All Of The Olsen Twins' Former Partners

For many millennials, the story of Mary-Kate and Ashley Olsen aligns with their own development into adulthood, with the sisters symbolizing the realization of girlboss aspirations. The twins were still in diapers when they first shot to stardom as Michelle Tanner in "Full House," and they were mere tweens when cast in a string of comedy flicks in the '90s and early 2000s. Having survived the pitfalls of child stardom, they ascended to the top echelons of business and founded numerous companies together, most notably the luxury fashion label The Row. In many ways, the sisters are trailblazers, killing it as celeb fashionistas in an era before fashion design became the mandatory side hustle of A-listers. "Dualstar started when we were six," Ashley told Vogue in 2011. "We had a collection with Walmart at twelve, which was the upper tier of the tween market. It was before celebrity designers."

Despite being in the limelight from the moment they left the womb, Mary-Kate and Ashley have largely kept their private lives under wraps. Both sisters are surprisingly tight-lipped when pressed on their relationships, opting to be known for their professional output as opposed to their romantic conquests. But in January 2023, Ashley found herself generating headlines when it was revealed that she'd secretly wed her long-term boyfriend, artist Lou Eisner, a few days after Christmas. Now that Ashley is off the market — and, if rumors are to be believed, her sis may be following suit — let's take a look at all of the Olsen twins' former partners.

Film producer Matt Kaplan is believed to be Ashley Olsen's first boyfriend. The pair met when they were in high school and began dating circa 2003, when Olsen was 16 and Kaplan was 18. Despite her A-list status, Olsen was adamant that she and Kaplan were like any other teen couple, opting to forgo fancy dates. "We go out to dinner, go to a movie. It's pretty boring," Olsen told Rolling Stone of her love life. She also noted that her twin would often accompany her on said dates, testament to their close bond.

Unfortunately, this youthful romance was not to be. In 2004, the couple called it quits. The split was amicable, but the teen twosome struggled to maintain a long distance relationship. Olsen had alluded to these struggles when speaking to People earlier that year. "It's been hard," she conceded. "A long-distance relationship is tough, no matter what." In an unusual twist of fate, Kaplan reportedly began dating another 2000s teen star, Lindsay Lohan, following his break up with Olsen (interestingly, there's a fair amount of overlap between these two former child stars' love lives), per SFGATE.

Shortly after her split from Matt Kaplan, Ashley Olsen found new love with restaurateur Scott Sartiano, who is over a decade her senior. It was Olsen's "Full House" co-star, John Stamos, who introduced her to Sartiano.

The couple courted controversy when tabloid the National Enquirer published a story alleging that Olsen was misusing drugs, which she supposedly procured from Sartiano, an alleged drug dealer, as People reports. The Enquirer published an unflattering photo of Olsen apparently looking "drugged." She denied the claims and subsequently sued the tabloid for $40 million. However, the lawsuit was soon dismissed.

After a few months of dating, Olsen and Sartiano broke up, with sources suggesting that the relationship soon turned toxic. She was peeved that Sartiano sought to surround himself with models despite having his stunning girlfriend by his side. "Scott's constantly surrounded by models who are all over him and desperate to get into clubs," an insider dished to Star (via Glamour). "Ashley didn't understand why Scott hangs out with people like that." Meanwhile, another source explained that Ashely grew sick of constantly being compared to and pitted against said models: "Every weekend it's all about these supermodels who are hotter, older, more mature than Ashley is — and taller. Ashley just didn't want anything to do with it anymore."

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Ashley Olsen swiftly moved onto another older man, actor Jared Leto, who is 15 years her senior. In 2005, the New York Post did a profile on Leto's alleged predilection for teenage girls, noting that he and Olsen had recently dated (Olsen was 19, while Leto was 33). The romance appeared to fizzle for a bit, lasting all but 30 seconds, until the couple reunited in 2008. Olsen and Leto were spotted locking lips at an art gala. "They looked like a couple and they were making out," a source dished to Us Weekly (via Observer). However, Olsen insisted that they were just pals.

The former couple appeared to reignite their romance in 2012 when they were seen grabbing dinner in Beverly Hills. Insiders claimed that the pair couldn't keep their hands off each other, with Leto allegedly playing with Olsen's hair and Olsen putting her head in her beau's lap. Four years later, they had a surprise reunion at the Met Gala. Leto resembled a sort of Svengali Mad Hatter as he posed between the forever frowning Olsen twins. However, this appeared to be nothing more than an impromptu reunion, and there were no suggestions that Olsen and Leto were rekindling their on-again-off-again fling for a fourth time.

