I have a serious question for you: are you someone who plays to win, or who plays to avoid losing?
Most folks would say that, yes, they absolutely play to win. Even if they’re not the sort of min/maxing, loophole-finding, cutthroat gamesman who makes board game night a flaming hellscape, people will generally say that when they play, their goal is to make a sincere effort at winning.
However, if you look at people’s dating life, you’d be forgiven for thinking that not only are they not playing to win, they’re playing in a way that’s designed to ensure they won’t find a long-term partner. To be blunt, a lot of the ways that people approach dating actively works against them. They are, for all intents and purposes, focused on not losing. That is: they’re focused more on avoiding rejection than they are on finding a potential partner. And to be fair: this is understandable. If you don’t have a lot of social experience, you’re just starting to date or you’re finding yourself back on the market again, rejection can be scary. It feels like the worst thing that could happen to you. It’s natural to want to try to avoid it at all costs.
But the problem is that trying to avoid “losing” isn’t the same as winning; in fact, taking this outlook will actually cost you dates.
It’s time to stop handicapping your own love life. Here’s how to recognize and avoid these common dating mistakes.
#1: You Think You’re Pre-Rejected
Mistake number one, amusingly enough, could just as easily be boiled down to one of the most banal and overused quotes in modern history: you miss 100% of the shots you don’t take. It’s the exact sort of thing that sounds profound, looks meaningful and inspirational when printed on the side of a mug and gets tossed around in countless business meetings, planning sessions and motivational seminars.
It’s also not wrong.
I can’t count the number of men who act as though they’ve been rejected, before they’ve so much as opened their mouths. They believe that there’s no possible way that this person could ever be interested in them. Did they ask her out on a date? No. Have they so much as talked to them yet? Also no. But they know, in their heart of hearts, that rejection is inevitable, a lack of evidence — or even a lack of conversation — be damned.
The most obvious example of this outlook is simple approach anxiety; freezing up at the thought of trying to talk to someone or not being able to force yourself to go and introduce yourself to that cute woman at the bar. However, this mentality manifests itself in a number of insidious and subtle ways.
Take, for example, the question of “who has the power in dating?” This is a topic that comes up over and over again; it’s the assumption that since men either a) have to be the initiators or b) like sex more than women do, then women hold all the cards when it comes to dating. They are — so the theory goes — the gatekeepers of sex, the ones who get to decide who does or doesn’t actually get laid. As a result: they get to dictate terms, set the “marketplace value” of sex, and only those who meet their “price” get to have sex.
This, in turn, leads to any number of baroque explanations as to why this is the case, what they want and how guys can “win”; that is, get laid while paying the lowest possible “price”. Pick-Up Artists, for example, coined the idea of “displays of higher value” — ways of showing that you’re of equal or greater social value than they are and thus “worthy” of getting laid. Other folks convince themselves that women will only sleep with certain men — the mythical top 20% who “get” 80% of women. And while folks dress it up in any number of rationalizations, from “women get to choose” or “sperm is cheap, eggs are expensive”, it all comes down to the same idea: you’ve been rejected in advance and have to prove your worth to get UN-rejected.
This plays out in a number of ways. Guys who simply assume that there’s no way someone could be attracted to them and so they don’t bother making a move are simply the most obvious. However, another common example of this mistake are guys who feel that they have to “prove” that they’re worthy or “earn” access to sex. PUAs run canned material in an attempt to hit those supposed “attraction switches”, dropping leaden hints about model ex-girlfriends or trying to initiate “jealousy plotlines” through social proof. Other guys try their damndest to impress women with their jobs, their income, their accomplishments or acting like a supposed “alpha male”.
It… works about as well as you might think.
The problem here is that this is all one-sided; it’s a belief born out of projecting your own insecurities onto others and reacting accordingly. Women aren’t Mjolnir; sex isn’t a measure of your worthiness, nor are women out there wearing panties that read “whomsoever should part these thighs, should they be worthy, shall gain the power of Score.”
