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In late 2016, Ashley Olsen reportedly dated art dealer Richard Sachs. But, the couple called off their relationship after only five months.In an interview with SUN Magazine, She stated, The two was together since 2014.She continued with her acting career independently, appearing with a few guest-star roles in films and in a music video.

Ashley was enlisted in the 100 Sexiest Women in the World 2005.She with her boyfriend, Matt ended their relationship three years later in 2004. But, the two parted their path after two years of togetherness in 2011.The couple was rumored to be engaged before the news of their split hit the internet.She and her twin sister co-founded luxury fashion brands, The Row, Elizabeth and James, and more affordable fashion lines, Olsenboye and Style Mint.Along with her twin, Mary-Kate, they have an older brother, Trent Olsen, a younger sister, Elizabeth Olsen (who is also an actress), and younger half siblings, Taylor and Jake, from their father's second marriage.

After that, she was enrolled into New York University with her twin sister, but for a short time.