Tom Cruise, Age 58 – Single

Tom Cruise has certainly been part of many high-profile relationships, but what’s even more surprising is that during his 80s phase of being attracted to older women, he even dated Cher! They reportedly met at Madonna’s wedding in 1985, but clearly didn’t last that long. They do remain friends, however.

Probably his more public relationship was the one with Katie Holmes, especially after his public declaration of love in 2005. They got married, had a child together, only to split up in 2012. Tom is now revisiting his 80s days, getting ready for 2020’s Top Gun: Maverick.

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.

Sheryl 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.

Charlize Theron, Age 45 – Single

She’s been in many relationships, including with Sean Penn, Keanu Reeves, and Stuart Townsend, but it seems as though Charlize Theron is much more comfortable being single. She has barely enough time to focus on being one of the highest-paid actresses and being a mother of two, let alone dating.

Charlize is now expected to play in the upcoming film called The Guardian. She lives with her two adopted children in a house in Los Angeles. By focusing on what’s important, Charlize is now worth $130 million, so she must be doing something right!

Al Pacino, Age 80 – In a Relationship

Even though he’s always been a heart-breaker, Al Pacino, over the many years he’s spent on this earth, has never been married. That doesn’t mean, however, that he has never had serious relationships! As a matter of fact, there have been many women that stole his heart over the years.

His first public relationship started at the same time with The Godfather in the 70s, with Diane Keaton, but ended soon after the second movie was finished. He later went in a relationship with Beverly D’Angelo between 1997 and 2003, which ended in an ugly custody battle for their twins. He’s now rumored to be dating Meital Dohan.

Maggie Smith, Age 85 – Widowed

One would think that a beautiful, talented, intelligent and charming woman like Maggie Smith would have had a great love life. Alas, it is not quite so. Her first attempt at married life came with Robert Stephens in 1967. After having two sons, they ended up separating in 1975.

She later got married to Beverly Cross in 1975, but death, tragically did them part, when he passed away in 1988. Maggie has never been married since, having already found the person she considered “her one”. However, she’s not alone, given that she’s now a grandmother of five, and just finished playing in the Downton Abbey movie.

Queen Latifah, Age 50 – Rumored to be Engaged

To be fair, Queen Latifah has never actually spoken about her preferences, but there has been much speculation surrounding people that she might have been dating. For quite a long time, around when she was making her return in hip-hop music, there were rumors about her dating the personal trainer Jeanette Jenkins.

However, they reportedly split up when Latifah started a relationship with Eboni Nichols. Jeanette, on the other hand, has denied all the rumors. Even though there have been some whispers that Eboni is pregnant, and engaged to Latifah, nothing has been confirmed by either of them.