Meeting your ex after some time has passed and comparing details about your current lives - there is always a winner and a loser in a breakup. If your life is going significantly better than your ex's, then you "win the breakup" Coined by the TV show How I Met Your Mother.
I ran into my ex Susan the other day - she's working at a Dairy Queen and got knocked up by some douche. I totally won that breakup.
Man, stop watching TV and go get a job or something. Don't you want to win the breakup when you meet Jen at this year's reunion?