I just realized somehting about SPN 3x11 "Mystery Spot"
which would completely change the interpretation of it:; If you pay attention to the lyrics of both songs that had played in that episode, "Heat Of
The Moment" wasn't Gabriel trying to apologize to Sam. He was apologizing to Dean.
"Back In Time" was more of a cationary tale towards Sam, warning him to be careful with
what he messes with. Meanwhile, the other is basically Gabriel saying that he knows Dean's
pain and really hates having to be the cause of more pain but he doesn't see any other choice.