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For a long time, Andy Cohen and Anderson Cooper have been friends. It’s only natural that Cohen would interview Cooper’s famous mother, the fashion designer and socialite Gloria Vanderbilt, on his popular talk show, Watch What Happens Live. Vanderbilt desperately hoped Cohen wouldn’t ask her one incredibly personal question.

Anderson Cooper and Andy Cohen in New York City | Michael Loccisano/Getty Images

Anderson Cooper’s mother had a scandalous past

First, a little background. According to the Encyclopedia Britannica, Vanderbilt was open about her relationships with numerous Hollywood celebrities, including Marlon Brando, Gene Kelly, Frank Sinatra, and Howard Hughes. She also wrote an incredibly salacious book called Obsession: An Erotic Tale. As such, she’s had a bit of a risque reputation.

In a way, she was similar to Cohen. Watch What Happens Live is one of the defining talk shows of our era. Part of this is because Cohen will ask his guests R-rated questions which other TV hosts wouldn’t dare to ask. In his own way, Cohen encapsulates the share-it-all mentality of the social media age.

Perhaps the most infamous of Cohen’s interviews was with Nicki Minaj. Bustle reported that in 2014, Cohen asked Minaj about her carnal knowledge of men in the music industry. The question seemed to catch Minaj off-guard, and she emphasized that she had been with one man for ten years. To many, this question seemed degrading and rude.

What Andy Cohen wanted to ask Gloria Vanderbilt

Andy Cohen, Gloria Vanderbilt, and Anderson Cooper on Watch What Happens Live | Charles Sykes/Bravo/NBCU Photo Bank/NBCUniversal via Getty Images

Because of Cohen’s record and her own reputation, there was a good chance Cohen would ask Vanderbilt some lurid questions when she went on his show. USA Today reports Cooper prepped his mother for Watch What Happens Live by reminding her Cohen might ask her anything. According to The Hollywood Reporter, Cooper said before his mother went on Watch What Happens Live, she was worried Cohen would ask her about the private anatomy of Hollywood actors.

Cooper was very embarrassed she even brought up the subject. He told Cohen about his mother’s concern, and the talk show host wondered if he could actually ask Vanderbilt that question. Cohen’s interview with Vanderbilt didn’t actually go that far.

Andy Cohen and Anderson Cooper’s crazy New Year

Andy Cohen and Anderson Cooper on New Year’s Eve | Taylor Hill/FilmMagic

Cooper seems to be fond of this anecdote. He discussed it when he co-hosted CNN’s New Year’s coverage with Cohen. In fact, he spoke about the incident using particularly vulgar terms for a major news network. Later in the broadcast, he got a text message from a friend about his choice of words. Cooper said he might have “went too far” with his comments.

This wasn’t the only moment of the night that was a little less serious than CNN’s usual programming. Yahoo! Entertainment reported that, at one point, Cohen and Cooper decided to take shots of tequila on air. Cooper didn’t hold down his liquor particularly gracefully. In fact, he made a disgusted face and giggled. After downing the shot, Cooper declared “I’m just trying to breathe.”

Whether he’s hosting CNN or Watch What Happens Live, Cohen is a little less formal than your average interviewer. For millions, this is precisely what makes him so fascinating. Even the behind-the-scenes anecdotes from his show can be very entertaining.