How Do I Learn To Flirt Without Being a Creep?

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How Do I Learn To Flirt Without Being a Creep?


Estimated reading time: 13 minutes

Dear Dr. NerdLove:

You’ve said in several posts that bars aren’t the best place to meet women and that they’re more for going out with your friends and that one shouldn’t explicitly go to a bar with the intent of meeting women.

We also have the idea that it’s important to learn how to flirt.

We have the idea that social skills (like flirting) need to be built up with deliberate practice.

Finally, you’ve also said that the best way realistically to find a partner is to go to a social hangout or recreational coed sports and wait until chemistry develops with another person and go from there.

This realistically doesn’t work.

Given that socializing requires deliberate practice, this means that if I want to get better at flirting, then I need to flirt. This is not something to be done at my preferred social hangout though. If you ask a girl out or hit on a girl and you’ve misread the situation and she doesn’t like you back, the most likely response is that she ghosts you, she now feels uncomfortable around you and she avoids you. You can be as respectful as you can and read all the signals as best you can and not cross any boundaries. It does not matter, it will still create a tension that won’t go away.

(Let’s assume for a second that this doesn’t happen, either way if you want to meet a woman through social hangouts as suggested, you have to find a new hobby or social group, start over, rebuild the social proof, etc. and hope that you correctly identify chemistry this time. If you ask out a second girl at said group then you will definitely be earmarked as a predator who is only there to meet women.)

So where do you go to get better at flirting?
Bars. Because now if you screw up, you never see the other person again, and you don’t have to rebuild your social life.

And are you going there with the primary intention of meeting women?
Yes.

The problem is this creates a contradiction with your other advice.

So how are you actually supposed to develop and practice things like “game”, flirting, correctly reading signals and social calibration if you’re bad at it? Especially when the very act of socializing without calibration makes people uncomfortable. Can’t get better if you can’t practice.

Social Calibration Subroutines

I see your problem, SCS: you’ve misread, misunderstood or misremembered a bunch of different columns and pounded them into a mash of incorrectness. Let’s start by teasing things back apart, and then we’ll talk about the other areas where you’re making things harder for yourself.

First: bars and clubs aren’t great places to meet potential partners for dating because those generally aren’t where most people go to find dates. More likely to find a potential hook-up, sure, but dates less so.  Most people tend to meet their partners through shared activities, mutual friends and dating apps. The number of people who start relationships from strictly cold approaches are relatively low.

The issue with trying to meet women at bars is, primarily, that it’s inefficient, as well as being a high-pressure environment. You are trying to convince a stranger to be interested in starting a sexual or romantic relationship with you in the span of anywhere from 20 minutes to an hour, in an venue where it’s frequently hard to talk, harder to be heard and that isn’t really conducive to getting to know someone at more than a very surface level. And unless you (and your potential snugglebunny) are both regulars, you also don’t have the advantage of propinquity and exposure, where folks get to know you over time and grow closer to you because of that.

They are, however, a place where the social contract says that talking to many different people in the span of a short period of time is not only common but accepted (depending on the bar), and that it’s understood that this is a place where people come to socialize. So yes, it can be a good place to practice making approaches, which can often involve flirting.

But on the other, other hand: singles bars and nightclubs are venues cater to folks who like singles bars and night clubs. Your success and/or enjoyment of practicing there can be very dependent on whether that’s your kind of hangout, too. So unless you’re already someone who is a bar and club kind of guy, you may not be meeting people you’re into and you may be trying to meet them in an environment that you may not be comfortable in.

Now the part about not going explicitly to meet women? That’s not about bars or clubs; that’s about social events like classes or meetups, places where people aren’t going expressly to flirt and meet people. The issue there is that if you’re the dude going to a hot yoga class to hit on women and doing lust laps like a horny shark, you’re making the experience worse for people who just want to do yoga. Please notice that’s different from, say, going to the class, saying hi to the people you already know or the folks next to you, taking the class as intended, then possibly talking to people afterwards… you know, like people do when they’re milling about, rolling up their mats, etc. If you happen to be talking with someone and the two of you are getting along well and you say “hey, I’d like to keep talking with you about X; do you have time to grab some juice after?”, that’s not going to raise an eyebrow.

Well, I guess unless you meet someone who’s grandfather was tragically crushed under an avalanche of oranges, but what are the odds of that?

