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Ashley Olsen Pair Up With Old Dudes AKA Boyfriends, Married Or Still Dating?

Date: 02 Dec, 2018

Ashley Olsen Pair Up With Old Dudes AKA Boyfriends, Married Or Still Dating?

Ashley Olsen's love habit has been in the limelight for a long time, and news about her hookups are not new to the media. However, her media presence after the latest break up has been rare arousing question marks about her dating life.

The Sherman Oaks native along with her twin sister, Kate Mary became famous after appearing in ABC sitcom Full House. Apart from the series, the sisters also starred in numerous movies together during the turn of the century including Passport to Paris (1999), Our Lips Are Sealed (2000), Winning London (2001), and Holiday in the Sun (2001). However, the sisters left acting for good in 2013 and Ashley is now a successful fashion designer, businesswoman, and an author.

Twins For Life: Ashley Olsen and Mary-Kate attends a promotional event for their fashion label The Row at Much Music studios on 15 June 2018 (Photo: olsensobsessive.com)

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Ashley was born into stardom as she began her first foray into the showbiz, just nine months into the world in ABC's Full House. After the series, the twin sisters were in demand and acted in several movies including To Grandmother's House We Go (1992), Double, Double, Toil and Trouble (1993). 

After the conclusion of Full House in 1995, The sisters founded an entertainment company Dualstar, which produced numerous successful videos and full-length films, with the sisters starring in lead roles. The company along with other independent movies established Ashley and her sister as the most marketable preteen stars around the turn of the century. 

Born on 13 June 1986, Ashley was the younger of two homozygous twins. Born to real state mogul father of Norwegian ethnicity, Ashley was educated in a boarding school at a posh area of LA. 

Despite a hugely successful career in her preteens and teenage, Ashley found harder to make her mark as an adult leading her to get tired of acting. And when the sisters announced in 2007 that they were leaving the industry for good, audiences were left aghast. However, Ashley remained in the industry and acted in guest roles in The Jerk Theory (2009), and I'm Still Here (2010) before announcing that she was leaving the industry and pursuing a career in fashion designing in 2012.

Ashley along with her sister founded fashion labels The Row, Elizabeth and James, and more affordable fashion lines like Olsenboye and StyleMint. The brand is a massive hit in the US with more than 3000 stores in the states and 5300 worldwide. The fashion designer and her sister's combined net worth of $400 million is reflected in their success. 

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When Ashley Olsen & Mary-Kate Made Rare Joint Appearance

Ashley Olsen and her twin sister Mary-Kate had retreated from the limelight, making their choice to turn the focus away from their lives and onto their award-winning design endeavors instead.

But on 7 November 2018, the two made one of their absolutely rare public appearances to support their friend Jonah Hill at WSJ Magazine’s Innovator Awards at the Museum of Modern Art in New York City.

Rocking Fashion: Ashley Olsen and her twin Mary-Kate appear at the Innovator Awards at the Museum of Modern Art in New York City on 7 November 2018 (Photo: wmagazine.com)

The duo coordinated their oversize black and white outfits; Ashley embraced an ankle-length white skirt under a matching white long-sleeve tunic top while Mary-Kate opted for a wide-leg black pant under a long black overcoat and highlighted the twins’ monochrome moment with bright-red snakeskin boots and coral earrings.

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At the event, the twins were seated at Jonah’s table and in the actor’s speech, he reportedly thanked the sisters for inspiring him as fellow innovators as he accepted the night’s Film Award.

Dating Old Dudes, Focused On Her Career Now

Ashley is famous for her colorful dating history, and a penchant for dating men much older than her age. 

Ashley Olsen's dating history can be traced back to 2001 when she was linked with actor Matt Kaplan, who is the only boyfriend gossiped to be dating Ashley; resembling her age. After dating for three years, Ashley and her boyfriend parted in amicable terms in 2004.

After the actor, she was linked with nightclub owner Scott Sartiano, actors and entrepreneur Greg Chait in the time interval of 2005 to 2008. The striking similarity with all three was they were all much older than Ashley. 

Her long line of rumored boyfriends also included Lance Armstrong, Justin Bartha, and David Schulte from 2008 to 2014. She was again linked with director Bennet Miller, who was 19 years her senior in 2014. After being connected with George Condo, a whopping 29 years older than her, Ashley seemed to have settled with art dealer Richard Sachs. 

The duo was seen displaying PDA at a basketball game in November 2016 which confirmed rumors about their relationship. Richard and Ashley, who had an age difference of 27 years, looked every bit in love and it seemed that he was the man Ashley would finally turn her husband. 

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What's more, her sister, who also has a long history of dating old dudes, married banker Olivier Sarkozy in 2015, leading calls for Ashley to get married and settle down. However, Ashley's relationship with the art dealer too did not last long, and the boyfriend-girlfriend duo split in March 2017, citing that she wanted to focus more on her career. 

After the high profile breakup, news about Ashley's boyfriend has not made the limelight. This time she could be focusing on her career, and after numerous failed relationships, her wanting to be single is understandable.