I have been thinking a lot lately about an old friend from high school who I haven’t seen or talked to (aside from social media,) in a while. Although we never were in an exclusive relationship, we have a romantic history in which we were more than friends – a typical fling.

It never became anything serious because my feelings for him weren’t as strong as his were for me, and I guess you could say I just didn’t give us a chance. After a few years of him expressing his feelings for me and trying to pursue a relationship with me, he finally gave up and moved on. It has been a few years since we’ve seen each other, mainly due to the fact that he now lives in another state, and has a girlfriend. I still think about how great of friends we were, and the fun times we had in high school with each other and our friends, and even got to hang out a few times in college. Although I always saw him as more of a friend than anything, I do sometimes think about how things could have been different if I would have seen past my own insecurities and given a relationship with him a chance.

I would really love to reach out to him and get together to catch up – not to tell him any of this for closure, but just because I don’t like the idea of never seeing or talking to him in person again. I would just really like to catch up as friends, and see how he is doing. I am actually going to visit another friend soon who also lives in his state, and I thought that would be a good opportunity to reach out to him and see if he is interested in grabbing coffee and catching up, or even just getting a group of friends together to hang out. However, I do not want to cross any lines or disrespect his girlfriend, who also went to our same high school. I don’t know if I should act on the thoughts I’ve been having about contacting him, or if I just shouldn’t even go there, and risk starting any drama or misunderstanding. Hopefully I’ve explained the situation well enough – some unbiased advice would definitely be helpful.