Dating an Older Man – The Good, the Bad and the Ugly

Dating an Older Man – The Good, the Bad and the Ugly

Dating an older man comes with a stigma, but that doesn’t make it wrong. Science has studied this phenomenon and has come up with some interesting conclusions.

While an age gap in dating isn’t uncommon, it’s more unusual for a woman to be older than a man. The more common age-gap relationship is for a man to be the more senior party. Then, you see terms like cradle robber and gold-digger, neither of which is favorable, both of which are judgmental.

Are Negative Stereotypes True or False

Thank heaven for scientific research to help us uncover fact versus fiction regarding a woman dating an older man!


When an older man dates a younger woman, it’s said he’s robbing the cradle. This stereotype falsely and automatically places the man in control of the relationship through the eyes of naysayers.

While older men seek out younger women, it isn’t to make a power play. Generally speaking, younger women have more energy, are more attractive, and have less baggage than women closer to them in age.

For these men, dating a younger woman makes them feel more alive and vibrant.


While the man is a cradle robber, the woman is a gold digger. This stereotype, of course, assumes that the only reason a woman would date an older man is for his money. Some dating sites even promote the idea of women finding a sugar daddy.

In other instances, it’s assumed that the man has some currency to offer the woman, if not money. It may be social status or professional assistance.

The truth is that younger women aren’t dating older men because they have more money or status. So why do women date older men?

Why Should You Consider Dating an Older Man?

He’s Moved Past the Crap

Let’s face it, if you’re a woman in your twenties or even young thirties, more than a few men in your age group still live at home or have a roommate. They want to come home after work and play video games or go out drinking with their friends.

They’re either immature or too wrapped up in themselves to be the man you want them to be.

An older man, one in his fifties or beyond, has moved past the crap. He understands the value of working to earn things and is self-sufficient. If he isn’t, he’s not your guy!

Many, but not all, men in this age group have been married before, perhaps profoundly in love, and want to experience that again. They’re serious about a relationship and want to find someone fun and vibrant to spend time with.

He’s Mastered Romance

When you’re dating an older man, you’re dating someone who’s figured out romance. He knows just how to woo you and says all the right things.

I know this is starting to sound like a player, but there’s a difference. A player wants something from you, often sex or money.

Dating an older man provides you with the opportunity to be in a grown-up relationship. He isn’t in this for sex or money. He’s interested in you because something about you piques his interest.

Dating an Older Man | He’s Patient

An older man isn’t in a hurry to advance your relationship. He wants to get to know you and spend time with you. Sure, he’s getting older, but we all believe we will live forever! This guy knows how to date you the right way.

He’s dating you because he finds you interesting, and he’s willing to take his time getting to know you. You should exercise patience as well and match his pace. This is true in any relationship.

An Older Man is Familiar

Some women in a 2016 study have familiarity with the older man. While many argue that women seeking out older men have daddy issues, the study proves this incorrect. Many of the women in the study had great relationships with their fathers, and the maturity of their chosen partner is familiar because of that relationship.

He’s More Stable and Secure

Just because a man is older doesn’t mean he’s wealthy, but it should mean he’s stable and secure, financially and otherwise.

By the time he hits his forties or fifties, he’s made most of the big life mistakes and found his stride. This makes the relationship less stressful and younger women feel more secure.

Dating an Older Man for Reproductive Reasons

Many reasons above indicate that an older man is better father material than a younger man.

Of course, in this case, you need to have a heart-to-heart conversation about whether he wants children this late in his life. Some men will, and some won’t. Be sure your guy doesn’t have a been there, done that attitude about children if you want a family.

Most Older Men Have Higher Confidence

There are exceptions to every rule, but older men generally have higher confidence. It goes back to making many of life’s big mistakes and learning from them.

His confidence helps you feel more confident as you explore life from the opposite side. You still have mistakes to make but having a seasoned veteran by your side enables you to get through.

He Wants Companionship and Conversation, Not Just Sex

An older man is less likely to want in your pants on a first date. He will enjoy the companionship of having you with him just as much as he’ll ultimately enjoy sex with you. Sex isn’t his number one goal. Again, there are exceptions to the rule.

When you’re dating an older man, you’re dating someone who enjoys the process of getting to know you and bonding with you just as much as sex.

dating an older man

The Cons of Dating an Older Man

While there are pros to dating an older man, there are also cons.

