How To Be Fearless With Women

Trying to meet amazing women can be incredibly intimidating, even terrifying. There’s an understandable fear of judgement or rejection, especially since meeting women requires deliberately making yourself vulnerable to a relative stranger. There’s also the understandable worry of what your social success says about  you and your worth as a person.

However, so much of why it can be so intimidating is because we put unrealistic expectations on ourselves. We feel as though that we need to be “perfect” in order to get people’s interest, and in order to do that we need to know exactly what we’re doing. And we often don’t.

In fact, it’s that sense of not having an explicit road map or set of instructions that leaves them feeling terrified when they even think about trying to meet women. And to be sure: much of this fear comes from trying to avoid the hard stuff – being willing to be vulnerable, being willing to risk rejection and or even humiliation. This is precisely why so many people want scripts and one-size-fits-all rule sets to follow. If you have rules, then success is supposed to be assured… theoretically.

The problem with this outlook is that humans aren’t meat robots that follow algorithms and relationships don’t follow the if/then patterns that scripted routines and “secret seduction technique$” claim. There’s no escaping the inherent messiness of the human condition; accepting that risk is part and parcel of the whole adventure.

But imagine how much easier it would be to date if you weren’t having to fight through the fear first.

Meeting and dating women isn’t about being perfect or knowing exactly how to act at every second of the interaction. Being an incredible catch, the kind of guy that women would be lucky to date, isn’t about technique, it’s about your mindset. When you’re hung up on the outcome, rather than just connecting, you create barriers between yourself and the very people you want to match with. When you have the right outlook and approach to dating and meeting people, you remove the fear and anxiety and let your best and most authentic self shine.

Here’s how to change the way you think about dating and unlock your inner dating Jedi.

Don’t Approach

So let’s start with the big one right off the bat: part of why guys psych themselves out is because they don’t think about meeting people. They think of it in very mechanical terms: doing approaches, on the prowl, picking girls up, whatever term you want to apply. And to be fair…

…I talk about it in these terms often, so I’ve certainly contributed to the problem. And also to be fair1 , there’s nothing inherently wrong with going out specifically to meet folks to date or hook up with. However, for a lot of men – especially men with relatively little social experience – thinking of these interactions as “doing approaches” puts you in a different headspace. Because the interaction now has a specific goal – to get a number, a date, or get laid – the tenor has changed. The interaction is now something you can screw up; it’s become pass/fail in a way that we simply don’t encounter in other circumstances.

Small wonder, then, that it feels so intimidating. When you consider the pressure that men place on themselves to be “good” with women and the way our sense of value gets conflated with our sexual success, “failing” becomes an existential issue. If you feel as though any interaction with a woman is difference between “becoming a real man” or missing your window and getting stuck being forever alone, it’s not a surprise that it feels like you need the technical perfection of an Olympic athlete paired with the unbelievable confidence and suavity of golden-age Gene Kelly.

Now to be sure, if men actually needed to perform at that level to date, the human race would’ve died out before we ever left the savanna. But we don’t and never have; it’s a self-imposed pressure that men put on themselves because of the belief that women have all the power in dating. It’s not hard to see how these beliefs combine into an epically shit version of Devastator, comprised of anxiety, neurosis and incel subreddit threads.

The problem is that, when you come to dating with a pass/fail approach mindset, you often end up making things harder on yourself… especially when you don’t have much social experience already. You’ve added a completely unnecessary level of pressure to a basic human interaction, and looking for ways to alleviate that pressure works against you. Trying to apply rules, routines and pre-scripted material in order to critical-path your way to a date can actually work against you. Now, instead of having a human connection, you run the risk of coming off like a social robot trying to apply an algorithm that doesn’t match to the situation.

Never mind that you don’t actually know the people you’re approaching. You don’t know what they’re into, what turns them on, or even if they’re a decent human being. You’re worried about trying to impress them or pass the interaction when you don’t even know if they’re the sort of person who dog-ears their books or uses as bookmark, never mind whether they use goslings for games of pickleball or something. Focusing on the end goal isn’t just adding unnecessary pressure, it’s the wrong goal. You should be more interested in getting to know them and if they’re even right for you in the first place.

