The two celebrities were together in 2009 following a brief encounter on the set of her show Chelsea Lately.
The 45-year-old writer and actress went on to reveal a recent conversation with the rapper, after he made a controversial statement on Twitter, publicly supporting current president Donald Trump before the elections.
Chelsea was quick to comment on his post and wrote “you used to be my favorite ex-boyfriend,” with fans of the rapper and the comedian getting caught up in the dramatic social media exchange.
You used to be my favorite ex-boyfriend.— Chelsea Handler (@chelseahandler) October 20, 2020
However she later explained during an appearance on The View that the entrepreneur “wasn’t serious” and described a phone conversation after the viral post, where she asked if he was really supporting the Trump administration.
50 also said that “he was just screwing around on his Twitter,” with Chelsea adding that he was “supporting Joe Biden.”
The rapper also highlighted the fact that he “turned down a million dollars to go to the inauguration,” in 2017, and there was no way he would start supporting the Republican candidate in 2020.
When he was asked the reason for not seeing a possible romance with the comedian, he said it had to do with her support for New York governor Andrew Cuomo, but despite everything he thinks of her as “a good friend” and complimented her by insisting that “part of her show is almost to be unpredictable, and unpredictability is what makes a comedian.”