5 Mistakes That Men Make Approaching Women

So, I have a confession to make: I have a perverse love of weird, dumb or just plain batshit dating advice that gets passed around like golden nuggets of wisdom. This means that Twitter is a bonanza of bullshit to comb through for laughs that range from “wait, this has to be fake” to “oh God you’re serious.”

Now, occasionally this means that you get things like the Green Arrows dude who goes on and on about where people’s junk is pointing.

Other times,  however, you get the “How Do You Open” meme. The format is incredibly simple: a would-be nu-PUA guru posts a picture of an attractive woman (usually yanked from Instagram models’ Twitter feeds) with some weird backstory to set the scene. Each ends with the same question: “How do you open?”

These are a series of thought experiments that are intended to get you to apply the poster’s lessons on talking to women, while also goosing the algorithm via cheap engagement. And while their chief value is in the parody posts that are so absurd that you can’t be sure if they’re jokes, I find them kind of fascinating on an anthropological level.

However, the thing that makes these interesting to me is how much they contrast with the number of folks who are terrified of approaching women.

That’s not a joke; I hear from guys all the time who’ve mainlined hundreds of Reddit posts and TikTok videos from women complaining about guys hitting on them. This often gets paired with dudes who go trawling for more “proof” of the “It’s Not Creepy When Brad Pitt Does It” argument.

What makes this interesting to me is that both of these groups have a large stumbling block in common: they get the concept of “approaching” wrong. And to be fair: I’ve made that mistake too. Hell, I’ve promoted many of those mistaken ideas myself. But what’s significant is that these shared misconceptions make it harder to meet women, particularly in person. The issue isn’t that approaching women you find attractive is inherently bad, it’s that their technique, their mindset, even their very conception  of “doing approaches”, “opening” or what-have-you is wrong.

So let’s talk about the mistakes men make when approaching women, and how to fix  them.

Mistake #1: You’re Approaching Women The Wrong Way

Let’s get this  one out of the way first: the single biggest mistake men make is that they’re “doing approaches”.

Yes. Really.

Here’s the issue: when you hear women complaining about guys hitting on them, 9 times out 0f 10, the issue isn’t that “a guy found her attractive and had the temerity to talk to her”. The issue is that most guys do this incredibly badly. There’s no social calibration, no attempt to read the room and ask whether this is an appropriate time, or even consider whether the person they’re approaching even wants to talk to anyone just then.

Much of this comes down to the fact that they’re thinking about this as “an approach”. That is, they’re turning what should be a basic human interaction into an attempt to shoot their shot, regardless of circumstance. While I fully acknowledge that this seems like a weirdly hair-splitting position, the truth is that the way you think about this changes how you behave. The outlook of “how do you open” or “doing approaches” causes a mental shift from normal behavior to “how do I get what I want from this stranger” — often with little to no regard for the other person’s feelings.

You’re coming into an interaction with a stranger with an obvious agenda, and often at a time when they’re not interested in being hit on. Many times, they’ve already dealt with random guys hitting on them just because they had the temerity to exist in public. That’s going to be enough to make anyone keep their guard up; they’re just trying to avoid having to extract themselves from another tedious and annoying conversation from yet another guy who thinks that she exists for his consumption.

This is why so many PUA techniques — such as the ones you’ll find in those “how do you open” posts — are so glaringly absurd. They’re about trying to obscure the painfully obvious, while being blatantly manipulative. In fact, more often than not, the techniques are all about interacting with women as though women were particularly convincing chatbots, rather than treating them like people — reducing conversation to if/then flowcharts.

It works about as well as you might think.

While, yes, there are times when people meet, mingle and approach each other with the explicit intent to get laid, that’s incredibly dependent on the social context. After all, the expectations at bars or parties is vastly different from, say, getting some fresh zucchini and goat cheese at the farmer’s market. In the vast majority of your daily life, rolling up on folks with the end goal of getting laid will backfire on you, messily and all over the place.

The truth is that people waiting for their morning lattes or who’re browsing the aisles at Target aren’t there to be hit on, nor are they looking for dates. They’re just trying to go about their lives with as little friction as they can manage.

