Ashley Olsen's Complete Dating History

Although Ashley Olsen has an extensive dating history, the "Double, Double Toil and Trouble" star has consistently remained private when it comes to her love life. In fact, she keeps a low-key profile in every avenue of her adult life. "We were raised to be discreet people," Ashley's twin sister, Mary-Kate, told i-D. Even in her work, Ashley, as well as her sister, prefer to be behind the scenes. "We didn't want to be in front of [our brand], we didn't necessarily even want to let people know it was us," Ashley said. "It was really about the product."

If she's that quiet about her work, you can bet she's even more guarded when it comes to her personal life. While you may have to keep on waiting for the fashion mogul to gush about all her former beaus in a tell-all interview, her exes haven't exactly been a secret.

So what kind of guy does this Olsen twin favor? Well, she's certainly not picky when it comes to her partner's occupation, as she's dated everyone from actors to artists to even CEOs. Here's a look at her former flames and current partner.

One of Olsen's oldest known relationships was with Matt Kaplan, whom the actor started dating back in 2001 (via People). According to a 2003 interview with Rolling Stone, Olsen met Kaplan while attending high school. She was introduced to the then 18-year-old Columbia University freshman by none other than her sister, Mary Kate, as she confirmed in the interview. According to Ashley, their relationship was pretty ordinary. "We go out to dinner, go to a movie," Ashley told the publication. "It's pretty boring," she added.

As reported by People, the young couple's relationship ultimately came to an end in 2004 after three years of dating. According to one of Olsen's reps, the Columbia University QB and the "Full House" star had an amicable split and parted on friendly terms. "They wish each other the best," spokesman Michael Pagnotta stated, adding that the pair had found it hard to maintain a long-distance relationship and that there were no hard feelings between them.

After her breakup with Matt Kaplan, Ashley Olsen began dating Scott Sartiano, according to America's Star (via Glamour). However, by summer 2005, it was reported that Olsen and Sartiano had split and had been separated for quite some time. The "New York Minute" star reportedly grew tired of her former boyfriend's club owner lifestyle. An insider alleged, "Scott's constantly surrounded by models who are all over him and desperate to get into clubs."

According to People, The Row founder later sued the National Enquirer for $40 million after the tabloid published a story along with what she claimed was a misleading photograph. The article in question alleged that Olsen was part of a drug scandal that involved Sartiano. The publication claimed that they discovered documents that proved Sartiano was a drug dealer. However, it's noted that the article never stated that Olsen was doing or selling drugs herself. Still, a rep for Olsen explained why the star felt compelled to file a lawsuit, saying that freedom of the press doesn't give anyone a right to ruin someone's reputation with false claims.

After splitting with Scott Sartiano, Ashley Olsen ended up being romantically linked to Jared Leto, according to Us Weekly (via Hollywood.com). The pair were reportedly spotted together in New York, and according to a source, Olsen was like a "giddy schoolgirl who has a new man." Nevertheless, the pair's reported romance ended up being relatively brief, according to Huffpost.

In 2008, the couple's flame appeared to have been reignited. Us Weekly reported that Olsen and Leto were seen holding hands at the Art of Elysium in Los Angeles (via HuffPost). Likewise, a witness who spotted the pair claimed, "They looked like a couple and they were making out." 

Still, a source reportedly close to Olsen has denied the claims, saying that the pair were just friends. But, even so, that wasn't the end of the speculation regarding the two actors. In 2012, the Daily News stated that Olsen and Leto again seemed to be reviving their old relationship. This time, the former couple was spotted enjoying a seemingly romantic meal together at the Polo Lounge in Beverly Hills. The pair reportedly reserved a booth for 5 p.m. and showed constant displays of physical affection, with Leto affectionately touching Olsen's hair and arm and even teasing her by poking the twin with his fork. Afterward, it's stated that Olsen hugged the "House of Gucci" star and put her head on his lap.

One of the famous twins' former beaus is a name you've probably never heard: Greg Chait. So, just who is this mystery man who managed to win the stylish businesswoman's heart? Well, according to Business of Fashion, he has quite an impressive resume. Chait is the CEO of the Los Angeles-based cashmere brand The Elder Statesman and previously established the Australian denim brand Ksubi in 2007. Though the pair might sound like a match made in fashionista heaven, the couple ultimately parted ways in 2007 after 18 months together, according to Page Six.