Notice the important words there: “for you“. Rather than focusing on whether you can bypass her rejection filter or hit the right “attraction switches” and coming to this from a place of supplication, you should be trying to establish whether they’re worth your time and if there’s more to their attractiveness than their looks. And this is much easier if you adopt a mindset of outcome independence, where you focus less on getting a date and more on just having conversations with people. Think of it as an opportunity to get to know a potentially fascinating stranger – a reward in and of itself. Rather than worrying about trying to force the interaction down one path or another or hit the high marks, you can just relax and get to know someone and decide if you’d want to take it further.

This is why focusing on your social skills and being able to talk to people in general is more much more important than any technique or bar-approach roadmap. Being able to just talk to people without an agenda beyond “are you as cool/interesting as you seem to be?” is a super power when it comes to dating. Instead of putting pressure on yourself to try to achieve an arbitrary goal with a stranger, you’re able to just relax and come to the interaction from a more confident and authentic place. If they are, in fact, as cool as they seem, then that’s great! If they aren’t… well, then hey, you didn’t waste your time trying to win over someone who thinks that JohnnyBunchaNumbers on Twitter is a more reliable source of medical science than epidemiologists with decades of education and experience.

Of course, this is also predicated on an incorrect idea: that people meet their partners by cold-approaching strangers at bars or in the street. Even in 2022, most people meet their partners via friends, shared activities and dating apps. Polishing your conversational skills takes you much, much further in these instances than trying to find someone at a bar and convince them to start a sexual relationship with you in the span of a few hours.

But while we’re talking about where you meet people…

Think Outside The Apps

Let’s be honest for a second: part of what drives the idea that you need to be the top of the top tier in order to date are dating apps like Tinder. Tinder has always prioritized shallowness and superficial attraction; it started off life as a hook-up app, with an emphasis on pictures over text and a “thank you, next” swipe mechanic that incentivized maximizing matches instead of actually, y’know, meeting people. Small wonder, then, that folks who know how to take a good photo have an advantage on there. It’s quite literally what the app was optimized for.

This was obnoxious enough on its own, but dating apps also lean hard into algorithmic feeds, controlling who you see in your timeline and who sees you. This isn’t speculation; this has been discussed at length by the engineers at multiple dating apps. Who you see is based in part on who you’re interacting with and for how long and who’s interacting with you. If you were to borrow your friend’s phone and check their account at the same time you looked at yours, you would be seeing entirely different people, not just the sexy singles in your area. If you tend to swipe a lot on brunettes, but mostly match with blondes… well, you’re going to be getting lower quality matches because the folks you’re actually interacting with aren’t necessarily the folks you’re into and vice versa.

Needless to say, this has the unintended result of giving you worse matches and showing you people who you’re either not attracted to or not compatible with. While it may show you more people than you might otherwise encounter in your day to day life, it puts additional barriers up that make it harder to actually connect with them. Small wonder, then, that online dating sucks for… well, pretty much everyone – including folks who could pass for models and Instagram influencers.

But online dating can still be an incredible option – one that actually can play to the strengths inherent in strong social skills and knowing how to be charismatic and charming in person. The key is to think outside the traditional apps. Now, this doesn’t mean using LinkedIn as a dating site – and yes, people do, in fact, try to use it that way.

Instead, consider this: more people met their partners and have ended up in long-term relationships on World of Warcraft than on Tinder. For that matter, people have met their partners on Discord, on subreddits, webcomic forums and (sigh) yes, even Twitch.

Of course, what all of these have in common is that they’re all communities, not dating sites – places where people are gathering to be social and talk about their shared interests. What’s happening is that these explicitly aren’t cold-approach scenarios, with randos rolling up to shoot their shot. What’s happening is much simpler, much lower-key and much, much more human: people are having longer, more meaningful interactions with folks with similar interests and outlooks on life. Because these are communities – not public facing performances like Instagram, TikTok or Twitter – people are letting themselves be a little more honest, a little more vulnerable and a lot more authentic.

