Sa-Fire - "Thinking of You"

What happened in 1989 when you went through a painful breakup?  Chances are you picked up the phone and called into your local radio station to request "Thinking of You" by Sa-Fire (pronounced "sapphire").  The sappy ballad spent 19 weeks on the Adult Contemporary Chart and peaked at #4.  By now, you've hopefully forgotten about that dude who broke up with you.

Gavin DeGraw - "Not Over You"

How many people have listened to Gavin DeGraw's "Not Over You' on repeat with tears in their eyes?  I'd guess: several.  

Chicago - "Look Away"

In order to survive a breakup, you have to dust yourself off, pick yourself up, and go forward.  It's a lesson that presents itself time and time again in life.  The same thing happened when lead singer (and genuine bad ass) Peter Cetera left the group Chicago.  The remaining band mates put down their trumpets and forced themselves to do some daily affirmation before going out and landing a #1 song in the post-Cetera era.  "Look Away", which coincidentally is a song about breaking up, was that song.  Stay strong, boys.