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Who has Ashley Olsen dated? Boyfriends List, Dating History

Fact Checked by TDPel News Desk
By Jane Mayer

Ashley Fuller Olsen is an American child actress and fashion designer, who rose to fame along with her twin sister Mary-Kate, gaining worldwide recognition as a Dualstar act as the stars of several popular films in which they always appeared opposite each other. The twin sisters began their career as actresses in 1987 as baby Michelle Tanner in the popular sitcom ‘Full House’, with both of the twins sharing appearances on the show.

Though only nine months old at the start of filming, their appearance in the sitcom nonetheless ensured them a future as child actresses. Recognising their potential, Ashley and Mary-Kate began their own brand known as Dualstar, which ultimately aided in the production of many titles starring the Olsens, and gained them world renown for credits that include ‘Passport To Paris’, ‘Billboard Dad’, ‘It Takes Two’, and so many more.

 

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Naturally, all the many Olsen fans and followers would be familiar with every credit on their resume, and the twins certainly established an enormous fan base over the years. Mary-Kate and Ashley earned joint third place on the 100 Greatest Child Stars of all time list, and have appeared on every Forbes Celebrity 100 list since 2002.

Unfortunately, the two brilliant actresses would eventually announce their retirement from the entertainment business, though they then began pursuing an influential career in fashion designing. Born on 13 June 1986, in Sherman Oaks, California to Jarnette Jones and David Olsen, the twins spent most of their early life in Los Angeles, where they attended Campbell Hall School.

Mary-Kate and Ashley also have a younger sister, Elizabeth Olsen, who also pursued a career in entertainment and made her acting debut at the age of four.

Though it’s clear to see that the Olsen family simply overflows with talent, the twins further developed their abilities by attending New York University where they enrolled into the Gallatin School of Individualised Study program in 2004, shortly before the girls announced their retirement from acting.

Despite the announcement, Ashley continued to make appearances in films, and even starred in the 2013 music video for 30 Seconds To Mars’ ‘City of Angels’, however, she hasn’t taken up a substantial role since.

Although the Olsen twins retired from acting, they maintained the interest of gossip outlets and the media, this time around because of their influential beginnings in the fashion industry.

In 2005 the twins established their brand, The Row, and later expanded to include perfume lines, as well as other affiliated brands such as Olsenboye, Elizabeth and James, and StyleMint.


While the twins certainly had an interesting acting career, becoming child stars who developed into eclectic fashion designers, most fans would be more interested to know about Ashley’s romantic success, and for good reason.

Although Ashley’s dating history may not have endured the kind of heat other celeb couples have, her history includes several interesting names, including rumours concerning Jared Leto and Johnny Depp, and then, of course, there was the time she dated the famous cyclist, Lance Armstrong, however, this was before Armstrong’s doping scandal made headlines. Naturally, an A-list celebrity like Ashley would have no shortage of Hollywood’s most handsome bachelors standing in line to ask for her hand.

Ashley’s First Love

Ashley’s first notable romance was with the film producer and CEO of Chapter One Films, Matt Kaplan.

The pair famously dated back in 2001, when both Olsen and Kaplan’s careers entered the early stages of their rise to fame.

Unfortunately, many fans most likely forgot about this match-up, or perhaps never even knew about it. It’s true that their romance never gained too much attention, despite their influential positions and Ashley’s prominent fame, though for them the relationship was significant.

The couple dated for three years, most of which was spent happily together, and because of a lack of details the reason behind their split can’t be confirmed. However, according to certain reports, Kaplan attended Columbia University in New York, while Ashley focused on her acting career in Los Angeles, and their decision to assume a long distance relationship placed too much stress on them, and it eventually fell apart.

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While this is the commonly accepted reason for their split, it sounds rather too speculative to be the truth, though according to statements released by Ashley’s representative, Kaplan and Olsen’s break-up was amicable and on mutual terms. Ashley’s twin, Mary-Kate, later confessed to Rolling Stone magazine that she was the one who introduced Kaplan to her sister, and believed that the couple could make things work.

The exact truth about their relationship will remain a mysterious affair, with the only evidence and confirmation of it happening left behind in the grainy photos of nostalgic memories. Although the details might be obscure, it seems certain that Kaplan and Olsen enjoyed a very special time together, especially considering that their relationship lasted more than three years.

Of course, Kaplan went on to marry and later divorce the ‘Vampire Diaries’ actress Clair Holt, while Ashley moved on to her second public relationship, with Scott Sartiano.

Ashley Olsen

Guilty By Association

Throughout their career, the Olsen twins never gained a reputation for being scandalous, at least when compared to fellow child stars such as Macaulay Culkin and Lindsey Lohan. However, this didn’t prevent the tabloids from publishing scandalous speculations about them, even implicating Ashley in particular as an accomplice to narcotics trafficking.

In 2004, following her separation from Kaplan and Ashley’s retirement from acting, she became involved with New York Nightclub owner Scott Sartiano, a famous restaurateur well known in the hospitality industry. Sartiano’s clubs have become quite popular among celebrities, both local and visiting.

At the time, Ashley relocated to New York to attend varsity, and most likely became acquainted with Scott while enjoying the local nightlife. Unfortunately, their relationship didn’t reach the tabloids for romantic reasons, as the sweeter details seemed less entertaining than publishing speculative accusations.

Instead, Sartiano and Olsen made the news after Olsen filed a $40 million lawsuit against ‘The National Enquirer’ after they published accusations suggesting that Ashley assisted Sartiano with his alleged drug dealing.

Sadly, three months after filing the lawsuit, Ashley and Scott ended their relationship after dating for less than a year. This time, it didn’t seem that the break-up was as amiable as before, with some sources claiming that Ashley grew tired of Sartiano’s partying lifestyle.

Others, though, would suggest that the accusations published by The National Enquirer were the reason for their split. Either way, things between Scott and Ashley didn’t end kindly.

Seeking Security

Following her relationship with Scott, Ashley moved on with Greg Chait, the owner of The Elder Statesman, a luxury clothing brand.

 

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