So about three years ago, I dated this guy. He was a good boyfriend and he cared so much about me. But ready for this? I ended things. Years later, I still don't know why. I think I was too young and I was afraid, maybe? I don't know. Over the years our paths have crossed a little bit but nothing major. However, recently we started talking again and even made plans to see each other. I didn't expect to feel anything besides just happiness that we were friendly again. But that night we spent hours together and it just felt normal and really nice.
It would have been nice to keep things that way and remain friends, but things progressed. I was scared again – but this time because I didn't know how he felt. I could have sworn he felt something too, but he said he wasn't looking for a relationship. Which, to be honest, I wasn't either. I don't know if that means he doesn't have any feelings at all, but I never told him how I felt either. We saw each other again but it wasn't the same. That was just a few weeks ago. We kept in touch, but I feel as though he's losing interest in me and the friendship entirely.
A lot is going on in his life right now. I'm not sure if he's just very occupied or if he's just not interested in moving forward with me in his life. I know these are questions to ask him, but I feel as though I've already asked enough and I don't want to overcomplicate things. So I'm wondering ... was it even a good idea to re-enter each other's lives, knowing our history? Also, what do I do now? Should I give him space, as he is very busy, or decide to mentally walk away? Or physically walk away? I don't know if I want to. I believe there was always something between us, but what if he doesn't think that? I still feel guilty for breaking his heart years ago. But I feel like ... I let someone/something go that was very special years ago, and now it's too late to bring back. Or is it?
"I know these are questions to ask him, but I feel as though I've already asked enough and I don't want to overcomplicate things."
It doesn't sound like you've asked him much at all. Your letter is a lot of "I don't know," "I'm not sure," and "I'm not certain." You're overcomplicating things by staying silent. If you want to know what happened here, please ask (him, not me).
I can make a bunch of guesses about his feelings based on what you shared in your letter. It's possible he feared getting hurt again so he backed away, or maybe he's long over it and when things "progressed," it was really just nostalgia. He said he's not interested in a relationship right now, but does he want anything? Why guess when he has answers?
Tell him you’d like to see him again. Admit you've been confused – about your past and present. Remember that you're not asking for a serious relationship yet either, because who knows if you're compatible? All you know is that you're interested in learning more about him now. Is he open to that? Find out.
Readers? He said he's not looking for a relationship. Is that the answer?