I’m a straight guy and I have no problem getting dates on dating apps and stuff, but once I’m on the date I feel like I just have a “vibe” that is not flirtatious at all. I listen to my date, ask questions, smile a lot, make eye contact (but not too much eye contact) and will make a few jokes and get a few laughs. One might even say we’ll have a good conversation. But for whatever reason there is nothing flirty about the evening – it all feels very prescriptive and rigid.

If I try to compliment them, or do one of the “flirting 101 gently touch their shoulder while sharing a laugh” stuff, I feel sort of nervous and unnatural doing so and I’m sure it comes off stilted and uncomfortable too as a result. So I shy away from doing this stuff; we always part ways at the end of the night, there’s NEVER a kiss or invite back to someone’s place or anything like that because frankly it would feel like going from 0-60. I only know 0, I don’t even know what 20-30mph looks or feels like.

I sometimes text them to follow up and let them know it was nice meeting them, and I usually get a polite “thanks, same!” about half the time but I’ve found that if I don’t text anything, I NEVER hear from my dates otherwise – no “thank you for drinks” or anything along those lines. That’s not to say I’m offended or think I’m \*owed\* a Thank You, I just mean that I take it as sort of a sign that there wasn’t much interest (if someone took me out for drinks and I had a legitimately good time/wanted to see them again, I would probably send them a Thank You text to show my interest but maybe that’s weird of me).

Anyway I think I’m doing something really wrong and just going on very aggressively average and boring and repetitive dates with people who I do find cool and nice and attractive but I can’t figure out for the life of me how to “escalate” anything in way to show real interest. Everyone explains flirting like it is a type of “energy”, a “vibe”, something one can not merely follow a script or be disingenuous about, it has to be natural and come from a natural place, and that does make sense to me – but I feel like I just don’t have “it”. I see other people out on dates sometimes and it actually depresses me to watch how their body language changes from reserved to extremely intimate by the end of the evening (leaning in toward each other, or even hands on each others legs, or even making out etc) and I feel like an alien who can’t understand humanity and wants to scream “HOW???”

So TLDR: “HOW???”

3 comments
  1. Read Mark Manson’s Models. I read that book years ago and tried my best to apply the principles in it to my life. I also started therapy around the same time to deal with some underlying anxiety. Those two things really changed my dating life for the better.

  2. I think that flirting is a two players game. Sometimes you might attempt flirting with someone, but if the vibes are not reciprocated, then anything you do will feel weird and unnatural. So just keep in mind that an “unsuccessful” flirting might not be solely your fault.

    In my personal experience I proceed a similar way to yours. Just start a nice conversation, keep eye contact, smile, add some jokes in the mix. If I feel that things are flowing naturally, then I try to turn the conversation towards more personal topics (nothing sexual). Namely, topics that display a genuine interest to getting to know the other person at a deeper level than just as an acquaintance (thats the point of a date anyways). I use the received information both to provide compliments and to tease the other person an try to make them laugh or getting to tease me as well (I am careful not to joke with sensible topics though). After that, things usually unfold naturally and I just flow with it. Always being respectful and keeping your boundaries, of course.

    There have been a couple times where I felt that everything was right but things did not escalate at all. In those cases I have found that being direct pays off. For instance, when driving them home, after arriving I might directly say that I had a great time and that I would like to kiss them if thats okay (say it in a gentle non threatening way). Although I know it might come off a little strong, so far I have had only positive responses to that.

    One final comment, although many men might advice you to add more physical contact while flirting (e.g., touching her arms or lower back), I think that such touching should only be done if she touches you first. That is, match her energy and body contact. In fact, one of the most amazing things a girl I was flirting with at a bar has ever told me was: “I love how you flirt with me without being all touchy like most guys”. I felt like a king after that.

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