Now, besides the aforementioned fact, what are some of the other dating older men pros and cons?The truth is that it’s not about age, it’s about the personality type you’re dealing with.When you meet a new guy, ask yourself three key questions to determine his personality type: First look at the way he speaks about his future.Maturity means he’s experienced the world, he knows what he wants and most likely…he knows how to get it!He’s comfortable being a man and knows the right things to say and do to make a woman feel like a lady.Here are few good examples: Michael Douglas and Catherine Zeta-Jones or Geogre Clooney and Alamuddin with 17 years of gap in between them.