Inside Chelsea Handler’s wild dating history — from 50 Cent to Bobby Flay
Chelsea Handler has openly discussed her dating history, emphasizing her preference for short-lived romances. In a recent podcast, she clarified that she is not a commitment-phobe, stating she enjoys her independence and knows when to end relationships. Handler's longest relationship lasted four years with Ted Harbert, and she has had notable flings with celebrities like 50 Cent and Bobby Flay.
- ▪Chelsea Handler has been candid about her dating experiences over the years.
- ▪She claims not to be a commitment-phobe, enjoying her independence.
- ▪Handler's longest relationship was with Ted Harbert, lasting four years.
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Celebrity News Inside Chelsea Handler’s wild dating history — from 50 Cent to Bobby Flay By Riley Cardoza Published May 26, 2026, 12:38 p.m. ET See more of our coverage in your search results. Add Page Six on Google Who is in Chelsea’s (love life) lately? The comedian has spoken candidly over the years about her short-lived romances — and insisted to Kristin Cavallari in a May 2026 podcast episode that she is “not a commitment-phobe.” At the time, the Daytime Emmy winner told “Let’s Be Honest” listeners, “I don’t stay too late to the party. I know when to wrap things up. … My life is so f–king sweet and nice. I just don’t want any disruption to that.” 18 Chelsea Handler (pictured above in May 2024) hasn’t been shy about sharing her dating history over the years.
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