Ann Coulter, Age 58 – Single

Through her tendency to speak her mind, Ann Coulter has managed to become the center of attention on many occasions. She is 57 years old and currently works as a political commentator and author. On top of everything, much like most people on this list, she has never been married, probably because she’s waiting for the right person.

In the early 00s, there were many rumors going around that wanted Ann to be dating David Wheaton, however, given that she’s since established relationships with others, it seems like it didn’t work out in the end. The most recent gossip was that she’s, oddly enough, dating Jimmie Walker, rumors which she has also shot down.

heryl Crow, Age 58 – 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.