I’m curious to hear men’s perspectives on situations where two people have a history but never seem to make a relationship happen. I’ve known a guy since high school. We graduated in 2019, and after losing touch for several years, we reconnected in 2024 (he reached out to me and asked me out). Since then, things have been on and off, and we’ve never officially dated. We’ve always lived far apart, which makes things more complicated. He knows I’m interested in a serious relationship with him, but we’ve never gotten to that point. We also haven’t had sex, because I personally only want to have sex within a committed relationship, and he does know this. Another factor is that he had spent most of his life pursuing a career in sports, but things didn’t work out professionally. He’s now living at home, working a job he doesn’t particularly enjoy, and I’ve sometimes wondered whether being at a different stage in life could affect someone’s willingness to pursue a relationship. I’m trying to understand a few things from a man’s perspective: Can long distance genuinely stop a man from pursuing a relationship with a woman he has feelings for? Can a man feel like he’s not in the right place in his life to date someone, even if he’s interested in her? Why might someone repeatedly reconnect with a person without ever committing to a relationship? Can two people have genuine feelings for each other but still never make a relationship work? I’m interested in hearing about people’s experiences with situations like this, especially when distance, timing, and different expectations around commitment are involved I should also mention he lives in Boston and I live in NYC, so I suppose not too far. submitted by /u/Proper-Apartment1235
Originally posted by u/Proper-Apartment1235 on r/AskMen