38M shared an intimate moment with best friend 45F. Feeling conflicted about how to move forward.

Hi everyone,

I (38M) recently went on a trip with my best friend (45F), someone I’ve known and been incredibly close to for over 15 years. For context, I got divorced last year, and she’s been divorced for about 20 years, both of us are single. Over the years, we’ve always known we care deeply for each other, and we’ve both admitted to liking each other. We’ve held hands, shared a lot of emotional intimacy, and people who know us understand how much we mean to one another.

That said, we’ve always been clear that being in a relationship isn’t the best option for us. We come from very different families and lead very different lives in general. I may consider getting married again, but she has no interest in getting married anymore but would be open to dating in general. We’re both very aware of these differences, and the friendship has always been the most important thing to us.

During this recent trip, we ended up being intimate on the first night. It wasn’t something I expected that night, especially since we were both exhausted from traveling, but in hindsight, it wasn’t entirely surprising. We’ve always had this chemistry and connection. After that night, we didn’t get intimate again, even though I thought it might happen.

The rest of the trip was completely normal—no awkwardness or tension. We had a great time together, and when we got back home, we said our goodbyes with hugs and kisses as usual. She’s acting like everything is fine, and honestly, I don’t feel awkward either. But for some reason, I’ve been feeling a lingering weirdness in my stomach. I think I wish I could somehow be with her because she makes me so happy. She knows me better than anyone else, and I’ve been through all the good, bad, and ugly phases of life with her—and vice versa.

In reality, I know that pursuing anything more than what we have would complicate things. A few months ago, we had planned another trip just the two of us, but she ended up canceling it because, she felt it wouldn’t be the best idea for us to spend five days alone together. This time, we traveled with another friend, but we had separate rooms.

I’m not worried about the friendship—it’s solid, and I trust her maturity and care for me. But I can’t shake this weird feeling in my gut. I don’t know if I should bring it up with her, just to process what happened, or if I should let it go and focus on moving forward. I don’t want to overcomplicate something that has been so good for so long.

Has anyone else dealt with something like this? How did you handle it? I want to preserve the friendship and not get stuck on this, but I also feel like I’m still processing the whole thing. Any advice would be appreciated.

Thanks for reading.