7 Rules For Dating An Older Man

Yes, there will always be something slightly appealing about young, wide-eyed struggling artists and beer pong-loving frat boys with hearts of gold. But sometimes you want someone a little more settled and refined—someone who prefers a suit to a backwards hat and The New York Times to Maxim. Whether you have already snagged yourself a silver fox, or you are on the hunt for one, there are a couple of things you’ll need to take into consideration. Like all relationships, this could be long or short-term, but it is always nice to know how to act or behave when dealing with the majestic creature known as the older man. After the jump, seven rules.

1. Beware of pop culture references. Yes, you may be tempted to tell your older man the story of how when “Annie” came out, you were 5 and wore a red wig for an entire year. Only, when “Annie” came out, he was graduating from college. See the problem? Referencing movies, TV shows, and fads of yore only highlights your age difference. So focus on things in the here and now, which you are both experiencing as adults.
2. Do not take on the role of the kid. He may be older, but this man is not your father—it is not his job to take care of you. He should not be a substitute for any male adult figure that you are lacking in your life. If you are craving or missing that bond, make a session with a therapist. There is a good chance that your older man might have kids already, so don’t be more obnoxious and needy than his 10-year-old. The same goes for him—if he is trying to keep you in some creepy child-like state, ditch him. You’ve come so far as a woman, do you really want to be bossed and controlled like a toddler?
3. Ask what he’s looking for and make sure it lines up with what you want. Some older men date younger on occasion, when they meet a woman they find irresistible. Some do it all the time. If he’s 45 and only dates girls under 25, that should be a red flag if you want something long term. After all, why hang around if he is only going to turn you in for a newer model? And conversely, what if he’s ready for kids now and you don’t see that happening until years down the road? Find out what he wants from the beginning. Is he looking for wedding bells or arm candy? It never hurts to ask—that way you can make the decision to stick around.
4. Be yourself. Yes, this is a tired and cliché phrase, but it’s also true. It goes for all relationships, but especially with an older man. See, older fellows are far less prone to playing games than their younger counterparts. They usually know who they are and what they want. They want to see the same in you. Know that you are beautiful, smart and amazing. Stand up tall and be the woman that made him take a second glance.
5. Be yourself, just a slightly more mature version. Hopefully, acting like you involves some sort of grown-up behavior. You shouldn’t expect him to do car bombs with you on a Wednesday until 2 a.m.—have other friends on call for that. Here is where things get complicated. Some of the life experiences that you want, he has already had. Be understanding and considerate and he should do the same.
6. Speak up in bed. On the subject of realness, save the “Yes! Yes! Yes! That’s the spot!” theatrics for someone else. Odds are that he has been with enough women to know when you are auditioning for a horror film. He has been around the block long enough to know how to take constructive criticism in the sack. If you don’t like it, say so. His ego is less prone to be bruised if you tell him to move over an inch.
7. Take his lead on occasion. Hooray! No more jackhammer. Older men actually want to please you and know that you are capable of having orgasms in a variety of spots. An older man tends not to get all of his sex moves from porn. Relax and enjoy it — he wasn’t always a pro in bed and he obviously learned his way over time. Let him show off his skills.