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They were like, 'Chelsea, come on.' They were both laughing really hard at it…I mean, everyone was."So what went wrong?"We dated for a couple months and then we had a falling out," Chelsea explained."I like to have fun, and I'm really trying to not get into anything too serious."She also opened up about the fling during an episode of Oprah's Next Chapter in March 2013."He's a sweetheart, and he's so cute," Handler told Oprah Winfrey at the time. He came on my show [in 2010], and he sent me flowers.But it was the same lady who sued because of huge amount of money; she said that he did not take care of her for life.The suit was dismissed by a judge, their tale of a love relationship just gone sour."My friends all loved him, my friends fell in love with him," she said.

Then that taints the relationship," he added, which makes total sense.

In an interview with Vanity Fair, the G-Unit mogul said when he first became famous, he tried to bring his friends along for the ride, but others close to him got jealous.

Then he tried to hire a few of his buddies to help with some of his businesses but that didn't work well either."I went from a basement apartment in Queens to a 50,000-square-foot house and when you're successful, it's valuable to have people around who represent what was there before all the confusion started," said Fif."But you know what happens?

It’s not that I don’t appreciate the time we spent during that period. That might spin me right back into the actual relationship.”“You know what happens? Our lives would be moving us in different directions at the same time.

You usually find out about my relationships after they’re finished.”“That was an accident. So it’s enough space for us to actually still be into each other.

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