Women, like men and non-binary folks, are looking for potential partners they connect with, who they get along with and who excite them. They aren’t looking for excuses to pre-reject folks, they aren’t looking for reasons to not fuck them, nor do they choose who they date or sleep with by tallying up points on a spreadsheet. This belief creates a combative and antagonistic frame, where one of you wins and the other loses. This, needless to say, is the Anti-Sex Equation. It’s like being a magician; it’s an attitude that’s guaranteed to make sex vanish into thin air.
Women are trying to live their lives, the same as everyone else. When you act like you’ve been pre-rejected, all you’re doing is shooting yourself in the foot. At best, all you’re doing is signaling that you have low self-esteem and no faith in your own worth. At worst, you’re deciding how someone else feels for them, without ever so much as asking their opinion on the matter.
In both cases, all you’re doing is sabotaging your own success.
The key to avoiding this mistake is simple: don’t try to impress women. Don’t try to wow them with your accomplishments or “prove” your value to them. You want to come to dating from the position of “is she right for you? Is she someone you want to date?” and recognize that people you date should be worth your time. If they are, then the goal isn’t to bowl them over with your status or your wealth, it’s to try to connect with them. Find what you have in common, find what you both value and treat dating as a collaborative effort. If you are coming to any interaction under the belief that you’re pre-rejected, you’ll never succeed. Even if she does want to date you, you’ll never feel safe or secure in your relationship; you’ll just be spending all your time waiting for the other shoe to drop.
And with that outlook? It always will.
#2: You Hide Your Authentic Self
Like the previous mistake, this mistake ties into the idea that you need to fit a certain mold in order to date. Also like the previous mistake, it focuses on making decisions on behalf of the other person. The difference, however, is that in this case, folks who make these mistakes feel as though they have to be someone they’re not in order to date successfully.
Instead of trying to impress someone with status or wealth — whether you have it or not — people who make this mistake try to hide or play down the things that make them who they are. Sometimes this comes across as trying to create a false front, exaggerating accomplishments like you’re padding out your resume. Guys who noodle about with guitars or a sampler and Ableton Live become musicians and DJs, guys with cameras round up to being a professional photographer, someone working in the mailroom at a law firm may be on the “fast track to making partner” and so on.
Others, however, hide who they are; they push away or avoid mentioning aspects of themselves because they feel that nobody could possibly like that aspect of themselves. They worry that this side of them is “too beta” or that liking or enjoying this other thing is too weird or too niche or too… whatever. Male nerds, for example, have spent decades convincing themselves that women couldn’t possibly like them because they like nerdy shit and girls don’t. Other men feel that they have to avoid the things they love — whether it’s dessert, particular books or movies, sweet cocktails, even types of pets — because it’s not “manly” enough.
Other times, they feel like what they enjoy simply isn’t interesting or cool enough to be desirable and thus openly enjoying it would only be held against them by anyone they would want to date. Whether it’s coding, ballroom dancing, cooking, kink or musical theater, they believe that they need to push those aspects of themselves away in order to be a viable dating prospect.
Not surprisingly: this tends to backfire on them. But not in the way people think.
Now, if you’ve ever been told that the secret to getting women to like you is “just be yourself,” you’re probably rolling your eyes. After all, “Just Be Yourself” is one of the oldest, and most useless pieces of advice out there. Everyone who’s ever struggled with dating has been told this, and almost every time, it’s always come down to “…if being myself worked, I wouldn’t be asking you for advice!” And to be fair, that’s because most of the time, it’s advice that’s misapplied. What people mean when they say “just be yourself” is “don’t follow trends or try to be somebody you aren’t, just to impress people.”
What folks hear is “yeah, I got nothin’. Just keep doing what you’ve been doing.” Which, of course, hasn’t been working.
Small wonder that they feel like they need to try to be someone else.
