9 Surprising Pros and Cons of Dating Older Men You Should Know

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by Georgia Selih, relationship and dating expert of Highstylife.com. Intro & edits by Jeff Campbell

Looking for the Pros and Cons of Dating Older Men?

I think you’ll agree with me that there’s something intriguing about dating or marrying someone much older or younger.

As we get introduced to their world (and they to ours) it broadens our experience and perspectives. We find ourselves in new situations and looking at the world in a new way.

But dating someone significantly older or younger has its challenges too. Habits, pop culture interests, energy levels and what we do for fun can be radically different.

But fear not.

In this post, we’re taking a look at the world of dating older men. We’ll review all the top reasons this can work and some of the challenges they present.

That way as you review the pros and cons of dating older men, you can decide if that type of relationship is right for you.

Have you ever been so hooked on a TV show you couldn’t stop watching? But something at the end of each episode made you click “Watch Next Episode” again?

Dating expert Amy North analyzed the science behind binge-watching and figured out a fool-proof system for using it for texting men you are interested in.

Check out her FREE VIDEO to learn more about her amazing system!

Pros and Cons of Dating Older MenPROS

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There are many advantages to having an older partner, mostly thanks to all the lessons they’ve learned over the years.

1. They are more experienced in life

One of the good things about dating older men is that they can actually teach you a thing or two.

An older man probably made or seen all the mistakes that you are yet to make, so he will know how to guide you or advise you.

Whether in the bedroom or in life, older men don’t have a problem being leaders and helping their partners reach the next level.

Also, confidence often comes with experience, and there are very few things more attractive than that.

2. They know how to communicate

With younger men, there is always that issue of them not responding to your messages for hours, which can be quite frustrating.

On the other hand, one thing an older man is never going to do is ignore his partner. They understand the importance of communication & listening. They are also capable of expressing themselves much more clearly.

Most importantly, they actually want to talk about everything, and they are good listeners as well.

3. They are stable

Older men are much more stable, both financially and emotionally.

Now, just because a woman wants to be with somebody who has a nice job and a stable income does not automatically mean she’s a gold digger.

The thing is, older men are not only better at earning money but also at investing, spending it wisely and saving for the future, which is quite comforting regardless of the age.

Such a man is also less likely to play emotional games and has unrealistic expectations about love.

They know what they want, and thanks to the above-mentioned communication skills, they won’t leave their girlfriends guessing.

There are also benefits to being an Older Father. So if kids might be in the picture down the road, it’s important to know that too!

4. They are not afraid of commitments

As much as people dislike talking about this death, everybody has an “expiration date”.

An older man knows that his is just a bit sooner than his partner’s.

He’s been dating for a while, or already been married and divorced once. He knows his goals in life (and has probably already reached a few). Thus, he’s ready for a meaningful relationship with one person.

This means that if the girl has some of the soulmate signs coincidences, he will commit to her with all his heart.

5. They know how to please a woman sexually

Let’s be frank and call it what it is.

Older men have been around the block a few times. They may have been married once and have doubtlessly dated a number of other women.

Thus, in the bedroom, they just flat out have the experience that a twenty-something just isn’t going to have. His libido may have dropped a little, but he’ll more than make up for it with his intimate knowledge of how to please you.

Pros and Cons of Dating Older MenCONS

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The cons are where the taboos come from. Of course, they are just stereotypes and can occur in any relationship, but still, it’s good to keep them in mind.

1. Your parents may not approve

Meeting your partner’s family is always exciting, to say the least.

However, when your man is closer to your parents’ age than to yours, it can become a bit awkward. Not everybody understands such relationships, especially when their family members are involved.

However, if you and your partner keep showing them how happy you are together, the opposing family members will be more likely to come around.

2. Older men might not take their younger partner seriously

Unfortunately, age does not always equal maturity.

Instead of becoming wiser as they get older, some men just become condescending. This leads to them not taking their partner seriously.

They may even be patronizing to their younger partners because they think they always know better.

They sometimes are not even willing to try to see things from a different perspective, which nobody finds attractive.

