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Mila Kunis and More Stars Who Have Tried Friends With Benefits

Watch: Mila Kunis Reveals Why No One In Her Life Saw Ashton Kutcher Romance Coming

Sometimes life really does imitate art.

Such was the case when Mila Kunis and Ashton Kutcher entirely ignored the core messaging that was at the heart of their separate-but-basically-the-same 2011 rom-coms to take a stab at being friends with benefits—no strings attached.

“I did Friends With Benefits, he did a movie called No Strings Attached,” Kunis recounted to Howard Stern in 2016, detailing Kutcher’s January 2011 rom-com with Natalie Portman and her July 22, 2011, release opposite Justin Timberlake. “If we just paid attention to these movies, we should know that s–t like this does not work out in real life. Well, we clearly didn’t pay attention. We shook hands, we’re like, ‘Let’s just have fun!'”

Diligently following the scripts laid out in each film, about three months in, admitted Kunis, “I was like, ‘This isn’t fun anymore!'”

And so she paid a visit to her former That ’70s Show costar.

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Ashton Kutcher & Mila Kunis: Romance Rewind

“I was like, you know what, ‘I actually care about you. I don’t want to mess anything up so I’m just going to walk away before it becomes too much,'” she explained during a 2018 appearance on the WTF with Marc Maron podcast. “And he was like, ‘Got it.’ And the next day, he showed up to my house and he was like, ‘Move in with me’ and I said, ‘Okay.'”

Not that that every sealed-with-a-handshake pact ends with an 11-years-and-counting marriage and a couple of kids.

Long before he was giving Gigi Hadid a second look, Bradley Cooper was keeping things shallow with a high school BFF.

“Because we are both seniors, I realize that we might as well just enjoy the time we have left before we go to college,” the then-intern wrote in a 1993 op-ed for the Philadelphia Daily News. “Because once college hits our relationship will definitely return to ‘best friendship.'”

Not that there’s an age limit on casual situationships. Dyan Cannon revealed last year that she’s been seeing “several” special partners. As she put it to People, “I have friends with benefits, yes.”

And if you ask stars like Fran Drescher, Sonja Morgan and The Brady Bunch‘s Florence Henderson, there are plenty of upsides to that sort of arrangement.

Here’s how they play the game.

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Ashton Kutcher & Mila KunisNot only did future spouses and parents of two Ashton Kutcher and Mila Kunis live out the plots of their respective films No Strings Attached and Friends With Benefits IRL, they got the cinematic happily ever after. Years after filming That ’70s Show, the stars reconnected at the 2012 Golden Globes and made a pact. “We were just like, ‘Let’s just hook up. Let’s have fun. We’re both single. We both trust each other. Everything’s great,'” Kunis recounted on the WTF with Marc Maron podcast in 2018. Weeks in, though, she flipped the switch, admitting to having real feelings. “Three months later we’re living together,” she detailed during a 2016 appearance on The Late Late Show with James Corden. “Six months later we’re, like, married and have a kid. Like, literally, we clearly did not watch the end of either one of our movies.”

Photo by Amy Sussman/Getty Images

Dyan CannonWith a romantic history that includes former husband Cary Grant and talk show host Johnny Carson, “I’ve known a lot of special men,” Dyan Cannon admitted to People at the 2025 Hollywood Beauty Awards. “And there’s more to come.” Because as the Heaven Can Wait actress put it, she’s not just seeing someone special, she’s dating “several” standout guys, adding, “I have friends with benefits, yes.”

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Fran DrescherTurns out a lot of men find Fran Drescher beguiling. Still “very close” to ex-husband Peter Jacobson—they divorced after two decades of marriage in 1999 and he later came out as gay—The Nanny alum said the most she can offer other guys is a casual situation. “I have a little rotation,” she explained to Page Six at a March 2025 screening of The Friend, adding, “I’m Fran Drescher. What do you think?!”

Matt Baron/BEI/Shutterstock

Matthew PerryStarting in 2008, the Friends alum was there for actress Lizzy Caplan, ’cause she was there for him too. While Matthew Perry didn’t mention the Mean Girls star by name in his 2022 memoir Friends, Lovers and the Big Terrible Thing, he revealed that their six-year romance began as a “friends with benefits” situation. And though they nearly got engaged at one point, they ultimately separated in 2012. Admitting he was haunted by their breakup, Perry—who died in 2023 from acute effects of ketamine—said he frequently thought that if he’d proposed “now we’d have two kids and a house.”

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Florence HendersonHere’s the story of a lovely lady who was just trying to find some company after the 2002 death of husband John Kappas. “When we see each other it’s wonderful,” California-based Florence Henderson explained on Today in 2015 of maintaining a romance with an unidentified Florida resident. Comparing their connection to the 1978 movie Same Time, Next Year, the Brady Bunch alum added, I don’t know that I would want to be married again, but I do love companionship.”

Sonja MorganA little Sonja Morgan will spice up any party and apparently that’s all businessman Tom D’Agostino needed. Before his brief marriage to Luann de Lesseps and even shorter romance with Ramona Singer, the CEO enjoyed a no-strings-attached arrangement with Morgan. “He always had a girlfriend and I always had a boyfriend, so it was in between, as adults do at our age, you know,” The Real Housewives of New York cast member explained to E! News in 2016. “We’re both in our 50s, so it’s like…it is what it is. But it was a nice understanding, very discreet.”Though, admittedly, when she’d learned about his relationships with Singer and de Lesseps, “I’m like, ‘Oh my gosh, this is really crazy. Does he have a thing for Housewives?'”

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Bradley CooperLong before he crashed through the surface with now-girlfriend Gigi Hadid, Bradley Cooper enjoyed his time in the shallows. As an 18-year-old intern at the Philadelphia Daily News, the future Oscar winner wrote about romancing high school bestie Deborah Landes.”The reason that we are able to cross that line and obtain that great friendship is that we really don’t know how to be anything other than best friends,” he wrote in the 1993 essay, shared by Philadelphia Inquirer news writer Tommy Rowan in 2018. “I realize this when people ask me if we are going out. It sounds too weird to even imagine; however, to an outsider, it probably looks as if we are boyfriend and girlfriend.”

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Courtney LoveLooking to fill an, er, hole in her life, rocker Courtney Love came up with the perfect solution. “I’m a libertine,” Love shared during a June 2025 episode of Fashion Neurosis with Bella Freud, “and the person that I most do my romantic crap with is also a libertine, so we are really more friends with benefits.”But that’s all she’d like to say about that. Noted the mom to Frances Bean Cobain, her daughter with late husband Kurt Cobain, “I don’t like talking about them, because there’s jealousy around that person.”

(Originally published April 20, 2025, at 3 a.m. PT)

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