How Not to Lose it When Dating

How Not to Lose it When Dating

Over the years, I’ve gone through just about every permutation of dating frustration you can imagine – being unable to even talk to women, the dating site emails that disappear into the void, the first dates to nowhere, the second dates that never resulted in a third – you name it, I’ve done it. Even under the best of circumstances – and I’m saying this as someone who loves dating – it can be an infuriating, exasperating, exhausting process. And that exhaustion makes it even harder. Dating is a holistic experience; it’s something that encompasses your entire life, not just one sliver of it. Problems in your everyday life will be reflected in your dating life and issues in your dating life will affect your day to day existence, setting up a self-perpetuating loop of frustration.



This is why it’s important to recognize that sometimes the way we go about trying to date makes things harder on us. It doesn’t do any good to try to make dating simpler if all we do is end up shredding our souls in the process.

But we can avoid the most common ways that we end up complicating things needlessly and fighting our own progress. If we follow some simple rules, then we end up making dating easier… on ourselves.

Realize That It’s A Numbers Game

The first rule of dating is that you’re going to need to approach a lot of people to find love. Expecting to find The One (there is no One) right off the bat is a recipe for heartbreak. Going into every approach, every date under the assumption that this is going to be the last time you ever have to do this is going to drive you mad in short order. No matter how skilled you are of a Casanova, how good looking you are or how whatever-you-might-be, you’re not going to be everybody’s cup of tea. There will people who you simply aren’t compatible with or who aren’t going to like you no matter what you do.

This includes abject begging and straight-up bribery.

Sometimes it’s incredibly obvious from the start that things aren’t going to work These are going to be the people who reject you – or that you reject – right off the bat. But other times it isn’t obvious at all. Sometimes it may look like you’ve got some chemistry after all. Or that sure they trigger your Spidey-Sense but they’re so hot that maybe you’re willing to overlook it and see if that whole “only one head” rule you have is a deal-breaker or more of a guideline really.

This means that you’re going to end up with a lot of false positives. You’ll have long email conversations on OKCupid that trail off and never lead to meeting in person. You’ll have first dates that don’t go anywhere, second dates where you thought things went swimmingly but she won’t return your calls…

Yeah, it’s frustrating. But it’s also an inherent part of the process, and the sooner you recognize this, then the easier dating will be for you. A lot of people tend to have unrealistic expectations when it comes to dating success; they think that they’re supposed to meet their One True Wuv and live in fairy-tale happiness ever after, and that’s just not how the universe works. It’s very, very unlikely that you’re going to meet a soulmate on the first try. It’s akin to buying a single lottery quick-pick and expecting to hit the Mega-Millions jackpot; it happens, but the odds against it are so astronomical that I don’t think they make numbers large enough to actually express the concept.

Believe it or not, this is a feature, not a bug. The savvy dater knows this, because it makes dating easier in the long run. Remembering that dating is a numbers game helps you be outcome independent – you go into each interaction with the attitude of “well, let’s see what happens” rather than “this person may be THE ONE”. It helps absorb the sting of rejection because you didn’t over-invest in this person right off the bat. It empowers you to take risks and approach more people because the more people you approach means that you start that many more conversations. Those conversations mean opportunities to flirt and build chemistry which lead to more opportunities for dates. The cliche “you miss all of the shots you don’t take” is absolutely true. The more you put yourself out there, the more chances you have for success.

Now, I already hear the cynics among you saying “yes, and it gives you more opportunities to be shot down.” Which is true. But part of making dating easier means that you have to…

Learn To Handle Rejection

Rejection happens. It sucks, but it’s a part of the game. There’s absolutely no getting around this. You’re going to get rejected. Anyone who tells you they never get rejected is either lying to you or selling something.

Usually both.

Sometimes you will get rejected a lot. But if you’re going to let it destroy you, then you’re never actually going to improve; you’ll end up never taking chances unless there’s no risk and – spoiler alert – those don’t exist.

