Hi Meredith and crew,

I am almost 24 and have only had one serious boyfriend. I’m totally fine with my dating history, as I am a very independent person. In the past year and a half, I have lived in a couple of states and have been dating a bunch. There have been some short-term relationships, but nothing that materialized, partly due to the timing and location. Now that I’m back in Boston for good, I again have been meeting guys, having fun, and seeing where things take me.

One small dilemma is that I can’t stop thinking about my one ex and what it would be like to be with him now. We dated at the end of high school and into some of college. We were each other’s first everything. Because we were young and naive, we were convinced for a while that that was it and that we were going to get married, pop out some babies, and live happily ever after.

Obviously, that didn’t happen. We broke up for distance reasons (our schools were two hours apart), and for reasons related to future hypothetical careers and hypothetical locations of those careers. Now that those careers have begun, we are randomly both still in Boston. He had one serious girlfriend after me, and a couple longer flings. He broke up with the girlfriend because he didn’t see himself with her longer term. Some weird, hidden part of me can’t stop thinking about the possibility of being with him again. The few times we have seen each other in group settings, I find myself making eye contact with him a little longer, and smiling a little more when he talks. We don’t see each other often at all (every few months when our whole friend group comes back to the area for holidays), and do not ever really talk outside of this group. It would definitely be very weird, but while I haven’t had a serious relationship since him, and while I’m still very young, I am so much more mature and capable of being someone’s girlfriend than I was four years ago.

I guess my question is, do you think this is something I should casually try to pursue? I have no clue how he feels about me, but would it be horrible if the next time I find myself out with him, I try to maybe bring it up without sounding crazy and ruining the 4.5 years of “friendship” that have followed our breakup? Has anyone dealt with similar situations with exes?

– Thinking about him again