Dating Tips: Older Woman, Younger Man

  • An older woman dating a younger man wasn’t as accepted as older men dating younger women in decades past. But that changed about ten years ago with the emergence of the “Cougar." The recently separated power couple of Demi Moore and Ashton Kutcher showed us that relationships involving an older woman and younger man can flourish -- at least for a while.
    Dating a younger man can be fantastic for both parties for a number of reasons. Let's take a look:
  • Maturity Remember that age is just a number. In some cases, your young guy has gone through some life experiences which may have accelerated his outlook on things and may have already given him some wisdom that he wouldn’t have gained until later in life. Don’t let that sell you though. Spend time with him. See how he handles stress, finances, his job, and his friends and family. If you’re trying to keep it casual, then it probably won’t matter. Just beware of the “clingers”.
  • Spontaneity Younger men are usually still exploring what life has to offer and even more important, they want to discover themselves before they settle down. That means they are all about adventures, which can be appealing to an older woman. The thirst for adventure can be contagious to the woman and exploring life together offers excitement for both parties.
  • Match Your Expectations Even though you know what kind of man you want, you have to be sure to be aware of what you are looking for when you find him. If having a casual relationship is more for you, then make certain to put that out there first to avoid confusion. Being on the same page at the beginning will prevent frustration and eventual heartbreak later. So,in the early conversations, find out what he wants from the relationship. Is he marriage minded? Does he want children? Of course, this isn’t first date talk, but if there are more dates after, then these issues are something to discuss early on.
  • Same Energy Levels It’s not going to be fun if you date a guy who likes to make it to happy hour 3 days a week and then hits the bars and clubs on the weekends when you would prefer to stay at home and watch a movie or vice versa. Find someone who on the same level as you. Tell him the things you like to do as well, and make some compromises if you need to. Your happiness is what’s at stake, so it’s best to find someone who has the same energy as you do.
  • No matter how old they are, women are looking for a guy who is the whole package" Someone who likes to have fun, is self-confident, funny, sexy, and best of all respects and accepts you as you are. Figure out your deal breakers before you start dating a younger man because this will help you to decide who is worth the pursuit and who is looking for the fling.
  • Beware of Being “Mommy” Some younger men are looking to be with a mother type. It can be easy to get manipulated into that role. If you notice things such as his asking to borrow money, or if he needs a place to crash because his actual mother kicked him out, these may signs it's time to move on to the next candidate. That’s because this guy is simply looking for someone to fill the role that his mother used to have. You've already raised your own kids. Don’t bring on another one.
  • Beware of Booty Calls To young guys, going out with sexy older ladies is a huge turn-on. His friends will stroke his ego by agreeing and encouraging him to keep the “relationship” going. Or there is the stereotype that a woman who knows more sexually will teach him everything he should know. So if sex isn’t your top priority, then make sure it isn’t with him either. If you notice that he only calls late at night, or if he’s bold and says outright that all he wants is a “friends with benefits” relationship, then end it -- unless of course that’s what you’re looking for.
  • Let Him Chase You Even though he may be younger, he is still a man. The thrill of the hunt is encoded in his DNA. So let him take the lead by asking for your phone number and the first date. It won’t diminish your strong woman role, and the fact that he’s chasing you means that he really is in to you. Besides, you’re too busy to do the chasing with everything else going on in your life.
  • Keep Your Options Open Date other young men in order to figure out if the one you're dating is going to be worth the investment of your love and devotion. It will be hard, especially if you feel a connection, but it will prevent you from getting emotionally attached too soon. Younger men offer the Cougar an exciting dating life that she may have not experienced before. It may be likely that your boy toy won’t have any extra “baggage” like kids or ex-wives, which makes it more alluring and refreshing than dating men of your own age range. So be on the lookout for the cub of your dreams.

    Date younger men -- Yes! Marry them -- No.