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Chelsea Handler Dishes On Breakup With 50 Cent, Takes Shots At Joan Rivers And Mariah Carey

Back in 2010,  rumors were flying that Chelsea Handler was getting it in with rapper 50 Cent. She initially denied the reports and then later on downplayed their involvement, telling Esquire: “We had sex. It was fun.” Then, earlier this week, in an interview with Howard Stern, the late-night talk show host finally confirmed that the two were dating and spilled the beans on why she broke up with 50. Check out the excerpts below:

On Dating Another Celebrity
First of all, I really try to avoid ever dating another celebrity. Look at everyone, everyone is such a mess. That world is just not real and it’s very hard to maintain a relationship when you marry or get involved with another celebrity. It’s fun for a little hook up, but it’s not going to  ever be anything serious … but I definitely didn’t have sex with 50 Cent for attention. We dated for a couple months and we had a falling out. (laughs)

On Having Sex With 50
The sex was okay. It was just normal. It was fine. It wasn’t mind blowing … I’ve had much better sex with other people, but it was good.

On Their Brief Relationship
This is how it started, he was on my show. He was cute, and you know, I flirt with all the cute guys on my show. And I thought he was just adorable. Then he started sending me flowers, but ridiculous amounts of like 50 white roses, and it was like laughable. I’m like, “Get these out of my office! This is so embarrassing.” Then he started to call my office, and my assistant was like, “50 Cent is calling and I swear I think it is him.” And I’m like, “Oh, my God.” So I got on the phone, and he’s not a grammatical genius and it’s kind of like silly because I’m like, “This is so stupid.” You should’ve seen some of the texts he used to send me. I didn’t even bother [correcting the spelling], as if he’s all of sudden going to get an education now.

Finally I picked up the phone. I had avoided him for a couple of days. He said some silly line, but it was very cute and I was like, “He’s sweet. He’s not carrying a gun right now.”

It was pretty normal. We went out. We dated. We had sex. My friends all loved him. My friends fell in love with him. They were like, “This huge gangster guy is like the sweetest.” So we dated for a couple months. And this is the best part, he was going to come with my family, because I was going to Anguilla to go to Christmas vacation. I was going to bring him because he had met my family at one of my shows in Newark. He would come to a lot of shows and he would come and meet me a lot of places.

On Why They Broke Up
It was so dumb. It’s almost embarrassing. I can’t really remember exactly the details, but I’ll tell you what I can remember. I think one of his ex-girlfriends was coming on my show and she’s one of those singers -I can’t remember her name. She’s really hot. He was dating her I guess previous to me.

Right before Anguilla, Ciara–that’s her name!–was coming on the show, and he called me to tell me something about her. Something about she still calls him all the time and shes like in love with him or something. And I’m at my job, and I go “Curtis, honestly this is like eighth grade sh*t. What is this?  Why are you telling me this?  This girl is coming on the show tomorrow, and now I have to look at her and think you guys have some weird thing going on or had going on or whatever.”  It was just so juvenile. I’m at my work and I work my ass off all the time. I have million different things and even though it’s not like important work, I am working hard. I’m doing shit. He said, “I want you to hear this conversation” and he was like calling someone like a 3-way phone call. I go, “So you’re telling me this girl wants to get back together with you but she’s upset that you’re dating me, is that what you’re saying?” He’s like, “Yeah, so I just want you to know when she comes.”

I think I called him, whatever I called him was probably the worst thing you could say to a black person short of calling him the N-word. I said something like you’re like a street person basically. Something along the lines of being a gangster, and it was really, really offensive and I hung up and I’ve never spoken to him again.

Listen to the audio after the jump:

Do you believe her that she didn’t call him the N-word?


Peep the video clip of her taking shots at Joan Rivers, Mariah Carey, and Nick Cannon:


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