How to flirt without being a creep

I had one of my most uncomfortable interactions ever with a stranger a couple nights ago. I was bar-hopping by myself on a Wednesday night, chatting up strangers, checking out the live music, and keeping my eye out for any pretty young ladies looking to dance. (didn’t see any who really struck my eye that night, sadly) The 6 shots of gin I’d rapid-fired down my esophagus before going out had already hit me hard. I’m a functional drunk though. Still basically sober aside from the alcoholic buzz in me.

One guy I wound up chatting with and sitting with was gay. So I assumed the usual thing would happen – I get into a friendly chat with him, he hits on me, “I like girls man, sorry”, friendly chat continues with no hard feelings and he ends up being my latest “cool stranger I got to know” story. I have no problem with gay guys hitting on me, as long as they’re gents about it and treat me like a person, not like solely a potential fuck. I believe that straight or gay, men should shoot their shot even if it means getting rejected.

This waste of oxygen wasn’t a gentleman.

He didn’t even know me for 10 minutes before he launched into a rant about all his sexual fetishes and kinks and fantasies, offered me a gummy edible uncomfortably close to my face, pointed me out to his friends like I was his adornment – the latest cute guy he’d picked up at the Potential Sexual Partner store, flirtatiously touching me on the chest as I leaned back on the couch as far as I could to preserve my personal space. He wasn’t interested in talking about much besides his depraved sexual fantasies.

I had an unfinished drink I still needed to pay for, so I spoke minimally as I let this creep talk. Basically just asked him “why do you think that?” a bunch of times. Pulled a bit of canned social game to lubricate the situation and keep it stable. Then as soon as I finished my tequila and my water, I politely said goodbye, warmly rejected him when he asked for my number, paid my tab, and fucked off out of the bar, on to the next one.

This guy didn’t force himself on me or anything. He wasn’t TOO pushy whenever I rejected any of his advances, though he’d always re-engage with me attempting to escalate. But I still left him thinking “thank fuck I don’t have to see that guy ever again”, feeling creeped out af.

I don’t have sympathy or empathy for this guy. I could try to understand him, dig deep into the root causes of his trauma and dissociation. Most definitely childhood sexual abuse. But I don’t believe in solving other people’s problems for them anymore, unless they’re paying me to. This piece of garbage violated my boundaries and didn’t show me anything about himself worth appreciating. He can burn in Hell for all eternity (not because he’s gay, because he’s an emotional rapist)

(and to the girls whose boundaries I’ve disregarded/been unaware of in the past as I’ve pursued them – I respect them feeling the same way about me, if that’s the case. I’ve had my own traumas and blind spots about relationships I’ve since overcome thanks to those experiences revealing them to me)

There’s a lesson in this story anyone can make use of – male, female, gay, straight, bisexual, young, old…

I have a major issue with the “yes means yes and no means no” model of sexual consent. It only addresses the SYMPTOMS of sexual harassment, not its root cause. Sure, yes does mean yes. No does mean no. But if we’re looking to determine what sorts of sexual behavior are acceptable or not – there’s more important variables determining that than whether someone says yes or no to your advances.

I’m all for bodily autonomy and sexual consent. Yet reducing wanted or unwanted sexual behavior to this “yes and no” dichotomy leaves out a vital part of the picture.

The root cause of sexual harassment

This guy superficially respected my “no”s whenever I brushed off his advances. But STILL, he was quite a creep. I couldn’t wait to leave him and was more and more disgusted with him the more he told me all about the dirty things he’s obsessed with.

He was a creep because he wasn’t attentive to MY needs. He only viewed me as an object he could potentially get off with, and satisfy his own needs with. Every word he said about his fantasies wasn’t an attempt to connect with me as a person – it was an attempt to rape me with his words if he couldn’t do it with his body. If he tried physically forcing himself on me, I could have easily left him bedridden. So he had to settle for penetrating me with his disgusting words. I really wish I could unhear some of the things he told me.

The fact that this creep wanted sex from me, or was open about his sexual thoughts, isn’t what made him a creep. That just means he’s human. People wanna fuck, and that’s that. He wasn’t a bad person for having sexual needs or for acting on them. He was unwelcome for not acknowledging my humanity as he attempted to do so.

I’ve talked sex with a bunch of girls myself. Whether I’ve known them for 5 minutes, 5 days, or 5 months. Whether I was banging them or simply befriending them. They enjoyed my company. They enjoyed hearing what I had to say about my own dating life, my wants, my needs, and they opened up about their own sex to me in return. In those cases, we both had social awareness. We made sure that the other person WANTED to hear our sexual thoughts aloud, and most importantly…

We recognized that there was an entire person attached to the set of genitals and secondary sexual characteristics in front of us.

That right there is what separates a welcome sexual advance (even if the recipient isn’t into it) from a creepy one. That creepy guy wasn’t trying to get to know me. He was looking to masturbate himself with me.

Recently, another gay guy slipped me his number at a cafe and we got on over text even if I’d much rather have been hit on by a girl. Before that, I was alone in a hostel room with yet another gay guy who wanted a piece of my squat booty and attempted to seduce me into bed with his words. Both of those experiences left me feeling better about myself, even if I don’t want to bang guys. In an energetic sense, those men were trying to dance with me, not to coerce me into anything. I respect them for shooting their shots and am happy to have met them.

Now imagine how women feel

If this one aforementioned experience creeped me the fuck out, imagine what a woman’s life is like. Women deal with this shit much more often than men do. When they go out, in the DMs, even during the day once in a while.

Talk to any woman ever, and she’s got at least a few “creepy guy” stories like mine from a couple nights ago.


