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, toldi-D.
Even in her work, Ashley, as well as her sister, prefer to be behind the scenes.
“It was really about the product.”
So what kind of guy does this Olsen twin favor?
Here’s a look at her former flames and current partner.
According to a 2003 interview withRolling Stone, Olsen met Kaplan while attending high school.
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.
The “New York Minute” star reportedly grew tired of her former boyfriend’s club owner lifestyle.
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.
Nevertheless, the pair’s reported romance ended up being relatively brief, according toHuffpost.
In 2008, the couple’s flame appeared to have been reignited.
But, even so, that wasn’t the end of the speculation regarding the two actors.
In 2012, theDaily Newsstated that Olsen and Leto again seemed to be reviving their old relationship.
So, just who is this mystery man who managed to win the stylish businesswoman’s heart?
Well, according toBusiness of Fashion, he has quite an impressive resume.
An insider who is reportedly close to Chait told the outlet that he wasn’t ready for a commitment.
“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 theDenver Post.
Ashley drank red wine, sat on his lap and they were making out all night.
Instead, she confirmed, “Ashley is dating Justin Bartha and they are very happy.”
However, there feels like no bad blood between the two.
Olsen’s rep provided no comment on the pair’s breakup.
Despite their split, the pair appeared amicable.
However, their relationship later appeared to sour.
Ashley Olsen dated director Bennett Miller
In 2014, Ashley Olsen began dating director Bennett Miller.
“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.
Olsen and Miller were also seen dining together at Dan Tana’s in West Hollywood.
Later that summer, theDaily Mailreported that Olsen had been spotted once again with Miller.
“It was obvious something was going on,” an insider alleged toPage Six.
The pair was reportedly spotted cuddling and holding hands just like a couple.
Anna claimed that before the rumors started, she and Olsen had been friends.
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.
However, the source added that the breakup was amicable and that Olsen and Sachs remained friends.
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.
“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.”
An insider reportedly told the outlet that the pair were “very much in love.”
The insider added that Olsen had a good relationship with Eisner’s family and even attended their Thanksgiving dinner.
That same year,Us Weeklyreported 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 feels like going strong.
In March 2021, the couple wasphotographedtogether in New York City on a date.
Then, in July 2021, the artist shared an image of Olsen on his Instagram Story.