But while they’re not interested in being hit on, you know what they would be open to? Having a nice, brief conversation with someone cool. Would they be up for more than that? Maybe, maybe not. But if you’re making “approaches”, then what you’re ultimately doing is signaling that you want something from them beyond a nice chat.

How Do You Fix This?

The answer here is obvious: you don’t make approaches. This doesn’t mean that you can’t or shouldn’t talk to women in venues that aren’t about hooking up; it just means that you just talk to people. Not women — people. Because here’s the thing: being social is great. Being social when it’s obvious you’re only interested in being social with the ladies? People pick up on that pretty quickly.

The key to getting out of the “approach” mindset is that you want to be outcome independent. Your goal should be very simple: you’re interested in meeting cool people and having great conversations. Maybe all that happens is you talk to someone for a couple minutes. That’s  great! Maybe you’ll get a cool story or experience out of it. You might make a new friend. That’s awesome too! But if you’re treating someone like a target or that they’re part of “a set”, then all you’re doing is creating a scenario where you’re entirely too concerned with the ultimate outcome. And while I completely understand wanting to connect with some sexy someones, that desire can get in the way of the end goal.

When you’re too focused on the outcome, you’ve set yourself up with a fail condition to… well, to basic conversation. Because you’re invested in getting a specific outcome, a lot of your mental bandwidth is going to be devoted to both achieving that outcome and gauging your progress. This, in turn, makes the simple act of talking to people far too intimidating. If you’re focused on making sure you do everything “right”, then you’re not being in the moment. You’re putting yourself in a position where you’re more focused on what to say or how to direct the conversation down the path you want it to go, rather than letting it just flow naturally.

If you want to have more success at talking to women that you meet in your day to day life, focus less on meeting women and more on getting comfortable talking to people in general. Let your goal be “enjoy this conversation”, instead of trying to steer things towards getting a number or a date. This makes talking to women when it “counts” less intimidating and lets everything flow easily and naturally.

On a related note:

Mistake #2: Women Don’t Want to Be Picked Up

So, let’s go back to the topic of “women hate it when guys hit on them”. This is a topic that causes no small amount of agita — both from guys who’re convinced this means that they should never talk to women ever and from guys who think it’s unfair they aren’t allowed to talk to women ever. But the folks who get the most spun up about it also tend to be the ones who miss an important bit of context: why women complain about this.

Women aren’t complaining about “guys I may or may not be attracted to want to fuck me and that’s rude”, they’re complaining about guys who are transparently hitting on them with no regard to their lack of interest. It’s not about somebody making small talk, it’s about guys who are actively trying to pick them up — often in places or at times when they aren’t even remotely interested. This would include at work, on public transit or just walking down the street. These are usually dudes who start hitting on them with absolutely no warning, warm up or anything resembling social foreplay. Just a guy rolling up to offer her some dick in this trying time.

The fact that they do it badly is just adding insult to injury.

Despite what folks will tell you, this has nothing to do with looks and everything to do with social skill. Part of the Celebrity Exception — “It’s Not Creepy if Leo does it” — that people miss is that whatever celebrity du jour they slot in usually isn’t going to just roll up on somebody… certainly not at random. Most of the usual suspects that get brought up — Brad, Leo, George, Michael, Tom, whomever — are not only perceptive and good at reading the room, they’re also good at building a connection with people. After all, networking and social skills are crucial survival skills, even in days when folks can be famous for… being famous.

That having been said: I’ve personally seen very famous celebrities — ones who are objectively hot as hell — get shot down over and over like a MiG-28 in contested airspace.

They may have been hotter than a four alarm fire, but they were acting like every stereotypical fratboy chud at the club after a 2-for-1 Jaeger night. Their looks, money and fame couldn’t overcome the fact they thought “not interested” was something that happened to other people.

Keep in mind that, again, there’re plenty of times, venues and events where the vibe is all about hooking up. These are places where folks are either expecting to flirt and hit on each other, or understand that this is accepted behavior. However, those are specific times and environments; most of the people you meet aren’t going to be at bars or clubs. They’ll be during your every day life. This makes hitting on random strangers an incredibly ineffective, even counterproductive approach.

…er, as it  were.

