Went to my (24M) good friend’s (Sally) birthday a couple nights ago. Met one of her friends, Olivia (23F), and we clicked right away. Lots of laughing, joking, little arm brushes, and even across the room I’d catch her looking at me. In a couple photos from the night she’s literally staring at me instead of the camera, which felt telling considering there's two photos of me with my friend who is a man wearing a dress. She’s super funny, really nice, and honestly attractive.
Relationships came up in conversation. I mentioned I broke up with my ex in July (I’m fine now, more relieved than sad). Olivia said she just got out of a 4-year relationship about two weeks ago. The last year with him was awful, she saw the red flags too late, but she feels much better now. Still, it’s obviously fresh.
Here’s where I fumbled: I was exhausted (long day, drove so I stayed sober) and around 11pm I socially shut down. Got quieter, overthought things, and convinced myself not to “push” anything in case I seemed weird. We drifted apart as the night went on, and I left around 1am without asking for her number or IG.
Since then I’ve been second-guessing: Did I imagine her interest? Should I have asked for her number? Is it too soon to reach out after such a fresh breakup? I did find her IG through Sally but haven’t followed her. Debating whether to ask Sally for her info directly so it feels less stalkery, then invite Olivia for a drink.
I don’t want to just be friends, because I know I’d catch feelings and that wouldn’t be fair to either of us. But I also don’t want to come off pushy when she’s still processing her breakup.
TL;DR: Met my friend’s friend at a birthday party, instant chemistry, lots of small flirty moments. She just got out of a 4-year relationship two weeks ago. I didn’t ask for her number because I overthought it and left early. Found her IG but haven’t followed. Should I ask Sally for her info and shoot my shot, or leave it be since her breakup is so fresh?