Looking might dapper, Winchester boys. They run into Cupid during the episode "My Bloody Valentine."
This is a scene from "My Bloody Valentine." It's the 2/11/10 episode of Supernatural.
This is a scene from the February 11 episode of Supernatural. In it, Lex Medlin guest stars as Cupid.

Supernatural Season 5 Episode 14 Quotes

Dean: Where am I going?
Sam: Dean, it's Valentine Day. Your favorite holiday, remember? I mean, what do you always call it - uh, Unattached Drifter Christmas?

Castiel: This is their handshake.
Dean: I don't like it.
Castiel: No one likes it.