In a very real way, it’s easier to be more yourself when nobody can see you or has as much of an idea of who you are. And that actually pays off. Because people have good interactions with someone in their community – whether it’s their Discord server or a Facebook group – they start to chat in DMs. They talk, they share, they get to know each other. We like folks who are similar to us, after all, and those shared interests and values often reveal other, deeper and more meaningful commonalities. Those moments of unguardedness and authenticity allow for moments of genuine connection… even a certain spark. And sometimes, especially when online friends finally meet offline, those sparks will catch and turn into a flame.

What’s significant here, is that the ways these relationships come to be is very much the same with how most of us meet our partners in physical space. Familiarity and propinquity increase comfort and breed attraction. Shared interests and good conversations lead to moments of chemistry – good conversation and laughter promote the generation of oxytocin after all. Those moments of chemistry add up to mutual interest and, before long, mutual desire.

Now, if all of this sounds a lot less stressful than swiping, matching, unmatching and trying to move from the app to in person… well, yeah. It’s incredibly organic; there’s no script or series of techniques, just two (or more) people getting to know one another and bonding over shared interests.

Just like people do in person.

That fear – the fear of rejection, of judgement and so on – isn’t as prevalent because these aren’t dating sites. These aren’t people going into those interactions with an agenda other than “I really like talking to this person.” Because they’re not putting on a mating song and dance routine, they’re being their honest selves and their connections are the better for it.

This is why I tell people, over and over again: success in online dating comes from being good with people, not with your pictures or putting the right attraction triggers in your profile text. If you can have conversations – even private conversations – with your friends on your gaming Discord channel, you can have conversations with the folks you meet in the real world too.

And while we’re on the topic…

Be In The Moment

Let’s go back to the topic of mindset, attitude and technique. Part of why things like pick-up artistry or shit like Red Pill techniques are so popular is because they fill that vague fear of “I don’t know what to do or say.” They’re all a way of trying to not just avoid the possibility of rejection, but to quiet the core anxiety of “I don’t know what I’m doing and I’m terrified I’m doing it wrong.” While general guidelines can be useful, they don’t offer the same comfort of “OK, say these things and you’re golden.”

But as most folks who’ve tried using canned material or other people’s lines can tell you: it doesn’t work. Even if you were to actually hook them with the initial script, you’re going to run out of material very quickly. At that point, you’re going to realize that all you’ve done is delayed the inevitable. You’re right back at the “don’t know what to say or do” part, except now you’ve created this Potemkin version of yourself, instead of your authentic self.

So, y’know. Good luck on getting your ass to live up to the person you were just pretending to be.

But beyond the inevitable running out of things to say, let me give you the real secret to why scripts and canned material don’t work: because you’re too busy focused on what you’re supposed to say or do next, instead of on the other person. Relying on scripts and routines may help you with the whole “running out of things to say” issue, but you’re going to end up missing what the other person is all about because you’re too lost in your own head.

However, even without the (dubious) benefit of having material to riff from, those moments of being lost in your own head are part of what makes meeting women so intimidating. Whether you’re using canned material or freestyling it, if you’re too caught up in your own head, you’re actually making things harder for yourself. It’s understandable that you feel like you need to watch for every possible micro-expression to read her mind or figure out the perfect thing to say… but unfortunately, that’s precisely what’s keeping you from connecting with them. You only have so much bandwidth, and if you’re using it to think about what you need to say next, you’re not using it to listen. And that’s a problem.

The way you can avoid this pitfall is to stop trying so hard. It seems like cruel irony, but the fact that you’re so focused on saying the right thing or trying to make sure every joke and comment is landing just right is working against you. To abuse a metaphor: it’s much like a first-timer’s mistake when they study improvisation; they’re trying to be clever or funny and they fail, miserably. Part of the point of improvisational exercises isn’t to think about the great laugh line or clever comment, it’s to work with your scene partner. Rather than having lines you’re supposed to hit, you stay in the moment, responding without thinking to what your scene partner has just contributed.

