Some of these relationships lasted years.
Others were gone in a New York minute.
Ashley Olsen has hooked up with some of the biggest celebs around.
One of Olsen's oldest known relationships was with Matt Kaplan, a producer whom the
actor started dating back in 2001.
According to a 2003 interview with Rolling Stone, Olsen was introduced to the then 18-year-old
Columbia University freshman by none other than her sister, Mary Kate.
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.
After her breakup with Matt Kaplan, Ashley Olsen began dating Scott Sartiano, according
to America's Star.
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.
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.
The pair were reportedly spotted together in New York, though the relationship didn't last long.
In 2008, the couple's flame appeared to have been reignited briefly.
And again, in 2012, the Daily News stated that Olsen and Leto seemed to be reviving
their old relationship for yet another time.
This time, the former couple was spotted enjoying a seemingly romantic meal together at the
Polo Lounge in Beverly Hills.
Afterward, Olsen reportedly 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?
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.
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.
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, in his words, "15 [or] 16 years ago."
"I dated Ashley Olsen.
She's just the most wonderful person.
She's fantastic."
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.
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.
"You got it, dude."
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.
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.
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."
"She's a brilliant, talented woman.
I mean, amazing woman."
"She's an entrepreneur."
"Oh my God."
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.
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.
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.
Notably, 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 together in various spots around NYC.
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.
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 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.
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.
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.
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.
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.
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 new ring.
However, neither has confirmed the rumors.
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 a drink and a machete — though no explanation was provided.
Eisner and Olsen went far more public in September 2021 when they appeared together at the YES
20th Anniversary Gala.