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A big relationship/friendship milestone for me is when you text the person about random stuff happening in your day, stuff you're excited about, stuff that's annoying you, random thoughts that occur to you, everything, without worrying if you're bothering the other person. I consider quite a few people to be close friends, yet I've achieved this milestone with a small subset of them, and sustained it with even fewer.
Another big milestone for me is breaking the touch barrier. I don't touch people willy-nilly, so if I touch you intentionally, either: (1) we are already very close, or (2) I'm interested in becoming close to you, either platonically or romantically. If we're not already close, it will just be something like a touch on the arm when I'm emphasizing a point in our conversation or when you say something funny, or punching your arm when you tease me. Perhaps too subtle. Greeting/parting hugs don't really count as they might just be dictated by the norms of how we know each other--hence not really under my control.
A sufficient but not necessary condition for knowing I think you're attractive is if I am extremely startled if you unexpectedly touch me, like on the shoulder to get my attention or something.
There was this guy who had been flirting w me for a while, but one day, he did that and I practically jumped out of my seat, and he hasn't flirted w me since. Sigh.
I'm so awkward!
Personally I could ask anyone a lot of personal/even intimate questions to get to know them; it's just how I make conversation and not a sign of particular interest from me.
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