Girls’ Andrew Rannells Says He Dated Anderson Cooper

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Andrew Rannells has the scoop on Anderson Cooper.

Okay, so this just came out – apparently, back when I was in my twenties, I had a short fling with a journalist! It’s been rumored for ages that one of the storylines on Girls was actually based on our connection, and now it’s confirmed. It feels good to finally put that speculation to rest.

On a recent episode of The Daily Beast’s podcast, Obsessed, actor Patrick Rannells, 47, described telling creators Lena Dunham and Jenni Konner about his past relationship with a former CNN host. He said they responded by calling it “a fun story.”

He added, “It became the story that Elijah had in the series.”

In season five of the HBO series, Rannells’ character, Elijah Krantz, dated a news anchor named Dill Harcourt, played by Corey Stoll. However, they eventually split up because of their age gap, with the older Dill saying he was looking for someone with more direction in life.

Back in 2016 when the show first came out, Cooper, who is currently 59 years old, dismissed speculation that he was the basis for the character of Rannells’ partner on screen.

He said he initially saw the person as resembling Bill O’Reilly, telling the New York Post, ‘I’m friends with Andrew, so I should probably ask him about it.’

Cooper said he’s a big fan of the comedy and would be honored if his work influenced the creation of the Dill character by Dunham and Konner.

For Stoll’s part, he said he “did not base this character on anybody.”

In a 2016 interview with Queerty, the actor playfully avoided answering the question, stating, ‘I was playing Dill Harcourt.’

Currently, Jonathan Rannells is dating Tuc Watkins, who he starred with in The Boys in the Band. They’ve been together since 2019.

Bradley Cooper was in a relationship with Benjamin Maisani from 2014 to 2019. Even after they broke up, they decided to co-parent their two sons, Wyatt, who is 6, and Sebastian, who is 4.

Cooper, whose parents were the late Gloria Vanderbilt and Wyatt Emory Cooper, shared on The Howard Stern Show in 2020 that he doesn’t have a traditional family, and considers his friends to be his family instead.

He said he wants his son to have as much love and support as possible, regardless of what happens to him. He also spoke highly of his ex-partner, saying it’s beneficial for a child to have two involved parents when possible.

For more surprising celebrity couples who dated, read on.

Although Brad Pitt and Juliette Lewis played tragic lovers in two films—Too Young to Die? (1990) and Kalifornia (1993)—they actually enjoyed a great connection off-screen.

I’ll always have a soft spot for Juliette Lewis. We were together for a while, even attending the Oscars back in ’92 when she was nominated for Cape Fear – I took her as my date! She’s incredibly talented and we had an amazing time together; honestly, it was one of the best relationships of my life. But you know, growing up, you’re taught that love can solve anything, and I learned that just isn’t true. It doesn’t always work out, no matter how much you care.

It wasn’t just a nostalgic rumor – Matt Damon and Jennifer Garner were actually a couple at the end of the 1990s. The story goes that Gwyneth Paltrow set them up, as she was famously dating Ben Affleck, who is Damon’s close friend. However, they broke up in 2000.

Years later, in a 2004 interview with Playboy, Damon described Ryder as a “great woman.” Ryder herself told Black Book magazine in 2009 that Matt was “a really nice guy” and she felt fortunate they remained friendly.

Oh my gosh, you guys, I was watching the 2003 Kids’ Choice Awards, and the way Justin and Cameron looked at each other when she gave him that award for… Best Burp?! It was electric! Seriously, they were together for almost four years – four years! It wasn’t just some fling. When they actually broke up in 2007, they put out a statement, you know? A whole statement about still loving and respecting each other, even as friends. It was so mature, but also… heartbreaking! I knew it was something special, even then.

While self-love is incredibly important, actress Kristin Davis (known for Sex and the City) enjoyed dating Alec Baldwin during her time on the HBO show.

Kristin discussed an ex-boyfriend on the Literally! With Rob Lowe podcast in February 2025, clarifying that he wasn’t the famous actor—the same man she’d previously loaned $5,000 to before their relationship ended.

Kristin recalled that when she dated Alec Baldwin, he was already very wealthy. She jokingly added that she would have never had to loan him $5,000 if that had been the case.

Kerry Washington, known for her role on Scandal, graced the cover of InStyle Weddings back in 2005 when she was engaged to actor Boris Kodjoe. However, the couple ended their engagement in 2007.

Madonna didn’t publicly talk about her relationship with the rapper, who died in 1996 at age 25, until 2015. During an interview with Howard Stern, she explained that when she appeared on David Letterman’s show in 1994, she was dating Tupac and he had a way of getting her energized and passionate about everything.

Before marrying Jim Toth, Reese Witherspoon starred alongside Jake Gyllenhaal in the 2007 thriller Rendition, and the two were in a relationship for about two years, following her divorce from Ryan Phillippe.

Jake spoke fondly of his ex, saying, ‘She’s one of the most intelligent and resilient people I know—and that goes for a lot of the women I’ve been close to.’

In her 2025 memoir, My Good Side, the former Vanderpump Rules star shared details about her relationship with the Desperate Housewives actor, which happened in the mid-2000s.

One of my favorite parts of dating him was how cozy and normal things felt. We’d often order takeout with his parents at his place, and when it was just the two of us, he’d play guitar and sing to me—’Hey There Delilah’ was a regular! Honestly, it felt like a dream come true, being with someone I’d admired on screen for so long. It was like living a real-life movie!