The mistake people make when they run from their authentic selves is that they’re making it impossible to find people they would actually be compatible with. When folks suppress their authentic selves and interests in the name of trying to appeal to more people, they’re often doing so in order to appeal to people who aren’t right for them. They’re trying to force themselves to become, or at least appear to be, someone they’re not. If that works — and it doesn’t, but if it did — then what they’ve done is end up matching with someone who likes their fake self, not who they actually are. And, speaking from experience, it’s impossible to keep that facade up for very long. People are bad at lying, especially over the long term, and it fucks with our heads. The truth almost always comes out, and the stress of living up to that fake persona ends up blowing up in your face… usually taking the relationship with it.
But more importantly: you end up in relationships with people you have very little in common with. Yes, they may be the sort of partner that makes your friends jealous, but it’s the sort of relationship that makes you miserable. Even if you click on a sexual level but no other, the New Relationship Energy fades. Without a deeper connection… that leaves you with nothing left to keep you together.
Worse, hiding your authentic self makes it impossible for the right folks to find you. When you’re trying to force yourself into the mold of “most generically acceptable person”, you end up missing out on the folks who are looking for exactly what you have to offer. Hiding your geeky interests makes it that much harder for geeky women to connect with you. Trying to pretend that you’re less sensitive or emotionally open than you are means that people looking for a guy who’s in touch with his gentler side never find you. There might not be a lot of straight guys who love musical theater and dig on modern art, but there’re a shitload of women who’d love to date a guy who wants to go to museums and camp out at TKTS for discounted Broadway tickets.
Not to mention, being your authentic self, even when it puts you outside the mainstream, is a sign of strength. Having the courage and the strength of character to be who you are and to love what you love, regardless of what the world thinks, is a rare and valuable commodity. It’s a mark of just how secure you are and how confident you are.
And confidence is sexy.
#3: You Aren’t Polarizing Enough
A variation on hiding your authentic self — a mistake that often comes hand-in-hand with it, in fact — is an attempt to be broadly appealing. It’s the desire to want to appeal to as many people as possible, to cast your net as far and wide as possible in order to maximize your chances at finding love… or at least someone to bang. You see this a lot on dating apps — guys whose profiles are so broad and unspecific that they comes across as generic. They’re clearly trying to reach the widest possible number of potential matches and — in doing so — have profiles that don’t say anything substantive about them.
This also tends to tie into the belief that you need to fit a particular mold in order to find love and sex. Women don’t like guys who do X, women only date guys who do Y, and so on. Never mind that if this were actually true, humanity would’ve died out as a species, never mind that this is cultural and not biological… it’s a belief that has clung to guys like a lovesick lamprey. But many men believe it and try their damndest to appeal to as wide an audience as possible, the fabled Four Quadrant film except for relationships.
And it doesn’t work. Not with people, anyway.
Broad appeal tends to also be shallow appeal. When you try to appeal to as many people as possible, you may be pleasant enough, but there’s not really anything there to grab folks. There’ll be few reasons to say no, but no real reason to say “yes”. There’s little to engage with, little to hook anyone, and nothing that grabs the imagination, speeds up the heart or stirs the loins. And frankly, that shouldn’t be much of a surprise. When folks try to avoid being too divisive or polarizing and try to be as broadly appealing, they’ve almost always sanded down all of the edges, ridges and rises that make them interesting. They’ve smoothed themselves out to the point that they look no different than anyone else, with nothing to draw the eye or intrigue the mind. They’re pleasant enough, sure… but there’s a difference between “pleasant” and “desirable”.
And while I understand the impulse to want to appeal to as broad an audience as possible, it actually works against you. When it comes to dating, more is not necessarily better. Quantity doesn’t have a quality of its own, because quantity in dating often means dealing with bad matches. It doesn’t do you any good to get hundreds of matches on Tinder when 99% of them are folks you don’t actually click with. This, for example, is why women getting so many matches and so much attention on dating apps isn’t inherently a good thing. Being offered thousands of sandwiches isn’t a benefit when the vast majority are garbage or contain ingredients you’re allergic to, and trying to sort through them all to find the few good ones can be enough to kill your appetite all together.