Similarly, one doesn’t necessarily wait until chemistry “develops” ex nihilo. One of the points of flirting is to test for interest and start developing that chemistry if mutual interest there. Part of the point of flirting is that flirting is fun, and having fun with someone increases the odds that they’re going to want to spend time with you. This is the Reward Theory of Attraction: we prioritize the relationships we have with people who make us feel good when we’re around them.

Now, those are some pretty significant misunderstandings, but hey, maybe I could be clearer at times. However, here’s where you’re really shooting yourself in the foot: you’ve convinced yourself that talking to people is a skill based challenge with a DC of 18 and you’re rolling with disadvantage, regardless of circumstance.

You’ve created a hypothetical, one that doesn’t seem to have actually happened, but that you’re reacting to regardless, where you were The Perfect Gentleman and yet you were ostracized anyway because FUCK YOU PENIS, THAT’S WHY. Which, I hate to tell you, isn’t a thing that happens – certainly not out of the clear blue sky with no previous warning or issue.

If you’re talking with someone, generally being polite and considerate, ask them out and they turn you down and if you take that rejection with good grace, then the vast majority of time, what ends up happening is… nothing. Things continue on as normal. Maybe you meet someone who’s a little sensitive because of their own experiences and they pull back, but that’s usually a them issue, not a you issue. Similarly, if you meet someone who seems to react out of proportion to having just asked them out on a date… well, either there’s something going on with them, or you were behaving a lot more egregiously than you realized.

So if that’s an issue that you have been having over and over again… well, it’s probably a good idea to stop and talk to a friend whose judgement you can trust about how you’re behaving.

Similarly, you’re not going to be “marked as a predator” if what you’re doing is talking with people and only asking out folks if it seems like there’s some chemistry and they’re showing interest. That’s just socializing, and how we tend to meet our partners.

The people who make folks uncomfortable are the ones who don’t read the room, who bounce from woman to woman (making it clear that what they’re looking for is a warm body, not because they’re interested in that particular person) or who generally doesn’t give a shit about the activity that brought everyone together.

(Now, there are people who are perpetual flirts and the folks around them know that they’re flirts and that they flirt with everyone and without intent, because flirting is fun and that’s who they are. They’re also usually very socially well-calibrated. But that’s a very different situation than what you’re positing, and if that were who you authentically were, you wouldn’t be asking this question in the first place.)

Again, if you’re being drummed out of every social gathering you go to because you’ve been flirting with people… well, either you really need to pay attention to what groups you hang out with, or you need to do some long investigating into your behavior and making corrections.

But as I said: you’re positing hypotheticals as though they’ve happened and reacting to those – you are, essentially, just hurting your own feelings.

Now here’s the other thing about practicing flirting: you don’t dive in, guns blazing, telling women “Damn, are you OSHA compliant? Because I want to make sure you’re properly railed.” Part of flirting and learning how to flirt is pinging for interest and meeting people’s level. Flirting tends to start off mildly and seeing how the person responds. If they respond positively, you continue. If they respond neutrally or show they aren’t interested, you dial it back or stop, depending.

The key, is to pay attention and respond based on how the person you flirt with behaves. If they reciprocate, all is well, you can keep flirting. If not, the odds are good they’re not interested and you dial it back and just chat, or move on if the conversation is over. There’re clips of Don Draper flirting with Joan Holloway, where she signals clearly that she’s not into him and he rolls with it with good grace. That’s not behavior that’s going to piss people off, that’s someone reading the room and responding appropriately.

Now, part of practice is understanding that sometimes you’re going to do it wrong or make mistakes… but then again, part of the point of practice is to learn what mistakes you’re likely to make, when you’re likely to make them, how to avoid them, and how to recover from them. Comedians, for example, will bomb on occasion while on stage. Knowing how to pull out of the spiral is a skill, and one that requires practice. Johnny Carson famously used to deliberately bomb in order to work on winning the audience back. So failing at flirting or not flirting well is also part of the learning process. As is knowing how to handle when you mess up.

Now, if bars are a place where you’re comfortable and the people you meet at them are generally the people you’re compatible with, then by all means, go there. But flirting is really just conversation with a point, and that point is to have fun with someone while letting them know that you’re interested in them as more than just a friend or acquaintance. If you’re not talking to people in general, connecting to them and making friends, you’re going to have a hard time flirting.  

