“Should I reach out to my old boyfriend?”

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.

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One thought on ““Should I reach out to my old boyfriend?”

  1. Anonymous says:

    Just shoot him a hi text and see him on Facebook. He’s too far out of reach already if he has a girlfriend and if you had said your friend lived in the same town or going to a class reunion that he’s also attending that’s one thing, but you said state so nah. What you can do is say something on Facebook about heading out that way and see if he posts something on your actual time line or shoots you a message himself, but otherwise let sleeping dogs lie.

    If he does say something and wants to catch up, invite his girlfriend as well. That way she knows you are just a nice person who wants to say hello to a old chum, not a home wrecker. It’s on her then if she comes or not.

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