The thing is, when you’re trying to pick someone up — especially when the social context isn’t conducive to hook-ups — it can feel incredibly dehumanizing. You know next to nothing about them other than their looks. If you’re going to move straight to flirting with them, you’re telling them that you’re primarily into them for their appearance. Even people who are attractive and know they’re attractive don’t want to be valued just because they’re hot. They have more going for them than their looks, but those qualities — things that they care passionately about — get shorter shrift than their face or cup size. And while many people do enjoy knowing that folks find them attractive, there’s feeling pretty and then there’s a dude who thinks “you make my penis smile” is a compliment.

To make matters worse, the guys who do these sorts of approaches make it abundantly clear that they’re not interested in the women they hit on as people. They show absolutely no interest in getting to know her beyond the bare minimum. Most of the interaction revolves around her trying to get into her pants. She’s not a person so much as a warm temporary home for a lonely peen.

Small wonder, then, that many — if not most — women are instinctively on their guard around guys who want to talk to them. You may not be one of the assholes who started hitting on her when she was trying to pick up her order, but she doesn’t know that. And if you’re approaching her the way those other guys did… well, now you’re just one more frankfurter in the never-ending parade of sausage being thrown her way.

But, again: you aren’t an asshole. You’re not one of those guys. Yeah she’s got a body to make a bishop kick in a stained glass window, but you’ve got purer intentions than they do. This creates a frustrating catch-22: how do you hit on someone without hitting on them? How do you get somebody’s number — or a date, for that mater — without trying to pick them up?

How Do You Fix This?

Here’s the thing: when you’re trying to pick someone up — whether at the club or at the food court at Whole Foods — you’re asking a stranger to start a romantic or sexual relationship with you after having known you for less than an hour. Under the best of circumstances, that’s a pretty big ask. That’s also not how most folks decide to date someone. Or decide to go home with them for that matter.

So, you want to slow your roll instead. Nobody wants a stranger hitting on them when they’re trying to buy groceries, but they’re much more receptive to “having a great conversation with a fascinating stranger.” This is why you don’t want to think Ryan Gosling in Crazy, Stupid, Love, think Hallmark Christmas movies. The appeal of those isn’t “hot dude hooks up with the female romantic lead”, it’s the slow burn and build of the connection. The fantasy is all about how that relationship comes together over time, even if there’s attraction (spoken or unspoken) right from the jump.

Your initial goal is very simple: get a conversation going. You can use almost anything to start the conversation — an open question, an observation to nobody in particular, a context-relevant remark. If she responds, then let the conversation flow. You want to play things safe at first, especially during the day — choose obvious, relevant topics and non-threatening small-talk. You don’t want to flirt or hit on her… not at first. Instead, let things just warm up on their own. The friendlier or more invested she becomes in the conversation, the more leeway you have to add a little flirting in. Think of it like adding a strong spice; a little will do at first, too much too early on will ruin the entire dish.

Just as importantly: you want to respect her time. This means that you have to be willing to let her leave… even if you haven’t gotten to a point where you would feel comfortable asking for her number or to connect on social media. Ask her: “Hey, do you need to go? Because I’d love to stay and talk to you some more, but I don’t want to keep you.”

This can be tough. Part of why an approach mindset works against you is because there’s a pressure to get to the goal; you may never see this person again, so you need to make sure you shoot your shot OR ELSE REGRET IT FOREVER. This actually ends up reinforcing a scarcity mentality — not only is the only chance you may have with this person, but if you miss out, then you’ll be one step closer to dying alone and unloved.

Having an abundance mindset, on the other hand, does two things. First: it helps put you in the frame of mind that this chance meeting isn’t the end; the universe brought you together once, it again. Even in big cities, you run into people in the most unexpected places. If you believe that there will be other opportunities, you don’t feel the need to try to rush to get a number. Second: if things don’t work with this one person, there will be others. You don’t need to get focused like a laser on her and so you can just enjoy the time you have for its own sake.

In both cases, this mentality exudes a deep and authentic sense of confidence. And confidence is sexy.

Focusing on just enjoying the conversation and letting things build before you start to flirt has its perks too. It feels more natural and authentic, rather than weird or forced. It helps create the feeling of “fate brought us together”, rather than “rando started hitting on me in the frozen foods aisle of the Safeway”.

But while we’re talking about uncomfortable and off-putting…

Mistake #3: You’re Acting Weird

Here’s another classic example of why “doing approaches” often works against you: it changes your behavior… in a bad way.