Before he was hailed a national disgrace due to doping, Lance Armstrong was an American hero, the kind who dated Olsen twins. Armstrong and Ashley Olsen were first spotted together in 2007. According to eyewitnesses who spilled the tea to People, the twosome got super close during an outing in New York, with Olsen appearing visibly flirtatious and sitting in the cyclist's lap. Sources who chatted to the New York Post (via Stuff) echoed these claims, divulging that the loved-up couple spent the night locking lips. "Ashley and Lance settled in and within minutes, he was whispering in her ear and she was giggling like a schoolgirl," an eagle-eyed onlooker revealed. "Ashley... nuzzled up to him, sat on his lap and they were making out all night. They left together around 2am."

As with a number of Olsen's beaus, Armstrong is considerably older than her. This was reportedly the source of much contention within Armstrong's camp. According to the 2014 book "Cycle of Lies: The Fall of Lance Armstrong," the disgraced Tour de France champ was warned against dating the then 21-year-old Olsen, per E!. John Korioth, Armstrong's pal, feared that the romance would damage the cyclist's then glittering reputation. "Whoa, dude, bad idea. You've got to put a stop to this right now," Korioth reportedly told his bud. However, Armstrong would not relent, apparently replying, "She's 21... F*** you." He did eventually heed his friend's advice, with the couple parting ways after a few months.

"The Hangover" star Justin Bartha was one of Ashley Olsen's first serious boyfriends. The pair began dating in 2008 and stayed together for around three years. In an interview with Marie Claire, Olsen revealed that Bartha had provided her with some much needed stability. "It's more important than anything else in the world," she reflected.

In 2010, it was reported that the couple had been eyeing up a swanky New York pad together. Also that year, sources claimed Bartha was ready to pop the question, having been spotted looking for engagement rings. No doubt Bartha thought the second time's the charm, since he had reportedly asked for Olsen's hand in marriage in the past, only to be met with swift rejection. This time, however, insiders were sure Olsen would say yes. "Ashley has always been the more centered of the twins, and Justin is centered, too," a source revealed to Us Weekly. "They mix well with each other's friends and calm each other."

However, the pair opted to remain low-key about their romance. In an interview with the Evening Standard, Bartha refused to discuss his relationship with Olsen. "I don't understand it when celebrity couples pose for pictures and invite people into their home," he said. "But it is a very unfortunate part of the culture that has entered into our society which personally I find fairly disgusting." Alas, the rumored engagement never materialized and the couple parted ways in 2011.

Hollywood is in no shortage of odd couples, but Ashley Olsen and Dax Shepard are one couple we certainly didn't see coming. As Shepard revealed on an episode of "Armchair Expert," he dated Olsen many moons ago. "I just saw her at a party and I was kinda thunderstruck with the beauty," he recalled. He noted that he began dating Olsen when she was first formulating her fashion label, The Row, and he was mightily impressed by her work ethic and commitment to her craft. Olsen founded The Row in 2006, so she would have been around 20 when she dated Shepard, who was 31 at the time. Although he conceded that he and Olsen undoubtedly seemed like an odd pairing, Shepard said that they shared a sarcastic sense of humor and love of Scrabble, thus getting on really well.

Shepard added that he had never watched Olsen in "Full House" prior to dating her. "I luckily never saw that show because I probably would not have been able to be attracted to Ashley if I knew her as a baby," he remarked. At the end of his anecdote, he made a plea for Olsen to get back in touch so he could potentially buy her black DTS, which she purchased when they were dating. "I promise you that's the only DTS that was ever sold to a woman in her 20s," he joked.

In 2013, Ashley Olsen brought a new man into her life. The girlboss began dating fellow fashion exec David Schulte, the CEO of luxury sunglasses brand Oliver Peoples. Both millionaires, Olsen and Schulte made quite the power couple. However, it wasn't to be, and the pair marked the beginning of 2014 with a break up, having called it quits after just a few months of dating. "He was a great guy and cute, but it didn't work out," an insider told Us Weekly. Despite the split, Olsen and her ex were spotted getting cozy on a casual dinner date at the end of 2014.

Although their romance appeared to end on amicable terms, Olsen and Schulte's professional relationship soon grew sour. In 2016, Schulte was appointed president of The Row, in an effort to expand the brand's menswear range. However, he left the company without warning in 2019. Subsequently, he sued the Olsen twins the following year. Though details of the lawsuit are unclear, WWD suggests that there were ongoing disputes between Schulte and the sisters. The lawsuit contributed to the already uncertain future of The Row. As of 2023, the case is still pending.

