Dating: Do's & Don'ts
Dating: Do's & Don'ts

Worst Flirting Moves Men Make (And What Works Better)

A person who's sick of seeing flirting fails discusses the worst flirting moves men people make — and better options.

Worst Flirting Moves Men Make (And What Works Better)

If there's one thing that every girl (or girl-looking person) has experienced, it's the cringe, embarrassment, and discomfort that happens when someone tries to put the moves on you — and fails miserably. At times, it can be funny, but usually, it's somewhat scary.

Flirting fails happen to everyone, and while not all are preventable, some definitely are. Speaking as someone who's seen guys turn into total creeps when they tried to flirt, I feel like it's important to discuss ways that men can avoid flirting failure.

The worst flirting moves guys make are scarily common, despite the fact that they often alienate the guy and make him look bad. If you're on the prowl, here are the biggest flirting mistakes to avoid...

Admittedly, most men realize that this is one of the worst flirting moves to make — including catcallers themselves. Most men do not catcall women as a way to flirt unless they're totally clueless; they catcall because it's their way of trying to assert power over a girl.

If you catcall women, please, stop. This isn't cute. It's one of the worst flirting moves you can do. There's a reason why so many groups are starting to campaign against catcalling, and why women are beginning to speak up about it. It's street harassment, bro!

Most women who are catcalled feel uncomfortable at best and scared at worst, and it just doesn't bode well for your reputation if you do this. What would your mother say if she found out you behaved that way?

Sitting next to her, but not saying anything and hoping that she notices you.

Shy guys do this all the time. Unfortunately, girls might not actually be gutsy enough to make the first move — or, in cases with people like me, they may be too oblivious to notice. If you aren't saying anything to her, she's not going to notice you.

This is like the male equivalent of the girl who does hair flips and expects men to suddenly fall in love. It just doesn't work the way it does in rom-coms.

Ignoring her body language, or not taking "no" for an answer.

Many of the best flirting moves out there are foiled because guys also do one of the worst flirting moves out there: ignoring the fact that the girl's scared. If she's freezing up, looking elsewhere, backing away from you, telling you to leave her alone, or verbally shutting down, she's not interested.

This is where getting consent right matters. Silence is not a "yes." An aggravated, "Fine, just leave me alone," is also not a yes. If she's not interested, and looking uncomfortable, leave her alone.

If she says she's not interested, interrogating her as to why will not accomplish anything. You can't negotiate attraction; and doing this is only making the experience she has with you more uncomfortable. Besides, do you really want to grovel for validation like that?

An enthusiastic yes, means yes, and if you're not getting that, you need to back away. Your desire to get laid does not trump her right to be comfortable. If you think otherwise, you're part of the problem that's plaguing the dating scene, and you need to get help.

A while back, some "pick up artist" wrote a guide on how to talk to a girl with her headphones on. Let me tell you the real way to do it: DON'T. (Unless she's on fire.)

One of the worst flirting mistakes men make is approaching women at the wrong time. Headphones on her ears are a universal signal for, "Please leave me alone."

The same can be said for reading a book, playing a video game on her Switch, or talking on her cellphone with someone else. If she's clearly doing something else, she doesn't want to talk to anyone — you included.

Interrupting her just shows that you're unable to read social cues, and makes you look like a self-centered dolt. It also makes her uncomfortable, because, let's face it, if you're doing this, you don't understand boundaries.


Spilling your guts to a girl you like will not make her like you. It'll only make you look psycho. Trust me when I say that revealing too much, too soon, is one of the worst flirting moves you can make — and will likely make you get ghosted.

Trying to force drinks down her throat.

Once again, this comes to consent. No means no, and if she's drunk, she can't legally consent. Guys who tend to try to get girls wasted in order to get laid, also tend to act as if girls "owe them" for those drinks. Trust me when I say that this never ends well.

Whining about how "nice guys finish last."

This is one of the worst flirting moves a man can make, and also is one of the most cringe-inducing. There's even an entire Reddit forum dedicated to how bad a move this is. That alone should tell you something.

The thing that most guys don't realize is that women really do like guys who are genuinely nice. The guys who whine because they aren't getting laid despite being nice aren't nice. They're lacking self-awareness, don't actually care about the people they claim to be nice to, and may not even be mature enough to date.

If you're genuinely nice, people will pick up on that and will want to be around you. Whining that you're not getting what you feel entitled to doesn't make you attractive to women; it makes you repulsive.

This is so common these days, it's absolutely sickening. It's also one of the worst flirting moves you'll regularly find on dating sites. While it's totally understandable that guys would feel burned and frustrated by having girls suddenly vanish on them, it's never acceptable to lash out at them.

Girls who see guys that turn into balls of anger the moment they're denied aren't turned on by them; they're fucking terrified. Women in the dating scene have a real, legitimized fear of being attacked by men who can't take "no."

There's a reason why so many online dating safety tip guides exist. Women are scared that men will lash out at them, or that they will get killed by a potential "date" that turns out to be crazy. It happens a lot more than guys would want to believe.

When you flip out over something like this, you look psycho — and yes, people will talk. Apologizing also won't take back the amount of crazy you showed them, either. If she sees you in public, she'll probably avoid you and warn others. You can't blame her for reacting that way, either. You'd probably do the same in her shoes, wouldn't you?

It's totally okay to feel frustrated and angry with the dating world. However, if it gets to the point that you feel a need for payback, it might be a good idea to just take a break from dating for awhile.


I've actually heard of guys who took girls' numbers from company phonebooks, then approached them outside of work. As you can imagine, this is one of the worst flirting moves you can make — and for good reason.

No one wants to date a guy who'd pull this, because it crosses so many boundaries. Since boundaries are a foundation to a good relationship, it's clear that the person who does this can't have a healthy relationship. It's just not a good look.


This is another gem from the PUA scene — and it's kind of a mess. The idea of "negging" is supposed to be a slightly mean joke that lowers a girl's self-esteem and gets her interested in you. What actually happens is that it devolves into guys insulting women and expecting them to put out.

It's one of the worst flirting moves you can make because it's manipulative; and when it's a flat-out insult, it's also borderline abusive. Unless you're okay with girls looking back at you and thinking about you being an abuser, you'll skip this idea.

Any decent flirting guide for men will tell you not to do this. So, I'll tell you the same: DO NOT DO THIS.

Doing stupid stunts.

I'm pretty sure that the Darwin Awards got started because guys tried to pull ridiculous stunts to get girls' attention. Like, I've seen a lot of men do things that put their lives at risk due to the power of pussy.

Many guys have died because they tried to show women they could climb up something awesome, fight off a ninja, or piss off a bear, and survive. Needless to say, this is one of the worst flirting moves you can do for your health — and your insurance, too.

Bragging or flashing cash.

I'm going to pull an Archer reference and ask you if you want gold diggers; because this is exactly how you get gold diggers. You do not want gold diggers, and if you do, then you may want to re-evaluate what you want in life.

This is one of the worst flirting moves you can make, but not because it makes girls uncomfortable. It's because it's basically saying that you only have wealth or status to offer — and that's selling yourself short.

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Mackenzie Z. Kennedy

Socialite and dating guru Mackenzie Kennedy knows all about the inner workings of people and society as a whole. It's not only her lifestyle - it's her passion. She lives in Hoboken with her pet dogs, Cassie and Callie.

See all posts by Mackenzie Z. Kennedy