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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There are a few things you can do to accomplish this goal- first and foremost though, you need to bang a new girl(s). DO NOT, however, get a new girlfriend. This only exudes desperation and is a sure fire way to lose the breakup, miserably. Your Ex will think even less of you than when they broke up with you (another tip to win the breakup- initiate the breakup).
And if you do get a new girlfriend quick, make sure that they are at least better looking than your Ex, so your Ex isn't glad to see you stoop to new lows.
Bro 1: Dude she got right into another relationship. And with that guy? Damn, desperado much?
Bro 2 (initiator of breakup): Yeah, what a joke. She says she's winning the breakup. I call yet another victory in this breakup.
Bro 1: Yeah. That's just sad. You've definitely won the breakup.
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but is not included Heartbroken over her split with Joshua Bassett, composed a series of absolute bangers for what would become her record-breaking debut album, “SOUR.”

Sour is now the first debut album in US history to have every song debut atop the chart. It also broke the global record for the biggest opening week for an album by a female artist in global Spotify history.

One year after her split with Bassett, Olivia his now ranked the 5th most listened to artist in the world on Spotify with 60M+ monthly listeners. Olivia Rodrigo is, therefore, winning the breakup.

Bassett sits at ~5M listeners per month. He is not currently ranked on Spotify. Cry bitch
by MML141 June 26, 2021
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