There's no denying that Ashley Olsen has a thing for a silver fox. Following her split from David Schulte in 2014, she moved onto director Bennett Miller; at the time, Olsen was a mere 27, while Miller was 47. Us Weekly notes that the couple had been staying toasty together throughout the winter months, with Olsen keeping her man company as he finished off his film projects. Miller has directed a number of acclaimed flicks, such as "Capote," "Moneyball," and "Foxcatcher," all of which earned him Academy Award nominations. Olsen accompanied Miller to the funeral of his friend and collaborator, Philip Seymour Hoffman, who won the Best Actor Oscar for "Capote." The lovebirds were spotted on a casual date in New York, with Miller towering over his petite lady love.

The romance soon fizzled out, though it's unclear when these two parted ways — or why. However, the split may have had something to do with Miller's avowed commitment to minimalism, in contrast to Olsen's well documented love of luxury. "I am a tumbleweed... I don't own anything," he told Vulture in 2014. "I've never owned a car or an apartment. My entire life can fit into a knapsack." We guess Millermalism just wasn't for girlboss Ashley.

Speaking of older men, Ashley Olsen allegedly began dating artist George Condo in 2016. At the time, Olsen was just 30, while Condo was shy of half her age at 59. The duo were first seen together at the Mercer Hotel in New York, with Page Six reporting that they appeared to be on a romantic date. However, Condo's reps insisted that he was having a business meeting with the fashion designer.

The pair were soon spotted on what appeared to be a romantic dinner date at a fancy restaurant, with insiders telling Page Six that Olsen was cuddling up to Condo. "It was obvious something was going on," an observer said. "It looked like she was dining with her grandpa, but they were holding hands and snuggling." Onlookers who chatted to People corroborated the claims. One such observer claimed that Olsen and Condo were nestled in a romantic couple's spot at the restaurant.

Radar reports that the alleged romance was a little sketchy since Olsen was pals with Condo's ex-wife, Anna. Oof. Though Anna told the outlet that she was unsure whether the dating rumors were true, she also didn't rule out the possibility that her hubby was cheating with her now former friend. "When somebody becomes famous people gravitate around them," she said. "I realized that a lot of the people gravitating around him were not the people I wanted to be associated with. They were not my cup of tea."

It was Matthew McConaughey (by way of his resoundingly creepy alter-ego in "Dazed and Confused") who famously said, "That's what I love about these high school girls... I get older, they stay the same age." Well, in Ashley Olsen's case, she seemingly doesn't age, but her beaus sure do get older. In the fall of 2016, she forgot all about rumored lover George Condo and began locking lips with art dealer Richard Sachs, who was in his late 50s. They were first seen together in a spin class, where they exhibited palpable affection for one another, per Page Six. "They were canoodling and cuddly when they left holding hands. He looked like he could be twice her age. There's no way that's his natural hair color," an observer divulged, noting Condo's suspiciously jet-black mane. 

As Us Weekly reports, Olsen and Sachs were then spotted getting super cozy during a basketball game in New York. Sachs packed on the PDA as he kissed and cuddled his much younger lady love. "Richard had his arms all over Ashley, kissing and [stroking] her hair," an onlooker dished. "She was laughing and giggling. He's also close with Mary-Kate's husband and was chatting with him."

But after just five months together, the couple called it quits. Reportedly, Olsen split with Sachs in order to focus on her fashion career, but the pair reportedly remain pals.

Like her sister, Mary-Kate Olsen has dated her fair share of heartthrobs and cads. Her first boyfriend was filmmaker Max Winkler. As his name suggests, he is the son of Henry Winkler, aka The Fonz, but Winkler is adamant that he has never relied on the fame of others to bolster his own career. As he explained in an interview with New York Magazine, he fell in love with Olsen and had little interest in her A-list status. "I dated an Olsen twin because I was in love with an Olsen twin," he sweetly said. "But I wasn't in love with her because she was 'an Olsen twin.' I just thought she was so pretty and smart and cute."

Other than that, not much is known about the pair's youthful romance, though a number of photos of the loved-up couple, circa 2002, have surfaced on Twitter, suggesting that they were teens when they dated. A 2003 Rolling Stone profile notes that Olsen had her first kiss in 1999 (when making the film "Passport to Paris") and was single at the time that the interview was conducted, so she and Winkler likely dated for just a couple of years.

