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The prospect of dating an older woman can seem tantalizing. She’s more stable, more mature, and generally has less “drama” in her life. But just because it seems like a good idea at first blush doesn’t make it so, you know? Dig a little deeper and you’ll see that a relationship with an older woman is fraught with peril. Don’t believe it? Well check out this list of seven reasons not to date an older woman if you need a little more convincing!

Generation gap. Tired of her overplayed Christopher Cross album and all you want to hear is some T.I.? Is she always going to wear that leopard-skin pill-box hat? Older women may listen to music not timely familiar to you, dress awkwardly from another dimension and swing an entirely different jig.  But that’s what you get when you cross a younger breed with an older one. She calls a couch a “Davenport,” whatever the hell that means, and to her Robert Redford is a young, rising star. To you, these things exist sometime in Earth’s sepia-toned past.

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Entertainment. She likes to have a good time, of course, but your idea of what’s entertaining is going to differ wildly from hers. She may want to check “Lawrence Welk” re-runs, and that “Murder She Wrote” marathon is going to occupy most of her weekend. You, on the other like young guy stuff, like drinking, yelling, and video games. She was born well before “Pong” even existed, so “Call of Duty” probably isn’t on her radar, slick guy. Unless you like church picnics, you may want to look elsewhere for dates!

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Medical issues. The older we get … the older our bodies get. From hair to the toes, things can disappear and things can grow. Older date feeling a little pain? It could be an arthritis thing. Could be osteoporosis. Truth is, medical issues happen. They can get in the way, both financially and mentally. But how about physically? Chances are that all of your acrobatic sex moves aren’t going to come in handy if her hip is stiffening up. And forget about conception, because her child-bearing years are over.

Expectations. At her advanced stage in life, an older woman may have different expectations about where your relationship is heading. Maybe she wants to keep things casual and you’re looking for something deeper. Or maybe she has different expectations about how the relationship should progress? If she’s expecting an old-fashioned way of doing things but you’re a young man used to dating young women, chances are that you’ll be butting heads when it comes to the expected course of the relationship.

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Mother figure. She doesn’t want to be your mom, and you don’t want her to be. But guess what? The only older women in your life to this point have likely been care-takers, or perhaps co-workers. It can be tough to shake that perception, and it can be equally tough for her to avoid mothering you. On top of that, doing the nasty with someone who reminds you of Mom is definitely not cool.


Thought Process. As people get older, they tend to mellow. Young men can be a little head-strong. A little wild, if you will. Older woman can be more deliberate. While you’re ready and raring to go anywhere on a moment’s notice, she may want to slow down and consider things from all angles. The more you’ve seen, the more you have to mentally process, and at her age she’s seen a lot.


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Dies on you. Hate to be the one to tell you but the older she gets, the closer she is to flat-lining. Women have a higher chance of a heart attack depending upon the situation. It’s embarrassing to have to tell your buddies that your girlfriend died of old age, and forget about it she dies during sex. The last thing you need is two stiffs in one room. Plus, with her vision deteriorating, she might hit you with her car as she’s on her way to a DMV vision test!