3. They can be too possessive

An older man may feel threatened by your younger male friends. This can lead to him trying to control you.

Sometimes an older man dating a younger woman can be insecure. This is mostly because they are aware of their aging looks and their lack of energy. Thus, jealousy can spring up and turn your amazing older man into a Clingy Guy.

4. They are not the life of the party

A mature man sometimes prefers quiet evenings and dinner dates to partying in a club.

After all, they have already gone through the stage of their life where they were going out and living it up.

If you still like going out and dancing all night, try to find a balance between what you like and what your partner does. If he’s really not into clubbing, you can always call your girlfriends and make it a girls’ night out.

Did we cover all the pros and cons of dating older men you wanted to see?

In this post, we took a detailed look at relationships women have with older men.

Every relationship comes with certain challenges.

So we compiled a list of the top pros and cons of dating older men. That way you can really analyze whether dating older men or staying in your current relationship with an older man is right for you.

What is the age difference in your relationship?

Have you ever been so hooked on a TV show you couldn’t stop watching? But something at the end of each episode made you click “Watch Next Episode” again?

Dating expert Amy North analyzed the science behind binge-watching and figured out a fool-proof system for using it for texting men you are interested in.

Check out her FREE VIDEO to learn more about her amazing system!

About the author of this post:

Georgia Selih is author @highstylife.com. By nature an artist, by profession a journalist. An irreparable print lover who is enjoying this hot digital affair.
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Want to write for Middle Class Dad? Get all the info you need here: Guest Blog for Middle Class Dad!

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Photo credits which require attribution:

Torino. What else? (George Clooney) by Fulvio Spada is licensed by CC2.0


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Jeff Campbell

Jeff Campbell is a husband, father, martial artist, budget-master, Disney-addict, musician, and recovering foodie having spent over 2 decades as a leader for Whole Foods Market.

4 thoughts on “9 Surprising Pros and Cons of Dating Older Men You Should Know

  1. Thank you for this wonderful post. It hits home and is encouragement. I am a younger woman in a relationship with someone 26 years older than me. Our relationship is beyond great and we plan to get married, but like you said, there are cons, and that specifically is due to stereotyping and family. Thank you for getting awareness out there and sharing this.

    1. Thanks for taking the time to comment!

      As a husband who is 17 years older than my wife, I can definitely a test that the challenges are different when the two people are similar in age, but I definitely wouldn’t have it any other way and I don’t think my wife would either. We’ve been happily married now for over 12 years!

      Thanks for being here, Jeff

  2. So I been seeing this guy, we are pretty much good friends with benefits, he is 45 and I am 34, He doesn’t want to commit because he is worried about the age difference as far as me not being in my prime yet and worrying about when he gets older and has equipment issues. How do I make that not an issue to him?

    – Diana C

    1. Hi Diana

      Thanks for commenting. At the time of my response I’m 53 and my wife is about to turn 37; a 16.5 year age difference. In your case the age difference is barely over a decade. It’s also not uncommon for guys to be older in relationships, so my first thought, which admittedly could be totally off base, is that there is some other reason he’s scared to commit. If he’s concerned about ED issues, those will be concerns no matter who his partner is and there are manageable soltutions to that issue too. If it was a 20+ year age difference I could accept him being cautious but an 11 year difference is fairly common.

      You mention “seeing him” but also describe him as a friend with benefits, and to me, those are 2 different things. If you’re dating, then the relationship should be progressing and should involve more than just sex and would fairly quickly become exclusive. In the other scenario while you might hang out some platonically you wouldn’t be going on dates and the relationship would mostly be sexual. There would also not likely be any agreement about being exclusive.

      I suggest describing exactly what you’re looking for in the relationship, letting him know you’re prepared to be patient about issues relating to aging and see what his response is. Don’t put demands or expectations on him, just clearly and plainly say what you want from the relationship.

      If he’s not on board then I would probably end the relationship altogether unless you are able to separate the sexual relationship from your feelings.

      Hope that helps. Feel free to chime in with additional info if you think it helps or follow up after you’ve had that conversation.



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