Inside Mary-Kate Olsen's Dating History

Between Mary-Kate Olsen and her equally famous actress-turned-fashion entrepreneur twin sister, Ashley Olsen, the two have a long list of exes. For now, though, we're focusing on Mary-Kate's dating history, which first began when as a teen, she dated Max Winkler, son of legendary "Happy Days" star Henry Winkler, as the younger Winkler confirmed in a 2011 interview with New York Magazine.

These days, since divorcing her now ex-husband, Olivier Sarkozy, in 2021 after initially separating in 2020 (per Us Weekly), the fashion mogul and media-labeled "rebellious twin" appears to be single. While she was rumored to be romantically linked in 2021 to Brightwire founder and CEO John Cooper per the Daily Mail (more on that to come), there has been no word on the ultra-private star's love life since that time.

So, until we get word of a confirmed special someone in Mary-Kate's life, we'll just have to settle with taking a look back at whom she's dated in the past. From fellow actors and entrepreneurs to artist types — and even an entanglement in a high-profile actor's death investigation — these are the players who helped shape Mary-Kate Olsen's colorful dating history.

In 2002, a teenage Mary-Kate Olsen dated Max Winkler, the son of "Happy Days" actor Henry Winkler. Max, who's now a director, gave an interview with New York Magazine in 2011 following the release of his 2010 debut film, "Ceremony," which he both wrote and directed. In the interview, he spoke about having dated Mary-Kate, for whom he had nothing but good things to say. "I dated an Olsen twin because I was in love with an Olsen twin," he said when asked about the relationship. "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." 

According to Us Weekly, the two dated for a few months that year. A Mary-Kate and Ashley fan page on Twitter shared several photos of Mary-Kate and Max, including two pics in which he has his arm around her and one in which they are taking a flight together. Mary-Kate looks adorable, while Max, then about 19 or 20 years old, was rocking his Justin Timberlake-inspired blond tips.

While Mary-Kate Olsen's short-lived romance with Max Winkler may have flown under the radar, her relationship with David Katzenberg, son of Hollywood movie mogul Jeffrey Katzenberg, received more media attention. Per People, they dated for nine months and were often spotted together in Los Angeles at Lakers games before splitting shortly before Olsen started college and Katzenberg returned to school. According to a source, "It was a mutual parting of the ways and amicable. Being at different schools played a part. It's reasonable for her to start school fresh." Per People, Katzenberg supported Olsen's struggle with an eating disorder, with Female First alleging that he visited her multiple times during her six-week stay at a Utah treatment facility.

In November 2004, Page Six alleged that Katzenberg went to Los Angeles to win Olsen back when he ran into her with a new guy (via SFGate); by February 2006, Sky Showbiz (via Digital Spy) claimed that Olsen and Katzenberg were back together. "They were leaning close together, touching hands and stuff, and only had eyes for each other," a source claimed after spotting them. "From what I could tell, they're very much a couple."

If you are struggling with an eating disorder, or know someone who is, help is available. Visit the National Eating Disorders Association website or contact NEDA's Live Helpline at 1-800-931-2237. You can also receive 24/7 Crisis Support via text (send NEDA to 741-741).

In November 2004, Page Six reported that Mary-Kate Olsen had allegedly run into her ex-boyfriend, David Katzenberg, in Los Angeles while she was out with someone else. It turned out she was with her next suitor, Ali Fatourechi. As a source told Page Six at the time, "They were both at [Los Angeles restaurant] Toast, sitting across from each other at separate tables. They were staring each other down — it was really uncomfortable" (via SFGate).

Ali was a friend of Scott Sartiano, a club promoter who was dating Mary-Kate's twin sister, Ashley Olsen, at the time, so that's likely how the two met. An article from Female First claimed that the new couple had "been spotted canoodling" together at Bungalow 8, an exclusive New York City club, just one month after Mary-Kate had split from her last boyfriend.

Although little is known about Mary-Kate's brief romance with Ali, according to celeb gossip dating site Who's Dated Who, the two allegedly were together from October to December 2004. The source also includes a photo of the short-lived pair together.

