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Sheryl Crow is a Grammy-winning artist with over 20 years in the music industry. Her unique music combines several genres, including pop, country, and blues. She has released eleven studio albums, and also tried her hand at acting. 

Ryan Seacrest also has a long career in entertainment. He has become one of the most recognizable faces in the industry, hosting a variety of television and radio shows. 

Both of these celebrities have spent plenty of time in the spotlight, with their personal lives and relationships being scrutinized by the media. It’s interesting that the two were briefly linked–possibly romantically?—in 2006.

The many men of Sheryl Crow–some will surprise you

Sheryl Crow has spent many years in the spotlight, but she’s managed to keep her personal life fairly quiet over the past few years. The singer recently released her eleventh studio album, Threads. Threads is a collaboration with many of Crow’s closest friends and some newcomers to the music scene. She says this will be the last album she plans to create. 

Although Crow had her fair share of celebrity boyfriends earlier, she hasn’t been linked with anyone in quite some time. After adopting her sons — Wyatt, 13, and Levi, 10–she changed her dating style. Now, she wants to be sure she really knows the person before they come into her sons’ lives, so she’s probably been dating less in general. Plus, we all know that motherhood keeps you quite busy…

Crow’s most well-known beaus include Eric Clapton, Lance Armstrong, and Owen Wilson. In the 90s, Crow dated legendary artist Eric Clapton. Clapton is 17 years older, and the relationship didn’t last very long. There were rumors that he cheated, but Crow never confirmed them. 

After Clapton, Crow dated actor Owen Wilson. They met on the set of the psychological thriller The Minus Man. Crow played a junkie, and the first victim of Wilson’s psychotic serial killer. The two grew very close and dated for two years. The singer even wrote a song about their relationship — “Safe and Sound.”

Crow’s relationship with former cyclist Lance Armstrong garnered the most media coverage. The two met at a charity event in 2003 and hit it off immediately. Two years later they were living together in Austin, but the relationship ended soon after that. In an interview, Armstrong stated that Crow wanted to get married and start a family, and that was something he wasn’t ready for at the time. 

Ryan Seacrest: Julianne Hough, Shayna Taylor, and others

Ryan Seacrest is one of the most recognizable faces in America. The charming radio and television personality has hosted a variety of shows and events, including American Idol and the weekly radio countdown, American Top 40. Throughout the years, Seacrest has been linked with a number of love interests, including dancers, models, and actresses. 

Seacrest dated model and actress Shana Wall from 2003-2005. In 2006, he went on one date with Teri Hatcher, but despite what the tabloids would insist, the two never had a relationship. In 2009, he took a trip to Paris with Jasmine Waltz, and the two dated for a brief time. 

In 2010, Seacrest began dating adorable dancer, Julianne Hough. The couple dated for three years, but the relationship ended in 2013. Hough later opened up about the experience, stating that her fear of being vulnerable had inevitably damaged the relationship. After dating Seacrest, she married NHL player Brooks Laich, but they split up in 2020.

Shortly after his relationship with Hough ended, Seacrest began dating model and chef, Shayna Taylor. This was his longest relationship, with the two dating on and off for eight years. They went through two public break-ups in that time, finally ending things in 2020. Social media posts from Taylor indicate that perhaps Seacrest couldn’t fully commit, which does make sense, given that he has always seemed to be very dedicated to his career. 

Ryan Seacrest and Sheryl Crow?

RYAN SEACREST
RYAN SEACREST | ABC via Getty Images
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Why Did Ryan Seacrest and Girlfriend Shayna Taylor Break Up?

Way back in 2006–right after that date with Teri Hatcher–rumors swirled that Seacrest and Crow were dating. There was never much evidence to support this theory, though, and we’re chalking it up to internet rumors. 

So what are they doing now? Well, although Sheryl Crow said Threads will be her last album, she still plans to continue working in music and release singles. She explained that changes in the music industry have resulted in fewer people listening to a full album. “I don’t think people listen to albums as a full artistic statement anymore. They cherry-pick and make their own playlists…” She viewed her albums as a story, from beginning to end, and doesn’t feel like it’s worth the time anymore. 

As for Seacrest, he continues to host the popular singing competition, American Idol, as well as his morning show, LIVE with Kelly and Ryan. He keeps busy with his Emmy Award-winning production company, Ryan Seacrest Productions. He also serves as chairman of the Ryan Seacrest Foundation, a non-profit organization that inspires youth through entertainment.