I’m not here to educate you gentlemen (and curious ladies) about sexual consent, or to tell you not to sexually harass people. If you’re a human with a functional heart, you already fucking know not to engage in unwelcome sexual behavior. I don’t need to give you the “yes means yes and no means no” lecture. You already know this, and would never engage in behavior that violates someone’s sexual autonomy.

I’m here to break the bullshit idea that expressing your sexuality (especially if you’re male) automatically makes you a creep if the recipient isn’t into you like that.

For a fulfilling dating life, you need to be comfortable expressing your sexuality. Sexual repression tears apart many a dating life, many a relationship, and many a marriage.

Being afraid of rejection is a one-way ticket to a dating life full of regrets and missed connections, if you have a dating life at all.

Too many modern men have been programmed into thinking that male sexuality, the male gaze, the masculine desire to take a woman and make her yours makes women uncomfortable. That’s bullshit.

Women, healthy women, have a strong intuition. They have a visceral sixth sense like all humans do for when a man’s being a creep vs when a man’s expressing his sexuality respectfully. Don’t worry about a woman taking your sexual advance the wrong way, as long as you’re perceptive of what she wants and needs, and have some overall situational awareness.

Women like being complimented. Women love being hit on. Women want to be treated as sexual beings. Women want men to approach them and shoot their shot. Women fantasize about brave, handsome men locking eyes with them from across the room and desirously claiming them…

As long as that man desires HER.

As long as that man pursues her with HER NEEDS in mind, and pursues her for higher reasons than simply getting off or trying to make a selfish fantasy real.

It’s a lesson I’ve learnt through experience.

I’m personally quite into daygame. If I’m out and about and I see a pretty lady who strikes my fancy, I usually say hi and see what happens. I’ve had my fair share of approaches where the girl’s closed herself up, spoken minimally, and waited for me to fuck off. 

So what was the difference between those – and the approaches where the girl’s been smiling, laughing, receptive to my touch (even initiating it), and open to giving me her number in the end?

It was all in the WHY. The girl would be closed off and unreceptive to me when I’d approach her just because she was a pretty girl I was down to clown with, or because I wanted to get an approach in for the sake of doing an approach.

The girl would be receptive, open, and talkative when I found something about HER to appreciate. Whether it was how she dressed to a similar archetype as me, a hobby we had in common, or we had a unique personality connection despite having nothing superficially in common. She didn’t feel like a sex object I was trying to game into bed. She felt like I appreciated her for HER. She felt like I saw her for HER.

It’s all in the WHY, gentlemen. I know you want to get your sexual needs met, and to find women you appreciate whose needs you can meet in return. And the possibility of being some girl’s “that creepy guy who hit on me” story can very well be a confidence-killer.

Let yourself make mistakes. You don’t need to be perfectly calibrated when you hit on a woman, as long as you have an accurate sense of your values, her values, and her boundaries, are aware of when to be bold and escalate, and are aware of when to pull back or when to eject.

There’s no other way to figure out the steps of the dance of sexuality than through experience and intuition. You will step on some toes as you get your calibration right. So if/when that happens, take the L and learn something from it.

“Creepy” as a weapon

Even if you do everything right, some dissociated, manipulative women and men will consider you a creep for expressing your sexuality. Let them. I got major backlash once from old classmates of mine looking for a fight – over writing a newsletter about exactly this (that I’ve since taken down from the archive because I didn’t want to give that mob the satisfaction of seeing it anymore).

One anecdote I shared in that now-unavailable piece is when I apparently “creeped out” a girl by trying to flirt with her at a party, according to what her friend told me later on. When in my mind, I was making friendly conversation with no sexual intent, just trying to make her feel like she wasn’t left out of the party.

Some women attempt to gain power over men by playing social games, and by creating victim/perpetrator frames of reality. It’s these women, when they’re unfeminine, who perpetuate the “men are creepy when they hit on women” mentalities. But they’re still women. Their feminine essence still seeks to be the object of desire from men who see and meet their needs, however strongly they reject it.

Don’t let their existence discourage you. Let yourself offend them. They’re weak, fragile, and powerless. They’re only a minority of women. The genuinely creepy men such as the one who sexually harassed me a couple nights ago are only a tiny minority of men.

The majority of women are good, real people who want healthy connections with men, even if they aren’t entirely sure how to go about that. They want you to desire them for the right reasons.

Same for men. The vast majority of men are also good, real people who want healthy connections with women, even if they can be awkward or clueless in getting their needs met. We all want to feel empowered in pursuing the women we really want, and we deserve to find someone who works well with us.

Sexual harassment is an unfortunate reality that both men and women face, and we don’t need to get into the much worse reality of sexual assault here. Odds are harassment has happened to you at some point. Maybe you’ve unintentionally perpetrated it and if so, you better have learnt your lesson about boundaries and awareness from it.

The most valuable lesson here is to have some compassion. For the women and men who’ve experienced sexual harassment. For yourself if you’ve experienced it. You can choose whether or not to have compassion for someone who’s perpetrated it. These situations aren’t black and white. Not every man (or woman) who makes someone uncomfortable is built the same. Some sexual harassers are truly horrible people who would do horrible things if they could get away with it. Others are simply unaware and dealing with trauma and blind spots that are holding them back from success in their relationships. Some men who express their sexuality are good people who get labeled creeps by women playing manipulative games. Other men who get the “creepy” label are well-deserving of it.

Have some awareness. Think with nuance. The world and the realities of sexual harassment are more complicated than you may think.

So’s the dating world in general. I have much much more to say about that.

When you’re ready to develop your competence with women (and a holistic, integrated understanding of your own masculinity that no one taught you when you were younger), and never be hopelessly clueless in the dating world ever again…

See me.

– Ben

Leave a Reply