In 2004, Mary-Kate Olsen began dating David Katzenberg, who is the son of DreamWorks CEO Jeffrey Katzenberg. Katzenberg and Olsen got through some tough times together. Soon into their romance, Olsen was hospitalized after becoming seriously ill with an eating disorder, while Katzenberg supported his girlfriend throughout her mental health struggles. Reflecting on this difficult period in her life, Olsen told Elle that she found it difficult opening up about her illness to those closest to her, but doing so ultimately aided her recovery. "I think the hardest part to get to is that point of asking for help or reaching out to other people and being honest with yourself," she said. "I do not want to go through my life with my eyes shut."

After nine months together, the couple parted ways. The duo reportedly struggled to maintain their relationship after Olsen began attending New York University. "It was a mutual parting of the ways and amicable," an insider told People. "Being at different schools played a part. It's reasonable for her to start school fresh." Two years later, there were reports that the couple had briefly reconciled. Insiders revealed that they spotted the exes getting close, holding hands, and giving each other lovestruck gazes.

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Following her split from David Katzenberg in 2004, Mary-Kate Olsen reportedly set her sights on Ali Fatourechi, per the Chicago Tribune. Fatourechi was buds with Ashley's then-beau Scott Sartiano, so it's probable that she set her twin up with him.

However, by 2005, Mary-Kate had already moved on to a new man — Greek shipping heir Stavros Niarchos III. The pair were seen on a number of dates, cavorting on vacation in Hawaii and enjoying the finest eateries Los Angeles has to offer. Their fairytale romance came to an end, however, when Niarchos set his sights on another 2000s tabloid mainstay: Paris Hilton.

In an interview with W Magazine, Olsen revealed that she was distraught after discovering that Hilton, whom she considered a friend, was dating her ex. Subsequently, she admitted that she had fallen out with the heiress. "[Paris and I] always only had nice things to say about each other," she said. "Now I guess you can tell we're not talking ... I miss [Stavros] and I love him and I don't speak with him anymore. It's a hurtful and painful subject ... This is a hard time for me." Sadly, Olsen was so deeply affected by the betrayal that she made the difficult decision to drop out of college. "She's really hurt," her bestie, Hayden Slater, revealed. "Did I see it coming? Absolutely not."

Following the untimely death of Australian actor Heath Ledger, there was much gossip and speculation surrounding his relationship with Mary-Kate Olsen. The former child star was one of Ledger's last girlfriends, having spent a lot of time with her prior to his passing. "They had a bond that was based on partying," insiders told People, adding, "and they had the same tastes in partying ... like, in terms of where they liked to hang out in New York." 

In 2008, Ledger died of a drug overdose at the age of 28, his body having been discovered in his New York apartment by a masseuse. Before calling 911, the masseuse made a number of calls to Olsen, who was in California at the time and was on Ledger's speed dial. Rather than calling 911, Olsen advised the masseuse that she would call some New York security guards to arrive at the scene. These mysterious calls led investigators to believe that Olsen may have been Ledger's drug dealer. 

However, she strongly denied such claims. "Unfortunately, things will be written about whether they're true or false," she told the Irish Independent. "Sometimes, we do take action but sometimes fighting it is pointless and there's really no reason to engage." Over a decade later, there remains much mystery surrounding her relationship with the Aussie star. There is no mention of her in the 2017 documentary "I Am Heath Ledger," potentially fueling further conspiracies.

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Between 2007 and 2008, Mary-Kate Olsen was reportedly in a string of casual relationships. As noted in a profile by The New York Times, she dated photographer Maxwell Snow around this time. However, the relationship was short-lived and the pair called it quits in the fall of 2007. "They broke up mainly because she was in LA and Max was in New York, which made the long-distance relationship tough," an insider told InTouch (via Aceshowbiz).

The following year, there were rumors that Olson had moved onto Italian businessman Lapo Elkann. The pair allegedly dated for a few weeks, having been spotted together at Paris Fashion week a month after Heath Ledger's death. But in an interview with Elle, Olsen dismissed the rumors, insisting that she and Elkann were nothing more than great friends. "One week it's that one. One week it's another," she said in reference to dating rumors. "It's a good story, don'tcha know?" Chatting to Interview, Elkann also denied that he and Olsen were anything other than friends. "There is nothing to say. It's simply not true," he declared. 

Mary-Kate Olsen ended the aughts by dating artist Nate Lowman. Always a fan of packing on the PDA, the pretty pair were spotted locking lips at a New York restaurant in 2009. It was apparently a full house, with dozens of diners looking in on the make out sesh. There were even rumors that the pair were set to wed, though Olsen's reps denied this.

