Inside Ashton Kutcher's Relationship With Rumer Willis

It's a relationship that played out largely in the public eye, between two members of Hollywood's most intriguing extended family. In the years following Ashton Kutcher's well-publicized split from actress Demi Moore back in 2011 (and subsequent divorce in 2013,) the former star of That '70s Show has reportedly maintained a friendly relationship with Moore's daughter, Rumer Willis — the eldest of three sisters, all from Moore's previous marriage to Bruce Willis. (The other two siblings are Scout and Tallulah.) In September 2018, Ashton and Rumer inspired a fresh batch of headlines after The Blast reported that Kutcher and his wife, actress Mila Kunis, had signed over a Hollywood Hills property to Rumer, his former stepdaughter.

Although People reports Kutcher and Rumer haven't been seen in public together since he split from her mother (that's up for debate), the real estate news rekindled interest in their relationship, and for good reason. Before Kutcher started dating her way-famous mom, Rumer thought the actor was a "heartthrob." She's the first to admit the whole scenario was rather "weird," but the two bonded, and Kutcher proved to be highly supportive of Rumer's various creative endeavors. "When Ashton came into our lives, he was just an extension of our family," she told the Daily Mail in 2009. "He's like a friend as well as a stepdad."

Let's take a closer look inside the never-not intriguing relationship between Ashton Kutcher and Rumer Willis.

Did you have a celebrity crush growing up? Well, imagine if that crush showed up on your doorstep one day and started "hanging out" with one of your parents. If you pause to consider this scenario, you'll start to understand how Rumer Willis probably felt back in 2003, when Ashton Kutcher started dating her mom, actress Demi Moore. (Kutcher was 25, and Moore was 41 at the time.)

After a short period of adjustment, Willis reportedly took Kutcher's entrance into her celebrity family circle in stride. Powwowing with a Daily Mail scribe in 2009, she admits she once had a crush on Kutcher, long before he became part of her family. "Ash was a heartthrob to me," she confessed. "I had pictures of him on my wall at boarding school." Reminiscing about the day her mom announced a new "friend" named Ashton was coming by the house to "hang out," Willis said the news initially rattled her.

"I said, 'Whoa, wait — Ashton Kutcher?' and I kind of freaked out a little bit. I definitely blushed." But Kutcher and Willis quickly bonded: "We talk about everything — auditions, boyfriends, family. He understands more than my parents sometimes because he's closer to my age."

So when Demi Moore started dating Ashton Kutcher, Rumer Willis was out one poster, but she gained a new "father-slash-older brother figure," as she referred to Kutcher in an interview with Cosmopolitan in 2008. Speaking to Howard Stern in a 2015 interview, she recalled: "I feel like I told my sister that, 'Man, ugh, alright, gotta cross him off the list'" (via Entertainment Tonight.) It was a glamorous turn of events, yes, but also rather bizarre: "It was definitely weird for a minute," she acknowledged, "but I have to commend him, he was a really great stepfather and the perspective shifted very quickly." 

In order to cope with this adjustment, Willis made herself exorcise all carnal thoughts of Kutcher by scouring through teenybopper mags for a brand-new imaginary lover: "That's when you open up your Teen Beat and then you just take him down [from your wall], find someone else and put him up." (We have not all been there.)

Willis was also quite proud of her mom for snagging a specimen as handsome as Kutcher: "I feel like I was kinda impressed. I was like, 'Yeah girl, get it, alright.'" (You know — the whole "Get it, mom!" bit.) In 2009, Willis told the Daily Mail that she "got over any strangeness because I'd never seen my mom happier." She compared Kutcher and Moore's relationship to "two 16-year-olds who were going to the prom together."

Tabloid editors must have been disappointed in Rumer Willis and Ashton Kutcher. They reportedly remained on good terms — even after Kutcher and Demi Moore finalized their divorce in 2013, in the wake of several cheating allegations. 

