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.

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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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.

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.

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.

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.

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 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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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.

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.