Ashton Kutcher & Mila Kunis
Not only did future spouses and parents of two Ashton Kutcher and Mila Kunis live out the plot 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."
Dyan Cannon
With 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."
Fran Drescher
Turns 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?!"
Matthew Perry
Starting in 2008, the Friends alum was there for actress Lizzy Caplan, 'cause she was there for him too.
While Matthew Perry doesn'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."
Florence Henderson
Here'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 her 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 Morgan
A little Sonja Morgan will spice up any party and apparently that's all businessman Tom D'Agostino needed. Before his marriage to Luann de Lesseps and brief 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?'"
Bradley Cooper
Long 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."
Courtney Love
Looking 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."