I’m a divorced single mom and have been dating a divorced single dad for the last six months. In general, our relationship is pretty good. There are just a few things on the partner checklist that have not been checked. I’m starting to feel like I’m “settling,” and that makes me feel less than excited about the relationship, him, and going forward in the future. I want to be realistic, and understand that there is no perfect relationship or person, but I’m still having my doubts.

A little history: I was married for 14 years and was only with my ex-husband. Before I met my current boyfriend, I had some short-term romances, and went on about 15 or 20 first and second dates. I’ve always found that I’m extremely picky when it comes to attraction. Here is the problem: I think I’m a pretty good catch (attractive, athletic, well-paid, intelligent, witty, and fun). And on some level, obnoxiously, I feel as though I’m better than my current boyfriend (more educated, attractive, cultured, and generally skilled). Doesn’t that sound awful?

But I am attracted to him and he is decent in the bedroom. I know I sound like I’m full of myself, but believe me, I am totally insecure and full of self-doubt, which leads to why I’m writing. Together we have five kids. On some level that excites me, on another, I’m not sure I’m ready to take on his three – and his financial situation, which includes debt. He’s fun, funny, athletic, and smart so there is a reason we’ve maintained a six-month relationship. However, as he gets more attached, I’m not sure it’s fair feel the way I’m feeling or lead him on when I could put myself out there again to meet someone who is maybe more compatible. He is a good catch too, but there are certain things that I’m not sure about. Appreciate your thoughts.

– Skeptical