In May 2012, the Daily Mail tried making a big deal out of Willis and Kutcher being spotted in Kutcher's car in Los Angeles, even going so far as to suggest they were "meet[ing] secretly." According to the tabloid, "They didn't want to be spotted, and when they were, Ashton covered his face and Rumer tried to lie back in her chair ... to no avail." We imagine this had less to do with what they were doing, and more to do with the fact that the paparazzi was swarming the vehicle.

Willis congratulated Kutcher and his second wife — his former That '70s Show co-star Mila Kunis — upon the birth of their first child, Wyatt Isabelle. "I reached out to him when he [and Mila Kunis] had the baby, which is so awesome," Willis told Access Hollywood in November 2014. By the time of the interview, Willis had even seen some photos of Wyatt Isabelle. "She's very cute," she said. "I realized the other day, [Kutcher] was a year younger than me when he and my mom started going out. It would be like me meeting someone who already had three teenage kids."

In short: "Going into that situation was crazy."

It sounds like quite the night: Rumer Willis, in concert. Us Weekly boldly proclaimed it was a "showstopping performance," and on that fateful evening in March 2012, Kutcher reportedly slipped discreetly into The Sayers Club in Los Angeles to support his ex-wife's daughter. He was nonetheless spied on the premises in a "white T-shirt and a red flannel knit." (Noted!) An omniscient super-spy gave Us Weekly their full report: the former Two and a Half Men star "immediately joined Rumer's large table," and "Rumer seemed happy to see Ashton there, supporting her on her big night."

Apparently Willis "didn't say a word before taking the small stage," but she eventually burst into song, belting out such chestnuts as Otis Redding's "Sittin' on the Dock of the Bay." (She's classically trained, by the way.) Kutcher reportedly rose from his seat to get closer to the action. According to the source, who must not have been paying close attention to the actual show, Kutcher "smiled as he slowly bopped his head along to her song ... He was beaming!" 

Us Weekly's hawk-eyed celebrity sleuth also noted that Kutcher gave Willis a "solid ten-second hug" after the performance and then bolted, as "he was strictly there to support Rumer." Also worth noting: Kutcher was equally supportive of Willis' stint on Dancing with the Stars in 2015, tweeting: "Rumer I'm so proud of you. You are an artist of movement."

Despite the fact that Ashton Kutcher and Demi Moore divorced in 2013, Kutcher's bond with Rumer Willis reportedly remains tight to this day. In fact, in June 2015, Kutcher took to Facebook to praise a think piece by Willis and contributor Shaun Dreisbach in Glamour magazine. In the piece, Willis says, "When you grow up in the public eye the way that I did, everyone's looking at you and waiting for you to do something crazy or say something wrong or have a meltdown." She reveals that she was "constantly bullied" over her appearance while growing up and "struggled a lot with my body image." She insisted that "life's hard enough as it is. Let's find strength in the fact that we're different and unique."

"It's amazing that you're telling your story and speaking up for other women," Kutcher responded on Facebook. (The article was also shared and analyzed on Ashton Kutcher's A Plus website.) In response to a fan, Kutcher also wrote on Facebook (via E! News): "She's going against the grain and that's exactly what needs to be done. She's helping other girls realize that they don't need validation from others." 

One tabloid did manage to find a source who claimed things weren't always so fabulous between Ashton Kutcher and Rumer Willis. According to Celebs Now, Willis had something of a meltdown in 2011, and it allegedly had everything to do with the rumor that Kutcher had cheated on her mom, Demi Moore, with a woman named Brittney Jones (a claim Kutcher furiously denied.)

"Since those allegations, Rumer refuses to hang out with her mum and be at the family house," the insider alleged, conveniently dishing the dirt in thick slabs of scandalous copy: "Deep down [Demi] knows she's only mad because she loves her so much and hates to see her hurting, but she's going over the top by refusing to come to the house." In 2012, Star claimed "Rumer Willis wasn't by fragile Demi's side" when her mom got out of rehab (via Celebitchy.) That tab suggested Willis "was hanging out at a nightclub with the man who sparked Demi's breakdown in the first place — Ashton Kutcher!"

