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Lance Armstrong Broke Up With Ashley Olsen Over Their 15-Year Age Gap, Book Says

The cyclist and the fashion designer reportedly dated in the late '00s.

He was a 36-year-old globally known cancer survivor, cycling champion, and father of three. She was 21-year-old former child star who'd rebranded herself into a fashionista and businesswoman. For a brief moment in the fall of 2007, Lance Armstrong and Ashley Olsen made headlines when they were spotted "making out" around New York City. But according to a 2014 tell-all book, the romance came to a swift end after Armstrong's handlers urged him to consider the impact their age gap could have on his reputation. Read on for the full details on their unlikely fling and its abrupt ending.

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They were spotted kissing in NYC.

Lance Armstrong
Jon Kopaloff/FilmMagic

After a 2003 divorce from his first wife Kristin Richard and subsequent broken engagement with singer Sheryl Crow, Armstrong found himself living in New York City to be closer to his new love, fashion designer Tory Burch. According to an anonymous Page Six source, the pair had reportedly ended things after finding living in the same city to be too much, leaving Armstrong single and ready to mingle again. "He tried to make Tory happy when they were dating by buying a place here, but she couldn't deal with him not actually living in the same city, so they broke up," the source said.

Olsen and Armstrong were first spotted in the wake of that breakup in October 2007. An anonymous onlooker told Page Six that they had spotted the pair cozying up at the Gramercy Park Hotel's Rose Bar.

"They came together with a group of friends," the source said. "Ashley drank red wine, sat on his lap and they were making out all night. They left together around 2 a.m."

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Olsen went to school with his daughter.

Ashley Olsen in 2007
Jason Kempin/FilmMagic

Olsen, meanwhile, was no stranger to dating older men. At 18, she had dated 30-year-old nightclub owner Scott Sartiano before being linked to a then-35-year-old Jared Leto the next year, according to PopSugar. However, her time with Armstrong soon took her outside her usual NYC haunts when she did a special favor for one of Armstrong's six-year-old twin daughters from his first marriage.

According to an archived RadarOnline story, the New York Minute star was the subject of Armstrong's daughter's show-and-tell presentation during a visit to her Texas elementary school.

He said they were just friends.

Lance Armstrong in 2008
Jemal Countess/WireImage

An unnamed insider told Marie Claire UK at the time that the public cuddling may have been an attempt to get Armstrong back in headlines—or to heal his broken heart.

"He misses the spotlight now that he's not competing," they claimed, adding, "He doesn't handle loneliness well, so he overcompensates and makes poor decisions sometimes."

After Page Six posted an item claiming that Armstrong's ex Sheryl Crow called his dating Olsen "pathetic," the cyclist spoke publicly about his feelings for the former Full House star, denying any romance.

"Ashley Olsen and I are strictly friends," he said in a statement to the outlet. "We have hung out amongst other friends, and she strikes me as a nice, smart lady." (Crow meanwhile, denied ever commenting on the two.)

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A 2014 book claimed his handlers were wary of her age.

Mary-Kate and Ashley Olsen in 2007
Donato Sardella/WireImage for InStyle Magazine

But according to the 2014 tell-all Cycle of Lies: The Fall of Lance Armstrong by Juliet Macur, he and Olsen had done more than hang out as pals. And not everyone was happy to see Armstrong involved with the much-younger woman. The book claims that, perhaps wary of tarnishing his already precarious image amid persistent accusations of doping, his handlers urged him to end things before the wider public got word of his involvement with a former child star 15 years his junior.

Macur wrote that friend and Livestrong Foundation chief John Korioth brought the relationship up with Armstrong. "Whoa, dude, bad idea," Korioth reportedly urged Armstrong. "You've got to put a stop to this right now." Armstrong was reportedly unswayed, retorting, "She's 21…[expletive] you," according to the book.

Despite his nonchalant attitude, the relationship seems to have come to an end soon after. By May 2008, Armstrong was seeing actor Kate Hudson, according to People, while Olsen had moved on with National Treasure actor Justin Bartha, per Page Six.

Four years later, Armstrong's reputation took another blow when he was formally stripped of the seven Tour de France titles he won between 1999 and 2005 due to "doping and playing an instrumental role in team-organized doping," according to The New York Times.

Andrew Miller
Andrew Miller is a pop culture writer living in New York. Read more
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