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A Secret Hookup & Shag, Marry, Kill! Andy Cohen's Own Most Revealing Plead the Fifth Answers

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Over the years, Andy Cohen has found a way to pull scoop after scoop of juicy celebrity revelations out of his famous guests with his signature Plead the Fifth game — and now it’s time for him to dish the dirt.

PEOPLE and Entertainment Weekly‘s Editorial Director Jess Cagle turned the tables on the Watch What Happens Live host, and as expected, Cohen, 48, didn’t hold back — or plead the fifth!

First up? Naming one celebrity he’s hooked up with that people don’t know about.

“I made out with Jonathan Groff once,” he revealed. “That was in front of my apartment building. We went out for drinks. I don’t know if he thought it was a date, but I did! I think once I ended it in that way he definitely knew.”

“It was sweet,” he added. “Nothing else happened besides that, and we love each other to this day.”

  • Watch People Features: Andy Cohen, streaming now on People/Entertainment Weekly Network (PEN). Go to PEOPLE.com/PEN, or download the app for Apple TV, Roku, Amazon Fire TV, Xumo, Chromecast, Xfinity, iOS and Android devices.

FROM COINAGE: See Where 6 Stars Were Before They Were Famous

Up next, all about his dream WWHL guest Madonna — and whether he thinks she’ll ever actually come on the show.

“She’s Madonna! I mean, her whole brand is: ‘I owe you nothing, and I might be a little bit of a bitch,’ ” he said. “So she’s unfortunately being on-brand by not doing my show. It’s horrible. It’s a Catch-22.”

“The truth of the matter is, if she ever does do my show, it’ll wind up being a horrible disappointment,” he continued. “Because Madonna is someone who hates looking back at the past, and all I want to do is look back at the past! She’s going to hate it. But I look forward to her hating it.”

Then came a classic round of Shag, Marry, Kill with a particularly challenging trifecta: Cher, Oprah Winfrey and Meryl Streep.

“Oh my God. That’s really hard — they’re all perfect, and they’re all really rich,” said Cohen. “I mean … I think shag Cher, marry Meryl because she’s perfect, and kill Oprah? Ugh. There’s no happy answer.”

Cohen had no trouble with the next round: naming one celebrity he once loved and now wishes he had never met.

Scott Baio,” said Cohen without missing a beat. “He just was not into Watch What Happens Live. I played a game called Andy Loves Crotchy, like Joanie Loves Chachi. He didn’t like it. Mrs. Scott Baio was very offended — she blocked me on Twitter. I was a big Scott Baio fan.”

And last but not least, Cohen was tasked with naming the most difficult anchor he ever worked with during his years at CBS News.

“I think it would be when I did a story with Dan Rather, and only because it was like maneuvering a head of state,” he recalled. “We went to Monument Valley [in] Utah, he had his assistant Bill with him. We were shooting a profile on Don Imus and Don Imus’ private plane got a flat tire on the runway. It was a Sunday and Dan immediately was like: ‘Does New York know about this?’ I’m like: ‘No, it just happened, I haven’t talked to New York.’ ”

“It was literally like people in New York needed to know Dan’s whereabouts at every second,” he added with a laugh. “It was like being with the president. It was really intense.”

Watch What Happens Live with Andy Cohen airs Sunday through Thursday (11 p.m. ET) on Bravo.