And I get it: rejection hurts. It feels personal, and sometimes it is. But often it isn’t a judgement on your worth as a person, just on how you’ve been presenting yourself to them. Many rejections are either a result of poor performance or a fundamental incompatibility. In the case of the former, you can learn from it; failure is how you refine your approach. In the case of the latter, then all that’s happened is that you’ve confirmed that it wouldn’t have worked in the first place. And often, your getting rejected has absolutely nothing to do with you. You may look like her ex. She may be in love with someone else. She may have had a bad day and didn’t want to deal with anyone. She might not want to date, might be gay, might be asexual or just straight up doesn’t want to talk to another carbon-based lifeform for the next several days.

Here’s some cold hard truth: you can do everything right and still get rejected. You can be the most objectively good looking, suavest motherfucker ever to glide into a room, who knows exactly what to say and when to say it…

"Someone say my name?"

…and still get shot down.

"Someone say my name?"

That’s just life, and either you can get up and try again or you can just lay there and bleed.

Here’s a secret though: the guys who can handle rejection with grace? The ones who can take a “no, thanks” with a smile and a nod and move on? They’re the ones who’re the most in demand, because they’re showing a level of confidence and an abundance mentality that is veryattractive.  That one person may have shot them down but trust me, other people noticed how they handled it.

The better you can handle rejection, the easier dating will be for you.

Watch Your Attitude

You know who is pretty much always unattractive? Captain Negativity. You know the guy: the one who’s pissed off and bitter about everything. Give him a moment and he’ll talk your ear off about how life sucks and everything’s unfair, how women are cruel because they won’t give him a chance and it’s all about those 20% of guys who get to fuck 80% of the women and everyone else is justscrewed man. He’s the one who’s the first to complain about his dating life and then turn right around and get angry when you try to help him fix it. Everything’s too hard, or too arbitrary or too something and there’s no point in trying to fix it because reasons and also misandry so there.

"Maybe I should just not date anyone. That'll show them."

Can’t imagine why they don’t have women lined up around the block, huh?

Dating is about 10% looks, 20% skill and 70% attitude. Your attitude is, hands down, the biggest indicator of whether or not you’ll succeed in dating. A positive attitude goes a very long way towards helping you improve, and makes people want to hang around you more. A negative attitude helps ensure failure by creating a self-fulfilling prophecy and ensures that people will avoid you. See, studies have found that emotions are contagious; the moods of the people around us affect how we feel. We like positive, friendly, optimistic people because they make us feel good too. On the flip-side, we try to avoid negative, unhappy people because they drag us down with them.

"Entitlement leads to resentment. Resentment leads to bitterness. Bitterness leads to suffering..."

Your attitude will make or break you, no matter how good looking you are or how superficially charming you may be. No matter how hot somebody is, nobody is going to put up with their shit for very long if all they do is moan and cry and complain.

Don’t get me wrong: nobody is saying you can’t be frustrated or confused or upset  or that you have to be a complete Pollyanna in order to make dating easier. But people respond to your attitude, and a bitter, resentful outlook on life is going to push even the most determined of individuals away.

Keep It In Perspective

One of the issues I see come up when people are trying to get better at dating is that they get tunnel vision. This happens all the damn time in the pick-up scene; their entire lives is about being a PUA. Everything they do revolves around trying to pick up women. It’s all they talk about with their friends. It’s all they read about. It’s all they think about. Just about every waking moment in their lives is focused on getting women to fuck them. I should know. I was one of them. And you know what? Despite focusing their entire lives on the subject of getting laid like an especially horny laser, they weren’t doing all that well.

It happens in regular people too. They’ve become so determined to find a girlfriend that it becomes all they talk aboutall they think about… and that’s a problem.

It’s easy an easy trap to fall into. On the surface, it feels like you’re throwing yourself into it, as though you were trying to train like an Olympic athlete. But what you end up doing is retarding your own progress. Devoting time and energy to practice is good – it’s a vital way to improve any skill and dating is a skill – but there comes a point when you’re overdoing it… on just about every level.

I realize this is an odd thing for a dating coach to say but: dating isn’t the most important thing in the world. In fact, when you’re putting your entire focus on your dating life (or lack thereof) then you’re actually doing yourself a massive disservice.

