Dating should be fun. Done right, it’s a blast. There’s a thrill in meeting someone awesome and getting to know them. There’s the excitement of discovering the fascinating side of a new person. And of course, there’s the exciting nervousness that comes as a relationship progresses and goes from “dates” to “this may be serious…”
But a lot of guys struggle to make that initial connection. Dating can be a serious challenge for a lot of men, who may struggle even with that initial connection — whether it’s meeting women in person, or through dating apps. It’s incredibly frustrating, especially when you don’t know what you’re doing wrong. The things that seem to come so easily to other men feel almost impossible for you.
Many times, the issue is that men who struggle with dating are making things harder on themselves. The problem is that they’re making incredibly common mistakes — mistakes that could easily be avoided. Here are some of the mistakes that make dating harder for men and how to avoid them.
Dating Mistake #1: You’re Trying to Run Before You Can Walk
The first and most common mistake guys make is that they get impatient. They want to be the Duke of Dating, the Cavalier of Courtship, the Suzerain of Seduction right now.
The problem comes when they’re laser-focused on being The Guy Who Gets Laid, they’re ignoring the part where they can’t string three words together with a woman they’re attracted to.
A lot of men see dating as being a series of disparate and discrete skills that they can pick up in any order… so naturally, they want to jump straight to the sexy, flashy bits. In a real way, they treat dating like the social equivalent to a trip to a Vegas buffet where they can go straight to the crab legs and eclairs without bothering with the other courses.
Unfortunately, social skills don’t work that way. Learning how to meet amazing women, build a powerful connection and turn those meetings into dates and more aren’t separate skills that you can pick and choose. You can’t skip around to all your favorite parts and make actual progress; there is no critical path that lets you skip all the “boring” bits. Dating isn’t a buffet, it’s a skill tree, where unlocking the advance skills requires that you learn the prerequisites first.
All of the sexy parts of dating — the flirting, the seduction, all of it — are built on a foundation of mundane and basic social skills. The skills that you take for granted are, in fact, the most important. The ability to approach and charm beautiful women at the bar or at Starbucks are born out of just being able to start a conversation. The “opener” that people stress on is ultimately just the way you make folks aware that you’re there. It doesn’t do any good to approach somebody in a noisy bar if you can’t get their attention in the first place, after all. Flirting is born out of just talking to people and knowing how to connect with them on an emotional level. Social calibration is built out of basic experience and observation.
Michael Jordan didn’t become the greatest by just focusing on doing amazing dunks. The secret to his learning how to pull a perfect crossover-to-fadeaway came from relentless practice of the basics. If you aren’t able to start a good conversation with an acquaintance at a party or classmate, you aren’t going to be able flirt with the woman of your dreams when you see her at the bookstore. Drilling the basics is what makes it possible for you to move up to the “advanced” maneuvers.
That’s the bad news.
The good news is that you already have most of those basics down. They’re how you make friends and how you interact with your coworkers. If you can tell when it’s a good time to tell a joke to cheer your buddy up and when it’s time to just listen, then you understand social calibration. If you can joke with your coworkers and make them feel good, you know a lot of how flirting works. Like Mr. Miyagi teaching you “Wax On, Wax Off’, you’ve built up those skills until they were practically muscle memory. Now it’s just a matter of learning how to apply them in a different context.
The hard truth is that there is no short cut. You have to build those social muscles by drilling the basics. The urge to skip this step is why so many pick-up artist and Red Pill gurus sell “magic formulas” for how to seduce women. Not only do they not work, they actually make you worse at dating.
In fact, speaking of…
Mistake #2: You’re Trying to Avoid All Risk
This mistake is one that tends to come up often, especially with men who have little social experience. They want to avoid any chance of risk or the possibility of making any mistakes. They don’t want to try flirting with somebody because they’re worried they’ll screw it up if they don’t do it perfectly. The are afraid of getting rejected or — worse — laughed at. Their nightmare is to make an approach and have it go so badly that they have to change their name, get plastic surgery and move to another state to escape the shame. If they don’t have 100% certainty of success, they don’t want to even try.
The problem is that, frankly, this is literally impossible. There’s no such thing as a 100% chance of success, and there’s no way to eliminate risks from any encounter. This is how people get suckered into PUA; they’re hoping to find a formula or step-by-step flowchart that they can follow without having to think or worry.
The hard truth is that the risk of rejection or making a mistake is baked into everything. It’s part of the human experience; we’re all flawed and fallible, and even experts can make mistakes. Trying to avoid all risk just makes you worse at talking to people. Either you hesitate, hem and haw and hold back or you don’t make the attempt at all. In fact, for many people, trying to avoid making a mistake — whether it’s getting rejected or creeping someone out — becomes their excuse for not trying in the first place.
