Sheryl Crow has had a number of high-profile relationships and has been engaged three times but the 62-year-old singer has been unattached for a while as she focuses on bringing up her two sons at their Nashville home.
While she has been open about some of her romances, even drawing on them for inspiration for her songs or putting pen to paper as a cathartic exercise to get over painful breakups, many of her relationships remained private - especially those from the pre-fame days.
Crow has had several meaningful liaisons with fellow musicians. She was in a relationship with pianist/composer Kevin Gilbert when both were members of the Tuesday Night Music Club collective - a group of musicians who worked on her debut album. As an item, Gilbert and Crow were over by the mid-90s - he died in tragic circumstances in 1996 aged just 29.
First love in St Louis
A few years earlier, when Sheryl was working as a schoolteacher in St Louis, Missouri, she was living with and engaged to a born-again Christian boyfriend, as she admitted in Amy Scott’s 2022 documentary Sheryl. “God love him… he was born again but he also partied,” she remembered. “There was a cycle of drink, smoke weed, repent and repeat.” It came to an end when he confronted her: “If you’re not going to sing for the Lord, maybe you shouldn’t sing at all?”
Nothing is known about the next mystery boyfriend who popped the question but Sheryl was romantically linked to Eric Clapton (1998-1999) despite the fact that the English guitarist was 16 years her senior. They performed live together at the time and continued to do so when both had moved on to find new partners.
The singer met actor Owen Wilson on the set of 1999 film The Minus Man in which Wilson played a serial killer and Crow his first victim. The two hit it off, enjoyed an electric, on-screen chemistry and started dating. They attended numerous red carpet events together but their whirlwind romance lasted barely 12 months. Sheryl wrote a haunting breakup song about their time together, Safe and Sound - the fourth track on her 2002 album C’mon, C’mon which included the lyrics: “Maybe this is forever/Forever fades away/Like a rocket/Ascending into space/Could you not be sad/Could you not break down/After all I won’t let go”.
The singer turned up at the 2003 Grammys at Madison Square Garden with new flame The Good Wife actor Josh Charles in tow. The fling was short-lived with Sheryl realizing that Josh wasn’t ‘The One’, and split amicably after a few months together.
Sheryl meets Lance
Cupid’s arrow struck when Crow attended a charity event a few months later. In October 2003, she met cyclist Lance Amstrong and the pair started dating almost immediately. By January they were an item and went public for the first time at the Los Angeles premiere of Along Came Polly. The loved-up couple were inseparable and in August 2005, Lance proposed and they got engaged. “We took this boat out to the middle of the lake, and this is one of these little fishing boats with the motor behind going,” Armstrong told Oprah Winfrey. “It ran out of gas in the middle of the lake, and so I thought, you know, we’re stuck here. I may as well ask her now.”
But by February 2006, their affair had hit the rocks. “After much thought and consideration, we have made a very tough decision to split up,” they announced in a joint statement. “We both have a deep love and respect for each other, and we ask that everyone respect our privacy during this very difficult time.” Some claim that Sheryl’s desire to have children of her own with Lance was a contributing factor as the cyclist already felt his three kids was sufficient for him.
Sheryl Crow 2024 Tour dates
- June 13 The Piece Hall Halifax, United Kingdom
- June 15 Black Deer Festival 2024 Tunbridge Wells, United Kingdom
- June 16 Blenheim Palace Woodstock, United Kingdom
- June 18 Hampton Court Palace Surrey, United Kingdom
- June 21 Auditorio Starlite Playa Duque Marbella, Spain
- June 22 Azkena Rock Festival 2024 Gasteiz / Vitoria, Spain
- June 24 Alma festival 2024 Barcelona, Spain
- June 25 Noches del Botanico 2024 Madrid, Spain
- June 27 L’Olympia Paris, France
- June 28 Paradiso Amsterdam, Netherlands
- June 29 LIVE IS LIVE 2024 Antwerpen, Belgium
- June 27 Chris Stapleton's All American Road Show Seattle, WA
- August 10 The Dome at America's Center St. Louis, MO
- August 11 Mercedes Benz Stadium Atlanta, GA
- August 14 Rogers Centre Toronto, Canada
- August 18 Lincoln Financial Field Philadelphia, PA
- August 21 Gillette Stadium Foxborough, MA
- August 24 Soldier Field Chicago, IL
- August 28 Washington-Grizzly Stadium Missoula, MT
- August 31 Commonwealth Stadium Edmonton, Canada
- September 11 Petco Park San Diego, CA
- September 13 Allegiant Stadium Las Vegas, NV
- September 15 Dodger Stadium Los Angeles, CA
- October 1 Hersheypark Stadium Hershey, PA
- October 3 MetLife Stadium East Rutherford, NJ
- October 6 JMA Wireless Dome Syracuse, NY
- October 12 Lucas Oil Stadium Indianapolis, IN
- November 6 Globe Life Field Arlington, TX
- November 18 Camping World Stadium Orlando, FL
- November 23 loanDepot Park Miami, FL
Since then there have been a string of short, one-off relationships with Hank Azaria (2006), Ryan Seacrest (2006), Steve Bing (2007-2008), John Cassimus (2008) and Doyle Bramhall II (2011) but Crow is believed to be happily single right now and has never married. She admits that she probably had some part to play in why her romances fizzled out and even tried to make sense of it and try to break the chain in her song My Favourite Mistake.
“If I knew the secret to a happy relationship, I wouldn’t have been engaged three times while somehow ending up single. I’ve had amazing relationships, have loved and been loved, but I’ve had a weird life with a job that kept me traveling. I’m content and happy, but would I like someone to join our little family? Of course,” she confesses. “Every person I have loved, I love [and] still love. I don’t have any terrible feelings about anyone. That sounds really woo-woo. There was a reason why I loved them.”
Sheryl has two young sons who she adopted - Wyatt in 2007 and Levi in 2010. With a new album Evolution out tomorrow and a lengthy promotional tour that will take her across Europe then back to the States, Sheryl’s got plenty to keep her occupied but she hasn’t given up on finding love yet.
