Sheryl Crow thanks God she never got married: ‘I almost did, three times’

My jaw dropped when I read this article and realized Sheryl Crow is 60 years old. Obviously celebs get older just like the of us, but some seem to stay the same age forever and she’s one of them. I really thought she was 40.

Anyway, Sheryl has an eponymous documentary coming out soon and appeared on Howard Stern’s show to discuss a range of topics. Aside from talking about her career, Sheryl talked to Howard about her personal life and why she never married despite being engaged three times. Turns out she doesn’t feel like she missed out on anything.

Ahead of the release of her documentary, Sheryl, music legend Sheryl Crow is opening up.

The singer stopped by The Howard Stern Show on Wednesday where she reflected on her love life, her legacy in music and why — at 60 years old — she has yet to marry.

“I’m hot. Even at 60, I’m hot, right?” she told Stern. “Honestly, I even scratch my head and go, ‘How did I get here without getting married?’ … I almost did, three times.”

One of those men was cyclist Lance Armstrong, with whom she got engaged in 2005 before calling it off in 2006 — around the time Armstrong fell into controversy surrounding his highly publicized doping scandal.

“Everyone eventually grows up, figures out who they are,” she said of the men in her life. “I give people a lot of leeway when they evolve.”

Looking back, though, Crow doesn’t regret her choices.

“I go, ‘Thank you God. Thank you. I didn’t get married,'” she said. “I got breast cancer at the end of one relationship and it was horrible but when I came through it, I was like, you know what? I’d still be in that relationship had I not had breast cancer. So in a weird way, I’m grateful. And you think you’re gonna be like, ‘Oh, F that guy,’ or whatever, but by the time you get to that point you’ve moved on and you don’t really care anymore.”

Still, despite the ups and downs in her personal life, Crow remains optimistic about the future — especially when it comes to love.

“I like funny people,” she said. “I’ve dated famous people, I’ve dated athletes, I’ve dated not-famous people,” she said. “It’s an open opportunity for anyone to be in the category of my next ‘favorite mistake.'”

[From Yahoo! Life]

The guy Sheryl is thanking god she didn’t get married to is none other than Lance Armstrong. They were engaged and together for about three years (2003-2006) before breaking up. I read some reports that their relationship fell apart over children — he had three already and wasn’t sure if he wanted more, but Sheryl wanted them. She seems to attribute their breakup to her breast cancer diagnosis, but both can be true. In any case, Sheryl did adopt two boys — one in 2007 and one in 2010 — and has been raising them on her own. I’m glad she made it happen and got what she wanted on her own!

I tried to figure out who the other two engagements were but couldn’t find anything conclusive. Sheryl did date Eric Clapton and Owen Wilson, but in what I read both of those relationships were characterized as brief, so who knows. Great mystery! Sheryl’s no regrets, “my favorite mistake” outlook is a pretty positive way of looking at things. Honestly, a favorite mistake is probably better than a favorite “what if.” Seems like her vibe toward relationships at this point is YOLO and she’s focused on raising her kids. And as she mentioned she’s definitely hot at 60!

Photos credit: Instar and via Instagram

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31 Responses to “Sheryl Crow thanks God she never got married: ‘I almost did, three times’”

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  1. Pinkosaurus says:

    She’s absolutely gorgeous, maybe even more attractive than decades ago. I’m sure she’s had a few things done but so glad it’s not terrible fillers and excessive disfiguring surgery to get rid of every wrinkle.

  2. Amy T says:

    I think one of those close marriage calls was when she was very young and her fiancé said they should only ever make music that praised God, she reassessed the relationship.

  3. liz says:

    My recollection is that the original “favorite mistake” was Clapton. She had just come out of that relationship when the song was released. That was a bullet well dodged.

    Given her history/taste in men, not getting married has been a very good call for her.

  4. AlpineWitch says:

    To be honest, I totally agree with her even though I got married after the third engagement…. but so happy I didn’t go ahead prior to that.

    Better to stay on your own if things don’t work out.

  5. Dlc says:

    She really dodged a bullet with Armstrong. He is SUCH an *sshole. Not for the cheating, but for the bullying to hide his cheating. He terrorized people and tried to destroy their lives.

  6. Orangeowl says:

    I was thinking about her and Armstrong yesterday after hearing an interview with her on NPR. They were so public, she seemed to fall so hard, I remember being a bit nervous for her as I always had my doubts about Armstrong’s integrity. To say she dodged a bullet with that guy is a huge understatement.

  7. CMChat says:

    Sheryl wanted kids, Lance didn’t, then he had 2 kids with his next girlfriend. My guess is that Sheryl wasn’t into entrapment!

