Ashton Kutcher's Marriage Is Full Of Glaringly Obvious Red Flags

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The following article contains mentions of sexual assault.

For people of a certain age, films like "Dude, Where's My Car?" and "The Butterfly Effect," and television series including Fox's "That '70s Show" and MTV's "Punk'd" were practically required viewing. That's because they all starred Ashton Kutcher — one of young Hollywood's "it" actors during the Y2K era of entertainment. From his earliest days as a sitcom star, Kutcher won hearts with his boyish charm and innate comedic timing. As the years have passed, though, he has matured as a leading man and allowed his dramatic chops to shine through. Eventually, he parlayed his fame into success as a venture capitalist in Silicon Valley.

Behind the glitz, the glamour, and the second career as a tech investor, though, Kutcher has been the subject of rumors we couldn't ignore. And his marriage to his former "That '70s Show" castmate, Mila Kunis, has been put under a microscope by observers. While their romantic journey from co-stars and friends to lovers, parents, and partners feels like the stuff Hollywood scripts are made of, Kutcher and Kunis' marriage may even have major cracks hiding in plain sight. 

Here are some of their awkward moments and red flags that have fans questioning what's really going on with the Kutcher's marriage.

Long before there were actually any romantic feelings between the two, Ashton Kutcher and Mila Kunis' characters, Kelso and Jackie, had an on-again, off-again romance throughout "That '70s Show's" timeline (and into its "That '90s Show" spin-off). So, when the two actors shared their first kiss, it actually happened in a scene when they were both young actors. However, if their age gap at the time of the lip lock doesn't induce a double-take — Kutcher was 19 when it happened, while Kunis was just 14 — the circumstances surrounding it surely will.

While guesting on "The Rosie O'Donnell Show" in 2002, the future couple claimed that their "That '70s Show" co-star Danny Masterson nudged Kutcher to get the most out of the moment, offering him a questionable proposition. "I've never kissed a guy," Kunis recalled (via Variety). "I was a 14-year-old little girl and I was extremely scared for my life. [Kutcher] was very nice about it, like, 'Don't worry about it.' Then Danny goes to him and goes, 'Dude, I'll give you $10 if you French kiss her.'" Kutcher confirmed during the 2002 interview that he and Masterson did indeed have a "side bet." However, he and Kunis quibbled about whether Kutcher did enough to win the bet.

Although the anecdote was played for laughs at the time, it hardly elicits the same response today, as evidenced by the reaction it gets when it resurfaces on social media.

Years after their respective breakouts on "That '70s Show," Ashton Kutcher and Mila Kunis — now legitimate movie stars — found themselves appearing in shockingly similar movies in 2011. For his part, Kutcher starred alongside Natalie Portman in "No Strings Attached" while Kunis and Justin Timberlake led the cast of "Friends with Benefits." And in a bizarre case of life imitating art, the former TV co-stars engaged in exactly the kind of relationship that was portrayed in those films around the time of their release.

"If we just paid attention to these movies, we should know that s*** like this does not work out in real life," Kunis said on "The Howard Stern Show" in 2016 (via SiriusXM). "Well, we clearly didn't pay attention, and we shook hands and were like, 'Let's just have fun.' I mean, literally, we lived out our movies." Kunis made it clear that, to that point, even though they had remained friends after "That '70s Show" came to an end, she had never considered getting into a relationship with him, until a chance encounter at an awards show where the two caught the love bug. After the show, the two decided to keep the party going. 

"Long story short, I didn't leave 'til the next morning," Kunis added. "Then we ended up having a lot of talks about how this is a huge mistake and how he needs to go and be single, and I need to go and be single."

Trust, loyalty, and faithfulness are key pillars to any successful relationship, and Ashton Kutcher may have entered his partnership with Mila Kunis at a deficit in those areas, if some of the allegations made by his ex-wife and Golden Globe-winning actress Demi Moore are to be believed. In her 2019 memoir, "Inside Out," Moore wrote that Kutcher talked her into two threesomes that left her feeling shame for having participated. She further alleged that Kutcher later used these experiences to justify his extramarital activity.

"Because we had brought in a third party into our relationship, Ashton said, that blurred the lines and, to some extent, justified what he's done," Moore wrote (via People). Moore further noted that Kutcher admitted to having been unfaithful when she confronted him with the claims of a 21-year-old woman who said she had been with Kutcher. For her part, Kunis apparently left little mystery regarding her feelings while discussing Kutcher's reported infidelity after the fact.