Before marrying Livia Giuggioli in 1997 (they later separated in 2019), Colin Firth was in a relationship with Tilly for five years. They have a son, William Joseph Firth, born on September 20, 1990, who is also an actor and appeared alongside his father in Bridget Jones’s Baby.

The U.S. Open tennis champion dated actress Mandy Moore from 2003 to 2004, but their relationship didn’t last.

In 2018, Moore shared with Howard Stern that a past relationship had been very painful. She explained that she began dating him at age 18, and he broke her heart. She also noted they were both young at the time.

It’s a long-standing question among music fans: who inspired Alanis Morissette’s famous 1995 song “Ironic”? Many believe it was the Full House star, though Morissette claimed it wasn’t in her 2021 documentary, Jagged. However, some find that hard to believe.

Back in 2005, Ryan Reynolds told People magazine that he was a big fan of his then-fiancée’s music. He jokingly admitted it could be embarrassing when she walked in on him listening to her songs and dancing around in his underwear.

The Canadian band stopped making music together in 2007, and their split after four years was remarkably amicable.

It’s no surprise the Mad Men actress has a type – she likes funny men! She dated Jason Sudeikis for a few months in 2010, and five years later had a short relationship with Will Forte.

Oh my gosh, can you believe it? Matt Damon and Minnie Driver, Will and Skylar from Good Will Hunting—they actually dated in real life! It was like a dream come true for us fans, seeing their on-screen chemistry spill over. But sadly, it wasn’t meant to be. They didn’t get their happy ending, you know? No riding off into the sunset for these two, which totally breaks my heart, honestly.

As a longtime fan, I remember when Damon spoke on The Oprah Winfrey Show back in January of ’98. He shared that he was currently single and had previously been with Minnie, but they’d decided to just be friends. He made it clear how much he cared for her – they were very close and loved each other deeply, but ultimately weren’t a romantic match. He seemed really at peace with that, saying if something isn’t meant to be, you have to accept it.

Okay, seriously? When Matt went on Oprah to talk about us breaking up… it just felt SO wrong! I mean, could he not have handled that privately? Later I told the LA Times how awful it was – honestly, it felt like a really inappropriate place to announce something so personal. It genuinely upset me; it just wasn’t okay!

Liam Neeson and Helen Mirren first connected while filming the 1981 movie Excalibur. They later became a couple—Neeson recalls Mirren teaching him how to drive—but their relationship ended in the mid-1980s.

In a February 2023 interview with ET Canada, Liam Neeson said he felt incredibly fortunate to have shared three or four years of his life with her, describing her as truly special.

Finding love in Jurassic Park? What a meat cute.

Jeff Goldblum and his co-star started dating after they finished filming their hit 1993 movie. Goldblum told the Chicago Tribune he had long admired her talent and personality. He said he was immediately impressed, but they didn’t realize they had a romantic connection until after the film wrapped.

The couple became engaged in 1995, but their relationship ended after two years. They didn’t share the screen again until 2022, when they both appeared in Jurassic World: Dominion, the sixth film in the Jurassic Park series.

Gillian Anderson, known for her role in The X-Files, dated the creator of The Crown from 2016 to 2020. She won an Emmy Award in 2020 for her portrayal of Margaret Thatcher in the popular Netflix series.

According to Arquette, the two dated while filming their 1995 Western Wild Bill.

During a Reddit question-and-answer session in November 2015, the actor from Clueless confirmed a surprising fact: he and the actress had previously dated. They had both appeared in the 1992 TV movie Desperate Choices: To Save My Child.

I dated an actress early on, and we maintained a long-distance relationship for quite a while. I was really head over heels for her.

TopMob News was the first to report that the star of Real Housewives of New York and an actor from Modern Family were dating back in 2015. However, their relationship ended by 2016.

The former student of Southland High School and the actor known for his role as Theo Huxtable on The Cosby Show were a couple for several years, but they broke up in 2013.

Before he became widely known as a bachelor, this celebrity was living with Preston as early as 1987 – well before John Travolta gained fame. They even shared a home and a pet pig named Max, but their relationship ended in 1989.

Yes, Cher truly believes in finding love again. She famously dated actor Kelly McGillis (known for Top Gun) in the 1980s, after her divorces from Sonny Bono and Gregg Allman.

Before he was Heidi Klum‘s ex, the “Kiss from a Rose” musician romanced a different supermodel.

They apparently began dating after working together on the 2005 movie Brick, though their relationship lasted only about six months.

The Dawson’s Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.

Reese Witherspoon and the NCIS: LA actor began dating in 1993, shortly after the then 17-year-old Witherspoon relocated to Los Angeles.

Robert Downey Jr., best known as Iron Man, has spoken openly about how his struggles with drugs and alcohol led to the breakup of his seven-year relationship with Sarah Jessica Parker. In a 2008 interview with Parade magazine, he explained that his lifestyle was incompatible with hers. He acknowledged she attempted to help him but felt frustrated when he couldn’t overcome his issues.

Matthew Perry, best known for Friends, and Zach Galifianakis, famous for The Hangover, reportedly had a brief romantic encounter in 2003, but it was just a short-lived fling and didn’t develop into anything serious.

Kat Dennings, known for her role in 2 Broke Girls, had a short romance with her Thor co-star in 2010. They seemed very close while promoting the Marvel movie at Comic-Con, but the relationship ended before the film came out the next year.

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2026-06-16 05:21