I'm to lazy to actually write a story for these characters but I wanted to do something for Valentines Day sooooo here is this. I'm also rushing this so sorry if its crappy. I literally wrote this in maybe 10 minutes, and in class.
Sam: He gets you your favorite flowers and then spends the entire day with you. He also makes you your favorite breakfast and dinner.
Dean: He lets you drive Baby, takes you fishing and then hunting. Later that night you swing by a restaurant and you guys eat burgers and pie.
Jack: After hearing Sam and Dean ranting to him that he has to get you something, and after long explanations on why he has to get you something, he gets you a necklace that he noticed you were looking at, chocolates, and roses.
Castiel: He takes you to the mountains with a picnic.
Gabriel: Gets you enough candy to fill a large candy store for a few weeks.