Artists, Heirs, and More Men Who Mary-Kate and Ashley Olsen Have Dated

Ashley began dating Columbia University quarterback Matt Kaplan in 2001. They were together for three years before splitting in 2004. A rep for the New York Minute star released a statement at the time, saying that the breakup was “amicable,” they “parted on good terms,” and “they wish each other the best." Matt is now engaged to The Originals actress Claire Holt.

In 2004, Ashley moved on to nightclub owner Scott Sartiano, who she was introduced to by none other than her former Full House costar John Stamos. The two dated for nine months before calling it quits, but their relationship took a very public turn when, in February 2005, Ashley sued the National Enquirer for $40 million over a story that claimed she was "caught in a drug scandal" and linked Scott to "alleged drug dealing."

Jared and Ashley seemed to have had an on-off friends with benefits sort of thing over the years; they were first linked in 2005 after being spotted on a date in LA but came back together in 2008 when they were seen holding hands and "making out" at the Art of Elysium Gala in LA. An eyewitness told Us Weekly at the time that they "looked like a couple," but a source close to Ashley insisted they were just friends. Cut to 2011, and the "friends" were reportedly seen enjoying a "very flirtatious meal" at the Polo Lounge in Beverly Hills.

In September 2005, Ashley hooked up with Tsubi jeans CEO and Elder Statesman designer Greg Chait. Though they split in January 2007 due to "commitment issues," the two have likely run into each other at the CFDA Awards over the years.

Ashley began dating disgraced cyclist Lance Armstrong in 2007, but the romance only lasted for a few months. In 2014, a tell-all book claimed that Lance was "urged to dump" Ashley because of their 15-year age difference. Allegedly, his handlers convinced him that "a May-December romance could damage his cancer work."

Ashley's most public relationship was with The Hangover's Justin Bartha, who she began dating in 2008. The two were reportedly planning to get engaged but split up in March 2011. Justin went on to marry fitness trainer Lia Smith in January 2014, and the two welcomed their first child three months later.

After her split from Justin Bartha, Ashley was rumored to be hooking up with Johnny Depp (though the reports were never confirmed). It wasn't until 2013 that she stepped out with David Schulte, the CEO of luxury eyewear brand Oliver Peoples. Their romance lasted less than a year, but in 2016, David was named president of Ashley and Mary-Kate's fashion brand The Row.

In 2014, Ashley started up a relationship with 47-year-old director Bennett Miller while he was filming Foxcatcher with Steve Carell and Channing Tatum. Their relationship lasted a year. Oddly enough, Bennett is currently romancing Sienna Miller, who also starred in Foxcatcher.

Ashley was linked to the renowned artist in Summer 2016 when she was 30 and he was 59; the two were seen lunching in a "cozy" booth in NYC. Ashley and George, who split from his wife of 26 years a year earlier, had previously worked together on her fashion house The Row and created a sketch of the brand's NYC boutique. Their relationship fizzled out a couple months later.

In October 2016, rumors swirled that Ashley was dating 58-year-old art dealer Richard Sachs when the two were seen "canoodling" during a Spin class (how do you even do that?). They all but confirmed their romance a month later when they showed PDA in the stands at a NY Knicks game and were photographed on a hike in St. Barts over the New Year. Sadly, news of their split broke in March 2017 when a source revealed that Ashley "wants to focus on her clothing line right now."

Mary-Kate dated Henry Winkler's son Max for a few months in 2002.

Mary-Kate moved on to David Katzenberg, son of DreamWorks cofounder Jeffrey Katzenberg, in June 2003. He stayed firmly by her side during her battle with an eating disorder the following year, though they ended their relationship in August 2004 before both leaving to attend college — Mary-Kate at NYU and David at Boston University. He later went on to romance Nicky Hilton.

In 2004, when her sister Ashley was dating nightclub impresario Scott Sartiano, Mary-Kate struck up a brief (like, two-month) romance with his business partner, Ali Fatourechi.

In April 2005, Mary-Kate began seeing Greek shipping heir Stavros Niarchos; perhaps their most memorable moment as a couple were photos of them making out while jumping on a trampoline during a Hawaiian getaway in July. After five months of dating, Stavros carried on a very public affair with Paris Hilton (who was Mary-Kate's friend at the time). The incident compelled Mary-Kate, who was then a college sophomore, to take leave of absence from NYU and move back to LA to pursue her acting career. Needless to say, she and Stavros ended things.

Of their split, the 19-year-old told W magazine, "I miss him 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." As for her friendship with Paris, she said, "[Paris and I] always only had nice things to say about each other," adding, "Now I guess you can tell we're not talking."

Yes, this means Mary-Kate has dated two guys who have also dated Hilton sisters. Small world.

Mary-Kate dated photographer and oil heir Max Snow (who also happens to be Uma Thurman's nephew) from October 2006 to April 2007.

While they were definitely close friends and party pals, Mary-Kate and Heath Ledger were also rumored to be a couple back in 2007, just months before the actor's tragic death. A source told People at the time that the two were "casually dating, but neither were particularly interested in making it exclusive."

Mary-Kate became unintentionally involved in the investigation surrounding Heath's passing in January 2008; it was revealed that the masseuse who found his body in his NYC apartment made two phone calls to Mary-Kate, who was in California at the time, asking for help. It was then reported that she and Heath were a couple.

Mary-Kate was linked to Lapo Elkann, the sole heir to Fiat's billion-dollar auto dynasty, for a few weeks in February 2008.

In October 2008, Mary-Kate met artist Nate Lowman through mutual friends. They dated until February 2010, and People reported that she didn't seem to broken up over the split, as she and actor Josh Hartnett were spotted "making out in a dark corridor" at a London party weeks later.

Mary-Kate was linked to artist Dustin Yellin for a brief time in 2011. Dustin began seeing Michelle Williams in 2013, meaning she and Mary-Kate have dated two of the same guys.

Mary-Kate began dating Olivier, a businessman and the half-brother of former French President Nicolas Sarkozy, in 2012. Despite a 27-year age difference, the couple got engaged in 2014 and tied the knot in a private Manhattan ceremony in November 2015. Mary-Kate opened up about her marriage (and becoming a stepmother to Olivier's two children) for the first time in a March 2017 interview, telling The Edit, "I have a husband, two stepkids and a life; I have to go home and cook dinner. I run on the weekend. You find the thing that helps you relax and if you don't have it, you have to look for it. Or you get burned out and then you're not productive."