TBT: Ashley Olsen Dated Dax Shepard While She Was Launching The Row

Who: Retired actress, fashion designer, and co-founder of The Row, Ashley Olsen, 36, and actor, comedian, and podcast host Dax Shepard, 48. 

How They Met: The year was 2006 — Shiloh Jolie-Pitt was born, Britney Spears and Kevin Federline broke up, Paris Hilton was the queen of clubs, and, apparently, Dax Shepard and Ashley Olsen dated. 

Fast forward to 2022, and Dax shared a few details about their relationship during an episode of his Armchair Expert podcast. During a chat with his co-host Monica Padman, the comedian admitted that he and Ashley met at a party “about 15 or 16 years ago,” and he was immediately “thunderstruck” by her beauty. 

It was around the same time that Ashley and her twin sister Mary-Kate were launching their high-end fashion brand, The Row. Dax said to witness her being a boss at the time was “very impressive.” 

"When we were dating, it was when she was putting all her energy and focus into launching that in a big way," Shepard explained. "So, I was able to see her meet with design teams and, like, run her s— and she handled her B, and it's very impressive."

Why We Loved Them: Dax is the first to admit that while he and Ashley were seemingly an odd pairing on the surface, they actually shared a similar sense of humor. 

Dax, whose big break came while appearing in Ashton Kutcher’s practical joke show Punk’d in 2003, says contrary to what people may think, Ashley is actually really funny. “[She’s] super funny and sarcastic and intelligent,” Dax said. And we imagine that humor probably came in handy while the two played Scrabble, which Ashley apparently won often. 

When They Peaked: Another fun tidbit about Ashley and Dax as a couple: They both loved cars, and Ashley was a major collector. 

As it turned out, she just so happened to own one of Dax’s dream cars. “You’ve got to be a car person to dig this. When I met her, a favorite car of mine, which nobody would get, was the Cadillac DeVille DTS. It’s like a businessman's, f—ing Tony Soprano luxury sedan,” said Dax. “I promise you that was the only DTS that was sold to a woman in her 20s in the history of the Cadillac DTS.” 

Ashley also let Dax test-drive her black-on-black G Wagon AMG. He revealed, “That was the first time I drove one.”

The Breakup: It’s unknown how long Ashley and Dax dated, but it couldn’t have lasted more than several months. By 2007, the fashion entrepreneur was in a new relationship with Lance Armstrong, while Shepard was dating Kate Hudson.

As for the reason behind their breakup, that also remains a mystery. Neither Dax nor Ashley has publicly commented on the matter. 

Where They Are Now:  After her fling with Dax, Ashley moved on with another unlikely suitor, Lance Armstrong, and in the years following, she was linked to The Hangover actor Justin Bartha, director Bennett Miller, and financier Richard Sachs. Last month, Ashley married her longtime boyfriend, artist Louis Eisner, during a private ceremony in Los Angeles. 

Ashley’s career shifted from acting to fashion design in the mid-2000s. In 2006, she co-founded the understated luxury label The Row, and six years after launching, Ashley and her sister Mary-Kate were honored with the CFDA Womenswear Designer of the Year award. The brand has continued to grow and is now available at 188 stores in 37 countries. 

Dax dated Kate Hudson before meeting his wife Kristen Bell in 2007. They got engaged two years later but didn’t marry until same-sex marriage was legalized in 2013. The couple shares two daughters, Lincoln, 9, and 8-year-old Delta. 

Since his relationship with Ashley, Dax has shown off his comedic chops in blockbuster movies, like Baby Mama, When In Rome, and Buddy Games, as well as TV shows — including Parenthood, Bless This Mess, and most recently, Stoner Cats. In addition to acting, Dax launched his Armchair Expert podcast in 2018. 

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.