"You were an a**hole," Kutcher recalled Kunis telling him afterward (via an Esquire feature). "Was I?" Kutcher remembered asking her in response, to which Kunis reportedly replied, "Yeah, you were an a**hole for a good two years."

Before he had ascended to the ranks of Hollywood's A-list, one of Ashton Kutcher's claims to fame following his initial "That '70s Show" breakout was his work on MTV's "Punk'd," which saw Kutcher and his co-conspirators (including a young Dax Shepard) play elaborate pranks on celebs. One of the more notable targets during the show's multi-season run was Hilary Duff, who appeared on the show's Season 2 premiere at the height of her Disney fame.

And while fans may or may not recall the prank they pulled on her, Kutcher has been dragged on social media in recent years for a comment he made about Duff (who was then just 15 years old) on the show. As he's setting up the segment with Duff, Kutcher refers to the "Lizzie McGuire" star (via Mr. Pop on X) as "one of those girls that we're all waiting for to turn 18. Along with the Olsen twins." Needless to say, some of the modern reactions to that sentiment have been pretty negative.

"Disgusting then and disgusting now," wrote one X user in response to the clip. "All the Kutcher lovers jump on the 'it wasn't that bad' bandwagon, just because he is who he is," another user commented. "It was not an appropriate comment, then or now." Regardless of the fan responses, though, it's not the kind of statement someone wants to see in connection with their spouse.

When Ashton Kutcher and Mila Kunis finally started dating in 2012, they didn't exactly enter the situation as cleanly as they could have. Rather, both parties were carrying the baggage of their very serious and very public previous relationships. For her part, Kunis had recently split with "Home Alone" star Macaulay Culkin, with whom she had spent the better part of a decade before hooking up with Kutcher. Their split wasn't a happy one, either.

"I had a horrible, horrible, horrible breakup," Kunis revealed during a 2018 appearance on Dax Shepard's "Armchair Expert" podcast. "I f***ed up. Like, I was an a**hole in my 20s, and I'll be the first to admit it. And that's something that took me a long time to come out and be like, 'Yeah, you know what, I was a d***,' and I accept it, and I own it now." Of course, Kunis wasn't the only one who had experienced a messy exit with their previous partner.

Kutcher and Demi Moore officially separated in 2011 — their divorce wasn't finalized until 2013 — and had gone through a lot during their time together. In addition to the alleged infidelity that occurred, Moore reportedly broke her longtime sobriety while they were together. Moreover, the ex-couple suffered through the pain of a miscarriage and years of failed IVF treatments together.

While one might have expected a young couple in love to shout from the rooftops about their relationship, that wasn't the case with Ashton Kutcher and Mila Kunis. As reported by Entertainment Tonight, the couple wed in secret in July 2015 after Kunis had previously been spotted wearing what appeared to be a wedding band. Months earlier, James Corden inquired about the ring on the "Forgetting Sarah Marshall" star's finger when she appeared on "The Late Late Show." But Kunis offered only a "maybe" when Corden asked whether she and Kutcher had tied the knot. 

By that point, the couple had already started their family (despite vastly different parenting styles). It would be almost a full year, though, before Kutcher and Kunis actually acknowledged that they had gotten married. Nevertheless, Kunis maintained that there was no hidden agenda or funny business going on with their relationship during a 2016 interview with Glamour. "We never denied it; we just never talked about it. It was something that didn't have anything to do with anybody else," Kunis told the outlet.

When Ashton Kutcher and Mila Kunis began dating — and later when they started having children together and eventually got married — it was like a Hollywood love story come true. Fans had already seen their electric chemistry as Kelso and Jackie on "That '70s Show;" now, there were real-life fireworks happening.

While the press and the actors' fans were fully on board with the A-list pairing from the jump, though, people in Kunis' life were reportedly taken aback when she and Kutcher escalated their relationship. While guesting on "Armchair Expert," Kunis recounted her mother's NSFW response when the "Jupiter Ascending" star first told her she was dating Kutcher (via Glamour). "We were driving up Laurel Canyon, and I was like, 'Mom, I have to tell you, I'm dating somebody.' And she was like, 'Oh, tell me! Who are you dating?' And I was like, 'You've got to brace yourself for this one. I'm dating Ashton Kutcher.' And she literally was like, 'Shut the f*** up,' in Russian."

More recently, Kunis told the Wall Street Journal (via Q107.5) that her parents "were in shock" when they started dating, leaving us to speculate about what potential red flags may have cropped up in the beginning. At the very least, it is another strange thing about their relationship.

