Jeremy Piven – 55, Actor

For someone in his fifties, Jeremy Piven could be happily married with a few children. But nope, the actor is still a bachelor. He recently confronted personal problems involving many lawyers, but thankfully, he was able to get back up on his feet.

The former Entourage star has developed an off-screen reputation as a ladies’ man, but recently, he admitted that he wants to settle down and start a family. He has been linked with several famous personalities, including model Rachel Hunter, model Ashley Chontos, socialite Erica Lancellotti, and X-Factor winner Alexandra Burke. The 55-year-old actor said he would begin to consider marriage once he is sure he has met the right girl. He even honored his parents as his role model for marriage, saying, “My parents were devoted to one another. That’s my reference for marriage.” Piven is set to star in the films Ghost Killers and American Night.