Look at this shit, for example:

Does any of this seem like a way two humans actually interact with each other? Does this strike you as “strong social calibration” or more “well look at the time, gotta go mow my cat…?”

I have a lot of sympathy for folks who find trying to meet, flirt with and date women to be scary and intimidating. I have been there, done that and quite literally built a career out of it. However, while trying to gamify human interaction can help make it less daunting, it often creates scenarios that feel fake and unnatural. Doubly so if you’re relying on routines, pre-scripted material or structured processes that… don’t really bear any resemblance to basic communication skills. Half of the material out there tries to hide your true intentions and relies on manipulation or weird high-pressure sales tactics, and none of it sounds normal or like something people actually say in casual conversation.

Even if you leave out weirdness like “alpha confusion”, the truth is that it takes a lot of work to make a memorized script feel natural and unforced. A skilled actor can make it work. Most folks out there aren’t skilled actors. Especially when they’re trying to flirt with a hottie at the club.

And I know from which I speak. Early in my PUA days, I used to use a lot of canned routines and material. However, trying to actually make any of it work was a challenge. In fact, one of my regular sticking points was how much it sounded like I was doing a bit. I had women ask if I were rehearsing something or if I were practicing a comedy routine, which… didn’t do great things for my ego.

It was, needless to say, the antithesis of sexy.

But then again: I was using other people’s (equally bullshit) stories and material in order to create the image of being someone I wasn’t. This is the literal opposite of what you want. When you’re trying to meet someone, you want to be authentic. People aren’t stupid; they can tell when you’re trying to direct the conversation like a flow chart. They can also tell when the stories you’re telling and how you present yourself are incongruent with who you actually are. You want to be authentic with the people you’re trying to hook up with, and for them to be interested in talking to you. What you don’t want is to make them feel like you’re workshopping your tight five on them.

At best, all routines actually do is buy you time to think. However, the drawbacks negate any benefits you may get because, quite frankly, they come across as fake as hell. Random things like “cut the thread”, or compliance checks or “hoop theory”and “frame control” make you sound like a weirdo.

How Do You Fix This?

Look, there’s no other way to say this: you’re gonna just have to get comfortable with improv. That is, you want to put improv techniques into practice.

You want to learn to stop thinking so much about what you’re going to say and focus on being in the moment. When you’re hung up on saying the “right” thing or planning the next clever phrase or waiting for your chance to “cut her thread” (or whatever weird shit Green Cock Arrow goes on about), you’re being the opposite of authentic. You’re too focused on the outcome instead of the process and on the end game instead of just getting to know the person you’re talking to. More often than not, you’re only listening with half an ear — waiting for your turn to talk instead of enjoying getting to know this person.

All of that gets in the way of building a connection with people, finding commonalities and building mutual chemistry.

Now, having some structure to guide you does make the process of talking to new people — especially people you’re attracted to — seem less daunting. But rather than relying on routines and cold-approach flash cards or whatever, you could try this one weird trick to make talking to women easier: assume that they like you already.

If you go into a conversation with someone with the assumption that you and they are already friends, it changes everything about the interaction: your behavior, your body language, even the way you interact with them. Think of how you talk with your friends across the gender spectrum — the banter and jokes, the gentle teasing and easy camaraderie; you want to bring that energy to your interactions with people you find attractive. Think of it less as talking with someone you hope to date and more about reconnecting with a friend you haven’t seen in a long, long time. This not only help you relax, but the focus on “catching up” helps you keep your attention where it should be: learning more about this old friend you’ve only just met.

Not only does this help you relax and keep the conversation flowing in a more natural manner, it also means you don’t trip her pick-up filter or demand an answer to “why is he talking about this weird little kid on a tricycle?” instead.

And speaking of getting to know folks…

Mistake #4: You’re Trying to Impress Her

Let’s talk about something I think a lot of folks don’t realize they’re doing when they make approaches. One of the reasons why people strike out or end up creeping women out is because of the mindset they’re bringing to the interaction: they’re trying to win her approval. While this may not seem like something inherently off-putting, it has less to do with the actions and more about the attitude behind it. Regardless of whether it’s framed as “trying to flip her attraction switches” or “demonstrations of higher value”, in practice it actually betrays a sense of neediness and insecurity.