I mean, sure, you’re here because you’re trying to date better…

Or maybe you just really love my carefully curated array of stock photos.

…but rather than making dating easier, making getting better at dating the center of your universe actually makes it harder.

I want you to try something here. Just trust me for a second, I promise this will be relevant. Stand up, walk into the next room, then turn around and walk back. Pretty easy, all things considered, right? Now I want you to do the exact same thing. Stand up, walk into the next room, then turn around and walk back… except this time I want you to do it while tensing every single muscle you can at the same time. Notice how much harder it is to move at all? This is because you’re having to push past the resistance that your body is producing through dynamic tension. You’re fighting against  yourself and it’s making it harder to do something as simple as “walk in a straight line”.

...and really, who HASN'T had that issue before?

The point of this exercise is that it’s possible to end up getting in your own way, and people who don’t keep things in perspective tend to do just that. In every skill progression, there are plateaus; it’s just part of how we work. You improve to a certain level and then your body and mind acclimate to the new level of mastery. Suddenly you’re not improving the way you were before. You’re finding new sticking points that you just can’t seem to get past.  And when nothing seems to go help you get past that new plateau… well, you grit your teeth and try harder… and then again and again and… well, pretty soon, you’re actually going backwards. You end up frustrated, and like a gamer who can’t get past that one fucking platforming section, you start getting impatient. You start rushing things to try to get to that sticking point and in your rush you get sloppy. You develop bad habits as you try to cut corners and then you get even angrier because you know you can do this goddamnit and even the things you’d thought you mastered are failing you.

You’re pushing muscle against muscle. You’re fighting against yourself.

So how do you avoid this problem? Well… by not focusing so goddamned hard. See, getting better at dating is a holistic practice. If you want to get better at dating, you want to be a better person and that means leading an interesting, fulfilling and well rounded life. Getting more involved in your life as a whole makes dating easier because it makes you a more interesting person. Dating and relationships are a part of life, not the entirety of it. Yes, you want to practice. But if you don’t have things going for you in your life besides whether or not you’re railing chicks or whether you have a girlfriend, you’re going to be fighting against yourself.

And that’s why sometimes it’s good to…

Take A Break

Sometimes the most important part of trying to get better at dating is to stop. It can be easy to get frustrated, especially when you’re constantly working at it. Practice is all well and good but you need time off to recover; in fact, if you’re not taking any time off from practice then you’re actually not going to improve. You need time to process what you’ve learned, to recoup your mental and emotional energy.

This is doubly true if you’re having problems with your dating life. When you’re experiencing nothing but failure again and again and again, throwing yourself back into the pit is going to shred your ego and destroy your confidence. NerdLove’s Rule #357: If you find yourself constantly beating your head against a wall, then it’s time to stop. Take yourself out of the game for a little while. Stop focusing on dating, on sex, on… well, everything related to your love life and just be for a while. Give yourself permission to sit out for a while, even if that means chilling at home with a Teen Wolf marathon on Netflix while all of your friends and wingmen are out at the bars downtown. Sometimes you need to take a step outside of the dating world and practice a little self-indulgence for a while.

"Maybe this is the episode when Ollie finally realizes he's in love with Felicity!"

Taking a break lets you relax and gain some much needed perspective. It lets all of those emotional muscles unclench and loosen up while you put your focus elsewhere. It frees up emotional and mental bandwidth that you can devote to other aspects of your life, allowing you to reprioritize and work on yourself a little. Taking that time off helps you improve. A little vacation from your dating woes means when you do come back, you’ll be feeling tanned, rested and ready to give the old town a wedgie again.

But most importantly, that break can make dating easier on you. It lets you rebuild your ego and restores your confidence. You’ll find those sticking points aren’t quite so bad after all; a little break to relax and suddenly you’re blasting through them on the way to your next level of mastery. It helps refresh your attitude, gives you distance on your failures ad better perspective on your successes.

Like I said: dating is a holistic exercise; when you’re suffering in one area, you’ll wind up suffering in all of them. The best way to make dating easier is to make it easier on you.


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