see far, far too often amongst men: the belief that they’re helpless victims in a cold universe; poor hapless players in a game where the deck is stacked against them. It’s not their fault; women are too bitchy or demanding or only date X guys[2] or some other reason why they should be absolved of responsibility for their lack of success. 

I get the appeal. I mean, shit, was one of those guys for an embarrassingly long time.

But it’s all smoke and mirrors. It’s a way of deflecting the truth and protecting yourself from the fact that you are the sum total of all of your choices in life, both good and bad. No matter how much you wish you could blame it on something, anything else.

It’s great when you can blame everything on someone else; women only like assholes, women are crazy, they can’t appreciate nice guys like you, it’s not your fault. But at the end of the day, the thing that every rejection, breakup and heartbreak has in common… is you.

This doesn’t mean that you’re just some loser or creep who deserves to be alone, but it does mean that you need to examine what you’re doing. Sometimes it’s a case of things you’re doing wrong – you’re coming across as too needy or being too sexual too quickly. Sometimes it’s a matter of the choices you make; you may be pursuing women that you’re not suited for or who aren’t suited for you. Sometimes it’s a matter of lifestyle or even a matter of your personality. At which point you have a choice: do you continue to just wail about the unfairness of life… or do you accept that you and you alone are responsible for your life and take control in order to make things better? 

Are you going just suffer the slings and arrows of outrageous fortune — to quote the Bard[3] — take up arms against a sea of unending troubles and by opposing, end them?

Sure, sometimes shit happens that’s out of your control — you get laid off from your job, your girlfriend suddenly dumps you out of the blue because she’s decided to pursue her dream of living in Williamsburg and starting a throat-singing folk band, a meteor falls out of the sky and destroys your house.

That sucks. But you can either whine or you can do something about it.

If you don’t take responsibility for your life, you can’t control it. You can’t blame all of your failures on God, the Universe and everything and still take credit for your successes.

So you can accept responsibility for your failures in your dating life or you can never get better. Your choice.

2. Set Firm Boundaries

A lot of socially inexperienced guys, especially those who have low self-esteem, have a hard time setting boundaries. These are the people who let others walk all over them, who constantly put other people’s needs ahead of their own, who are always balls-deep in drama.

It can be hard to feel as though you deserve to be respected, to be willing to take a stand and say “No, this isnot my responsibility” when others try to shift it onto you. When you don’t feel as though you have anything to offer, or that you don’t have a right to refuse others, it’s difficult to draw a hard line and say “This far, no farther”.

Being overly obliging is actually an incredibly common way people try to get others to like them. In theory, it seems obvious: do nice things for people and they’ll appreciate you. In practice, it’s quite the opposite; when you don’t respect yourself enough to say “no”, then others won’t respect you. After all, you’re telling themthat you have nothing else to offer.

Not having strong boundaries leaves you vulnerable to manipulative assholes, passive-aggressive victims and emotionally abusive shitbags.

I should know. My weak boundaries left me stuck in an emotionally abusive and life-draining relationship for years. Being able to stand up for yourself and demand that people respect your limits and wishes speaks to confidence and, critically, will help ensure that you aren’t being pathetically needy in an attempt to get people to like you.

1. Stop Thinking It’s All About You.

Here’s what a lot of people don’t realize: you’re not the only one freaking out about dating. Everybody else is too.

A date isn’t a competition or an audition for a role, it’s a way of getting to know somebody. You’re not trying to prove something or meet some arbitrary and random standard to prove yourself worthy of a second date, of sex, of a relationship; you’re trying to form a connection with another person.

Every single date you’ve ever gone on, you’ve been sitting across (or next to) someone who is just as nervousand just as anxiety-ridden as you are. They’re sitting there wondering what you’re thinking, cringing inside as they made a joke they’re convinced just fell flat, worrying that they’ve got something between their teeth, wondering what that pause in your story meant, praying that their hair looks ok, that their dress doesn’t look as bad on them as they imagine it does and that you’re not going to think that they’re some crazy, creepy loser.

Just like you are.

You know why?

Because your date wants everything to go well just as badly as you do.

People don’t go on dates with folks they don’t like[4], they go out with people they like and want to get to know.

If she said “yes” when you asked her out, you’re half-way there! You already know that she’s interested in you and wants to get to know you better. All you have to do is relax and let her know you are the cool, funny, charming person she’s been hoping to meet.

When you’re so caught up in your own anxieties and worries that you think that every date is a referendum on you as a person, it’s going to come out in your behavior, in your body language and in the way you speak. You need to be willing to realize that she’s right there with you. She’s cheering you on. She wants to like you and she wants you to like her, too.

Take a deep breath. Accept that you’re nervous and that’s ok. So’s she. Accept that things can get awkward.

Accept that she wants to be there.

Stop making the mistake that you’re the only one who’s freaking out inside.

You’re both hoping for the same thing. Thought Catalog Logo Mark


[1] If I could remove one concept out of the dating scene, negging would be it
[2] where X= some value of “not me”
[3] It never fails. Scratch an English major, get a Shakespeare reference.
[4] Yes there are assholes out there who are just out for sex, obligation, pity, free dinners, whatever. These are the exception, not the rule

Join the Patrón Social Club to get invited to cool private parties in your area, and the chance to win a four-person trip to a mystery city for an an exclusive Patrón summer party.

This post originally appeared on Paging Dr. NerdLove. Follow them on Facebook and Twitter.

image – Simon Clancy

Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and at He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.

Keep up with Harris on Twitter and

More From Thought Catalog