I don’t think he is ever going to be on the same line as you regarding kids and marriage. Not at this age. Unless you can adjust your future plans without resenting him for it later, it might be best to find someone more compatible while you still have time.

And you want to be married to a compulsive gambler because...?

I hope he’s been betting on UConn; otherwise you might want to kick his ass to the curb.

Are you sure you really want a guy like that to propose to you? First of all, you should never force a guy to propose. You'll both wind up miserable. Second of all, if you two clearly have different goals in life for something so serious, you should probably re-evaluate the whole relationship. If he's spent his paychecks on March Madness, it sounds like his priorities are wrong and he's essentially a man-child. Trust me, you don't want to be tied down with that.

He wants to spend his money on what he chooses. Kids are ridiculously expensive and at least he acknowledges that and isn't forcing a life of poverty on a blameless child. He's actually being responsible.