But just as importantly, those matches aren’t as solid, even if you do want to take a chance on them. That broad but shallow appeal also has very little staying power in and of itself. Without having more reasons to be interested — more “yes'” rather than fewer “no’s” — those are matches that usually don’t last beyond the first date or two. And why should they? It’s the dating equivalent of Applebee’s; broadly acceptable with something most folks could eat, but nothing that folks really crave.
When it comes to dating, there’s good reason to be more divisive and polarizing. While yes, it means that you get fewer matches and more people who aren’t interested, it also means that the people you do meet are the ones who crave what you have to offer. It means that those connections are stronger, the compatibility runs deeper and the attraction tends to be that much more powerful.
It’s like a famous story about the Velvet Underground: their first album only sold 30,000 copies which is… not great. But everyone who bought that album went out and started a band. They may not have had the broad appeal that, say, Eric Burdon and War had at the time, but the impact they had on people’s lives was immeasurable.
Now, being polarizing doesn’t mean being an asshole or not trying to present yourself in the best light. It doesn’t mean that you don’t polish yourself up or that you go out of your way to offend people. But what it does mean is that you want to lean into the things that make you unique. You want to emphasize what makes you different, what makes you special and what you love. As with being your most authentic self, it means presenting yourself as you are, without worrying that it may diminish the overall pool of potential dates.
Some women may not be into bald guys; that’s fine, if you’re bald or losing your hair, it’s better to embrace the beauty of being bald and avoid the women who dislike it. Some women may not like guys with tattoos, but if you’re inked up, then it’s better to show them off than to worry about the folks who would swipe left over those.
Because while you may not be everyone’s cup of tea, you will definitely be someone’s shot of whiskey.
And while we’re on the topic.
#4: You Play It Safe. TOO Safe.
Raise your hand if this sounds familiar: you’ve seen a sexy someone at the bar and you’ve actually had the guts to go over and talk to her. But now that you’re talking to her, you’re hyper-aware of everything — how you’re standing, how dry your mouth is, the ratio of how much you’ve been talking to how much she’s been talking. Now you can’t get out of your own head and you’re starting to panic and so you eject.
Or maybe you’ve matched with someone hot on Tinder and you’re agonizing over exactly what to say, to the point that every message takes you up to a half-hour to write.
Or you’re on a date and you’re so worried about saying something weird or strange or off-putting that you barely talk at all.
The odds are good that these scenarios speak to you in a deep and painful manner. You may well be feeling called out in a way that you really don’t appreciate. Welcome to the club; we have shirts.
Just as folks tend to be too afraid of standing out or being too polarizing, a lot of people are entirely too terrified of making a mistake. So terrified, in fact, that they end up over-correcting in the opposite direction.
Now, as with the previous example, this is an entirely understandable mistake to make. It seems like the most obvious thing in the world; the last thing you want is to say or do the wrong thing, so you play things as safe as possible. If you don’t make any mistakes or do anything off-putting, then the other person won’t have a reason to dump you or reject you.
But — say it with me now — that’s not how it works. That’s not how any of this works. In fact, playing it safe actually tends to work against you.
The most obvious example of why this is a mistake is how much it pulls you out of the moment. A lot of guys, especially guys without much social experience, tend to focus like lasers on not doing anything “wrong”. They’re worried about saying or doing the wrong thing and that if they don’t do everything perfectly, then they’ll have lost their one and only chance at love. As a result, they become hyperware of everything… how they’re standing, how sweaty their hands are, every micro-expression on their date’s face.
Everything, that is… except what to say or do next. They are so focused on trying to critical-path their date that they can’t actually enjoy it or even hold a conversation.
And then, wouldn’t you know it? There’s no second date.
Ironically enough, it’s that hyperfocus on perfection that doomed the date. If they hadn’t been so lost in their own head, they could have focused on having a good time. But instead, they ended up with a stilted, fairly boring conversation that ultimately went nowhere.
