How to Date an Older Woman

Updated on November 22, 2017
Mystee Crockett profile image

Mystee is a writer, entertainer and entrepreneur. Her column, Ask Mystee, has a large following. You can ask her questions: askmystee@gmail.

How do I Date an Older Woman?

My inbox has been filled lately with young men asking me how they can attract and keep the interest of an older woman. This article is an attempt to answer those many emails.

You Can Date an Older Woman


Benefits of Dating Older Women

1. They know what they want

2. Lots of experience

3. A new perspective

4. No Drama

5. They appreciate your attention

Older Women Make Beautiful Lovers

Older Women Know What They Want

Whether it's in business or in bed, we know what we want. As an "older" woman, I know what I want in life. I know how I like to be treated, not only on a date, but after the date too.

I'm not interested in playing games. I know what I want and I know how to get it. If you want to date an older woman, be direct. Don't be weak and pussyfoot around. Be direct, be honest, and be sincere. This goes a long way for women of any age, but especially mature women.

You don't have to create a false pretense. If you invite me back to your house, we both know why we're heading there, and it isn't so we can watch reruns on TV, or play video games. Let's cut to the chase and get down to business. Life is short, and older women don't like to waste time.

If you want to date an older woman, know what you want, and don't be afraid to ask for it. Be strong, bold, and decisive.

Date A Cougar!


Older Women Have Great Experience

Most older women have had lots of experience. We have been married, divorced, had children and raised them, had jobs, run businesses, and best of all for you, we've had lots of sex.

This means you might learn a thing or two about life, love and sex. Pay attention to your older woman. Listen to what she says, watch what she does, and try to learn something.

We've seen a lot, we've done a lot, and we've been around the corner a time or two. You probably won't surprise an older woman, with what you think are new pick-up lines. We've heard it all before. Rather than try to be funny and flip, be sweet, sincere and passionate.

If you want to date an older woman, don't act like you already know it all. Pay attention to what she likes, what she says, and what she does. Be ready to learn some new tricks, and finally, be willing to be flexible.

Madonna on Dating Younger Men

Older Women Bring New Perspective

As you age and grow, you develop a different sense of what is important and what matters most. For older women, sex is fun, but we also like to have interesting conversations, new experiences, and fun.

Don't think that because we have a lot of experience, older women don't want to do new things. As a matter of fact, older women are braver and more adventurous than our younger counterparts. We are more likely to take risks and we love to have fun, because we don't really give a damn what people think.

If you want to date an older woman, be adventurous. Be willing to take risks and throw caution to the wind. Don't think dating an older woman means sitting around watching television and playing cards all day. Instead, be ready for exploring and expanding your horizons.

Why I Date Younger Men


Older Women Don't do Drama

Drama is for kids. Older women don't have time to waste getting upset about what someone said, or what someone did to someone else. Who cares?

If you are into drama, then don't even try to date an older woman. She will toss you aside. We don't typically make a big deal out of little things. You didn't text? Who cares? I have plenty to do on a Friday night. You made plans with your friends? So what? I made plans of my own.

Older women don't need you to complete their lives. You are around because she chooses you. She wants you. While younger women are busy playing games and using emotional sabotage to control you, older women just love spending time with you when they can. We don't need to manage every second of your day, or the weekend.

Older women don't usually get jealous and catty, the way younger women do. We know that men like to look at beautiful women. We also know that if you are with us, it's because you want to be. And we are with you because we want to be. And we are not intimidated by young, insecure women. We already know we are beautiful, sexy, smart and desirable. If you want to date us, you must be strong, secure and bold.

If you want to date an older woman, ditch the drama. Older women have neither the time nor the desire to play games. Be upfront, be honest, and be yourself.

Dating Older Women

Have You Ever Dated an Older Woman?

See results

Your Attention Please!


Older Women Appreciate Your Attention

Older women love to hear that they are beautiful, smart, sexy, funny. All of the same things younger women love to hear. The difference is, younger women hear it all the time and they become hardened to it. As we get older, we don't hear it as often.

Although we may still be very sexual, very sensual, and attractive, people don't always tell us how cute we are, the way they do with younger women. Many older women work hard to maintain their fitness and health. We appreciate it when men take notice.

If you want to date an older woman, pay attention to her. Compliment her strengths, whether they are physical attributes or personality quirks you enjoy. Older women appreciate genuine compliments and will open like a flower toward the sunshine.

If You Want to Date an Older Woman

Know What You Want

Be Bold

Be Ready to Learn New Things

Forget the Drama

Give Her Lots of Attention


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    • profile image

      S. Marcelino 

      11 days ago

      Am 37 she is 52 n there's not a day she cant do without me. I only wish i could impregnate her i love her so much. But our sex is great. No complaints she got naturally sweet lips.... marriage is in the pipeline around july to December 2021 God spare

    • profile image


      3 months ago

      Nice article

    • profile image


      2 years ago

      Hi there, are there any real sites where I can meet older/mature woman to date? Most of the websites says free and when you register on these websites they will then send you fake messages that showing these woman are looking and interested to meet you. When we become paid member and all of a sudden reality changes and none of them response.

      Are there any dating sites where they don’t charge and have real people?



    • Mystee Crockett profile imageAUTHOR

      Mystee Crockett 

      2 years ago from Everywhere You Want To Be

      Thanks for reading and commenting George.

      Good luck with your dating.

    • GeorgeEddieRay profile image

      George Eddie 

      2 years ago from Georgia Atlanta

      Cute pics. I need a good dating


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