I’m in my 30s and have been dating a guy who’s in his mid-twenties. We’re having a great time, we get along very well, and he’s a nice refreshing change from my past relationships. The problem is that I can’t just enjoy it for what it is, and I can’t stop thinking about the fact that it seems inappropriate to be dating him. I don’t know what’s going to happen in the future, and I don’t know how serious I am about this long-term. But I don’t want to ask him because I don’t want to either hurt his feelings if I’m not serious enough, or scare him away if it seems like I want to get married. Should I just break up with him and move on?
Yes. Dating a fun, young, attractive man is a really bad idea. I think you should break up with him and go find a guy in his fifties who has three teenagers who hate you and an ex-wife who wishes you were dead.
Having fun when you’re dating is just wrong, so I’m glad you’re spending your time worrying about whether you like him too much or not enough, and that you’re going to sit him down for a conversation about where your relationship is headed even though you don’t really care. I’m sure that while you’re spending your free time fretting over what it all means, he’s at home doing the same thing. I’m sure he’s not watching TV with his hand down the front of his pants, or golfing with his friends and talking about the Celtics, or doing whatever else it is that normal, functional people do.