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Chelsea Handler Talks To Tiffany

Chelsea Handler is coming to Milwaukee. She talked with Tiff about her new boyfriend and her numerous trips to our fabulous ...
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Chelsea Handler Praises Ex-Boyfriend 50 Cent for His 'Relentless' Trolling of Sean 'Diddy' Combs, Jokes She 'Should Probably Revisit' Relationship

Chelsea Handler applauded her former boyfriend for trolling Sean "Diddy" Combs amid the music mogul's fall from grace. Combs, 56, was convicted on two prostitution-related charges in July 2025, though ...
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50 Cent 'convinced' Chelsea Handler to date him - but their romance was short-lived

Chelsea Handler has opened up about her brief romance with 50 Cent as she revealed how the rapper "convinced" her to date him. The 50-year-old comedian had a whirlwind romance with 50 Cent, real name ...

Chelsea Handler, 50, says she took parenting classes — even though she doesn't have kids

"It's not that I don't have a maternal instinct. I do, I just don't want children," Chelsea Handler said.
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Chelsea Handler says 50 Cent was "so sweet" and is her "favorite ex" [VIDEO]

Celebrity relationships are always a fascination, but the ones that never fully took off are sometimes the most interesting. Comedian Chelsea Handler has always been candid about her personal life, ...