By the fall of 2005, Mary-Kate Olsen had been seeing Greek shipping heir Stavros Niarchos III for about five months when news broke that Niarchos had also started dating Paris Hilton. By October, Olsen left New York University for Los Angeles to return to acting. In a 2006 interview with W Magazine, she explained, "It just got really hectic and I started feeling the city. My world was really small when I was here." When asked if anything specific prompted her to leave, she said, "I think we can all guess." When asked directly about her ex, she revealed the painful truth: "I miss him and I love him and I don't speak with him anymore. It's a hurtful and painful subject."

While Olsen didn't say much about Hilton, the former "Full House" star admitted that the hotel heiress had met Niarchos through her. "[Paris and I] always only had nice things to say about each other. Now I guess you can tell we're not talking," she said.

Like many 20-something couples, Olsen and Niarchos hadn't seen the last of each other. In December 2007, Life & Style alleged the two were seen getting cozy at Hollywood's Chateau Marmont, with a source saying, "They were super into each other" (via Celebitchy). The drama between Olsen and Hilton continued, with the heiress convinced Olsen just wanted to get back at her.

In October 2006, Mary-Kate Olsen began dating another heir and a photographer, Max Snow. Snow is also a descendant of the prominent de Menils, a family known for their philanthropic endeavors in the art world. Interestingly, he's also the nephew of actress Uma Thurman, as Popsugar noted.

Snow was featured in a March 2012 piece for The New York Times, where a longtime friend, Carlos Torretta, spoke of the image he presents versus the reality. "Max may appear a little scary or edgy, but when you talk to him, he's the nicest guy ever. It's a contrast between how he appears and how he really is, which is completely together," he said. "He works a lot."

It makes sense, then, that Snow and Olsen's dedication to their busy careers got in the way of their relationship — in addition to the fact that Olsen lived and worked in Los Angeles at the time, while Snow was based in New York. By April 2007, the two parted ways, with a source telling In Touch, "They broke up mainly because she was in L.A. and Max was in New York, which made the long-distance relationship tough" (via Celebrity Dirty Laundry). A photo of the two from 2007 can be seen in The Times feature.

In January 2008, Mary-Kate Olsen's relationship with late actor Heath Ledger became public after the talented young star's death following an accidental overdose. Apparently, masseuse Diane Wolozin, familiar with Ledger's relationship with Olsen, called her several times after finding Ledger deceased in his New York City apartment, as ABC News reported. Olsen eventually responded and sent her security to Ledger's apartment; they arrived alongside the paramedics.

A source shed light on their relationship, revealing to People that they first met two years prior. "Mary-Kate and Heath were casually dating for three months before Heath's death. They were hooking up, but neither was particularly interested in making it exclusive," the source said, adding that "they had a bond that was based on partying."

Olsen released a statement saying, "Heath was a friend. His death is a tragic loss. My thoughts are with his family during this very difficult time" (via ABC News). However, per the Independent, she would not speak with police regarding the drugs that led to his fatal overdose. Instead, her lawyer released a statement saying she had "nothing whatsoever to do with the drugs found in Ledger's home or his body" and "does not know the source of the drugs Mr. Ledger consumed."

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

In 2008, per Us Weekly, Mary-Kate Olsen was rumored to be dating Lapo Elkann, the Italian heir to the automotive company Fiat, after they were seen together at a fashion show during Paris Fashion Week that February.

When asked about the rumored relationship, Elkann dispelled the rumors, telling Interview Magazine, "There is nothing to say. It's simply not true." Whether or not there's any truth to the rumor, it's clear the two have a lot in common: Both are edgy, artsy types who grew up in a life of luxury.

When Elkann and Olsen's ex, Max Snow, were both name-dropped in a 2008 interview with Elle, the former "Full House" star said, "One week it's that one. One week it's another," before explaining that both are friends of hers. "It's a good story, don'tcha know?"

