9 Surprising Pros and Cons of Dating Older Men


I am 17 years older than my wife. While we’re now well over a decade into our marriage, back when we first met, you can bet she was running down the list of the pros and cons of dating older men.

Here’s what those are and how they’ve turned out for us:

The pros of dating an older man often include maturity, financial stability, life experience, better communication, more experience in the bedroom, and they aren’t afraid of commitment. The cons, however, can include being too possessive, not taking their partner seriously enough, and not wanting to go out as often.

But there’s a lot more to the pros and cons of dating an older man than that!

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.

Co-authored with Georgia Selih, relationship and dating expert of Highstylife.com.

Is a 16 year age difference too much?

Since my wife is 17 years younger than me and we met in 2005 and are still happily married today, I’m going to say no.

But ultimately, it’s not so much the years of age difference as it is shared life goals, dreams, vision, and values. My wife and I have the important stuff in common.

Yea, she doesn’t always get my 80’s pop-culture references and I don’t always get her 90’s hip-hop references, but we “get” each other on the stuff that really matters.

So don’t focus on the age as much as the connection and how you each make one another feel when you’re around each other.

A great relationship should build you up.

It’s not your spouse’s job to make you happy; only you can do that. But it is important that they not knock you down, control you, or see you as less than equal. Ultimately things like respect for you don’t come from age.

However, you do often find that maturity, communication skills, and treating you the way you want to be treated are traits that come with age and time.

How can I impress an older guy?

When I met my wife, then 24 with me being 41, she approached me at a mutual friend’s birthday party which was at a bar.

At the time, she impressed me with her energy. She was highly charged, but while a little sassy, she was upbeat and positive.

We ended up talking for hours about who knows what.

I will also say that while we did kiss and get affectionate quite a bit that night, we did not have sex that night. As an older man who’s had 4 serious and a couple less serious relationships, it is impressive when a woman doesn’t have sex on the first date.

That doesn’t mean I wouldn’t have done it or wasn’t thinking about it.

But it does tell me that she doesn’t just give it away to anyone, and when it did happen it was that much more special. Plus we had gotten to know each other a little bit better too.

But the top qualities that a younger woman can show to an older man to impress him would include:

  • Confidence
  • Positivity
  • Sassy/flirty
  • Make him work for it a little

Why am I sexually attracted to an older man?

Why is anyone sexually attracted to anyone?

If we get a little metaphysical for a minute, let’s acknowledge that everything in the universe is made of energy. And like when you played with magnets as a kid, sometimes that energy repels and sometimes it attracts.

But we don’t usually know which until we try it.

Yes, there could also be childhood or daddy issues at play too, but if you’re in your 20’s and find yourself attracted to guys in their 30’s or 40’s, it could also just be that they seem like they have their act together better than the average 25-year-old guy.

A guy driving a late 90’s Toyota with bean bag chairs in the apartment he shares with 3 other dudes just isn’t as appealing as the guy who owns his own home and carries himself with more confidence and maturity.

Now if you do have a damaged or non-existent relationship with your Dad, that is worth exploring with a good therapist so you can work through that.

After all, when we bring unhealthy baggage into a relationship with anyone of any age, it stands a much higher chance of failure.

But it’s OK to be drawn to a sexy older man who has his act together.

How do you keep an older man?

I won’t lie.

When my wife and I were still dating, we did break up a couple of times. We had both exited relationships right before we met, and neither of us was in a great place mentally to start a new serious relationship.

That being said, we also both knew this was something special, like a soulmate. The signs of a soulmate (click to read them on my site) aren’t always clear, and they don’t always show up in our lives at the perfect time. But when they do, we often just “know”.

Just click the link to read all the most important soulmate signs coincidences in a recent article on my site.

But to keep an older man engaged and getting him to see you as a serious partner and not just a fun fling, use these tips:

  • Be yourself – Be confident, engaging, and upbeat. You want him to fall for the “real” you
  • Take an interest in his world, likes, and passions
  • Avoid insecurities – He may have kids, or an ex, or female friends. These things sometimes come with age. They don’t mean you can’t be his everything eventually. But jealousy and being neurotic can definitely push him away.
  • Spend time doing a variety of things and not just going out
  • Ask questions. While you also have a lot to share, there is wisdom just in the sheer number of extra years he’s been around
  • Engage with his friends and co-workers – show him you’re serious about getting to know his world
  • Avoid childish behavior – Everyone of every age sometimes does this, but nothing will remind him more of the age difference than you doing this with any frequency

What are the advantages of dating an older man?

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 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 good listening skills (click to read my article on how to improve your communication skills.)

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 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.

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 several 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.

What are the disadvantages of dating an older man?

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Of course, they are just stereotypes and can occur in any relationship, but still, it’s good to keep them in mind. And there are challenges and risks with dating anyone – which is why I always recommend running a personal background check on someone before you get serious, especially if you two first hit it off online.

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 (click to read my article about some of the clear signs of a clingy guy and how to handle it).

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 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?

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

Jeff Campbell

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

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