So, I’ve had a friend whom I’ve known for around 5 years now. We both went to college with each other and were pretty good friends, and still are pretty good friends until now. He’s one of the few people I trust and get to open up to about very personal matters, and the same goes for him with me.

Back when we were in university, at some point during a night out, we both admitted to one another that we’d liked each other at some point, and ended up making out. We talked about it after and decided not to pursue anything because it’d be a waste of our friendship to risk dating and not working out in the end.

Flash forward to present, we’re still very much close. He’d broken up with his long time girlfriend a few months ago, and we’ve been talking much more than we used to. We never flirted or skirted anywhere near flirtatious joking in the past, but recently there has been a change in the way we converse. I’d normally take it as flirting if it were anyone other than him, but since it’s him, I don’t know how to take it.

He has stated he’s been casually talking to a new girl, but isn’t really feeling it, he’s just seeing where it goes. This further makes the situation confusing on my end because I’m not sure if the change in the way we talk is because we’re talking more in general, or because he’s actually interested.

Either way, I don’t know if I should shoot my shot. I’m both worried that things may escalate with the new girl he’s talking to, but I’m more worried about me being mistaken by his “flirting” and making things awkward between the both of us and ultimately losing him as a friend.

I really only have a select few people I trust, and a relatively small group of friends, so I don’t want to lose him by making the wrong move but i’m also afraid of regretting not taking the opportunity to take things further if I was reading into the signals correctly.

Update: Thank you all for your wonderful advice and different takes on how to tackle it! I went and casually dropped a few hints jokingly the other day, to see how he’d react, and I didn’t really get much of a reaction.

The anxiety leading up to his reply kinda sold the idea of me trying to get over the whole thing. Partners come and go, but genuine friends are hard to come by. So I choose not to risk things and just genuinely be happy for him regardless what happens to him next.