Sheryl Crow, Age 57 – Single

While Sheryl Crow has managed to maintain her single status over many years, that doesn’t mean she hasn’t had her fair share of public relationships. It all started in the 90s when she was dating Eric Clapton. While they were touring together, they were also criticized for their age difference.

She later had a brief relationship with Owen Wilson, and later with Lance Armstrong. To be fair, she almost got married to Lance, and they had even announced their engagement but split up in 2006. Sheryl has released a new album called Threads in 2019, that even features a collaboration with her ex, Eric.