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WOW!: Chelsea Handler Talks About Sex With 50 Cent & Why Ciara Broke Them Up! On if 50 Cent was the First Black Guy She's Dated. No, I dated black. E!'s resident late-night funnylady opens up on her short-lived coupling up with the rapper. Chelsea Handler. 50 Cent and Chelsea Handler dated in Chelsea Handler has become one of entertainment's most sought-after and versatile rising stars. This list of Chelsea Handler's boyfriends and exes includes Bobby Flay, 50 Cent, André Balazs, and Ted Harbert. Bobby Flay is listed (or ranked) 1 on the list.