As I said, however: you do best to practice in places where people are expecting to talk and flirt and meet people. If you’re at a place where folks aren’t going explicitly to flirt and meet potential dates, then hopping around the room like an oversexed Daffy Duck runs the risk of making people uncomfortable. Talking with them like a normal person, however, doesn’t.

But do yourself a favor: focus on what’s actually happened, rather than creating increasingly improbably worst-case scenarios based on shitty TikTok ragebait accounts and dodgy subreddit threads.

Good luck.


Dear Dr. NerdLove:

I ran across your article from 2012 called “Do you have White Knight Syndrome?” and it was an interesting read, and I have a bit of a problem with one right now actually. I am shacked up with a guy who is a self-acknowledged White Knight, in recovery. I am exactly the kind of woman a man who is NOT a white knight would get involved with, very self-reliant, exactly what you describe as being terrifying to the white knight – if I didn’t need him to rescue me, what use would he be to me?

This is kind of where we are at in the relationship, because without the rescuing, he doesn’t really bring a lot to the table in the relationship. He’s not really taking care of himself, if you know what I mean, or any of the things that a cohabitating sort of relationship would require – household responsibilities.

Is there some way that a former white knight could refocus his energies into like… real world helping that doesn’t involve attaching to a problem woman that he can save? Or is real-world helping just too boring?

Is this the kind of stuff that Jordan Peterson is talking about in 12 Rules?? I would hate to have to read that, or give it to him as a self-help book for problem men.

Not A Damsel, Not In Distress

I have questions, NDND, starting with “how did you end up shacking up if you’re not in need of being ‘rescued’” and then following up with “why are you with someone who isn’t bringing anything to the table?”

But that’s not what you wrote in about. You wanted to know what to do about a would-be White Knight and how to redirect their efforts.

Well.. about that.

The thing about White Knights is that it’s not really about being an overly-enthusiastic do-gooder who would otherwise be volunteering at charities or leading anti-police-brutality protests. White Knights try to “rescue” women or look for women who need “saving”, not because they’re inherently heroic and virtuous but because they don’t believe they are desirable in and of themselves.

White Knight Syndrome is an end-stage result of “men feel like they must be needed because they don’t feel wanted”. The reason why they zero in on women who “need saving” is because they feel like this is how they show their supposed value; if they “save” someone, then they’re rewarded with sex and a relationship. It’s a form of neediness; they’re seeking reassurance and validation because they don’t believe that someone would love them or want them for themselves. But if they’re “of service”, then people would keep them around, because their value is in what they do for others, not who they are.

The problem is: that’s not a great place for a relationship. Most people don’t want or need saving, nor do they appreciate someone rolling in with “solutions” that the supposed damsel in distress already tried or discarded. And nobody likes feeling like somebody’s project, rather than a person.

The ones who do want or need help tend to require more help – and more specialized or specific assistance – than the would-be White Knight can provide. When their damsel (or bachelor) doesn’t “recover” quickly enough or completely or relapses or otherwise isn’t magically healed or restored, they tend to react poorly – both out of frustration with their partner not holding up their end of the agreement they never made, but also because of what it says about them and their worth. And to make matters even more complicated, the efforts of trying to “save” someone can often backfire, not just on the person being “saved” but on the supposed “rescuer”, too. As the saying goes, there’s a reason why you’re supposed to put your oxygen mask on first before you help someone else with theirs.

But to make things even more dire, a lot of erstwhile White Knights end up in toxic relationships with people who take advantage of their weak boundaries and low self-esteem. When all you have is a hammer, everything looks like a nail; when your self-worth is just about “saving” people, toxic folks can look a lot like someone in need… and they love folks with low self-worth and high levels of neediness or loneliness.

As for your supposedly recovered white knight, if he’s not maintaining his hygiene or his health or contributing to the general upkeep of the house or the relationship, the issue isn’t that he needs to have his energies directed elsewhere. That’s usually an indication of personal issues. So rather than pointing him at some worthy cause, it may be better to aim him at a therapist and some counseling instead. He can find a worthy cause after he’s in good working order; otherwise he runs the risk of causing more problems than he solves.

But it still sounds to me like maybe this isn’t a great relationship to begin with. If he doesn’t make some improvements, then you may be reaching a point where it might be better to do this from a distance, instead of a shared living space.

Good luck.



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