He’s a lawyer and proud of it

I've been dating this guy who is a young, successful lawyer for a couple of weeks. I really like him but whenever we go out with my friends, he talks A LOT about the fact that he went to law school and is a lawyer. He doesn't even talk about specific law experiences. He just continuously reminds people that he is a lawyer. Most of the time, it doesn't even relate to the conversation, he just throws it out there.

Don't get me wrong, he should be proud because he worked really hard to get where is, but it just comes across as too much. Even my friends have noticed and have said how they really like him but "he talks about being a lawyer a lot." They weren't mean about it and just dismissed it as his way of trying to impress them, but he does it often, even among his own friends or new people he meets.
The fact of the matter is that I hang out with very down-to-earth people who aren't pretentious. So here is my issue: some friends and I are planning on going away and sharing a vacation house. I don't know everyone in the group that well and I am concerned that this problem will happen again, only it's a bigger deal because we'll all be stuck together for a few days. One friend even said "just make sure he doesn't constantly talk about being a lawyer."

I definitely don't want him to hide who he is and what he does, but I don't want him to gloat about it either. How do I tell him to cool it with the bragging without hurting his feelings or undermining his success?

– Cool It, Boston

You have to say something now, CI, while it's early. Something like, "Hey, I know you're proud of your profession – and I've been fantasizing about dating a lawyer ever since I fell for Corbin Bernsen on 'L.A. Law' -- but I notice that you bring it up a lot. I know you don't mean to brag, but sometimes the lawyer-talk is a bit off-putting." Be prepared with some specific examples so he knows what you're talking about.

The trick is to keep a soft tone so that he doesn't go on the defense, "Law & Order"-style. Make your gripe sounds like a concern, not an accusation. He's going to feel foolish, so you need to let him know that you're willing to forgive, and more importantly, to forget
I empathize with him, of course. It's incredibly difficult to become a lawyer (try taking a practice LSAT), and these days, it's a challenge to keep a law job without getting laid off. I understand why he's proud. But lawyers who don't mention that they're lawyers are cooler than lawyers who do. You have to talk to him before you take him to that vacation house. Don't set him up to fail.

Readers? How do you tell a bragger to stop bragging without making them feel stupid? Does someone who brags about being a lawyer understand that it's also cool to be a musician -- or a social worker? Does his behavior mean he's too competitive? Any lawyers want to weigh in? Does the bragging mean they're doomed? Discuss.

– Meredith