Anderson Cooper Talks Dating, Death, and Drinking on New Year’s Eve in Stern Show Return

Veteran journalist sits with Howard following the release of his new book, “Astor”

September 26, 2023

A frontline correspondent bravely reporting from dangerous conflict zones, a straight-laced anchor who calls it like he sees it while doing his best not to take sides, or a silver-haired “twunk” who throws back shots on TV with his best friend Andy Cohen (almost) every New Year’s Eve—call him whatever you like, but Anderson Cooper is the very model of a modern broadcast journalist.

The 56-year-old CNN host and longtime “60 Minutes” contributor returned to the Stern Show on Tuesday morning to shine a light on topics ranging from his unconventional upbringing as the great-great-great-grandson of business magnate Cornelius Vanderbilt to the converted firehouse where he and his ex-boyfriend cohabitate and co-parent their two children. Cooper also clued listeners in on the state of his oft-scrutinized network and some of the many projects he has in the works, from the next season of his podcast “All There Is” to his latest biography about an ultra-wealthy family, “Astor: The Rise and Fall of an American Fortune.”

Photo: Getty Images

If it seems like Anderson has a lot going on, it’s because for much of his life he was more of a doer than a feeler. However, he hopes the self-exploration he’s done on his podcast, which takes a hard look at loss and sorrow, can help him overcome that.

“It’s unlocked something in me that’s made me really reflective,” Cooper told Howard.

Anderson is no stranger to grief. His father died when he was just a boy, and his only brother took his own life when Cooper was 21. “I came to realize that I had never really grieved my dad or my brother,” he said. “It’s only recently … I realized there is an ocean [of feelings] I have pushed deep down, and I think I need to deal with it.”

“I’m doing another season of this podcast because I want to talk to people about grief and these are not conversations I would normally allow myself to have,” Anderson continued, explaining that in the one episode he invited listeners to call in and share their own stories of heartache, and he received 46 hours of calls.

“I’ve spent the last couple of months listening to [that] 46 hours, and it has clearly impacted me very strongly,” Cooper said while beginning to get emotional. “I started to realize how little I had actually allowed myself to feel this stuff,” he continued, adding, “I don’t allow myself to feel joy, and I don’t allow myself to feel pain, and so I live in this middle ground … and with kids I want to allow myself to feel the full range of feelings.”

“I don’t want my kids to see the sadness that I saw behind my mom’s eyes,” he concluded before sharing a few wild anecdotes about his mother—renowned artist, fashionista, and heiress Gloria Vanderbilt.

That Time His Mom Offered to Be His Surrogate

There’s no telling what a guest might say on live TV, but Anderson credits his eccentric mother with helping him maintain his composure in just about any situation.

“People ask me, ‘How do you not react on air?’ I’ve spent my life not reacting to my mom’s crazy statements,” he told Howard with a laugh.

Even so, Cooper was hardly prepared for the conversation he had with his mother when she was 85 and he still hadn’t decided whether he’d have children. “She was like, ‘The most amazing thing happened … [The gynecologist] told me I could still bear a child,” Anderson recalled. “I’m immediately thinking, ‘How do I stop my mom from bearing a child?’ Which is a thought I’m sure we’ve all had … But then she said … ‘What I was thinking was you get an egg and, you know, fertilize it with your sperm, and I’ll carry your child.’”

Howard and co-host Robin Quivers could barely believe it.

“I said, ‘Mom, I love you, but even for you this is batshit crazy,” Anderson said.

Charming Prince

Cooper has crossed paths with countless entertainers, athletes, and even heads of state over the course of his long career, but none of that could prepare him for a chance meeting with the legendary recording artist Prince. “He sat down next to me, and he goes, ‘Uh, I moved to L.A. to be around people who are in it—and you’re in it,’” Anderson recalled, adding, “I was so nervous. I was like, ‘Yeah, I know totally what you mean,’ … And then I could not stop talking.”

Anderson apparently made quite the first impression because after that Prince wouldn’t stop inviting him to exclusive concerts and parties. Unfortunately, his demanding TV news career frequently got in the way.

“I felt like such a nerd saying, ‘I actually have a show at night. I can’t miss it for a party.’ And then finally … I went and it was incredible,” he told Howard, explaining he saw Prince perform in 2008 at the Gansevoort Hotel.

Photo: Getty Images

Cooper recalled being equal parts excited and exhausted when His Purpleness took the stage at around 1 a.m., but his night was far from over. “One of his people came over to me and said, ‘Prince would like you to stay afterward because he’d like to talk to you about the financial crisis … and I know nothing about the financial crisis,” he recalled. “I was like ‘Uh, okay. Yeah, sure.’”

As Prince’s performance continued until the wee hours of the morning, Anderson was forced to change his tune. “He kept playing and playing,” Cooper said. “I finally went to one of his people and was like, ‘I have to work at like 6 a.m. tomorrow. I can’t stay to talk about the financial crisis.’”

To Drink or Not to Drink?

CNN has ousted several big names in recent years, from chief executives Jeff Zucker and Chris Licht to on-air personalities Chris Cuomo and Jeffrey Toobin. But perhaps no departure shocked the world quite so much as that of the alcohol which once contributed mightily to CNN’s New Year’s Eve Live broadcast, hosted by Cooper and his dear friend Andy Cohen. Last year, then-network president Licht infamously banned booze from any part of the broadcast.

Now? It’s a new year and CNN is under new leadership, so Howard wondered whether Anderson and Andy might let loose on their live New Year’s Eve special.

“I don’t know,” Cooper said, adding, “Nobody has said anything to me [about alcohol] … We will see what happens.”

“Did you think this was a mistake that you could not drink on TV?” Howard asked.

“I think the whole thing was poorly handled,” Cooper said. “If someone had just come to me and said, ‘Look, I don’t think it was a good idea to do this,’ that would’ve been fine … But it became sort of a public thing … it became a thing that it didn’t need to become.”

Regardless of whether he’d wind up shooting tequila or sipping on non-alcoholic sparkling cider, Cooper wasn’t worried. “[Last year] I thought we had a show that was just as good, and we came up with ways to get around it,” he said.

More Single, Less Mingle

Living with his ex-partner Benjamin Maisani and their two children in his firehouse-turned-residence, Anderson broke the news to Howard that he’s single – and not doing anything to change his relationship status. “I’m not dating,” he said matter-of-factly. “I’ve got two kids who I can’t imagine not spending every minute with, and I’m working all the time,” he said. “I’m happy.”

In fact, the anchor can’t even remember the last time he went on a date. “It’s just not in my purview,” he insisted before politely brushing off Howard’s offer to set him up with someone. “When straight people try to set gay people up, it rarely works … I’ve got a great love affair with my kids right now — it’s the best thing ever.”

“Astor: The Rise and Fall of an American Fortune” is available now. Listen to “All There Is With Anderson Cooper” here and watch “Anderson Cooper 360” weekdays at 8 p.m. on CNN.

You Give us your email Address we'll give you even more howard!

By signing up, I agree to receive newsletters and marketing emails from the Howard Stern Show and accept the Terms of Use and Privacy Policy