The Boyfriend Trap (HS AU)

Gabriel Novak always had a theory about everything. Over the years Sam Winchester has come to learn that his best friend’s theories are almost never wrong. Gabriel’s newest theory has set both boys on a mission to reunite Dean and Castiel, who were once close friends but eventually grew apart as they
moved through high school. In fact, they want to do more than reunite them, Sam and Gabriel want their brothers to admit the love that they have both been hiding away from the other for years.

Fanart Credit: Priznik on Tumblr