Here’s the situation: Thanks to a great job opportunity, I recently moved back home after being away for 8 years. This past summer, I met my brother’s wife’s best friend who we’ll call “A”. Immediately was interested in A, but lived several states/hours away and didn’t think too much of it.

Fast forward to now, not only am I in the area, but I’m now a part of their friend group and we’ve hung out (in group settings) almost every weekend since I’ve been back. The entire time A and I have incessant banter back and forth - lot of teasing like little kids - to the point almost everyone has commented on it to me (so I’m not imagining it lol). It started out 100% as just a physical attraction, but now that I’ve spent actual time with A, I’m genuinely into her.

The tricky part is again, she’s my sister-in-law’s best friend, and that could lead to a complicated dynamic. I’m very close with both my brother and his wife, and they both support the idea, I’m just worried if things went poorly. Then of course there’s the self doubt/fear of rejection rooted in the fact I’ve never really “dated” but just went from one long-term relationship to another. My biggest worry there is creating an awkward dynamic if it is just a straight up “No”.

One last issue to mention is that I only ever see A with the group, and I don’t know if I want to ask her out in the middle of a hangout as 1: I’d like to be more respectful/intimate than that and 2: If she rejects me, that’ll make for one awkward game night. I do have her number as we’re in a bunch of group chats, but we’ve only texted 1:1 once after a night at the bars where we exchanged maybe 3 or 4 texts late at night.

I know I’m overthinking things - it’s who I am. But, maybe I’m not. So, here I am looking for any tips, advice or thoughts 😅 Much appreciated!