Chelsea Handler tells Howard Stern, a call from 50 Cent talking about his ex-lover Ciara — led to their fall out.
Howard asked Chelsea about her relationships with men. She said that a lot of men are intimidated by her. Chelsea loves men and being with men. She’s not a cheater either. Chelsea revealed dating 50 Cent. Howard asked how he is. She said, “he’s very sweet and has great energy.” 50 Cent is like a big, black Teddy Bear. She said she always had a thing for black men… it must run in the family because her dad is into black women. Chelsea said, she dated 50 Cent for a few months and then things just fell apart.
Chelsea said 50 Cent wasn’t into smoking pot or doing anything like that — she would smoke pot around him but he didn’t do it. She said 50 had no interest in it.
Howard asked if she notices that he’s black and she’s white all the time. Chelsea said you can’t avoid it. She said that she likes guys who are very masculine and that’s what 50 Cent was like.
Howard asked if she has ever had two guys on her. She said she hasn’t — 50 Cent… that was as close as she’ll get.
On how Chelsea and 50 Cent hooked up. She said he sent her flowers after he was on her show. She said that he was sending ridiculous amounts of flowers. Then he started to call the office. She said she got on the phone and he was very grammatically incorrect. She said you should have seen the texts he sent to her.
Chelsea said she eventually picked up the phone for 50 Cent. He said he wanted to take her out. She said that he was very sweet and she figured he wasn’t carrying a gun… Chelsea said that 50 asked to meet her in Nashville… She met him there and they had sex. She said it was pretty normal stuff. Howard asked if there was anal. She said there was nothing like that going on.
Chelsea told Howard that 50 wanted to go on vacation with her and her family. She said that he was coming to a lot of her shows and stuff. She said this girl Ciara was coming on her show and he called her to tell her some stuff about her. Chelsea told him that this was like 8th grade shit… She said that she didn’t want to hear it so she told him to knock it off. She said something to him about being a street person or a gangster… And she hasn’t spoken to him since. She said that he was so insulted that they never spoke again. She said that it was the worst thing she could have said to a black man next to the N-word. Chelsea said he was supposed to go on vacation with her but he didn’t even show up. She said that he didn’t come to Anguilla and that’s probably good because he couldn’t swim. She said that it was never going to be a long term relationship anyway.