If you’re focused on being funny, then you’re devoting more time to trying to steer things to the place where you can get your joke out. This comes at the cost of… well, the scene itself. Improvisation is supposed to be a collaborative exercise, where the point is to build on your partner’s actions. Trying to force things to where you get your moment to shine inevitably comes across as stilted and painful.

On the other hand, when you focus on being in the moment, you may not have the best wordplay or quippiest of quips. What you do end up with, however, is often funnier than anything you planned. Because it’s more unexpected and more organic, it builds and supports the thing you’re building together, instead of being your moment to shine.

The same is true for dating and meeting women. Dating isn’t about being the brightest, shiniest penny in the jar, it’s about building something with another person. It’s about collaborating with them and building something together, not practicing your tight five, dazzling them with your brilliance or baffling them with your bullshit.

Rather than focusing on being perfect or having the best line or cleverest insight, you want to just be present. The last thing you want is to be lost in your own head. You want to be in the moment, right then and right there, giving them your actual attention. Yes, it means you may flub a joke or say something inelegant; organic and authentic moments are often messy. But here’s the thing: those aren’t disqualifications. Nobody is expecting perfection, they’re expecting connection. They want someone who they can be real with and who can be real with them. You can’t give them that when you’re off in your own little world and running out of oxygen.

There’s not a person on this planet who hasn’t tripped over their own junk talking to someone they were into and – quite frankly – most folks won’t notice or care. Starting strong and finishing strong go much further to smoothing over any bumps in the middle.

But as long as we’re talking about connecting with folks and being present…

Embrace Your Curiosity

If you ever want proof that looks and money don’t matter as much as personality and charm, allow me to introduce you to Henry Kissinger.

Kissinger was many things: a devoted soccer aficionado, a survivor of the Third Reich, a tenured Harvard professor, Secretary of State to Gerald Ford and Richard Nixon and directly responsible for so many war crimes that it’s almost impossible to measure the blood on his hands.

He was also an absolute sex symbol… despite looking like a melting nutsack stuffed with evil. This is, sadly, not a joke; even profiles that acknowledged his less than Adonis-like features and build were almost unspeakably horny for him. Kissinger was known for his many, many female admirers, often being seen with celebrities on his arm including Diane Sawyer, Candice Bergen, Shirley Maclaine, Marlo Thomas and original Bond girl Jill St. John. And yes, this includes women who absolutely despised him for pushing the US to commit war crimes in Vietnam, Laos and Cambodia.

Care to know what his secret to being so irresistible was? It wasn’t that he had a massive Andrew Lloyd Webber-esque hog2 , nor was it – despite his quip – his being in a position of power. And while one could argue that someone who was able to negotiate detente with Russia or reopen China’s borders isn’t going to be intimidated by beautiful women, the secret was much simpler… and much more banal.

He listened to women when they talked. He’d ask them questions and solicit their opinions on the news of the day.

No. For real. That was it. He asked women their opinions and actually listened to them, taking them seriously and made them feel like the most intelligent and interesting person in the room.

And while you can joke about how low the bar must’ve been in the 60s and 70s D.C., the fact is that this is still remarkable is fucking astounding. The number one complaint I hear about from women who date men is very simple: it’s the guy who never asks any questions. They either talk about themselves exclusively or they only talk about things that interest them. This isn’t an exaggeration; I can’t tell you the number of women who’ve told me about dates they’ve gone on with men, dates that have lasted for hours, and their date never asked a single question about them. Ever.

And then had the audacity to tell them that they weren’t like other girls and to ask for another date.

