Her Past With Lance Armstrong and More – Hollywood Life

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Sheryl Crow’s music encompasses heartbreak and the joy of falling in love. From “If It Makes You Happy” to “My Favorite Mistake,” the Rock and Roll Hall of Fame inductee has poured her heart out into her songwriting throughout her career. Fans can watch Sheryl’s long-awaited induction into the HoF on January 1 on ABC.

Although it’s not currently clear whether or not she is in a relationship now, the “Strong Enough” singer has opened up about romance in past interviews. Despite enduring a few breakups, Sheryl noted that she “would love to get married” while speaking with Good Housekeeping in 2020. 

“I’m still old-fashioned. But I don’t think marriage is the be-all-and-end-all,” the Grammy Award winner explained. “It’s better to have three broken engagements than three divorces.” 

As for what she looks for in a partner, Sheryl noted that she has “always gone out with guys who were highly successful, which would seem like it would put me at an equal level.” However, she explained that “what ends up happening is that one of you becomes smaller — and it was always me. I do think that sometimes, in order for one person’s light to shine, everyone else has to dim theirs.” 

See Sheryl’s full public dating history below! 

Eric Clapton

Sheryl and fellow musician Eric reportedly dated briefly in the 1990s, despite their nearly 20-year age gap. The duo went on to perform live together a few times and collaborated on a handful of songs. 

Owen Wilson

In 1999, Sheryl met Owen on the set of The Minus Man. The two co-starred together as characters Vann (Owen) and Casper (Sheryl), making this the singer-songwriter’s on-screen acting debut. They reportedly dated for about two years until calling it quits by the early 2000s. 

Josh Charles 

Following her split from Owen, Sheryl started dating The Good Wife alum in 2003. They were spotted attending public events together, such as the 2003 Grammy Awards. However, they broke up shortly thereafter. 

Lance Armstrong

By the end of 2003, Sheryl met Lance, and the former pair’s romance heated up quickly. The rock star and the athlete were even engaged in 2005, but they called it quits the following year. Although the Missouri native has said that she’s been engaged three times in her life, her only known engagement was with Lance. 

Doyle Bramhall II 

Sheryl’s last well-known relationship was with fellow musician and music producer Doyle, which reportedly began in 2010 when they collaborated on her album 100 Miles From Memphis. After four years together, it appeared their romance fizzled out.