If the only reason you want to break up is to see if you can do better you will be very disappointed.

This is not why. Maybe I didn't articulate it correctly. There ARE things that concern me about my boyfriend. Mainly he seems kind of "lost" and not very motivated lately. He wants to take family money to invest in something that his family has suggested (which isn't terrible, it's just not very ambitious). He's very lucky to have this option, but it still seems like he is only taking it because it's easy. He hasn't tried to seek out his own options/ideas. And maybe that is too much to ask of a 23 year-old.

So I don't wonder "what if" so much as I wonder if my boyfriend is the one who I want to be with for the rest of my life. Sometimes I wonder if it's just a post-college slump. But I don't want to be with someone who doesn't have much ambition.

He treats me very well, we have a lot of fun together, and I think we were in a very good match in college. I just don't know if what I'm feeling is a legitimate concern or hypergamy or just a phase.