But as difficult as it can be to believe, taking chances and making mistakes is one of the most important parts of learning how to be better with women. Without making mistakes, you never learn how to recover from them. You never learn how to bounce back from rejection. And most importantly: you never learn how to succeed.
As counterintuitive as it can feel, mistakes are the most important part of learning a skill. You don’t learn from success; after all, you can succeed for reasons that are entirely outside of your control. It’s your mistakes that tell you where your weak points are or where you need to improve. And to be perfectly frank: without making mistakes, you’re in no position to actually gauge the level of risk or the potential consequences. Because they’ve never even tried, the folks most afraid of taking risks have no basis for comparison. Their minds rush to worst-case scenarios — or take the stories of strangers as gospel — because they have no idea what the risks actually are.
And so it becomes an excuse to do nothing. People who make this mistake will frequently find ways to give the illusion of doing something. They’ll study all books, watch all the videos and listen to all the podcasts in hopes of finding the perfect path to success. They hope that if they read enough, absorb enough then they’ll stop being afraid. But it never works. All the theory in the world does you no good if you don’t put it into practice. Like developing your skills, there is no substitute for boots-on-the-ground, ass-in-the-chair time. No amount of study prepares you for the complexity and chaos of the real world; only in-person experience does.
As it is, perfection is no guarantee of success. As a wise man once said: it’s possible to commit no mistakes and still lose. By courting failure — deliberately taking chances and making mistakes — you’re able to put yourself in the position to fine tune your skills, confront your failures and figure out why you failed. You learn how to bounce back from failures, even to snatch victory from the jaws of defeat by understanding how to recover from screw-ups. And just as importantly, you learn one of the most important lessons imaginable: that you don’t need to be perfect. You can make mistakes, even lots of mistakes and still succeed.
The issue isn’t a lack of knowledge, it’s about managing fear. It’s the belief that if they prepare enough in advance, they’ll be guaranteed results that they want. The problem is that in life, there are no guarantees. Conquering your fear doesn’t come before doing the thing; it only comes afterwards. Overcoming fear happens in hindsight, through experience. Fear + survival is what gives you confidence.
There are always risks; we’ve just learned how to assess them, manage them and chance it anyway. After all: driving is statistically the riskiest thing you can do and millions of people choose to do this every day. At first, it’s practically terrifying; you’re quite literally risking life and limb every time you get behind the wheel. But through practice, we build the skill and experience that pushes the fear away and gives us the confidence to head out on the highways and byways without thinking twice.
Yes, you’re afraid. You’re afraid of making mistakes. That’s real.
Just do it anyway.
And while we’re on the subject…
Mistake #3: You Treat Women Like Your Opponent
One of the biggest, and most damaging mistakes I see men make is when they treat sex and dating like a competition. The idea that women are the gatekeepers of sex — and by extension, the gatekeepers of men’s value — puts dating in an antagonistic frame… and women are your opponent.
This particular mistake comes in two flavors. The first — and most obvious — are the bitter dudes who think that women are somehow cheating the system. They think women have it easy, that they’re too shallow or self-absorbed or have other reasons why nobody wants to be within 400 yards of their penis.
The problem here is fairly obvious. Strangely women tend to be averse to being anywhere near men who radiate anger, entitlement and resentment like a leaky nuclear plant with rage issues. The men who display these attitudes tend to be presenting themselves as a threat — intentionally or unintentionally. Men carrying around and exhibiting that much anger tend to explode, messily and all over the place… and usually at women. It doesn’t take much to look at guys like that and see a potential Elliot Rodger or Marc Lépine or Alek Minassian. Even if those results don’t leap to mind, most women have had a man Hulk out at them, or have a friend who’s experienced it.
(This, incidentally, includes the “it’s just science/biology” types, the evo-psych bros who insist that women are hypergamous gold diggers or the people who want to teach you how to “sneak past her defenses”.)
However, that’s not the only version of “women are your opponent” that exist. The other flavor are the men who think they need to impress their dates or prove that they’re “worthy”.
This actually catches folks off guard; after all, how does feeling like you need to win her approval square with treating women like an opponent?
Well, I’m glad you asked, convenient rhetorical device.
The issue is that men who make this mistake feel like they’re coming to each interaction pre-rejected. They believe that they have to work up from negative points to get her attention, never mind to get to a point where she might be attracted to them. They worry that they just aren’t impressive enough, not high-value enough or that their relationship history (or lack thereof) will disqualify them. This puts them at a series of disadvantages. They don’t feel that they can be genuine with the people they’re attracted to. Because they believe that they’re being judged, they get too focused on trying to pass her “shit tests” (which, BTW, don’t exist) to actually connect with her. Worse, they can never feel secure talking to her because there’s always the risk that another man — one with more points on the metaphorical spreadsheet — will come by and steal her attention.