We live in a society where we very rarely actually converse with one another; most of the time, we’re busy waiting for our turn to talk. This is especially true for women, and particularly on the dating scene: a lot of guys show little to no interest in what the women they’re attracted to are thinking. They’re more interested in preening like peacocks and collecting all the praise and admiration about how amazing they are. Guys who actually listen and want to know what their dates thing, on the other hand, are a prize. A man who makes someone feel not just listened to but heard, who expresses genuine interest and respect for women’s insights and thoughts isn’t just rare but valued.

It’s part and parcel of the Reward Theory of Attraction: we instinctively prioritize relationships with the people who make us feel good. When someone makes us feel validated, makes us feel smart or insightful, we want more of that. We want to spend more time with them and soak in that sweet sweet dopamine hit. Prioritizing that good feeling doesn’t mean they just want a yes-man, orbiter or toady; it transfers to other areas of the relationship. We don’t associate those good feelings with the action, we associate them with the person… and that helps generate the literal and metaphorical chemistry we want.

The quickest and easiest way to become someone who is as magnetic as Kissinger (without all the dead civilians and devastated countries) is to engage your intellectual curiosity and get interested in other people. Everyone has something fascinating about them – so get to know them and find that cool fact. Ask them about themselves, get to know what they’re passionate about and what makes them tick. Invite their thoughts and opinions on a topic and actually listen, even if it’s something you know a lot about. In fact, especially if it’s something you know a lot about. Not only might they have an insight or way of looking at it that you’d never considered, but making someone feel smart is incredibly sexy.

Once you can fully embrace that understanding, it’s much easier to feel confident connecting with people. When in doubt, give women an opportunity to share about themselves and really listen; most of the men in their lives never do.

Date Slow

So let’s talk about one of the most ignored reasons why men get intimidated in talking to women: they’re trying to move at light speed.

No, for real. If you ask guys why meeting women feels like tiptoeing through a minefield, they’ll often tell you that they only get one chance. If they don’t get everything right, they’ll likely never see this person again. As a result, they feel a self-imposed pressure to beat the buzzer and lock down a date or else. Pair this with a classic scarcity mentality and you’ve got a recipe for disaster.

Now, an obvious question would be “well, what’s so bad if this one does get away?” After all, it’s a little absurd to think that you need to “get” this specific person. The world was turning before you knew she existed; the world will continue to turn if you don’t get her number. Since you weren’t exactly dating her before, not getting a date doesn’t mean anything besides a return to the status quo. So, moving at speed to try to get a date seems counterproductive at best.

The answer isn’t logical, but it is understandable.

Part of it is ego, pure and simple. The image most of us have in our heads when we think of “meeting women” or “getting a date” is the classic pick-up: you meet a sexy someone, sweep her off her feet and get rewarded with a number, a date, or thirty to forty minutes of squishing noises. And to be sure, the idea that you’re just so hot, suave or desirable that women you just met will go home with you is intoxicating.

However, a much bigger reason is the fear that time is running out. It feels so dire because it feels like this is your shot. And if you don’t make this love connection happen… well, who the hell knows when a chance like this may ever come around again?

Well, actually, it would come around far more often than you’d think if you actually made a point of going out and meeting women. But that’s a matter for a different column.

But if this were your only chance at love/sex/whatever for the immediate future, wouldn’t you rather make sure you get it right instead of trying to rush things? After all, slow is smooth and smooth is fast. But that’s where the next snarl comes into play. A lot of men genuinely believe that if a woman is attractive, then it’s not just you shooting your shot. You’re trying to get and keep her attention and build that attraction while potentially dozens of other men are doing precisely the same thing. If you don’t play it just right, someone else will snatch her out from under your nose. When that happens, then not only are you a loser (or worse, a cuck) but you also will see her with that other guy, constantly.

(How they square that with “but I’ll never see her again” is an exercise left to the reader.)

This is an understandably upsetting scenario. It’s also entirely in people’s heads. As I’m often saying, when you’re trying to charm a sexy somebody, you’re not in a competition with everyone else that she knows, or even everyone else at the bar. You’re in competition – such as it is – with Netflix or a book and an early bedtime. And that is if you’re talking about a standard cold approach situation.

