Should I make a move on my friend of 13 years? Or leave it up to him?

TL;DR: Known a guy for 13 years. I’m 34F he’s 42M. He asked me out 7 years ago and I said no because I was seeing someone. We’ve both since had long-term relationships. We’re both now single (or about to be). We’ve started hanging out one-on-one again and I think I like him, but I can’t tell if he feels the same. Do I make a move, or wait for him?

I’m in a bit of a weird situation and would love some outside perspective.

So I met this guy in 2013 on holiday. We’re both from the same city and got chatting. We stayed in touch, and although we’ve never been super close, he’s been a constant person in my life ever since. Just one of those people who somehow keeps reappearing in your life. He’s really lovely — kind, thoughtful, funny, decent. Smart, successful and reliable. We have great conversations and I always feel like I can be myself around him.

I moved abroad for a few years and when I returned to our home city in 2019 we reconnected, and he asked me out one day after a picnic with friends. I wasn’t really feeling it / was chasing after another guy at the time, so I said no. He took it well and we just stayed friends.

We then both got into long-term relationships and lost touch for a few years. Then those relationships both ended in the last 1-2 years. I messaged him after my breakup because I genuinely just wanted to reconnect. We went for a walk and had a really good chat. A few weeks later, he suggested going to comedy which turned out to be at a private members club. It felt pretty date-like, but I couldn’t tell if that was intentional or just him taking me somewhere he likes.

We then met again a few weeks ago. He told me he was seeing someone and it sounded quite serious. I felt slightly jealous, which made me realise I might actually like him. I was also seeing someone at the time, but that has since ended.

Then I saw him yesterday. We went for a walk then a quiet drink. I told him I was single again, he told me he’s about to break up with the woman he’s been seeing. He’s not ready to take it to the next stage, particularly because she has a kid, and he doesn’t know when he’ll be ready to essentially become a stepdad.

I obviously didn’t make a move. That would have felt wrong when he was still in the relationship and dealing with all of that. But now I’m wondering whether I should**.**

The thing is, I genuinely cannot tell if he likes me. He has asked me out before, but that was many years ago. He consistently chooses to spend time with me one-on-one. Our meet-ups sometimes feel quite date-like. We have a really easy connection and are very open with each other. He knows I’m single. And now he’s about to be single. But he hasn’t actually made any romantic move this time around. So I’m wondering whether I should just leave it completely in his hands, or whether that would be silly given I was the one who declined last time! Eg he could be thinking “She said no before, so I’m not going there again.”

Part of me thinks I should wait and see if he reaches out after his breakup. If he does, that might tell me something. Another part of me thinks: Jesus, you’ve known this man for 13 years. He literally asked you out once. You now think you like him. What exactly are you waiting for?

I don’t want to put pressure on him while he’s ending a relationship. And I def don’t want to be the rebound or the person hovering around waiting for him to become available.

But once some time has passed, should I actually make a move? Or should I do absolutely nothing and see whether he comes to me?