The infidelity that cropped up during Ashton Kutcher's previous marriage to "G.I. Jane" star Demi Moore is practically public record at this point. For her part, Moore spoke out about the darker aspects of their relationship, including extramarital activity, in her memoir "Inside Out." Kutcher, meanwhile, was forthcoming about his bad boy period in the aforementioned Esquire feature. However, the cheating allegations didn't end with Kutcher's divorce from Moore.

In 2013, when Kutcher's romantic relationship with Mila Kunis was still in its nascent stages, one of the women who he was said to have cheated on Moore with reportedly spilled the beans on a new affair. As reported by Hollywood Life, the woman, Sara Leal, was shown a compromising photo of Kutcher by a friend. The picture was said to be accompanied by claims of a relationship between Kutcher and another woman. "It could just be an innocent picture, but I think it's also possible he's not dating Mila exclusively. Not just because of that photo, but because he's cheated before," Leal told Star Magazine (via Hollywood Life). "That would definitely be a red flag for me, if I were dating someone who'd cheated on their wife."

Whether or not those rumblings resulted from true events is difficult to say. A few years later, Star Magazine reported on a potential affair that turned out to be Kutcher hanging out with a relative. "You should have heard how upset Mila was that I spent the day with our cousin," Kutcher later quipped on X. "Sorry Aunt Jodie these magazines lack integrity."

When footage of Ashton Kutcher's inappropriate commentary on Hilary Duff and also the interview where he confessed to trying to tongue-kiss a very young Mila Kunis on a bet resurfaced, it didn't happen randomly. Rather, old skeletons were being pulled from the closet in response to Kutcher and Kunis' move to write letters of support for their former "That '70s Show" co-star and friend Danny Masterson.

In 2023, Masterson, who played Hyde on "That '70s Show," was convicted on two counts of rape and sentenced to 30 years in prison. Despite the heinous crimes he was accused of and the guilty verdict, Kutcher and Kunis both wrote letters to the judge in the case to be used as he weighed the actor's punishment. As noted by The Hollywood Reporter, which obtained the letters, Kutcher called Masterson a "role model" and praised his character, while Kunis referred to him as an "exceptional older brother figure."

Their support of the convicted rapist ignited a firestorm, prompting the couple to post an apology video via Instagram. "[The letters] were intended for the judge to read and not to undermine the testimony of the victims or re-traumatize them in any way. We would never want to do that. And we're sorry if that has taken place," Kutcher said in the video (via "Good Morning America").

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Ashton Kutcher's close relationship with convicted rapist Danny Masterson isn't the only problematic friendship from his past. The "What Happens in Vegas" star also has an extensive history with rapper and music mogul Sean "Diddy" Combs. While many celebrity friendships are, at worst, fodder for the occasional tabloid blurb, Combs was sentenced in 2025 to 50 months in prison after being convicted on two counts of transportation for prostitution. And Kutcher's connection to him and past attendance of Diddy's infamous White Parties, which have been described (via Grazia) as "elaborate and produced sex performances," has raised eyebrows.

During his 2019 appearance on "Hot Ones," Kutcher did little to dispel the mythos surrounding Diddy's parties when he was asked about them, telling host Sean Evans, "Wow, okay, I've got a lot [of stories] I can't tell," Kutcher said. "Diddy parties stories. Man, that was, like, some weird memory lane." In the years since the interview was uploaded to YouTube, fans have raised questions about what the actor may have seen or been involved in.

This much is certain — between Kutcher's friendship with Diddy, attendance at the rapper's parties, and his association with and support of Masterson, there's no shortage of potential red flags.

Perhaps the biggest red flag regarding Ashton Kutcher's marriage to Mila Kunis is the fact that divorce rumors have swirled around them at various junctures throughout their partnership. As noted by The Latin Times, the two were said to be on less-than-great terms and even considering divorce back in 2019. The couple's problems were reportedly being exacerbated by Kutcher seeing no reason to go to marriage counseling, per a so-called insider. "Their issues are always bubbling under the surface," the insider reportedly told L&S, "and sweeping them under a rug is not a solution for Mila."

The couple has remained married despite those rumors, but rumblings of discontent have persisted amid the intense scrutiny Kutcher and Kunis have received via their connection to Danny Masterson and Sean "Diddy" Combs (who's now having a harrowing experience in prison, according to his lawyers). In 2024, a source told People that there was no truth to online rumors that Diddy's legal trouble was putting a strain on their marriage. However, in 2025, a potential separation was still being written about in the press, with sullen-looking photos of the actors fanning the flames.