An insider who is reportedly close to Chait told the outlet that he wasn't ready for a commitment. "When they were together over the holidays, she told him she was looking for something more permanent," the source claimed. The insider then added that Chait wasn't prepared to do that for the "It Takes Two" star. "So they decided on an amicable parting," the source said.

In 2012, Chait did settle down — but not with Olsen. Instead, he married the mother of his daughter Dorothy, actress Laura Ramsey, according to the Denver Post.

In 2007, Ashley Olsen was romantically linked to cyclist Lance Armstrong. According to Page Six, the then 21-year-old fashionista was spotted with Armstrong at the Rose Bar at the Gramercy Park Hotel in New York. A witness who reportedly observed the pair told the news outlet, "They came together with a group of friends. Ashley drank red wine, sat on his lap and they were making out all night. They left together around 2 a.m." Olsen's rep did not offer comment on the situation, per Page Six. Not long after being spotted with Armstrong at the Rose Bar, Page Six reported that the pair dined together at Graydon Carter's Waverly Inn.

Years after their reported romance, the book "Cycle Of Lies" by Juliet Macur claimed that Armstrong's people worried about how his fling with Olsen, who is 15 years younger than the cyclist, would affect his image. Allegedly, Armstrong's longtime friend and head of the Livestrong Foundation, John Korioth, told the cyclist to end the relationship.

After being romantically linked to Lance Armstrong, Ashley Olsen began a fairly public relationship with actor Justin Bartha. The pair's romance even led to rumors of an engagement in 2008, after tabloids reported that Olsen and Bartha were planning to have a luxurious million-dollar wedding in the South of France. However, Olsen's rep, Nicole Caruso, denied the claim telling People, "Contrary to several tabloid reports, Ashley Olsen is not engaged to be married." Instead, she confirmed, "Ashley is dating Justin Bartha and they are very happy."

In a rare move, Olsen even mentioned her partner during a 2009 interview with Marie Claire, in which she called her and Bartha's relationship "more important than anything else in the world." Still, despite appearing to have plenty of fondness for each other, Us Weekly reported that the pair had broken up in 2011, with two sources confirming the news to the outlet. Star magazine later alleged that the former couple's separation was the result of Bartha's partying lifestyle, and Olsen had gotten tired of waiting for him to settle down (via SheKnows).

However, there appears to be no bad blood between the two. During an interview with Larry King in 2017, Bartha praised Olsen and her accomplishments, calling the star "a brilliant, talented woman."

In 2013, two years after the "When in Rome" star split from Justin Bartha, Us Weekly reported that Ashley Olsen was dating Oliver Peoples' CEO, David Schulte. "Ashley is dating David," one insider alleged to the outlet, before adding that the pair's relationship was a pretty recent occurrence. 

Despite sharing a love for luxury fashion, The Row founder and Oliver People CEO split up less than a year after their relationship began, Us Weekly reported. According to one insider, "He was a great guy and cute, but it didn't work out." Olsen's rep provided no comment on the pair's breakup.

Despite their split, the pair appeared amicable. As Business of Fashion reported in 2016, the Olsen twin's luxury brand, The Row, named Schulte president of the company. However, their relationship later appeared to sour. In 2020, Women's Wear Daily revealed that Schulte had abruptly stepped down from his position as president of The Row and later filed a lawsuit against the company.

In 2014, Ashley Olsen began dating director Bennett Miller. The news of Olsen's romance was confirmed by Us Weekly, with multiple sources reportedly telling the outlet that the "Two of a Kind" star and the "Moneyball" director were indeed an item. "They were introduced and have started dating," an insider alleged. It was noted that Olsen and Miller were spotted together at the funeral of Philip Seymour Hoffman. Miller was considered a close friend to the late actor and also directed the 2005 film "Capote," which won Hoffman his first and only Oscar award. Olsen and Miller were also seen dining together at Dan Tana's in West Hollywood.

Later that summer, the Daily Mail reported that Olsen had been spotted once again with Miller. In July, the pair were seen shopping together at a Whole Foods Market in New York City, and later that August, the duo were photographed looking casual as they left Olsen's NYC apartment. Still, despite appearing to have an envious romance, the star and the director seemingly parted ways, though it's unclear precisely when they separated.