We have no idea if any of this is true, but Kutcher apparently feels that this kind of negative press nurtures the soul. Upon accepting the Robert D. Ray Pillar of Character Award in 2017, he reportedly said: "Character comes when those magazines tear you apart for something you may or may not have done and you gotta go out and perform tomorrow — with everyone looking at you like you might be an adulterer."

It's a tiny tidbit that cooked up a tremendous amount of headlines: In September 2018, The Blast reported Ashton Kutcher had effectively let go of one of the last Earthly objects tied to his previous marriage to actress Demi Moore: the house he'd co-owned with Rumer Willis.

In 2009, Willis and Kutcher plunked down $971,500 to purchase a sprawling Hollywood Hills home, but documents filed Aug. 3, 2018, indicated that the co-ownership was effectively dissolved: "All debt owing under the note, deed of trust and any related loan documents has been deemed paid and satisfied in full," it read in part. As Nicki Swift previously reported, Kunis also signed onto the property back in 2015, when she and Kutcher got married. The couple went ahead and filed new grant and quitclaim deeds (reportedly at the same time Willis' court documents were filed.) Without getting too deep into the legalese of it all, the bottom line is that Willis is now the sole owner of the two-bedroom, four-bathroom property.

As Vanity Fair dramatically puts it, "Ashton Kutcher Finally Let Go of One Last Thing from His Marriage to Demi Moore" — a headline that suggests VF editors have been primly ensconced in their offices since 2011, patiently waiting for the actor to get his life together.

Expect great things from Rumer Willis — just don't count on her to look after Ashton Kutcher's children. Babysitting daughter Wyatt Isabelle and son Dimitri Portwood Kutcher is reportedly out of the question for the foreseeable future. "I mean, I have so many babies to babysit, I don't know if I have time," Willis told Access Hollywood in November 2014 (via Us Weekly.)

She had a point. At the time that article was published, her half-sister, Mabel, was only 2 years old and her other half-sister, Evelyn, was six-months old. (They're both the children of Bruce Willis and his second wife, model Emma Heming.) In case we haven't yet painted a chaotic, overstuffed portrait of Rumer's familial life, we'll go ahead and once again mention her two younger sisters, Scout and Tallulah, who were 23 and 20 in 2014, respectively.

In the same interview, Rumer talked about Scout's "Free the Nipple" campaign, a micro-controversy at the time. "Scout has always been one of those people that whenever she has an idea or wants to stand behind something, she's always that way," Rumer said. She also discussed Tallulah's recent stay in rehab: "I think when you grow up the way that we have and you have such attention focused on you, you get to the point where if you hide things, it does no good."

Ashton Kutcher and his second wife, Mila Kunis, welcomed their first child, Wyatt Isabelle, on Oct. 1, 2014 ... but Kutcher already felt like he had plenty of experience as a father, thanks to his time helping raise Rumer Willis and her two sisters. "I'd been a parent to teenage girls before in my life," he told The Talk in 2014 (via the New York Daily News.) Raising babies, on the other hand, was altogether new: "We really started studying what it is to take care of a baby and how you do it, and the whole thing."

The relationship between Rumer and Kutcher has inspired plenty of speculation over the years, but as E! Online's Ted Casablanca put it in 2012: "It's not as scandalous as [some] make it seem. [Willis and Kutcher] have a relationship and it makes sense that they would have contact even after Ashton's marriage to her mom ended." As Kunis told the WTF with Marc Maron podcast in July 2014, Kutcher's relationship with all three of Moore's daughters was a meaningful one and not mere tabloid fodder: "They had three kids they were raising," she said (via People.) "It was, like, a normal life. He was younger but he loved those kids."