Should I Date An Older Woman?

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Do Older Women Make Better Partners?


Hi, Jack,

I’m 29, straight and single. I’ve dated a few different types of girls, but I’ve never dated an older woman before. I usually date women my age or a few years younger.

Honestly, things are just getting weird. All the women I date now seem to be evaluating me for a job.  I work really hard in life but there’s all this pressure from my family and friends to settle down and get married, buy the house, have the kids, etc.

Should I be dating an older woman? I hear that older women are more chill and really appreciate a younger man.

Would I be compatible with an older woman?

Is it hard to date an older woman or is it just like dating a woman my age? 

Thanks in advance, Jack.

-Young Guy from Arizona


Hi Young Guy from Arizona,

I’m glad you reached out with your question. Lots of guys face pressure to have everything figured out by the time they reach 30 and it can throw a real monkey wrench into your dating life.

If you’re thinking about dating an older woman, then get ready for a wild ride. It could be a satisfying experience for you, but it’s still a relationship. There will be certain pitfalls and drawbacks to dating an older woman. She’s still a woman.

First, let’s talk about the reasons why dating an older woman could be excellent for you. Older women are wise, confident, and they have powerful sexual energy.

You might also like to know that the odds are in your favor when it comes to finding an older woman. A survey conducted in 2017 by the online dating platform Zoosk found that 31% of older women preferred dating younger men.

They’ve figured out what they want out of life and they won’t waste your time with wishy-washy intentions. Older women don’t have time to play games and they won’t tolerate any head games from you either. In fact, most of your tricks won’t even work on them. They’ve been there and done that.

What a relief, right? A straight-forward, experienced woman who knows what she wants out of life. Well, it goes on, my friend.

One thing that you’ll find with older women is that they are typically better conversationalists than younger women. They have more experience in life and that generally translates to a much deeper, more meaningful exchange of ideas.

Older women are usually more financial stable than younger women and less likely to put a great deal of pressure on you to be the bread winner of the relationship.

You might even find yourself in a sugar momma type of relationship where the older woman is willing to put a ton of extra cash into your pocket. It has nothing to do with how well you’re putting it down in the bedroom either.

Even though she comes off as confident, you’ll find that older women have some insecurities about their appearance and age. You might not notice those tiny wrinkles around her eyes, but she might be obsessed with them. She might try to compensate by keeping you flush with cash.

Related: Women OK Dating Men Who Are Younger and Earn Less (Study)

More than anything else, older women want attention and to have a rich life experience through you. They want to be treated like a precious gemstone, so you don’t necessarily need to buy precious gemstones to prove your love for them. Get it?

She’s gonna be attracted to your fresh perspective and your youthful take on life. She might be more experienced, but she also wants to experience new things, to taste life in a new way. She wants your vision, your hope for the future, your zest for life.

That’s where you come in, Young Guy from Arizona. Give an older woman these things and you will have great success, trust me. Now I know it sounds like dating an older woman is the way to go, but there are some things you need to carefully consider first.

Things to Consider Before Dating an Older Woman

You wanted to know about compatibility. So, here goes. I know you’re probably wondering about the age gap. Well, this is a unique time that we live in. People are more connected with social media and more people are in touch with popular culture than ever before. So, even older women won’t necessarily be out of touch with what’s trending or cool in today’s society.

Now, having said that, if you are dating a woman in her 40s or 50s then she’ll probably have experienced life way differently than you have. You could learn a lot from her if you’re willing to let her drive the car so to speak.

That doesn’t mean you have nothing to offer her. It just means that she’s had more time to develop a settled life. She’s worked out what she wants from life and has had time to go out there and get it.

Young women that you’re dating want to evaluate you as a potential life partner, but an older woman is going to look at your attractiveness, the chemistry between you, and your willingness to accept the reality of a relationship that she has set the terms and conditions for.

That’s right, buddy. If you’re dating an older woman she’ll probably have the upper hand in the relationship. She’s more experienced, more settled, and more assertive.

So, if you’re super concerned about the power structure of the relationship, then you’d better think twice about dating an older woman. She’s not going to tolerate any aggressive masculine posturing on your part.

Communication Has Always Been the Key. Now, it’s an Even Bigger Key

Women in general place a high value on communication in relationships. One of their biggest gripes about men is that we don’t communicate well. That concern isn’t going anywhere, dude.

Older women value good communication even more than the types of women you’re accustomed to dating. So, if you have trouble talking about your thoughts and feelings, then you will run into problems when you attempt to date an older woman.

Little Kids and Big Kids

Another thing that you should consider is children. You mentioned that you’re already under a lot of pressure to start a family, so I’m sensing that you don’t necessarily feel ready for fatherhood and the settled life.

When dating an older woman you should find out whether or not she wants to have children because you could be running into the same situation that you’re trying to avoid with younger women.

Women are having children much later in life these days, especially women who might have chosen to work on their career during their 20s and 30s. Now they can easily catch up on a family life, later in life.

She might already have children; adult children and you need to gauge how her offspring are going to feel about you dating their mom. Some children are appalled at the idea of their mom dating someone in their age range. So, you should try to get as much clarity about that issue as you can in the early stages.

The Cougar Myth

Now, I mentioned earlier that older women have powerful sexual energy. I don’t want you to think that you’re going to find a man-eating cougar who devours you sexually on a daily basis.

No, in fact, that’s pretty rare. The powerful sexual energy of older women has more to do with the intensity level of the sexual encounters. Sex with an older woman could be more passionate.

Don’t expect that she will be able to outperform a younger woman. In fact, if you’re a young guy in your late 20s, the chance is high that you’ve had way more sexual partners than she has.

Wrap Up

Dating an older woman could be exactly the thing you’re looking for, especially if you’re not ready for the life commitments that women in their 30s and late 20s are pressing upon you.

Just don’t disillusion yourself into thinking that older women just want sex. You could be setting yourself up for disappointment with that line of thinking.

I hope this response was helpful to you.

Need some dating help? Email Jack, the Dating Coach at: [email protected]

About Jack Eagle 21 Articles
Jack is a wise but mysterious figure whose exact whereabouts and identifying details remain unknown. What we do know is that he's really, really good at relationship challenges. He’s been on more dates than you can shake a stick at, and he’s here to help men from all walks of life step up their game.