20 Weirdest Celeb Couples – You May Be Surprised

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3) Chelsea Handler & 50 Cent

This peaches and cream talk show host certainly surprised tabloids with her choice in beau. The two met when 50 Cent came on her show in 2010 and, afterwards, sent her follow up flowers. Handler admits to some amount of trepidation because she didn’t want to date someone “whose name is a number”, but eventually she fell for his charms when he made the trip to New Orleans to see her. Later in 2010, they made it official.

Handler says that the rapper is a “sweetheart” and that he’s so very adorable; a nice guy; smart; pretty much everything you’d want to bring home to mom. Their relationship ended when Fiddy’s ex Ciara came on Handler’s show. Fiddy called Handler to warn her about the awkward situation about to ensue, and Handler admits to flying off the handle a bit. She insists that she was tired, on set, and trying to prepare for a long day when she got the phone call and that, in her rage, she insulted him deeply. After that, they didn’t see much more of each other (though Handler now claims that she still thinks her ex is a good person).