  8. Flo FLo says:

    Did she date Kid Rock?

    • lucy2 says:

      I don’t think so, but I remember them doing a song together.

    • Lizziebuck says:

      She was pretty serious with Dwight Yoakam at one point. They even did a duet or two while they were dating.

  9. HeyKay says:

    I enjoy her music.
    She has come thru after cancer = excellent.
    More power to her.
    Yeah, she was with some interesting men in her past.
    I thought her and Owen made a fun, cool couple.

    Clapton, ah Clapton, who the hell didn’t he hook up with back in the day?
    Most of whom he treated like crap.

    Lance Armstrong = no thank you. She deserved better, that douchebag ran when she was diagnosed with cancer, IIRC. #1. Asshole move.

    • Isadora says:

      She had relationships with some people who turned out to be assholes. I’m glad she’s doing great on her own.

      I’ve had one “close call marriage”. I was heartbroken at the time (I was barely 20) that we broken up but now I’m grateful not being stuck with him because i recognize now that he was an asshole.

      I’m in my 40s now, want to have children, am single and haven’t met a guy who is serious about starting a family. But much like Sheryl I’m toying with the idea to adopt. I haven’t given up on love but I’m also not sad if it doesn’t happen.

  10. HeyKay says:

    Btw, was she ever involved with Lenny Kravitz?
    Maybe I just remember them being on a summer tour together?

  11. AmelieOriginal says:

    She looks great! I know they don’t look alike all that much but I did think the headline pic was Meredith Vieira for a second before I clicked. And she def dodged a bullet with Lance Armstrong and all that doping stuff that came out!

  12. Elsa says:

    I love her and she looks great. I have a few favorite mistakes too. Always loved that song!

  13. DrFt says:

    As is the modus operandi with awfull men. What he should have said os that I do not want children with youuuu.

  14. Bre says:

    She looks like the coach in Netflix’s Cheer!

    • Amilu says:

      That’s it!!! I was looking at these photos thinking she looks just like someone! I’m so glad you commented!!!

  15. lucy2 says:

    She looks great. I’m interested to see her documentary, I’ve liked a lot of her music over the years. I saw her in concert once, and she did a Led Zeppelin song at the end that blew the doors off the place, I always wished she’d done more rock after seeing that.

  16. She was initially engaged to a man she went to college with in Missouri, pre-fame days. I went to high school with his younger brother. This was in the late 80’s

  17. Tiffany:) says:

    I’m so back and forth on her music. Some songs, like Favorite Mistake, I really love. But some of her songs are just so terrible. The lyrics to Soak Up the Sun are so incredibly stupid! And the straining sound of her voice on Leaving Las Vegas used to drive me insane as a kid.

    She seems like a relatively low-key celeb, though, and I respect that she stays focused on the music.

  18. Kristen says:

    Meh – anyone that proclaims ‘I’m hot’ is annoying. Honestly, get over yourself.

    • blacktoypoodle says:

      You may not realize, if you are not there yet, that over 50 we are “erased”, “UnF-able” and ignored by much of the population. Yes, she’s had work done but her attitude is a defiance I enjoy as a (nearly) 60 myself. Just wait until you hit menopause, are expected to shop at J Jill, Talbots or Chicos, yet you actually follow fashion, enjoy style but don’t want to dress like an instagrammer. For people of my age to actually have dating lives and romance is described as “cute” and “you go girl”. F that. She looks hot.

    • Jaded says:

      I’m pushing 70 and I think I’m still hot. My guy says I’m still hot. There’s nothing wrong with a little self-appreciation in a day and age where what’s shoved down our throats is that only young, gorgeous women can be appreciated for their looks.

  19. JFerber says:

    But Clapton is a world-class asshole, too. In addition to his anti-vaccine stance and a concert in England in which he (drunkenly?) shouted, “Let’s keep England white,” Patti Boyd said that about a week after she married him, he called up a groupie for a date. Her take was it was all about taking her away from his friend/rival George Harrison. The thrill was gone once she married him. How is that for a shit guy?

  20. JFerber says:

    blacktoypoodle, Yes to everything you said.

  21. Jaded says:

    Clapton is a horrible, HORRIBLE human being. I read Patti Boyd’s autobiography after which I threw out my Clapton and George Harrison CDs. Both of them were utterly despicable to her.

  22. Bread and Circuses says:


    She definitely doesn’t look 60, and she also doesn’t look tweaked into the Uncanny Valley either.

    Whatever she did worked. Maybe it was just being calm and living well.