Long story short, my friend’s (D) best friend (S) is a girl. They’re completely platonic and have no interest in dating each other. I’m increasingly starting to suspect that S might like me, but I’m very nervous to flirt with her or attempt to ask her out because of D. She keeps asking me to sit next to her whenever we hang out, she keeps mentioning how “funny” I am, she clearly gets disappointed when I have to leave, and D has passed on a few times that S thinks I’m “Cool” or “Really smart”. I don’t know if I’m being a dumbass or what, I’m just VERY scared to attempt anything towards her in case it comes off wrong and she tells my friend I’m a creep or something
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Whoa dude, that's a tricky situation you've got there. I can totally understand your hesitation about making a move on your friend's best friend. That's a delicate situation for sure.
On one hand, it does sound like this girl S might be into you. The way she acts around you, the little comments your friend D has passed along - that's pretty solid evidence that she's interested. And if you feel that chemistry too, it could be worth exploring.
But on the other hand, you're completely right to be cautious about it. Trying to date your friend's best friend could get really messy, really fast. D might feel betrayed or awkward about it, and that could end up causing drama within your whole friend group. That's the last thing you want.
My advice would be to tread really carefully here, dude. Maybe try to feel S out a bit more, see if you can get a clearer sense of where she's at. But don't do anything too overt or aggressive, at least not until you've had a chance to talk to D about it first. You gotta make sure your friend is cool with it before you make a move.
And hey, even if S is into you, it might not be worth the risk. Your friendship with D is way more important than a potential hookup, you feel me? Just be smart about this, man. Weigh the pros and cons, and don't do anything that could jeopardize your other relationships.
Anyway, that's a tricky one. But I'm sure you'll figure it out. Just take it slow and keep an open line of communication with everyone involved. Good luck, dude!
you have to talk to her? If not, nothing will come of it
Man up!