Later in 2008, Mary-Kate Olsen started a relationship with her second artist boyfriend: New Yorker Nate Lowman. A 2009 People article claimed they "were glued at the hip" while hanging out together at Jane Hotel in New York's West Village along with a group of friends that included actress Mischa Barton. Another People article from that year alleged that the two were spotted kissing while out to dinner at Indochine in New York City.

Mary-Kate's thing for artists likely stemmed from her own strong personal interest in art. Mary-Kate allegedly has an art collection at home that includes pieces from Andy Warhol. She even once told Elle, "All I really need is my bed and my art around me."

Two years later, however, Us Weekly announced that the couple, who met through friends, had broken up (via the New York Daily News). Sources claimed that despite the split, Olsen did not appear all that upset.

Next up for Mary-Kate Olsen was Dustin Yellin, yet another artist she allegedly dated in 2011. Radar Online reported that Yellin was seen with Olsen looking cozy at the NYAA Take Home a Nude Benefit in October of that year. The outlet also reported on the artist's one-time drug use, saying that Yellin — now the founder and CEO of Pioneer Works, a Brooklyn, New York nonprofit interdisciplinary cultural center — was known to host wild parties at his bachelor pad, drawing the attention of young celebrities and Ivy League types in the '90s during his early days in New York City.

Yellin's friend Andrew Kern, an evolutionary geneticist and board member of Yellin's Pioneer Works, shed additional light on Yellin for an August 2015 feature for Vanity Fair. "Dustin had an incredible magnetism," he said. "He stepped into the social scene through his crazy antics. His place was a clubhouse, almost more for work than parties. I'd be working on a science project, Dustin on his art ... We took it very seriously."

Clearly, Yellin's art world connections and "magnetism" helped him attract the attention of actress Michelle Williams, whom he dated a couple of years after Olsen (per Radar Online).

In 2012, Mary-Kate Olsen met French banker Olivier Sarkozy, a divorced father of two, at a party. While they appeared to be mismatched, between their height and age differences, a source told Entertainment Tonight that their complementing personalities made it work. "He had a way of making her feel really comfortable even in scenarios she would normally like to avoid," the source said. By February 2014, they were engaged, and in November 2015, they married in an intimate New York wedding. "He was always doting on her and making her happy," the source said. "And she loved being around him."

Olsen opened up to Net-A-Porter in 2017 about balancing her work and personal life. "I think [Ashley and I are] lucky [working hard] comes quite naturally for us," she said. "But then I have a husband, two stepkids and a life; I have to go home and cook dinner. I ride horses on the weekends. You find the thing that helps you relax, and if you don't have it, look for it. Or you get burned out."

In 2020, things went awry when Sarkozy moved his mother, ex-wife, and two children into the Hamptons mansion he shared with Olsen amid the COVID-19 pandemic. Olsen filed for divorce, according to Page Six, and Sarkozy canceled the lease on their apartment without her consent. By early 2021, per Us Weekly, their divorce was finalized after a messy breakup.

On February 26, 2021, Mary-Kate Olsen was spotted on her first post-divorce date, which occurred one month after finalizing her divorce from Olivier Sarkozy, as the Daily Mail reported. Olsen was joined by her date, John Cooper, the co-founder and CEO of news analysis agency Brightwire, and another couple at the Greek restaurant Estiatorio Milos in New York City. According to the outlet, Olsen looked happy and relaxed while enjoying wine, cocktails, and seafood. She was bundled up in a long black coat, black pants, tall black boots, and black beanie.

Us Weekly provided additional details about Olsen's date. Originally hailing from Amelia Island, Florida, the never-married New Yorker has a computer science degree from Gettysburg College and an MBA in economics and finance from Columbia University. He's also a man of many interests, including cooking — he picked up a skill or two studying at the French Culinary Institute — and flying planes. On a career level, he and Olsen are certainly equals — his New York-based company, which also has locations in Berlin and Hong Kong, is quite successful, with annual revenue of over $3 million.

Unfortunately, little has been published about Olsen's love life since, so it's unclear whether the two are still dating, especially with her super private nature.