Dating Older Women: 8 Tips You Must Know

So you want to try your hand at dating (or sleeping with) older women? You’ve heard the stories about how they’re more experienced, how they know what they want, how they’re more confident in bed!

Maybe your friend’s Mom is a milf that you can’t take your eyes off, or maybe you’ve heard enough about your friends dating cougars that you want to give it a go yourself.

I can tell you this, if you’re tired of dating younger women, especially in today’s society, that have lost the ability to converse in a meaningful way or care more about their social media following than they do about you, then you’re in for a treat!

Why Men Like Dating Older Women

As an older, experienced woman myself, I can tell you that you won’t regret it. I’m not going to bore you with too many details but here are just a few reasons why dating older women is awesome:

  1. They’re more confident: Older women are generally more confident than their younger counterparts. They know what they want and they’re not afraid to go after it. This confidence can be a turn on for some men.
  2. They’re more mature: This goes hand in hand with being more experienced and more confident. Older women are generally more mature than their younger counterparts. They’re not into drama and they don’t play games.
  3. They have their shit together: Unlike some younger women, older women usually have their lives together. They’re not always looking for a sugar daddy or someone to take care of them. They’re independent and they can take care of themselves.
  4. They’re not afraid to speaking their minds: Older women are usually more vocal than their younger counterparts. They’re not afraid to speak their minds and they’re not afraid to tell you what they want. This can be a refreshing change for some men.
  5. They’re far better in bed: This is probably the most important reason why men want to date older women. They’re simply better in bed. They’re more experienced and they know what they’re doing. This can be a major turn on for some men.

So without further ado, here’s my top tips for you younger men out there:

1. Dress to impress

A stylish well dressed man

The first step is to dress appropriately. Older women are attracted to men who dress in a classy, sophisticated way.

Avoid wearing too much streetwear or athleisure; instead, opt for classic pieces that will make you look like a gentleman. A well-fitted suit is always a good choice, or you could try a tailored blazer with dress pants.

When it comes to shoes, avoid sneakers or anything that looks too casual. Loafers, dress shoes, or even boots can work well.

And make sure your clothes are clean and wrinkle-free!

2. Know what you want

If you’re thinking about trying your hand at dating older women, the first thing you need to do is know what you want.

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Are you looking for a fling? A one-night stand? A friends with benefits situation? A relationship?

There’s nothing wrong with any of those things, but you need to be clear about what you’re looking for before you start pursuing older women.

Why? Because older women are usually clearer about what they want. They’re not going to waste their time on something that they’re not looking for.

So, if you’re clear about what you want, you’ll have a better chance of finding an older woman who wants the same thing.

3. Be a gentleman

One of the things that can be a turn-off for older women is when you act like a child.

And guys, older women have usually been around the block more than a few times and they can spot a player a mile away.

If you’re looking to date an older woman, you need to be a gentleman and leave any ulterior motives at home.

What does being a gentleman mean? It means opening doors for her, pulling out her chair, and being respectful of her boundaries. Older women aren’t looking to be treated like a queen, but they do want to be treated with respect.

If you can’t do that, you’re not going to get very far.

4. We Love Confidence

If you’re thinking about trying your hand at dating older women, there’s one thing you need to have: confidence. Older women are attracted to confident men.

They want a man who knows what he wants and isn’t afraid to go after it. They don’t want a man who’s going to shy away from a challenge or who’s going to be afraid to take risks.

So, if you’re lacking in confidence, now’s the time to work on that.

The good news is, confidence is something that can be developed. Start by working on your body language and the way you carry yourself.

Stand up straight, make eye contact, and speak with conviction.

Then, work on your conversation skills. Be interesting and engaging. Show her that you’re someone she wants to get to know.

And finally, don’t be afraid to be a little bit flirtatious. Older women love feeling desired and appreciated. So, let her know that you find her attractive and that you’re interested in getting to know her better.

If you can do all of this, you’ll be well on your way to success when it comes to dating older women.

5. Be interesting

A passionate man sitting at a piano

If you want to date older women, you need to be interesting. Older women have usually had their fair share of boring, unimaginative boyfriends and are now looking for something different.

They want someone who can hold their attention and keep them interested. So, if you’re boring, you’re likely to get dumped pretty quickly.

To be interesting, you need to be engaging and enthusiastic about life. Be curious and ask lots of questions.

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Be passionate about your hobbies and interests. Show that you’re excited about the things you’re doing and the places you’re going.

6. Give her a challenge

One of the things that can be a turn-on for older women is a younger man who is willing to give them a challenge. They’re used to being pursued by younger men who are trying to impress them with their looks and their money.

But if you’re willing to show her that you’re not just another pretty face, you’re going to stand out from the crowd.

One way to do this is to start a conversation with her that isn’t about the usual topics. Ask her about her favorite book, or her favorite movie.

If she’s into art, ask her about her favorite artist. If she’s into movies then you pretty much have an endless amount of material to discuss.

Show her that you’re interested in things that she’s interested in.

Another way to challenge her is to play games with her. If she’s competitive, she’s going to love a good game of chess or Scrabble.

If she’s more laid back, she might enjoy playing Cards Against Humanity or something similar.

The important thing is that you’re not just trying to impress her with your intelligence or your wit, but that you’re actually trying to engage her in a meaningful way.

7. Don’t be afraid to show your own vulnerability

One of the things that can be really attractive to older women is a man who isn’t afraid to show his own vulnerability.

We all have insecurities, and being able to openly discuss them can be a really attractive quality.

It shows that you’re comfortable with yourself and that you’re not afraid to be open and honest. This can be a really great way to connect with a more mature woman on a deeper level.

8. Be patient

If you’re just looking for a fling or a one-night stand, then you’re going to need to be patient. Older women are not going to just jump into bed with you. They’re going to want to get to know you first.

Don’t try to push things too fast. Let things happen naturally and see where things go.

Another thing to remember is that older women are typically not going to be chasing you. They’re not going to be the ones who are constantly initiating contact.

That’s not to say that they’re not interested, but you’re going to need to put in some effort if you want things to progress. So, don’t be afraid to take the lead.

You can still be patient while pursuing. It’s just how you go about it.

Send the first text, make the first move, and see where things go from there.


Ruth Thomas

Ruth Thomas

Hi! My name is Ruth! I am a sex therapist and a happily married swinger (for 20 years now).

I have a PhD in human sexuality and a masters in counseling. I've been helping people improve their sex lives for over 25 years.

I am a member of the American Association of Sex Educators, Counselors, and Therapists (AASECT) and the International Society for Sexual Medicine (ISSM).

I'm here to help people explore their sexuality and find what works for them. Whether it's with one partner or many, in a committed relationship or not, I believe that everyone deserves to experience the joys of a fulfilling sexual life.