The fact of the matter is, if you’re trying to brag or show off how rich/ high-status/ important you are, you inevitably come off as a try-hard. Think about it; do you think that Idris Elba needs to brag about how awesome he is? Does Clint Eastwood need to sell you on how cool he can be? Of course not. They know who and what they are and don’t require other people’s approval to validate them.

Now this doesn’t mean that you can’t talk about the things you’re proud of or what-have-you, but the more you try to flex, the sadder it becomes. As the man says:

However, this goes beyond a simple “What Would Brad Pitt Do” thought exercise. Part of what makes this a mistake is what it says about you and the person you’re trying to impress. What, precisely, has she done that makes her approval that important to you? What is she to you that you feel the need to work to impress her?

The answer is equally simple: nothing. She’s a stranger. An attractive stranger, yes, but a stranger. You know literally nothing about her other than her looks. And while being attractive is nice, it’s only a part of who she is… and not even the most important part. Not only does this tie into the fact that she’s more than her looks, but there’s the fact that her looks don’t give her higher status to the point that you need her approval. Nor does it make her a good person or someone who’s approval you may want. Trying to impress her means that you’re giving her more importance than she deserves in that moment. It’s not that she’s lesser than you or that impressing someone is inherently bad… it’s that you know nothing about her.

Why is this bad? Well, ask yourself: why are you giving her this power over you? If it’s because you want her to like you… well, if you’re working that hard at it, either she’s predisposed to not like you — which makes this a waste of time — or you don’t have faith in your own value. That means you’re coming to this from a place of insecurity. If you need her validation and approval, then you’re putting yourself in a place where you’re never going to feel secure or confident with her.

But more importantly, ask yourself this: is she worth your time? Instead of trying to prove to her that you’re good enough for her, you should be finding out if she is good enough for you. Besides being hot, that is. As I said: you know nothing about her; for all you know, you’ve been supplicating yourself to someone who thinks horse dewormer is a superior option to vaccines.

How Do You Fix This?

Ideally, you want to be confident and secure enough in yourself that you don’t feel the need to “prove” yourself; your good qualities should be self-evident. And while not all your cool points will be obvious, there’re easier ways to demonstrate them than conspicuously angling for approval. But rather than focus on impressing someone, you want to focus on making them feel instead. Being impressed isn’t the same as being attracted; someone can be impressed by your badass car or your high-status job and still think you’re an unfuckable homunculus. Making someone feel good, however, makes you magnetic.

Your goal shouldn’t be to impress them, it should be to make them feel like you get them on a deep and meaningful level. Can you make them feel like you’ve known each other for years, despite having just met? That’s like magic. Can you make her laugh like she never has with anyone else? Or introduce her to incredible experiences? That’ll make her want to spend time with you over anyone else. The more warm, positive feelings you can inspire in her, the more she’s going to like you.

You also want to put your emphasis on getting to know her. As I said: she’s a stranger, and the last thing you want is to elevate someone who doesn’t deserve it. However, this isn’t about proving that you’re higher status or higher value than she is. It’s not about making her seek your approval or getting her to feel insecure around you so she tries to suck up to you. It’s about recognizing that, despite what some folks insist, women don’t have all the power in dating.

The truth is that men who think this are throwing their power away. Attraction and choosing a person is a two-way street. Yes, you may have made the first move… but that’s not the same as choosing her. That was the opening of the investigation, the start of getting to know her and gauging if she’s right for you, just as she’s deciding if you’re right for her. Yeah she’s hot… but you may well find far more dealbreakers than any amount of hotness could make up for. Yes, she could reject you, even before you start talking. But at the same time, you can still reject her. 

Now to be clear: not trying to impress someone doesn’t mean that you “put in no effort”. It doesn’t mean that you don’t do things for her that make her feel special or good. It just means that you’re not seeking the approval of a stranger. Find out if she’s worth putting the effort in, first, then impress her.

And finally…

Mistake #5: You Come On Too Strong

This last mistake tends to be one of balance. A lot of guys — especially folks who think of themselves as “doing approaches” rather than talking to people — tend to push things a little too far and a little too fast. They’re not quite human versions of Pepe Le Pew, but they’re not far off either.