The good news is: that’s not how most people date. Cold approaches in general are difficult and inefficient under the best of circumstances. As I said: the idea that you meet a stranger and convince them to start a romantic or sexual relationship with you in a matter of hours may make for compelling movies, but it’s much less common in real life.

Attraction may happen quickly, but relationships are built over time. People may know that they find someone cute or sexy or desirable after only knowing them briefly, but that doesn’t translate into “wants to actually do anything about it.”

Trying to turn a chance encounter into a full-bore relationship – whether for a lifetime or just that night – is very, very difficult. It’s even harder when you’ve put absurd and pointless amounts of pressure on yourself. And if you’re worried that someone else will snatch her away, then you’ve added another, even more pointless level of pressure to the whole shebang. Here’s a truth: nobody can “steal” someone away from you, and it’s so unbelievably unlikely that a different stranger is going to woo them so hard that they lose interest in you that I’m not sure there’re numbers small enough to accurately measure the likelihood of it ever happening.

(And before folks rush to tell me their experiences, I can guarantee you one of two things: either 1) they knew the other person already or 2) they didn’t go home with them either; you just saw the end of your interaction, not theirs. In either case, he didn’t “squeeze you out” or “steal” her, she wasn’t into you in the first place.)

So much of why guys think they’re under the gun is because of the weasels in their own head. They’ve convinced themselves of a narrative where every attractive woman is constantly in a relationship and the windows in which she’s single are vanishingly brief. As such, they need to shoot their shot right then and there or else regret missing it forever.

But that’s not how it works. That’s not how any of this works, even for incredibly beautiful women. Even the hottest of the hot don’t just bounce from relationship to relationship with no space in between – no matter what it seemed like in high-school. Most relationships are built over time, especially romantic ones. Some of the longest, strongest and happiest relationships are the ones that took time to come together, not the ones that started right then and there.

More importantly, however, is that prioritizing speed over letting things build is a mistake, especially when you’re inexperienced. When you rush, you are more prone to make mistakes, and when you’re trying to rush romance, then you raise the odds of tripping over your own dick exponentially. The relationships I mentioned in the “Think Beyond The Apps” section didn’t happen overnight; they percolated for months, sometimes even years, before they came to fruition. And while you don’t necessarily need to wait years, by taking a slower, more deliberate pace ultimately works in your favor.

One of the more important things to remember is that we actually prioritize uniqueness over looks. The idea that the more we’re exposed to people and the more we get to know them, the more we like them. You’re much more likely to get a date by striking up a conversation with the familiar face you see at the student union or the bookstore than the random babe you bumped into at the Peet’s Coffee. Giving folks time to get to know you works far better than trying to boss-rush dating, especially outside of bars or clubs.

Now to be sure: this doesn’t mean that you want to dither forever and never actually ask someone out on a date. But there’s a difference between “getting to know someone and building a connection” and “waiting for the perfect moment that will never come.” In the former, you’re actually working on building the connection; with the latter, you’re often coasting by on the ambiguity of “friend/interested?” and hoping to backdoor your way into her heart and pants.

(Pro tip: if you need “the perfect moment” to ask, then that’s a tacit admission that you know she’s not interested and don’t want to accept it. If she’s into you, the perfect moment is whenever you ask.)

By slowing your roll and giving yourself time, you give yourself room to breathe, room to savor the moment and – importantly – room to make mistakes and recover from them. Rushing, on the other hand, means that not only will you make more mistakes but you won’t even be able to stop and address them; you just end up compounding them and making things worse. This is why slow is smooth and smooth is fast. By taking a measured pace, you don’t need to spend your time correcting mistakes and losing even more time.

So to help take the fear out of dating, embrace dating slowly. You’ll have far greater success – and far less anxiety. And in the end, it’s the relationship that matters… not how fast you got there.

1. No, I’m not going to do this twice; I’m just going to revel in the knowledge that it’s in your head now. [↩]
2. Sorry, but if I have to bear the burden of this very cursed knowledge, I refuse to bear it alone. [↩]