Mila Kunis And Ashton Kutcher's Relationship Is Overflowing With Red Flags

Mila Kunis and Ashton Kutcher have been married for over a decade. Which, in Hollywood, is basically forever. Having first met in 1998 on the set of "That '70s Show," where the two played an on-again, off-again couple, it wouldn't be until 2012 before the two would get together in real life. In fact, when Kunis and Kutcher worked together, they weren't even friends.

"Everyone shakes their head over the romance," a longtime friend of the couple told Radar in March 2014. "Ashton and Mila were absolutely not friends during much of the making of 'That '70s Show'... they couldn't stand working together." Even Kunis has admitted that she was less than impressed with Kutcher for a while. "We went through a period where I thought he was crazy," Kunis told Glamour in 2016. "At the height of his career, I was like, 'Ugh, I don't like you. I don't even know you anymore. You think you're such hot sh**.'"

But somewhere along the line, after Kutcher's marriage to Demi Moore ended in divorce and Kunis' relationship with Macaulay Culkin had run its course, the two made their way back to each other. While Kunis and Kutcher may be the first to sing each other's praises, the reality is that their relationship is riddled with peculiarities. So much so that when it comes to red flags in Hollywood relationships, Kunis and Kutcher are pretty darn high up on the list.

Before Mila Kunis and Ashton Kutcher started dating, they decided to keep it so casual that they intended to only be friends with benefits. But is having sex with a friend ever a good idea? Frankly, it's complicated and requires some rules if it's going to work without anyone getting hurt. "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*** like this does not work out in real life," Kunis told Howard Stern on "The Howard Stern Show," in July 2016, about her reunion with Kutcher in 2012. "Well, we clearly didn't pay attention, and we shook hands and were like, 'Let's just have fun.'"

It didn't take long for the fun to evolve and for the two to begin officially dating, but without any long-term plans. "We started dating with the idea that we both were never going to get married," Kunis told Stern, explaining that she never believed in marriage, and because they'd both just gotten out of relationships, it wasn't even on their radar. "I was single and having the best time ever," said Kunis.

However, in 2014, the couple got engaged, then married the following year. However, they kept the fact that they were married a secret for over a year, not going red carpet official until 2017. "We never denied it; we just never talked about it," Kunis told Glamour in 2016. "It was something that didn't have anything to do with anybody else."

As much as one may want to dismiss the theory that once someone's a cheater, they're always a cheater, there is something to it. According to a 2017 study published in the Archives of Sexual Behavior, people who cheat in one relationship are three times more likely to cheat again in future relationships. That being said, Ashton Kutcher not only has a history of cheating, but he's also one of the handful of celebrities who have admitted to cheating on their partners.

In her 2019 memoir, "Inside Out," Demi Moore detailed how she found out that Kutcher was cheating on her with a San Diego-based administrative assistant named Sara Leal. As Moore told Diane Sawyer in 2019 on "Good Morning America," she found out about the cheating when she received a Google alert when Leal shared her story with Us Weekly in October 2011. Moore immediately confronted Kutcher, who didn't deny it.

Just two years later, in 2013, Leal again made headlines when she alleged that Kutcher was cheating on Mila Kunis with a friend of a friend, and that she had the pictures to prove it. "It could just be an innocent picture," Leal told Hollywood Life in February 2013, explaining that she wasn't sure about the relationship status of Kutcher and Kunis. "That would definitely be a red flag for me, if I were dating someone who'd cheated on their wife," said Leal.

Ashton Kutcher had been buddies with rapper Sean Combs, aka "Diddy," for years, having spent time with Combs one-on-one and attending multiple parties that Combs was known for throwing. Granted, their friendship didn't mean much until Combs was arrested in September 2024, having been charged with sex trafficking and racketeering, per The Guardian. When that happened, everyone with ties to Combs was suddenly under a magnifying glass, as the rest of the world wondered what these friends were privy to during those infamous parties.

In 2019, when Kutcher appeared on "Hot Ones," he basically said that what went down at those parties wasn't exactly on the up and up. When asked to share an anecdote, Kutcher couldn't. "Wow, okay, I've got a lot I can't tell," Kutcher said. After he started to tell a story, Kutcher stopped himself, saying, "I can't tell that one either ... I'm like cycling through them." Ultimately, Kutcher told a story about the two going for a run and how the experience inspired Combs to train for the New York City Marathon.

Even before Combs and his freak-offs came into the spotlight, both Kutcher and Mila Kunis wrote letters of support for convicted rapist and former co-star of "That '70s Show," Danny Masterson. According to the BBC, in Kunis' letter, she called Masterson 'an outstanding role model and friend,' as well as an 'exceptional older brother figure,' while Kutcher wrote that Masterson treated people 'with decency, equality, and generosity.' It was only after the backlash that followed that the two would change their tune. But the original letters had already spoken volumes.

If infidelity, being friends with Sean Combs, and defending Danny Masterson weren't enough, Ashton Kutcher has proven his shadiness in other ways. For example, when Kutcher and Mila Kunis were filming "That '70s Show," and their characters had to kiss, Kutcher was 19 at the time, and Kunis was only 14. Despite the age difference and Kutcher being aware that kissing a 14-year-old girl wasn't exactly kosher, because his co-star, Danny Masterson, bet him $20 he wouldn't slip Kunis the tongue, Kutcher did it.

When Kunis said on "The Rosie O'Donnell Show" in 2002 that Kutcher never kissed her with is tongue, Kutcher responded, "I so did it!" Just one year later, in 2003, while hosting "Punk'd," Kutcher, who was then 25, made a pretty disgusting comment about Hillary Duff, who was then 15, and the Olsen twins, who were 17. After he introduces Duff, who was about to be punk'd, Kutcher added, "She's one of the girls that we're all waiting for to turn 18 — along with the Olsen twins."

In 2015, Kutcher, who was already married to Kunis, was spotted leaving a massage parlor in North Hollywood, according to The Sun, via Daily Mail. While there's nothing unusual about getting a massage, there are two things that are suspect about this situation: a man of Kutcher's fame and fortune would probably patronize a high-end spa for a massage, and, secondly, employees at a nearby restaurant reported that only men frequented that particular parlor. "Men are in and out at all hours of the day [and] night," an anonymous source told Hollywood Life in 2016.

While there are many celebrity couples out there normalizing couples therapy, don't expect Ashton Kutcher and Mila Kunis to become members of that club. In 2019, divorce rumors about Kunis and Kutcher began to swirl, and some of that had to do with the latter not taking their relationship seriously enough. According to Life & Style, via Latin Times, a source close to the couple said Kunis had given Kutcher an ultimatum and was desperate to get the two into therapy.

"Her married friends and even some of her friends who aren't married are in counseling," the source said, adding that Kutcher didn't think they had problems worthy of counseling. "There's no stigma about it, but Ashton says he's just not into it or he's just too busy." As a way to get out of therapy, the source said Kutcher suggested they renew their wedding vows instead. Kunis nipped that in the bud, because she believed that would merely be a band-aid and not fix their core relationship problems.

In response to the rumors, the couple posted a video on Kutcher's Instagram making light of the headline. Good for Kunis and Kutcher for having a sense of humor about the whole thing, but as the saying goes, "there's a grain of truth to every rumor." Even if Kutcher refuses therapy, let's hope Kunis is talking to a professional to better navigate her partner's problematic behavior, of which there seems to be a lot of.