Dear Prudence,
I started dating a great guy about a month ago and I’m at a loss with how to approach Valentine’s Day. We’ve been on four fun and pretty amazing dates so far. I’m scared to bring Valentine’s Day up to him and have him reject me—whether it’s because he’s got plans with another girl (we haven’t had “the talk”), he decides to go out with his friends, or just isn’t invested enough in “us” to do something. He’s a romantic and sweet guy, so I’m sure he’s not oblivious to the fact that Valentine’s Day is coming up. Do I just keep my mouth shut and do my best not to be disappointed if he doesn’t mention V Day or plan anything? Or should I be brave and bring it up in a casual, playful way? Things are progressing very nicely between us and I don’t want this holiday to mess things up.