That moment after you break up with someone is always hard. Whether you broke it off or they did, it's a big decision to decide that you don't want to continue down the path you were going. Upon reflection of that decision, have you ever wondered "wow, I sure came out on top!" or do you feel that other person might be the one "winning" at life? Has any of your friends come to you telling you about the last person that you messed with and you thanked the lord you ended it before you got that far with them? This episode is all about the "shoulda / coulda / woulda's" and how we believe we might have fared off better without them regardless how of we felt about them at the time.