Celebrities Who’ve Dated Casually: Mila Kunis, Bradley Cooper, and More!

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Sometimes life really does imitate art. 

In this scenario, both Mila Kunis and Ashton Kutcher disregarded the main themes that ran through their individual romantic comedies from 2011 and decided to experiment with a casual friendship – devoid of any commitments or emotional entanglements.

In 2016, during an interview with Howard Stern, Kunis explained that she starred in “Friends With Benefits,” while he (presumably referring to a male interlocutor) was in “No Strings Attached.” She noted that if we had simply watched these films, we would have known that such relationships don’t typically work out in reality. However, it seems we didn’t take the movies’ advice to heart. We agreed to enjoy ourselves, and as she put it, “We shook hands, we’re like, ‘Let’s just have fun!’

After three months of diligent adherence, I found myself uttering, “This isn’t enjoyable any longer!” It seems the initial excitement had started to wane.

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

In a 2018 conversation on the WTF with Marc Maron podcast, she explained that she felt something like, “I think I should tell you this: I genuinely care about you. I don’t want to risk things getting complicated, so I’m going to take a step back for now.” The next day, he unexpectedly appeared at her house and said, “Let’s move in together,” to which she agreed.

It’s not the case that every agreement made with a handshake leads to a marriage lasting for over a decade and the birth of children, but it can happen in some cases.

Prior to developing feelings for Gigi Hadid, Bradley Cooper was maintaining a superficial relationship with his high school best friend.

In a piece he penned for the Philadelphia Daily News, the intern expressed, “Since we are both about to enter college, it seems sensible that we should make the most of the remaining time before we part ways. After all, once college begins, our bond is likely to revert back to being just good friends again.

It’s not as if there’s an age restriction for casual relationships. In fact, Dyan Cannon has openly admitted that she has several special partners. To quote her from People magazine, she confessed, “Yes, I do have friends with benefits.

If you were to inquire from stars such as Fran Drescher, Sonja Morgan, and Florence Henderson from The Brady Bunch, they would share numerous benefits associated with such a setup. They would explain their strategies for playing the game effectively.

In real life, just as the characters in Ashton Kutcher’s film “No Strings Attached” and Mila Kunis’ film “Friends With Benefits” did, these two individuals experienced a relationship similar to their on-screen roles. However, unlike those films, they ultimately found a genuine and enduring love, achieving a real-life cinematic happily ever after.

After wrapping up filming for “That ’70s Show”, the cast members rekindled their connection at the 2012 Golden Globes and made a decision. As Kunis shared on the “WTF with Marc Maron” podcast in 2018, they simply said, “Let’s hang out. Let’s enjoy ourselves. We’re both single, we trust each other, everything’s good.” However, weeks into their relationship, she started to develop genuine feelings.

In a 2016 interview on The Late Late Show with James Corden, she shared that three months after moving in together, they were already living as a couple. Six months later, they got married and had a child. Essentially, neither of them seemed to have paid attention to the endings of our respective films.

Reflecting on her romantic past, which boasts figures like Cary Grant and Johnny Carson as former partners, Dyan Cannon shared with People at the 2025 Hollywood Beauty Awards, “I’ve been acquainted with many extraordinary men. There are still more exciting relationships to come.

As the dedicated follower of Heaven Can Wait’s actress, I can relate to her sentiments. She isn’t merely seeing a single extraordinary individual; instead, she’s engaging in multiple striking relationships. Moreover, she confides that she has companions who provide mutual benefits, indeed affirming this fact.

It appears that many men find Fran Drescher quite appealing. Despite her divorce from ex-husband Peter Jacobson in 1999, who later revealed he was gay, the actress from “The Nanny” stated that she only offers casual relationships to other gentlemen.

At a March 2025 screening of the film ‘The Friend’, I shared with Page Six that I have a small routine going on in my life. I’m none other than Fran Drescher, so what are your thoughts?

From 2008 onwards, the former Friends star had Lizzy Caplan’s support, since she had offered the same to him earlier.

In his 2022 memoir titled Friends, Lovers and the Big Terrible Thing, Matthew Perry disclosed that he had a six-year relationship with a woman who is known for her role in Mean Girls. This relationship started as a casual “friends with benefits” arrangement. Despite almost getting engaged at some point, they parted ways in 2012.

Reflecting on his past relationship, Perry (who passed away in 2023 due to ketamine overdose) often mused that if he had proposed marriage at that moment, they would likely have two children and a shared home by now.

Here is a tale about a charming woman seeking companionship, following the passing of her husband named John Kappas in 2002.

In a 2015 interview on Today, Florence Henderson from California described her romance with an anonymous Florida resident as delightful each time they met. Comparing their bond to the 1978 film “Same Time, Next Year”, she expressed that while she may not wish to remarry, she does cherish companionship.

At a small gathering, the vibrant woman named Sonja Morgan is bound to liven things up, and it seems that was exactly what wealthy entrepreneur Tom D’Agostino was seeking before his marriage to Luann de Lesseps and short fling with Ramona Singer. Before these relationships, the CEO had an uncomplicated relationship with Morgan.

We’ve each had romantic partners throughout our lives, and as we’re both in our 50s, it’s natural for adults our age. You understand. It was an unspoken agreement, quite discreet.

Initially, upon discovering his connections with Singer and de Lesseps, she exclaimed something along the lines of, “Wow, this is quite astonishing! Could it be that he has an affinity for the ‘Housewives’?

Way back when he hadn’t yet made a splash with my current crush, Gigi Hadid, Bradley Cooper spent his time in the shallow waters of life. At 18, I was just an intern at the Philadelphia Daily News, and this future Academy Award winner was penning tales of young love with his high school BFF, Deborah Landes.

He expressed in a 1993 essay, later shared by Philadelphia Inquirer news writer Tommy Rowan in 2018, that the reason they could surpass that boundary and forge such a strong friendship was because they couldn’t conceive of being anything other than best friends. This becomes clear when people ask if they are dating. To an outsider, it may appear as if they are a couple, but to them, it feels strange to even entertain the idea; yet, from an outside perspective, it might seem like they are boyfriend and girlfriend.

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2025-04-20 10:17