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?
by mowgli27 June 29, 2009

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