There’re a lot of reasons for that. There’s the scarcity mindset — the feeling that you need to lock this down because you only ever get once chance with this person before she disappears for ever. There’s the outcome dependence and the feeling that you need to “win” this encounter. Sometimes it’s even just a case of excitement and enthusiasm running away with you. But regardless of the reason, the end result is the same: guys ask for too much, move too quickly and often push a lot harder than they intend to.

And, quite frankly, all of that is unattractive. Most of the time, this ends up being a case of snatching defeat from the jaws of victory. Sometimes it happens because you ask for more than you should; you would’ve been better off going for a number than trying to get a date — or, worse, trying to get her to come home with you. You may have missed (or ignored) a soft “no” and kept trying to get her to go out on a date with you. Sometimes it’s the case of getting too physical or putting her in a place where she felt like she had to kiss you or make out with you so that you’d leave.

Or it could have been that you were angling for more than she was ready to give… yet.

A lot of times, what’s ended up happening isn’t that she disliked you or she rejected you. What actually happened is that she liked you and might have been interested in more — a date, a makeout session, forty five minutes of squishing noises — if you’d given her and the moment room to breathe. But because you pushed harder than you should have — intentionally or otherwise — you ended up with nothing after all.

While this is commonly a rookie mistake, it’s one that happens to the best of us when we let our excitement get ahead of our good sense. And it’s something to be mindful of… especially if you’re meeting someone in a place that isn’t conducive to hook-ups.

How Do You Fix This

As I said: this is a question of balance. You need to find the right balance between active interest and not giving too much. Part of what guys often misunderstand about dating women is that while women may make quick judgements about whether they’re into you or not, that’s not always their final decision. Many times, a guy they weren’t necessarily into right off the bat ends up being someone who grows on them. Or they may assume that he’s kind of a jerk or blowhard at first, but he demonstrates a lot of emotional intelligence and charm as they talk. She might not be interested in dating anyone but then she discovers she can’t get him out of her mind.

The key, however, is giving her both motivation to change her mind but also the room to do so. You can’t start a fire if there’s not enough air flow to reach the spark in the tinder, after all, and the same is true about attraction. Even if the spark is there, it’s very easy to accidentally smother it and put it out without meaning to.

It’s also not always a matter of changing people’s minds. Some folks need time to decide if they’re ready or willing to take a chance on a stranger. Some folks may find that cool, fun guy intriguing but not necessarily date material yet… but they might get there if they see him again and if he doesn’t push her. And still others take time to develop attraction to folks, even folks who they really like.

However, it’s all too easy to overwhelm folks like an overenthusiastic puppy.

Or a skunk, I guess.

In many cases, approaching an attractive woman is — pardon the problematic metaphor — like making friends with a strange cat. Some cats are cuddlebugs and will leap into strangers’ laps. Some are incredibly suspicious and will keep their distance until they get to know you. Still others will never like you. However, even the friendliest cat can be overwhelmed by too much attention. The key is to strike the right balance: show interest and make the initial contact, but give the cat space and the opportunity to make the next move. If you want to befriend a cat, you don’t want to leap to trying to scratch its ears or rub its tummy; you want to hold out your index finger and then let it decide what it wants to do next. Maybe it’ll come over, sniff your finger and then rub up on you. Maybe it’ll hiss and run away. Either way: that’s the cat’s decision; trying to force it only ends up with your getting covered with scratch marks… and not in a fun way.

So it is with meeting incredible women. While every fiber of your being may be screaming that you need to get her to agree to a date before she vanishes forever… sometimes what you need is to give her room to breathe, to think and to feel. Maybe this will be the only time you ever see her. But then again: maybe this is only the start. If you have an amazing time when you first meet but she doesn’t give you her number, that may not be the end of it. If you had that great time… well, she may make a point of coming back in hopes of seeing you again. Or she may take your number instead and will reach out when she’s ready.

Or maybe this really was just a fleeting moment, two ships passing in the night. You can’t know for sure one way or another… but coming on too strong will guarantee that she doesn’t want to see you again.

So strike the right balance. Show your interest, show her a good time… then show her you can back up and give her room. That willingness to let the moment be, rather than to keep pushing, could make the difference between a fun, but brief conversation… or something long-lasting and magical.