I don't know how anyone can't love A Christmas story! Although admittedly I've never lived in NYC but I never lived in the 1940s either and I still enjoy the movie.
Uh oh, this may be a red flag!

What if you're dating a grinch?
You should see if he's willing to take you to see The Santa Clause 2. If he can't appreciate one of two cute Christmas movies, you've got a serious problem!