Last year, Dax Shepard shocked listeners on an episode of his Armchair Expert podcast by revealing that he once dated actress-turned-fashion mogul Ashley Olsen. This previously unconfirmed coupling apparently met at a party sometime around 2006.
Shepard spoke highly of Olsen, commending her for her business expertise, sense of humor, and taste in cars. However, this was a pairing clearly not meant to last. By 2007, both Shepard and Olsen had moved on with other people—and their rebound relationships are somehow even less expected.
Dax Shepard Dated Kate Hudson For A Few Months
Shepard has admitted that he wasn’t a fan of monogamy in the early 2000s, so his relationship history gets a little bit fuzzy around that time. His next confirmed relationship, though, was with Kate Hudson in 2007. While this coupling had been cloaked in mystery, Hudson actually appeared on Shepard’s Armchair Expert podcast in 2019, and they took a stroll down memory lane.
As Shepard tells it, he and Hudson met in Toby Maguire’s backyard and immediately hit it off, but they were in relationships with other people. About a year later, they met up for dinner—although they still weren’t looking for something romantic. However, as they were leaving the restaurant that night, they thought it would be funny to trick the paparazzi into thinking they were on a date.
“While we were there, we said, ‘Wouldn’t it be funny if we came out holding hands and I was your new boyfriend?’” Shepard recalled. “We were just pals.” However, in typical rom-com fashion, they weren’t able to deny their very real chemistry. The pair dated for a few months before ultimately realizing they had different priorities. Shepard credits Hudson with helping him realize he wanted to settle down and have kids.
Hudson, on the other hand, already had a son and had just finalized her divorce from Chris Robinson. According to the actress, she wasn’t looking to start all over again so soon. Thankfully, both Hudson and Shepard can look back on their time together fondly. Later that same year, Shepard met his wife Kristen Bell at a party and the rest was history.
Ashley Olsen Had Brief Fling With Lance Armstrong
It’s clear that, like Shepard, Olsen had no problem moving on from their short-lived romance. In 2007, Olsen made headlines for her rumored relationship with professional cyclist Lance Armstrong. According to a Page Six report from the time, Olsen and Armstrong were spotted getting cozy at a bar.
There weren’t many other credible sightings of the couple from the time. However, in 2014, an investigative tell-all about Armstrong later alleged that the then-36-year old father of three caught flack from his friends and co-workers for his fling with the 21-year-old fashion designer.
According to the book Cycle of Lies, Armstrong’s friend John Korioth told him, “Whoa, dude, bad idea. You’ve got to put a stop to this right now.” Apparently, Armstrong’s friends were worried about what the relationship would do to his public image. However, undeterred, Armstrong allegedly responded, “She’s 21 … F*ck you.”
It’s unclear when their fling fizzled out, but it couldn’t have been long after they got together. By 2008, Armstrong had moved on to his next high-profile romance with…wait for it…Kate Hudson! It just goes to show that, in Hollywood, everyone knows everyone.