He Has Lots of Baggage

Living a longer life means more baggage. There are pretty good odds that he’s been in at least one long-term relationship, and those usually have their own baggage. He may have older children who are opposed to dad dating someone close to their age.

Kids may also be concerned that you’re out to steal their inheritance. The only way to soothe these worries is with time. Once they realize you aren’t in it for the money, they’ll settle down.

He Might Fear You’ll be Unfaithful

Everyone has their moments of insecurity in a relationship. An older man might fear that you’ll leave him for someone younger with more vitality.

This is especially true if you’re still hanging out with your younger friends at bars and clubs. Trust in any relationship comes with time, so prove your trustworthiness, and he’ll probably settle down. It may be time to find a new relationship if he doesn’t.

Dating an Older Man | You May Have Less in Common

While his age and experience are appealing, the chances of the two of you having a lot in common are slim. He’s probably into movies made before you were born and isn’t into the latest hip hop or whatever new-age music is popular.

This doesn’t mean an older man is out of the question. Be open to watching his 80’s movies and listening to his jazz or classic rock. You may find you enjoy it too. Also, introduce him to your likes; he may surprise you and come to enjoy them too.

His Partying Days are Probably Over

While you may enjoy hanging with your friends at a club or bar once in a while, he’s probably going to take a pass. He’s been there and done that and prefers a classic movie to headbanger music.

A compromise might work in your favor. He might not want to go clubbing, but he will appreciate it if you’ll join him for a quiet dinner somewhere special. He might even join you and your friends for a little while.

You’re Likely to Grow Apart

As you both age, you may grow apart. After a couple dozen years, many women report feeling duped or tricked. The shine has come off the superhero her older husband once was. Now, he’s just an ordinary man, an older man.

Sex Probably Isn’t What It Once Was

Women peak sexually in their late thirties to early forties, while men peak much younger. Therefore, dating an older man means he’s already past his peak by the time you meet him.

Dating an Older Man | He’s Not as Much Fun

While dating an older man was fun, a few years down the road, he’s less interested in doing anything too risqué and more into a quiet, settled life.

The problem is that you might not yet be ready for that settled feeling. Your same-age friends and their partners are still having fun together while you’re sitting at home watching reruns of Law and Order.

How to Succeed at Dating an Older Man

If you want to pursue dating an older man, you can do a few things to ensure your success.

The first is to ensure you align on the important things. You might not like the same genre of movies or music, but do you share the same goals? Do you both want to travel? Do you both enjoy weekend vacations in the mountains?

The next is to be yourself, but this advice goes for any relationship, regardless of the age gap. It’s never a good plan to try to be who you think a man might want you to be rather than just being yourself. Let him fall in love with the real you!

While you might not share some of the same interests, it will help if you take an interest in his likes, hobbies, and passions. He will most likely reciprocate, so it’s a win-win. As a bonus, you learn new things and maybe find a new hobby or passion too.

Next, avoid jealousy and insecurity. He has a past, and you weren’t part of it. He may have children or female friends who have been in his life for years. Jealousy won’t get you anywhere except dumped, so don’t bother.

Get to know the people in his world. Just because he’s older doesn’t mean all his friends and coworkers are older. These people are important to him. By getting to know them, you’re showing him that you’re serious about getting to know him.

Is Dating an Older Man for You?

Ultimately, only you can decide, but I encourage all women to try it at least once. I encourage women to date many different types of men. That’s how you discover what you like and don’t like.

Dating an older man can have many rewards, but there are pitfalls, so try to avoid them. Meanwhile, have fun!

To date a man, you must understand a man. Men and women do almost everything differently, and sometimes for different motivations. To a man, his financial status indicates how well he can take care of you and your family. It's a source of pride for him to be able to do so, even if you make your own money and can support yourself.

It's how he was raised.

Men also love differently. Many relationships breakup for the simple reason that a man is showing a woman how much he loves her, but he isn't saying the words she longs to hear. He's taking her car to get the oil changed, building the shelves she desires in her office and helping with the outside chores. You're probably missing many of these signs that he loves you.

You gain so much insight into the male mind that you'll be amazed at what you suddenly see and understand in the behavior of all men around you. Not just the man you're in a relationship with, but the men you work with and those in your family.

Read more about the book here or click the buttons to buy it today!

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