Sadly, this proved to be another short-lived romance, with reports that the couple had parted ways in 2010. Us Weekly suggested that Olsen had already begun seeing another man, 2000s heartthrob Josh Hartnett, whom she was allegedly smooching at a glitzy party in London (via Daily News).

A few months after their split, Olsen and Lowman very nearly had an awkward encounter following an Edward Sharpe and the Magnetic Zeros concert, which they both attended. According to Page Six, Olsen, who was living her best life as a newly single gal, deliberately avoided bumping into her ex at the show's after party. "Without making eye contact or saying a word, Mary-Kate dodged in the other direction," an onlooker revealed. "The two didn't have any interaction — Mary-Kate was laughing, dancing and having a blast with friends while Nate was chilling at the table." Well, we've all been there.

Surprisingly, Mary-Kate Olsen has an awful lot in common with Oscar-nominated actor Michelle Williams. Indeed, the stylistically disparate women have two exes in common: Williams is the late Heath Ledger's baby mama, and she also shares ex-boyfriend Dustin Yellin with Olsen.

Yellin is a visual artist who has frequently showcased his work in his native New York. It is through the art world that he met Olsen, who is famed for her penchant for attending artsy events. Yellen was first linked to Olsen in 2011. The twosome were spotted getting super close at a NYAA Take Home a Nude Benefit. Just two years later, he had moved onto Williams.

A deeply private person, Yellin has not discussed his relationship with Olsen. However, he did divulge details about his personal life in an Interview profile, making some, erm, comparisons between his art and his sex life. "I don't know if I'll ever feel like it's finished," he said with regards to his latest architecture project. "You feel that maybe in a moment in nature, in meditation, or in a certain moment during sex — where the objective, if you will, is clear. But I think part of the process of making things is that you are always just making things." While it's unclear why he and Olsen split, he certainly knows how to utter the romantic words that every woman longs to hear.

The star of "Full House" dating the brother of the former French President? You got it, dude. In 2012, Mary-Kate Olsen was getting super cozy with Olivier Sarkozy, brother of the then newly-defeated Nicolas Sarkozy. At the time, Olsen was 25 and Sarkozy was 42, with the age gap apparently proving a welcome change for the former. "MK is constantly complaining about boys not being mature enough for her," a source divulged to Us Weekly. In an interview with The Wall Street Journal, Olsen dismissed notions that the age gap was problematic. "Everyone has an opinion," she said. "I find it's better to focus on what's in front of you and to keep putting one foot in front of the other." In 2015, the Frenchman put a ring on it and Olsen officially became a married woman following a low-key wedding in New York.

But things weren't all rosy with Sarkozy. As with many couples, the Coronavirus pandemic would prove Olsen and Sarkozy's undoing. In 2020, Page Six reported that, rather than quietly quarantining with Olsen, Sarkozy had decided to spend lockdown with his mother, ex-wife, and children, moving the family into the home he owned with Olsen. "It was too much to have his ex-wife living with them during the pandemic," a source said. "Would you want the ex-wife living with you for an unforeseeable amount of time in the middle of a crisis?" Their divorce was finalized in 2021.

Newly single, Mary-Kate Olsen set her sights on John Cooper in 2021. Those close to Olsen had previously told ET that she was ready to re-enter the dating scene after taking some time out for herself following her divorce. Like the fashion designer's ex-hubby, Cooper is a businessman (he's the CEO of technology company Brightwire) and, in his late 40s, he is quite a bit older than Olsen. A month after the Sarkozy divorce, snaps were published of the alleged couple dining at a New York restaurant. Olsen appeared in high spirits as she sipped wine and enjoyed her rumored beau's company.

Although neither party has confirmed the alleged romance, sources told E! that the twosome were clearly smitten on their dinner date. "It definitely looks like they are dating," an onlooker said. "There was a lot of flirting going on ... They were constantly looking over and smiling at each other."

Insiders told Us Weekly that, as two successful business people, Olsen and Cooper seemed like a perfect match. "He's not affected by fame and fortune because he does well himself," a source explained. "Business is attractive to him — if he's doing well, he would want to date someone who is also doing well in their career." Moreover, Cooper has never been married, so Olsen needn't worry about a Sarkozy 2.0. However, there has been little tattle about these two since the gossip first surfaced. Is Mary-Kate simply opting to keep things low-key? Her lips are sealed.