Rekindle things with an intense fling who recently popped back into my life?

About 4.5 years ago, I (35m) went on a date with a guy (32m) that went great. Really good conversation, lots in common, and I could feel a major spark. Only problem was I had just gotten out of a 3.5-year relationship (like a week before the date) and was still needing a lot time to process that before I was ready for anything serious. He asked when we could hang out again, and I was going out of town that weekend so I said we could hang when I got back. He pulled the old, "You're gonna make me wait a week to see you again?" I relented and agreed to a second date that week, which also went great. I remember he went out of his way to call me when I was out of town just to chat, and when I got back in town, things took off. We were hanging out a few times a week, sleeping at each other's places a lot, having sex, meeting each other's friends, etc., and it was great. Even gave me a key to his place. (He was in residency and would have to get up at like 4:30am, so on nights I slept at his place he wanted me to be able to sleep in and lock up when I left). I still had that thing in the back of my head telling me it was too soon to get into another relationship, but I decided to just see where it went since he really checked almost all my boxes. The longer it went on, the more I really started to fall for the guy.

Things were great for another few weeks, and then out of the blue he told me we needed to talk. Sat me down and explained he was struggling with stress, didn't have the energy to put into a relationship because of residency, and that he just didn't see things going any further & that we should be just friends. I was pretty devastated, partly because I was catching feelings, partly because in a lot of ways he was my rebound, and now I had to actually process the breakup I had just had a month or so before. We decided to stay friends, occasionally would sleep over at each other's places, but drifted apart quite a bit as far as hanging out. When we did hang out, it was quality, but it became sparse. About two years ago he started dating someone, so I really felt it was appropriate for me to pull back more and did just that. We texted here and there, I think we both went to a concert with a group of friends once, had dinner once or twice, ran into each other at the gym a few times, but that's about it in about a 2-year span.

Fast forward to about 3-4 months ago. I find out he and the guy he had been dating had broken up. Then fast forward to about a month ago, and he texts me and asks if I want to hang out. Like I said, it was normal for us to text here and there, but we hadn't hung out one on one in a long time. I agreed, and ended up going to his place, had dinner, smoked a bowl and watched a couple movies and just generally caught up and laughed and told stories. Then about halfway through the second movie, he asked if I wanted to cuddle. I said sure, and we fell asleep cuddled up. No hooking up, just cuddling and I slept over. Fast forward another few days and he wants to hang out again, so we did the same -- dinner, smoked, TV, and after an hour or so we cuddled up. Now we’ve gotten into a routine of hanging out and cuddling about once a week, almost always initiated by him. He’s even wanted to sleep over multiple nights in a row, and we did once. Never in a million years did I see our friendship taking a turn back to anything remotely romantic, and so all of this has really come as a major shock. I'm being cautious, but I'm now finding myself feeling the feelings I had way back when, maybe even more intense this time around. Of course, it’s a little different this time -- I'm older, I'm not freshly out of a relationship, we’ve both grown a lot professionally, and we know each other a lot better than we did all those years ago.

I'm enjoying it a lot, and he clearly seems to as well. We haven't kissed or hooked up with the exception of a little grinding here and there in the morning before we wake up (and he makes these little moaning sounds which lets me know he's into it ha..). Also, I now work an incredibly demanding job as a lawyer -- far more demanding than when we first hung out -- to the point that I have just about as little free time as he does since he's still in residency. That makes him even more attractive since it's been tough to date with my demanding work schedule. People want more time than I can give because of work, and only someone equally as busy can understand that.

Bottom line is I'm not quite sure where to go from here because I never expected this to happen, and he really is kinda my one that got away. I'm frankly afraid to tell him that I'm enjoying what we're doing and want more, mostly because he so abruptly ended things the first time around all those years ago, and it hurt. I don't want to tell him I'm feeling something and then feel like an ass if it's totally unreciprocated. But at the same time, he's the one who initiated the hanging out, the cuddling, and he's asked me to hang out really frequently in the last few weeks. Reddit, what would you do from here?

TLDR: I (35m) had an intense fling with another guy (32m) about 4 years ago after I got out of a serious relationship. It fizzled out and we became pretty good friends. A year or two ago, he started dating someone so we put some distance into the friendship, given our history. A few months after breaking up with the guy, he's been asking me to hang out, cuddle, sleep over, etc., once a week or more for the last month. And I'm really enjoying it and am catching pretty intense feelings again. Do I try to rekindle it?