Another common example is picking the “safe” topics. One of the oldest cliches about first dates is that you never want to talk about anything divisive, especially sex, money, politics or religion. After all, the last thing you want to do is to accidentally say the wrong thing or offend somebody because you and they have different politics or religious values.
But as it turns out, those “unsafe” topics are actually a great example of things you should talk about on a first date. Those supposedly ‘forbidden’ topics tend to be ones that are incredibly important to people — ones that align closely to their values and interests. When we talk about our views on, say, politics or religion, we’re talking about things that are meaningful to us, and that give us real insight into the other person. They tend to be more satisfying and interesting conversations precisely because we feel like we’re getting to know each other on a meaningful level and talking about things that have serious importance to us. Other, safer topics like, say, movies, are often less interesting and satisfying in the long run.
And let’s be real: if you and your date have diametrically opposed views about politics or religion, isn’t it better to find out right off the bat?
Part of the problem of trying to play it “safe” is that it falls into the mistaken idea that you’re trying to avoid “nos”, reasons to not like you or want to date you. But focusing on being “safe” means that you also miss the “yeses”, the reasons why people should like you. Not making mistakes isn’t a guarantee of success, or that people will want to see you again. A lack of reasons to say “nah, not into it” isn’t the same or as important as reasons to say “oh yes, definitely”. As a wise man once said: it’s possible to make no errors and still lose. That’s not weakness; that’s just life.
But just as importantly, when you’re so worried about doing things “wrong”, you lose your ability to be in the moment. When you’re focused on perfection, you can’t enjoy the here and now. You can’t connect with people, joke with them or flirt or even just have fun when your every thought is bent towards analyzing every twitch of their mouth and flutter of their eyelashes to see how you’re doing.
To make matters worse, trying to avoid mistakes makes it impossible to improve. If you are so focused on never making a mistake, you never take chances. You miss opportunities because you couldn’t trust yourself to read things accurately or to believe that no, she really does like you. And most of all, when you try to avoid any and all risks or mistakes you miss out on the most important lesson of all: mistakes aren’t fatal. You can make mistakes and recover from them, even in the moment. If you never let yourself risk making a mistake you never learn how to rescue a date that’s hit a road bump or how to pull out of awkward moments.
Here’s the thing: it’s understandable to be worried that you’re going to say the wrong thing or that some bit of awkwardness is going to break the mood. But the truth is that it’s actually really hard to ruin the mood. When someone’s into you and is having a great time with you, it takes quite a bit to mess things up. In fact, you really have to work at it… and in ways that go beyond saying something weird or a joke that goes flat.
Attraction’s not a soap bubble, something so ephemeral that it bursts with the slightest touch. Nor is dating a competitive sport of opposing teams. When someone’s flirting with you or on a date with you, they want it to work as much as you do. People who go on dates aren’t doing so because they had nothing else to do. They want to have a good time with you. That means that they’re just as worried as you and just as invested as you. A flubbed line or awkward moment just becomes something you two can laugh about together.
You just have to be willing to let go of being perfect. Trust in yourself, trust in your connection with the other person. If you can’t do that… well, just avoiding mistakes isn’t going to make things work, anyway.
#5: You Don’t Tell People What You Want
The last mistake is one that tends to trip the most people up: they’re not clear about what they want.
One of the most important parts of dating — one that can make or break relationships — is to be on the same page as your partner. And what makes this particular mistake so dire is that you often may not realize that you’ve made it. The other mistakes tend to ruin dates in the beginning. When you’re trying to hide your authentic self or you’re behaving as though you’re pre-rejected, you rarely get to the first date. In fact, most of the time, you barely make it through the initial conversation or even match on the app. Things get strangled in their infancy, potential matches fail to spark.
The consequences of this mistake aren’t immediately obvious. Sometimes you realize the problem by the second or third date. Other times? You don’t find out until down the line… when you’re much more invested. And then the fallout hits like a leopard leaping out of a tree.
