Dating an Older Woman? Here’s What to Expect

Dating an older woman can be exhilarating by concept alone. However, there are certain things to know before you’re ready to set sail and into her life.

Keep these older woman dating tips in mind, and you’re sure to not rock the boat (at least, not too much).


Although you may be a bit shy to ask an older woman out, I can almost guarantee she’ll be flattered – even if she isn’t into younger men. If she’s not interested, you have very little to risk here. Unlike a younger woman who can often turn a guy down hard, leaving him with a nice bruised ego, an older woman will likely be very polite to your flattering gesture.

Name Calling

Don’t call her a Cougar. Don’t call her a MILF, and especially don’t call her Mom. Although some women get off on such terms, many mature women still find it offensive. Wait to see if this is a phrase she wants to self-profess, then tread lightly.

Mind the Gap

You don’t have to mention the age difference. Although it can be fun to tease, or be some flirtatious banter between the two of you, sometimes drilling in the reminder of age can be hurtful to both parties. You both know how old each other is, so just enjoy it.

Her History

Mature women often have a lot to deal with. Some things to keep in mind: she may have been married, have had numerous boyfriends, have children, or have financial obligations. Now that you know? Don’t be alarmed. She will have a history that goes well past your years and experience, so respect the differences.

She’s Got Legs

Older women have experience in many departments, and one of them is style. A cougar has had the time to get to know herself; she’s had the years to work through her insecurities and become confident. She knows what clothes to wear, how to style her hair, and show the right amount of skin.

Gossip Column

Yes, people will gossip. And, although cougars have been in the spotlight with shows such as Single Ladies, Extreme Cougar Wives, and Cougar Town (yes, I know, even with shows naming themselves such, I still warn you about “Name Calling”), people will frown. It’s still taboo, and especially with these shows in existence, it can make your situation that much more spectacle-worthy. With outside attitudes, I say – who cares! – and embrace your cougar n’ cub relationship with pride.

The Sex

I’m often dumbfounded by nature’s choice to have women’s sexual peak occur twenty years later than a man’s, but you can certainly use this folly to your advantage. Simply put, if an older woman is looking for a younger man – she’s likely hot in bed. She’s got experience, and she’s looking for your younger body and stamina to compliment her drive. Go for it!

Anything I missed? Leave a comment below.

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