For a few months in 2002, Olsen was linked to Max Winkler — the son of famous actor Henry Winkler, who would eventually go on to become an indie film director.

“I dated an Olsen twin because I was in with an Olsen twin,” Winkler told New York Magazine in 2011. “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."

How sweet is that? Seems like there are no hard feelings there.

Um, remember when life imitated art and Olsen dated Genetic Denim founder Ali Fatourechi while her sister was seeing his business partner? They were reportedly only romantically linked for a few months in 2004, but still. It’s the perfect plot for a classic Olsen twins rom-com.

It's safe to say that Olsen's first *serious* relationship was with David Katzenberg, the son of Dreamworks co-founder Jeffrey Katzenberg. They dated for a little under a year, and Katzenberg stayed supportively by Olsen's side throughout her recovery from an eating disorder, which included a six-week stay at a treatment center. Then, in early 2004, news broke that they had ended things right before the twins started college at NYU and Katzenberg began studying at Boston University. According to a source that spoke to People at the time, "it was a mutual parting of the ways and amicable."

Even though Olsen’s romance with Greek shipping heir Stavros Niarchos III only lasted for about five months in 2005, this relationship managed to make more than a few headlines — mainly because Niarchos had a pretty public romance with Paris Hilton. Not only was Hilton her friend at the time, but she supposedly introduced them — so yeah, ouch. Niarchos and Hilton went on to date for a little while, and Olsen promptly decided to take a leave of absence from NYU and move back to Los Angeles to focus on her acting career.

In a 2006 interview with W Magazine, she spoke about the breakup candidly.

“I miss him and I love him and I don’t speak with him anymore,” she told the publication. "[Paris and I] always only had nice things to say about each other … Now I guess you can tell we're not talking."

When asked why she left school and moved back to L.A., she simply said, "I think we can all guess."

Fun fact: Niarchos isn’t the only guy she’s dated who’s been involved with one of the Hilton sisters — Katzenberg eventually dated Nicky Hilton Rothschild. Small world, eh?

Once she settled back into life in Los Angeles, Olsen started dating Max Snow — a photographer, oil heir, and nephew of Uma Thurman — in late 2006, but the romance fizzled out in April 2007.

"They broke up mainly because she was in LA and Max was in New York, which made the long-distance relationship tough," a source told In Touch Weekly. "Mary-Kate has been busy filming and working with her sister, Ashley, on their new fashion line, The Row, along with launching a new clothing line called Elizabeth and James."

Though neither star ever confirmed this relationship, rumors of a possible romance started after Heath Ledger’s tragic passing in January 2008. Here’s why: the masseuse who found Ledger in his NYC apartment called Olsen four times from Ledger’s phone before paramedics arrived. According to The New York Times, the masseuse apparently “knew they were friends,” and Olsen — who was in California at the time — had her personal security guards rush to the apartment to help with the situation.

At the time, a source told People that the two had been "casually dating” before Ledger’s death, but that “neither were particularly interested in making it exclusive."

Olsen was spotted with the sole heir to the billion-dollar Fiat dynasty during Paris Fashion Week in February of 2008. That spark reportedly only lasted for a few weeks, though.

After being introduced by mutual friends in the fall of 2008, Olsen struck up a serious relationship with Nate Lowman, an artist known for his satirical style and pop art aesthetic. They ended things in February 2010, and TBH, she didn’t seem too devastated by the breakup. People reported that mere weeks later, she was seen “making out in a dark corridor” with Josh Hartnett at a BAFTA after-party in London. How’s that for a rebound with no regrets?

Apparently, Olsen has a thing for artists. Because in 2011, shortly after her split from Lowman, she was briefly linked to Dustin Yellin — a contemporary artist who's best known for his glass veneer sculptures.

Olsen and Sarkozy reportedly met at a party in April of 2012, and before long, they were vacationing in the Hamptons together, attending swanky art auctions arm in arm, and canoodling in the stands at New York Knicks games. They tied the knot on Nov. 27, 2015, and the small (ish) affair reportedly included "bowls filled with cigarettes." Bizarre decor decisions aside, their relationship appeared to be going smoothly — that is, until news hit that Olsen reportedly requested an emergency court order, which would allow her to get a divorce amid the coronavirus pandemic. According to Page Six, Olsen officially filed for divorce when New York courts reopened on May 25, and Sarkozy moved his ex-wife and their two children into the mansion he and Olsen previously shared.

As for why their marriage dissolved, a source told Page Six: “It was simply erosion … growing apart. No cheating or betrayals … sometimes couples just run their course. The plan to move in his family was his way of moving on, and the final straw for Mary-Kate.”