Sheryl Crow – 59, Singer-Songwriter

Over the years, artist Sheryl Crow has made a name for herself in the fields of music and acting. She is best known for her chart-toppers that incorporate different genres, such as country, rock, and pop. Crow has certainly found much success on her own, but she has also left many people wondering about why she has not chosen to settle down. After all, throughout the years, she has been involved in a number of high-profile relationships, with some almost leading to marriage. Crow even had a brief relationship with fellow singer Eric Clapton, who was 17 years her senior.

She was also in a relationship with former cyclist Lance Armstrong. The pair began living together just two years after they first met. Many thought that they would stick it out, but they later split up as well. These days, while she’s not saying no to love completely, the singer is dedicated to caring and investment planning for her kids, Levi and Wyatt.