Eric Clapton
In the late '90s, Sheryl Crow had a brief relationship with legendary musician Eric Clapton, who happens to be 17 years her senior.
The romance didn't last long, though it was rumored to have inspired her hit song "My Favorite Mistake," which is about a philandering ex-boyfriend.
Despite the speculation, Crow never admitted who the song was actually about and even introduced Clapton as "a really good friend of mine" when her joined her during her 1999 performance in Central Park. His presence on her 2019 album Threads indicates that the friendship is still going strong.
Owen Wilson
In 1999, Crow began dating Owen Wilson after meeting on the set of the little-seen film The Minus Man, in which she made her acting debut as one of the victims felled by Wilson's serial killer character. The two dated for two years, even attending the Vanity Fair Oscar party together in 2000.
As she would admit in the liner notes on her 2002 album C'mon, C'mon, the song "Safe and Sound" was dedicated to him, serving as an account of their relationship.
Josh Charles
For a few short months in early 2003, Crow dated The Good Wife star Josh Charles, even bringing him as her date to the Grammy Awards that February. By April, though, they'd called it quits, with a source telling Us Weekly, "They are no longer seeing each other. She's looking for The Guy, and he wasn't it."
Lance Armstrong
Perhaps her highest-profile relationship, Crow began dating famed (and now disgraced) cyclist Lance Armstrong after they met at a charity event in October 2003, shortly following his divorce from the mother of his three children, Kristin Richards.
By September 2005, they were engaged and sharing a ranch in Austin. It wasn't meant to be, though, and in February 2006, they'd ended their romance.
"After much thought and consideration we have made a very tough decision to split up," their joint statement read. "We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time."
Ryan Seacrest
In the same year that the American Idol host briefly dated Teri Hatcher—2006—it was rumored that Ryan Seacrest romanced Crow, though there is very little information to corroborate this fact. Baseless internet rumor or well-kept secret? We may never know.
Hank Azaria
After Crow was spotted out at dinner with actor Hank Azaria in 2006, rumors began to fly that the two were seeing one another, despite the fact that Patricia Arquette was also present at said dinner. Neither have ever spoken about the rumors and they haven't been spotted together since.
Steve Bing
In 2008, it was reported that Crow had begun dating film producer and Elizabeth Hurley's ex Steve Bing after allegedly being introduced by mutual friend Jennifer Aniston in late 2007.
Doyle Bramhall II
After enlisting longtime friend and occasional Clapton bandmate Doyle Bramhall II to producer her 2010 album 100 Miles from Memphis, Crow took her relationship with the producer to the next level, making their first public appearance together at The Society of Memorial Sloan Kettering Cancer Center's 2011 Spring Ball.
That May, while speaking with Prevention Magazine, she detailed her relationship with an unnamed producer, telling the publication he was "really good" with her two boys. "I've been involved with people and their kids, and if the relationship doesn't work out, it's heartbreak," she continued. "So I'm keeping the relationship friend-based when we're around the kids. Luckily, we have a great foundation, having known each other for fifteen years."
No word on when the two officially called it quits, but by 2014, she was promoting her latest album, 2013's Feels Like Home, a single woman.