Submitted March 22, 2023 at 12:13AM

About 4.5 years ago, I (35m) went on a date with a guy (32m) that went great. Really good conversation, lots in common, and I could feel a major spark. Only problem was I had just gotten out of a 3.5-year relationship (like a week before the date) and was still needing a lot time to process that before I was ready for anything serious. He asked when we could hang out again, and I was going out of town that weekend so I said we could hang when I got back. He pulled the old, "You're gonna make me wait a week to see you again?" I relented and agreed to a second date that week, which also went great. I remember he went out of his way to call me when I was out of town just to chat, and when I got back in town, things took off. We were hanging out a few times a week, sleeping at each other's places a lot, having sex, meeting each other's friends, etc., and it was great. Even gave me a key to his place. (He was in residency and would have to get up at like 4:30am, so on nights I slept at his place he wanted me to be able to sleep in and lock up when I left). I still had that thing in the back of my head telling me it was too soon to get into another relationship, but I decided to just see where it went since he really checked almost all my boxes. The longer it went on, the more I really started to fall for the guy.Things were great for another few weeks, and then out of the blue he told me we needed to talk. Sat me down and explained he was struggling with stress, didn't have the energy to put into a relationship because of residency, and that he just didn't see things going any further & that we should be just friends. I was pretty devastated, partly because I was catching feelings, partly because in a lot of ways he was my rebound, and now I had to actually process the breakup I had just had a month or so before. We decided to stay friends, occasionally would sleep over at each other's places, but drifted apart quite a bit as far as hanging out. When we did hang out, it was quality, but it became sparse. About two years ago he started dating someone, so I really felt it was appropriate for me to pull back more and did just that. We texted here and there, I think we both went to a concert with a group of friends once, had dinner once or twice, ran into each other at the gym a few times, but that's about it in about a 2-year span.Fast forward to about 3-4 months ago. I find out he and the guy he had been dating had broken up. Then fast forward to about a month ago, and he texts me and asks if I want to hang out. Like I said, it was normal for us to text here and there, but we hadn't hung out one on one in a long time. I agreed, and ended up going to his place, had dinner, smoked a bowl and watched a couple movies and just generally caught up and laughed and told stories. Then about halfway through the second movie, he asked if I wanted to cuddle. I said sure, and we fell asleep cuddled up. No hooking up, just cuddling and I slept over. Fast forward another few days and he wants to hang out again, so we did the same -- dinner, smoked, TV, and after an hour or so we cuddled up. Now we’ve gotten into a routine of hanging out and cuddling about once a week, almost always initiated by him. He’s even wanted to sleep over multiple nights in a row, and we did once. Never in a million years did I see our friendship taking a turn back to anything remotely romantic, and so all of this has really come as a major shock. I'm being cautious, but I'm now finding myself feeling the feelings I had way back when, maybe even more intense this time around. Of course, it’s a little different this time -- I'm older, I'm not freshly out of a relationship, we’ve both grown a lot professionally, and we know each other a lot better than we did all those years ago.I'm enjoying it a lot, and he clearly seems to as well. We haven't kissed or hooked up with the exception of a little grinding here and there in the morning before we wake up (and he makes these little moaning sounds which lets me know he's into it ha..). Also, I now work an incredibly demanding job as a lawyer -- far more demanding than when we first hung out -- to the point that I have just about as little free time as he does since he's still in residency. That makes him even more attractive since it's been tough to date with my demanding work schedule. People want more time than I can give because of work, and only someone equally as busy can understand that.Bottom line is I'm not quite sure where to go from here because I never expected this to happen, and he really is kinda my one that got away. I'm frankly afraid to tell him that I'm enjoying what we're doing and want more, mostly because he so abruptly ended things the first time around all those years ago, and it hurt. I don't want to tell him I'm feeling something and then feel like an ass if it's totally unreciprocated. But at the same time, he's the one who initiated the hanging out, the cuddling, and he's asked me to hang out really frequently in the last few weeks. Reddit, what would you do from here?TLDR: I (35m) had an intense fling with another guy (32m) about 4 years ago after I got out of a serious relationship. It fizzled out and we became pretty good friends. A year or two ago, he started dating someone so we put some distance into the friendship, given our history. A few months after breaking up with the guy, he's been asking me to hang out, cuddle, sleep over, etc., once a week or more for the last month. And I'm really enjoying it and am catching pretty intense feelings again. Do I try to rekindle it?