To make matters worse, because they feel they have to prove themselves, they don’t try to actually connect with people. Flirting, after all, is about having fun with someone. It’s about expressing interest in a light-hearted and playful way. But flirting requires confidence and belief in your own value. If you feel like you have to “prove” your value to others, you’ll never have the confidence necessary to actually make your move.
The truth is that women don’t test men or try to make them prove themselves worth her time. Women aren’t looking for reasons to reject you and only accept you if they don’t find any. Women want to meet a guy who’s worth her time, yes… but that doesn’t mean that she’s giving shit tests. It means that she wants to find someone who she’s compatible with, who she likes spending time with and who excites her. When she matches with you on Tinder or has a conversation with you at a party, she’s hoping that this is going to work just as much as you do.
When you’re trying to pass her shit-tests, you’re not treating her like a person, you’re treating her like an opponent. If you are trying to demonstrate your “high value”, all you’re doing is coming across like you’re trying to mechanically hit switches until you find the combination that leads to attraction. You’re not being authentic or genuine. All you’re doing is sapping your own confidence and creating a frame of insecurity. You don’t need her approval, you need a connection.
The best way to approach any dating scenario — whether on a dating app or in person — is to trust to your own value and to look for someone who matches you. Want someone who meshes with you, someone who synchs with you like the proper gear. The question isn’t “am I good enough for you”, it’s “are you right for me?”
It’s not competition, it’s collaboration. You’re looking to build something together, whether it’s for a lifetime or just that evening.
Mistake #4: You Keep Watering A Dead Plant
Let’s talk about The Friend Zone for a second, and why so many guys stay in it.
There’s an understandable impulse for men to go for the proverbial bird in the hand. They represent a known quantity. They feel like safety and security… even though it means that you’re devoting time and energy to a relationship that will never happen. And most of the time, men know this. They won’t actively pursue the relationship — making it clear that they want something more than platonic friendship — because they know the answer will be “no”.
But men can leave the Friend Zone at any time. It just requires admitting to yourself that it will never happen and to move on. But they don’t. In fact, they often prefer to stay there, expending their resources on a relationship that will never be more than it is right now.
The truth is that it’s easier to keep a fantasy alive, even when you know it will never come true, than it is to face the consequences of letting it go. There are few things more terrifying than accepting a loss and starting over from zero. The false hope of the fantasy is perversely comforting, even as it aggravates and infurates you.
And so men will continue to put time and effort into keeping false hope alive… even when it denies them the chance of finding a relationship with someone who will love them back. The known, no matter how disappointing, is safer and less intimidating than the unknown.
But this applies equally well to other relationships that only frustrate you. How many times have you tried to keep a connection alive, even when getting so much as a response is like pulling teeth? How many times have you stayed in a quasi-relationship that only exasperated you with how slow it was progressing or how you and they seemed to want very different things? Maybe the sexual connection wasn’t there; they were never ready to take things further, while you craved more. Maybe you were dating someone who’s interests or ideas of fun were so different from yours that dates were a chore instead of something you enjoyed. Or perhaps you just kept trying to turn indifference into interest, even when they gave you no hope at all.
Too many men stick to hopeless crushes or frustrating relationships because they’re afraid to let go of them. It’s all too easy to get stuck on someone just because they were the first one who matched with you on Tinder. Or they’re the first person you had an actual date with, or progressed this far with. The idea of cutting this person loose and starting over is terrifying because of how long it took to get here. If it took that much work to get even this far, then what happens if you give that up? It’s the very understandable fear that this is the best you can do. That this is possibly the last or only relationship you’ll ever have.
But it’s not. Or rather… it will be, if you let it drag on and on. The problem with pursuing dead end relationships is that they’re a trap. Not in the sense that someone is working against you, but that it leaves you stuck. All of the time you spend trying to grow a dead plant is time you don’t get back. It’s time you could have used to find someone else — someone better suited for you. Those are resources you could have used to find a relationship that actually meets your needs. It does you no good to stick with a mistake just because you took a long time making it.
As tempting as it is to believe that you can somehow pull off a miracle and change things… you can’t. You’re only wasting time and energy. It doesn’t matter how much you water it, a dead plant will never grow.
The solution to this problem is simple: you need to change your way of thinking. Being in the Friend Zone doesn’t mean that you weren’t “worthy” or “good enough”. The fact that she doesn’t want you the way you wish she did doesn’t mean that there’s something wrong with you. It simply means that for all you had together, there was a missing piece necessary for a sexual or romantic relationship. That’s not your fault or hers, it just is. If she didn’t value you enough to want you in her life, she wouldn’t be your friend. The all-too uncommon match on Hinge is a sign that people out there are interested. That frustrating relationship isn’t all you can get; it’s proof that you can succeed.
