I tend to engage with people on either a fairly playful or intellectual level, and have a difficulty initiating things which might be seen as romantic/sexual. I'm by no means ugly, but I often feel like the goofy comic relief character in a movie. A friendly type who is somehow perceived of not having a need for romance.
There were occasions where I asked a girl out for a clearly datey outing only to find myself spending it in a discussion about our interests, politics, everything... but didn't know how to show I'm also interested in her sexually and/or romantically. I know it confused a few of them where they just assumed I wanted to be just friends.
I think I know how to respond to flirting when it's very clear and coming from the other side. But I feel like I need to learn how to initiate it, just because how societal gender roles still work (unfortunately).
So, how do I show that interest, still letting the other party gracefully refuse escalating it if so they choose?
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