Ashley Olsen appears to have a certain fondness for gentlemen with some life experience under their belts. In 2016, after her brief romance with director Bennett Miller, Olsen was spotted getting cozy with artist George Condo at Balthazar in New York. "It was obvious something was going on," an insider alleged to Page Six. The pair was reportedly spotted cuddling and holding hands just like a couple. Additionally, the source declared that the age difference between the pair was quite noticeable, with the insider saying that Condo, who was 58 at the time, looked like he could be Olsen's (then 30) grandfather. Previously that year, the outlet had speculated that there were sparks between Olsen and Condo; however, reps for both individuals insisted that the pair were simply having a work meeting.

Nevertheless, as noted by the Daily Mail, Olsen's aforementioned dinner with Condo seemingly indicated that the pair were involved in more than just business. Likewise, People noted that during the pair's dinner, Olsen and Condo were seated in a secluded booth typically used by couples.

In a 2016 exclusive, Condo's ex-wife, Anna, told RadarOnline she wasn't thrilled by the idea of her former husband dating Olsen. Anna claimed that before the rumors started, she and Olsen had been friends. However, Condo's ex also admitted that she didn't know if the speculation that her ex and Olsen were dating was true.

By fall 2016, Ashley Olsen had a new man and wasn't trying to hide it. As reported by Us Weekly, Olsen was spotted with her boyfriend, financier Richard Sachs, at a New York Knicks vs. Brooklyn Nets game at Madison Square Garden. According to the outlet, Olsen's twin, Mary-Kate, and her then-husband, Olivier Sarkozy, were also in attendance. Ashley and Sachs also weren't shy about showing off a little PDA. The new couple kissed and looked quite cuddly as they watched the game.

The double daters later attended an album release party for Sting at Irving Plaza. According to an insider who reportedly witnessed the group, the couples were definitely enjoying themselves. "Ashley's boyfriend had his arm around her and was nuzzling her," the source alleged. "Richard has his arms all over Ashley, kissing and [stroking] her hair. She was laughing and giggling." Still, despite appearing to enjoy their time together, the pair's relationship ended up being fairly short-lived. In March of 2017, Us Weekly revealed that Olsen and Sachs had broken up after only five months of dating. An insider who reportedly confirmed the news claimed that the pair split because Olsen wanted to focus on her fashion line. However, the source added that the breakup was amicable and that Olsen and Sachs remained friends.

Apparently, dating an Olsen sister is one amazing experience that even celebrities don't want to keep to themselves. In 2022, actor Dax Shepard revealed during a chat with his co-host on the "Armchair Expert" podcast that he dated Ashley Olsen "15 [or] 16 years ago" (via Us Weekly). From the sound of it, there are definitely no hard feelings between these exes. "She's just the most wonderful person. She's fantastic," Shepard declared while speaking about his former girlfriend. 

The "Without a Paddle" star said that at the time that the pair were dating, Olsen had been heavily focused on launching her luxury clothing line, The Row, with her sister, Mary-Kate. "She was putting all her energy and focus into launching in a big way," he said. Shepard added that the former television star had a fantastic work ethic when it came to business. Regarding his former partner, Shepard revealed, "She's super funny, and sarcastic and intelligent." The star also confessed that he'd never watched the show that made the Olsen twins famous, "Full House," claiming that he probably wouldn't have been able to have a relationship with her if he'd been watching her on tv as a baby.

In 2019, RadarOnline reported that Ashley Olsen was dating artist Louis Eisner after a year of friendship. An insider reportedly told the outlet that the pair were "very much in love." According to the source, the lovebirds had met through mutual high school friends in L.A. and had known one another for over five years. The insider added that Olsen had a good relationship with Eisner's family and even attended their Thanksgiving dinner. That same year, Us Weekly reported that Olsen and Eisner appeared to be getting serious with their relationship. Many speculated that they had gotten engaged, as Olsen was spotted wearing a ring on her left finger. However, neither has confirmed the rumors.

As of this writing, their relationship appears to be going strong. In March 2021, the couple was photographed together in New York City on a date. Then, in July 2021, the artist shared an image of Olsen on his Instagram Story. In the picture, Olsen is seen carrying what looks like a cup of beer and a machete — though no explanation was provided. The duo was snapped in a photo again later in July, having a dinner date at Balthazar in New York City. Eisner and Olsen went far more public in September 2021 when they appeared together at the YES 20th Anniversary Gala (via E! News).