It kind of does to me, although that's not necessarily a bad thing (mature names on babies are better than babyish names on adults for sure). I think it's because a lot of DH's family and our friends are academics, and we know people who are university/college deans. So it sounds more like a title than a name to me, and I always wonder what it would be like for someone named Dean to become a dean.
Heh. The dean at my college was a gentleman named Dean Bootman.
Most Deans I know are firmly in the age category as my father (who was born in the late 40s). As names go in cycles, it is just interesting how names that our mothers have are not on trend but names our grandmother's have are. However, for men, this doesn't seem to be as big of an issue.