Dean has had just about enough of Sam. Yeah, sure, he went through a break-up, but he's twenty-three for crying out loud! Sam has been driving Dean crazy, he never leaves, he never really moves, and Dean has been wasting away without his boyfriend Cas. Something has to be done. Sam just wants to know what went wrong. He's thankful for Dean's help, but that can only get him so far. Then one day Dean says that Sam is going on a date whether he likes it or not. And it's a guy. Sam has no idea what's about to hit him.

Dean and Castiel are married now, and they couldn't be happier. Their life is finally making sense. But then an old ex of Dean's, Angel, becomes a mechanic at the shop where he works, and he rekindles a friendship with her. Although Dean has no ideas of romance, Cas can't seem to let it go, and Dean must figure out how to convince Cas that there is only one angel he truly loves.