In a world where romantic comedies often blur the lines between fiction and reality, the love story of Mila Kunis and Ashton Kutcher stands out as a real-life reflection of their on-screen roles. After starring in separate but thematically similar films in 2011—No Strings Attached and Friends With Benefits—the two actors found themselves embarking on a casual relationship that quickly evolved into something much deeper.
Kunis recounted the early days of their relationship during a 2016 interview with Howard Stern, where she humorously acknowledged their disregard for the lessons taught by their respective films. "I did Friends With Benefits, he did a movie called No Strings Attached. 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!'
However, as Kunis later revealed in a 2018 appearance on the WTF with Marc Maron podcast, the fun didn’t last long. Just three months into their arrangement, she realized that it wasn't as enjoyable as she had hoped. "I was like, 'This isn't fun anymore!'" she admitted. Concerned about the potential for deeper feelings, Kunis decided to step back, telling Kutcher, "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." In a twist of fate, the very next day, Kutcher showed up at her house with a proposal to move in together, to which Kunis agreed.
The couple's relationship blossomed rapidly from there. Kunis shared on The Late Late Show with James Corden in 2016 that within three months of moving in together, they were already married and had welcomed their first child. "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," she quipped, highlighting the irony of their situation.
While Kunis and Kutcher's story is a standout example of a friends-with-benefits arrangement turning into a lifelong partnership, they are not alone in navigating the complexities of modern relationships. Dyan Cannon, a veteran actress known for her relationships with Hollywood legends like Cary Grant and Johnny Carson, recently opened up about her own romantic escapades. At the 2025 Hollywood Beauty Awards, she told People that she has been dating "several" standout men, adding, "I have friends with benefits, yes."
Fran Drescher, another Hollywood figure, has also embraced the casual dating scene. At a March 2025 screening of The Friend, she told Page Six that she maintains "a little rotation" of men. Her confidence shines through as she quipped, "I’m Fran Drescher. What do you think?!"
Matthew Perry, the late star of Friends, provided insight into his own complicated romantic history in his 2022 memoir, Friends, Lovers and the Big Terrible Thing. He revealed that his six-year relationship with actress Lizzy Caplan began as a friends-with-benefits situation in 2008. Although they nearly got engaged, the couple ultimately parted ways in 2012. Following Perry's tragic passing in 2023 from acute effects of ketamine, he reflected on their breakup, expressing a sense of regret over lost opportunities, stating he often thought that if he had proposed, "now we'd have two kids and a house."
Florence Henderson, best known for her role in The Brady Bunch, also shared her thoughts on companionship after the death of her husband in 2002. In a 2015 interview on Today, she spoke about her romance with an unidentified Florida resident, likening their connection to the film Same Time, Next Year. Henderson expressed that while she enjoys companionship, she is not necessarily seeking marriage again.
Sonja Morgan, a prominent figure from The Real Housewives of New York, recounted her own no-strings-attached relationship with businessman Tom D'Agostino before his marriage to Luann de Lesseps. In a 2016 interview with E! News, she described their arrangement as a discreet understanding, noting, "He always had a girlfriend and I always had a boyfriend, so it was in between, as adults do at our age, you know." However, she admitted to feeling surprised when she learned of his relationships with other reality stars.
Bradley Cooper, who has recently been linked to Gigi Hadid, also shared his experiences with casual relationships. As an intern at the Philadelphia Daily News, he penned an op-ed reflecting on his high school friendship with Deborah Landes, describing their dynamic as one where they could not easily transition from friends to something more. In a 1993 essay shared by Philadelphia Inquirer news writer Tommy Rowan in 2018, Cooper wrote, "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."
As the lines between friendship and romance continue to blur in the modern dating landscape, these stories illustrate the varying paths individuals take in their pursuit of love and companionship. From Kunis and Kutcher's whirlwind romance to Cannon's open dating life, each narrative offers a unique perspective on the complexities of relationships today. Whether through casual arrangements or deep emotional connections, one thing remains clear: love, in all its forms, continues to be a captivating subject for both the stars and their fans alike.
