Based on this picture (because tumblr cut off the ending of the tags I’d written)
If Dean is going to spend Valentine’s Day alone, he’s at least going to do it drunk.
He sets the bottle of Jack Daniels on the check-out conveyer belt along with a 12-piece box of fried chicken. Sam would say Dean is “eating his feelings”, but what does Sam know. He gets to spend Valentine’s Day with his beautiful wife and new baby daughter. He’s the last person Dean wants to talk to about his feelings.
Dean glances ahead of him in line, pleasantly surprised by the sight of a very attractive, dark-haired man glancing absently at the tabloids along the rack. For a brief moment, visions of typical meet-cute scenarios and cheesy pick-up lines dance through Dean’s head. That is, until he looks down and notices the man’s items: a bouquet of pale pink tulips and a dozen pink-frosted, heart-sprinkled cupcakes.
Dean’s face falls; of course this guy is taken. There’s no way he is buying those items on Valentine’s Day if he doesn’t have someone to share them with.