You don’t want to take these as proof of failure. It’s proof that you’re doing something right. Your next step is to try again. Learn from your experiences, apply what you’ve learned and try again. And next time, you’ll know what you want and what you need. And, just as importantly: you’ll be ready for a relationship that isn’t a constant struggle.
Mistake #5: You’re Trying To Squeeze Yourself into the Wrong Box
This last one is a big one. In fact, it’s possibly the most common issue I find in men who struggle with dating. But let me go off on a tangent for a second; I promise this will make sense in a minute.
On occasion, I’ll work with clients who’ve dealt with a particular breed of dating coach, and it fell apart. The clients are often unsure why everything they were taught didn’t work or why so much of what they were taught made them miserable in practice.
This is almost always because many, many dating coaches and PUA gurus take a one-size-fits-all approach, where they try to turn people into versions of them, rather than helping their client become the best, most polished version of themselves. If, for example, you try to follow The Game like an instruction manual, you just end up being a third generation photocopy of Mystery.
All that happens is you try to squeeze somebody else’s personality on top of your own. You’re functionally trying to subsume your own character and be someone you’re not. This is, frankly, a great way to drive yourself insane. And I don’t mean that metaphorically. I’ve seen far too many folks in the PUA scene — people I spent weeks and months with — hit the wall and suffer literal emotional breakdowns.
Unfortunately, this approach is very common — not just with dating coaches, but in general. I can’t count the number of times I’ve watched men force themselves to be someone they’re not in the name of meeting women. More often than not, this involves trying to contort themselves into somebody else’s idea of the man women want. It’s inauthentic at best, and the strain of trying to graft that artificial persona will stress you out like nothing else. At best, it makes you a manipulative and toxic person. At worst… well, at worst, you end up hurting yourself and people in your life.
And to add insult to injury, it’s not even accurate. You’re breaking yourself into pieces to match up with the idea of what women want from somebody who has never actually listened to women. You spend weeks, months or even years doing the psychic equivalent of squeezing yourself into shoes that are too small and it doesn’t even work.
But this goes beyond just how you act. The attempt to force yourself into the wrong box includes where you go to meet women and even the women you are trying to attract. Many men, for example, think they want the hot club girl. It’s understandable; she’s the one who is most frequently held up as the ultimate prize. Who wouldn’t want to be the guy who gets the hottest girl in the club?
Well… lots of people, actually. Most of the time, the women men are told they should want aren’t the ones they’re actually compatible with. If you’re not already in the clubbing lifestyle, the odds that you and random women you meet on the LA club scene are a match is very, very low. The push towards superficial hotness is strong. A lot of men, especially when they are younger, tend to pursue women based on how other people would react. They want the clout of dating someone their friends would kill to have. They want the validation that comes from dating someone that makes other men envious.
Hell, many times, they’re pushed to pursue women they’re not actually attracted to — or to avoid the ones they do want. Many men who have a genuine attraction to fat women will try to suppress it, because it’s not “cool”. They worry what other people will say and so, date women they aren’t actually into. Others will attempt to date women that they don’t find attractive because they feel that it’s their best chance. They de-prioritize their own desire in order to find someone who’s “gettable” and never stop to think how fucked up that is. It’s a lose-lose proposition. They get frustrated by their lack of attraction, while simultaneously shredding their partner’s soul and self-esteem. Worse, it keeps both of them from finding someone who’s right for them.
Another way that men try to force themselves into the wrong box is that they try to be somebody else’s idea of attractive. They aim for being broadly appealing — trying to maximize the people they may attract. The problem with this approach is that it almost always means that they have to suppress the things that make them special. By being broadly appealing, they lose their uniqueness. Instead, they aim for a bland-but-generally-acceptable version of attractiveness. But while this may bring some attention, it’s ephemeral. It’s a mirage, a bite-sized snack that leaves you without so much as the memory of flavor when you’re done. Broad appeal is shallow appeal with little staying power. There’s nothing there for people to latch onto, or to keep them once the fashion changes again.
As the saying goes, you don’t want to be everyone’s cup of tea, you want to be a few people’s shot of whiskey. Embracing your uniqueness and the things that make you stand out, on the other hand, is a power move. You want people who crave what you have, even if it shrinks your dating pool. While it means the overall number is smaller, the connections are stronger. The attraction is that much more powerful because they want you, specifically. You have genuine commonalities and genuine attraction, not broad acceptability.
Being your authentic self breeds confidence and makes you more attractive. Owning who you are, without hesitation or apology is extremely appealing. It shows that you have the courage, to be your best, most polished self, not a poor copy of someone else. Take that courage and apply it to your life and your approach to dating. You’ll stop making these common mistakes and start getting out of your own way. And when you do, you’ll see your dating life transform to something amazing.