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The Cut
 

October 22, 2026

 

PERSONAL FINANCE

When a Relationship Ends But the Venmo Requests Don’t “We broke up over two years ago, but he still owes me money.”

By Charlotte Cowles

Photo-Illustration: by The Cut; Photos: Getty Images

Breakups are complicated. When money’s involved, they’re even messier. If one person owes the other a debt — or the other claims they do — there isn’t much in the way of protocol: Unlike divorces, regular breakups involving unmarried couples aren’t governed by family law, so exes have fewer apparent ways to settle arguments over who paid for what. Civil court can be an option, but informal IOUs don’t always hold up — and the associated legal fees may not be worth the battle. (Of course, as any fan of Judge Mathis knows, financial disputes between former romantic partners are quite common in small-claims courts.)

Below, four women share their own experiences of owing (or being owed) money after a breakup, how they handled the debt, and what they wish they’d known before the Venmo requests began. 

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