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Dating : How do I (25M) practice flirting without making people uncomfortable?

Dating : How do I (25M) practice flirting without making people uncomfortable?


I spent the last 5 years in a LTR that really I was too young for and as a result I never learned about how dating works. I don’t actually know how to flirt, or really what flirting actually is.

I’d like to practice, but I don’t want to come on too strong and being some creepy weirdo that crossed a line. I don’t want to push away my female friends by flirting with them all of a sudden either. I’ve been told flirting with waitresses and people at the store is a good way to start but to me that seems a bit predatory and like a situation that might be quite uncomfortable for a woman. I don’t buy into that creepy pick up artist bullshit either.

My social skills are generally pretty good, I like talking to people and I’ve been told I’m a great conversationalist. I was an athlete in college too. So it’s not that spaghetti falls out of my pocket as soon as I start talking to people, I just have no idea how to do something other than a pleasant, friendly and interesting conversation.

Any advice or ideas would be greatly appreciated

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  1. Hi! Don’t flirt with waitresses/anyone working. It’s uncomfortable and it is their job to appear friendly.

    Do observe body language- if she is avoiding eye contact and seems more closed off, she probably wishes to be left alone.

    When approaching, always stay respectful and say something like “hi, I was just wondering if you’d like to get a coffee sometime?” and offer your number- this allows her to choose if she contacts you. Also doesn’t pressure her from giving her number. When complimenting a stranger, NEVER compliment their body- it’s weird. Complimenting their smile/eyes is all groovy.

    If they are wearing clothes with a reference to something you like (for example: a marvel top) you can say something like “hey! Your top is really cool, have you seen the Loki series?”.

    If rejected, just a “ah no worries, have a nice day” is fine and move onwards. Rejection isn’t always personal.

    Good luck! As long as you keep the conversation respectful, you should be ok.

  2. How about asking a female friend to practice with you? It could genuinely be a fun thing to do.

    Could also set your OLD profile to say something like « I’ve been told I need to practice my flirting. Help me out! ». Should take the pressure of being actually good at it off. And could spark some genuinely fun conversation, especially if you’re willing to laugh at yourself!

    Or if those don’t feel good to you, just find a partner from Reddit and practice with them.

    Just please don’t harrass the waitress. I promise you, they get enough of that. They’re there to work.

  3. Flirt with people you know or have at least been introduced to. Anything else is creepy – unless you are 70+ years old, cause then it’s just an old man being – creepy

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