Castiel: How You Get The Girl by Taylor Swift. You guys broke up tragically after Cas decided he wanted to go hunting more with Sam and Dean. You remember how you got together and now your breaking up. It happened too fast. Castiel realised how bad this effected you and you guys got back together.
Dean: Here Without You by Three Doors Down. Dean was a hunter obviously. He spent so much time away from you going all over the country saving people. Finally, you broke up with him because you couldn't take the pain. Dean never took his mind off of you. Never.
Sam: Amnesia by 5 Seconds of Summer. Sam, like his brother, went all over the country. You finally split because you couldn't handle his life on top of yours. He wrote you letters all of the time even after you broke up. You wrote back about your life; including your new boyfriend.
A/N sorry I didn't put lucifer in this one
