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How to Flirt Without Coming Off Creepy

How to Flirt Without Coming Off Creepy

When asked what was the most intriguing mystery in the universe to him, late theoretical physicist Stephen Hawking, who spent his life exploring things like black holes, the concept of time, and the origin of the universe itself, simply said “Women.” Indeed, the female sex is difficult to understand, especially for men, which makes engaging in romantic banter challenging. Here are some tips for flirting without seeming creepy to the object of your affection.

1. Don’t Flirt with People While They’re Working

Someone who’s being paid to be nice to you isn’t going to have genuine reactions to what you say, even if you’re genuinely trying to see if sparks fly between you. That means hitting on your waitress is a bad idea since she won’t be able to express disinterest without risking getting stiffed on the check. Even if you’re not the type of guy who would retaliate for being rejected, it’s best to leave women alone while they’re working.

2.  Don’t Be Mean

“Negging” is one of the most popular techniques among so-called pickup artists. Negging is described as being gently cruel to a woman in order to get her interested in you, but it’s easy to overdo it and come off as a jerk. Light teasing is OK, but rude comments about someone’s appearance or age will immediately put the brakes on things, so when in doubt, it’s best to just be nice.

3.  Practice Active Listening

One major turn-off for women is being ignored or talked over. When you don’t engage with what a woman is saying, it demonstrates to them that you’re not interested in them as a person and you’re just trying to get in their pants. Active listening means giving verbal cues to show you’re listening, instead of just waiting for your turn to talk. Try waiting until she’s finished talking to formulate a response. Many women find a man pausing to choose his words to be attractive, as it shows he’s not impulsive or self-centered.

4. Choose Your Compliments Wisely

Women like being complimented – who doesn’t? But when your compliment is superficial and focused on her body, like “Nice legs,” it’s a turn-off. Women prefer positive comments on things they have control over, like their outfit or choice of beverage, not their body.

5. Pick the Right Setting

Remember that if you’re trying to make a good first impression, the context matters. For example: approaching women in the gym is not a great idea. They’re there for a specific purpose, and they’re not going to be receptive to cold approaches. The same is true for situations where women might feel vulnerable, like when they’re walking home alone at night. But women who are in places that are intended for socializing, like bars, are usually more open to flirtation, as are women in public places during the day.


Flirting is a minefield for many guys, as it can be tough to express your interest in a woman without coming off like a weirdo. It’s not impossible, though. The do’s and don’ts above can help you avoid some common pitfalls.

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