Dating Older Women 101

There will always be younger men who are interested in dating mature women. They may know instinctively that this is a better fit for them, or it may take a few years of dating women their own age to realize that’s not what they want.

When I talk to cubs that are new to the cougar jungle, I like to share a few basic tips. Yes, older women are complicated creatures and the only way to really know what you’re doing is to get out there and explore. But before you head out on the journey, I’ll offer a little advice – not enough to overwhelm, just enough to help you avoid common mistakes.

Be Direct
An older woman is not shy about asking a guy out, but that doesn’t mean she always wants to make the first move. With younger men, she doesn’t! Confidence is sexy. Ask her out without hesitation.

No Labels
I use the cougar cub terms because I write about this particular relationship a lot, but I know many older women who don’t like the term cougar even if her preference is dating younger men. Avoid the term when speaking directly to an older woman.

Forget Age
You know you want or prefer being with a mature woman, but you don’t need to address that with her. Reminding a woman of her age isn’t polite. Compliments are always welcome, but never say “you look good for your age” – not cool. She knows she looks good, that’s why you want to be with her.

Grow Up
You may still act like a kid, especially with your buddies, but an older woman is not going to be impressed with childish behavior. Talk straight. If you say you’re going to meet or call her at a certain time, do it. She won’t put up with less than.

Outside the Bedroom
Older women like their sexual relationships with younger men, but they also want a little more. That doesn’t necessarily mean long-term or fully committed, but show interest in other aspects of her life – you’ll impress and turn her on even more.

Men: What lessons did you learn when dating an older woman for the first time?

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