The problem here is that you weren’t clear, from the jump, about what you were looking for. Maybe you were looking for something casual, without any sort of expectation of long-term commitment. Or you’re absolutely sure that you want the wife, the house in the suburbs with the white picket fence, the 2.5 kids and 1.88 cars. Alternately, maybe you’re 100% sure that monogamy is not for you. Or you might have decided that you were willing to roll the dice on dating someone in a polyamorous relationship, but you knew that you couldn’t do it long term.
What you didn’t do, however, is be clear about what you want or need from a potential partner.
Maybe you thought you didn’t have to. After all, you met on Tinder; you never talked long-term. You didn’t think you needed to say anything, since you never had the “are we exclusive” conversation. Or you may have figured that there wasn’t any need to talk about where this was going since it seemed like you were all on the same page.
Or you didn’t bring it up because you didn’t want to run the risk of tripping a deal-breaker or scaring someone off. Especially since it’d been such a long time since you last had a real connection like that.
And yet here you are, nursing a broken heart and a wounded ego, sitting in the tattered remains of what had been a promising relationship. At least until the time bomb at the heart went off, messily and all over the place.
If you want to date, and you want to date successfully, you need to be willing to be up front with what you’re looking for in a relationship. You need to risk losing a promising connection by being clear about what you are and aren’t open to, what you require in a relationship and what will make you peace out, Cub Scout. It’s very easy — incredibly easy — to try to coast on assumptions. After all, most people are going to assume that monogamy is standard, so do you even need to have that conversation?
Yes. Because you can’t be sure what monogamy means to them. What do they consider to be cheating, what do they consider to be in bounds? And at what point are you two going to be exclusive?
The same goes for sex. If you can’t talk about the kind of sex you want or need… then you’re likely going to end up unsatisfied at best. If you’re someone who needs time to develop attraction — or who doesn’t develop attraction at all — it’s important to be clear about that. Yes, that means that a lot of people will pass you by. But those are people who should swipe left; you and they were simply not compatible, and trying to start something with them would be an invitation to frustration at best. By choosing to pass you by, they’ve done you a favor; they aren’t wasting your time in a relationship that would ultimately go nowhere.
If you’re not looking or open to commitment, then you need to be clear and unambiguous about this. The same goes for wanting to get on the fast track to marriage. If you don’t know, that’s ok… but you need to be clear with people that you don’t know, not to let them assume one thing or another in the space you left unfilled. And if and when that changes… you need to tell them.
Don’t get me wrong; I know how intimidating the conversations can be. I know how easy it is to want to let things go and just coast on the ambiguity wave for as long as you possibly can. I know why you’d want to leave being in an open relationship off your account or why you might not want to tell someone that you aren’t interested in anything long-term. It can be awkward. It can be difficult. It can mean that a relationship you have high hopes for is about to come to a sudden and screeching halt.
But even if it does… it’s better to end it sooner, rather than later. Not when you’ve invested weeks or months into them, not when the relationship ending will hurt far worse than that momentary pain in the beginning. Because not being on that same page is a crack in the foundation, a flaw in the frame, rot in the support structure. Sooner or later, everything you built with them is going to collapse… and the longer you’ve let this go, the more you will have built on that flawed foundation. And all of that will be coming down on you both.
This doesn’t mean that you need to give a list of your dealbreakers or your must-haves at the start of your Bumble profile any more than you need to have the “where do you see this relationship going” conversation on the second date. Different needs and dealbreakers are best brought up at different times, and the ideal timing doesn’t exist. Some folks will want to know you’re in an open relationship from the jump. Some will want to know right away whether or not you want kids. Others won’t.
But you have to be clear, you have to be understood and you have to be honest. It doesn’t do you or them any good otherwise; all it does is make any future pain that much worse.
Like all of the other mistakes, avoiding them is a matter of courage. It requires a willingness to be direct and the confidence to court rejection directly, rather than trying to avoid it like a mouse avoiding a cat.
It can be scary. It can be intimidating. It can make you feel like you’re making things harder for yourself than they have to be. But as the saying goes: nobody said it would be easy.
They said it would be worth it.