Dating an Older Man: Pros, Cons, + Advice For The Modern Woman

I know a lot of women who prefer dating an older man. Remember when you were a teen and your mom said that girls were two years more mature than guys the same age?

Whether you believed it then or not, dating in your 40s or older reveals that dating an older man can have perks over dating a younger man.

The good news is: 60% of men are attracted to younger women, so you’re a hot commodity for anyone older, whether that’s two years older or, if you’re into it, 20.

Dating an older man can have some pretty great benefits. There are also, however, some drawbacks to be aware of. Let’s look at both so you can decide whether dating an older man is appealing to you or not

Pros to Dating an Older Man

You’ve dated your share of men your age…and even younger. Clearly, you haven’t found what you’re looking for yet, so why not go with someone older and more wiser? While all of these won’t be true of every older man (after all, many suffer from Peter Pan syndrome), as a whole, you’re going to realize more of these benefits with an older man.

1. He’s Financially Stable

An older man is past the early-20s “what am I doing with my life” phase. There’s a good chance he’s midway in his career, and therefore at least somewhat financially stable.

Being financially stable isn’t about making $300k a year. It’s about being smart with his money. Maybe investing it or buying a house.

It basically is the opposite of being broke, which is a libido-killer for most women.

It’s nice to date a man who can afford to pay for dinner.

Whose car doesn’t break down in front of your house…

Who has more than one shirt…

Who could afford to take a spontaneous weekend getaway with you…

There’s appeal in that, and you can’t always find it with a younger guy who’s still struggling to find his foothold in his career.

2. He Doesn’t Play Games

He’s already played games in his 20s…and he’s over it.

A young man doesn’t know what he wants, and so he plays those cat-and-mouse games we all hate. An older man, especially one

who’s already been married once, knows what he wants. If he’s ready for a long-term relationship, he’ll make it known. You won’t wonder. He’s not out to waste time; he wants to know within a few dates whether you have potential or not.

Now, I’m not saying every older man is ready to settle down again. Plenty want to continue to play the field. But they’ll be more upfront about it if they’re older. At least then you know immediately whether you want to pursue something with him or not, based on whether your goals are aligned.

3. He Has More Confidence

Chalk it up to older men having more life experience: they tend to be more confident. They’ve been around the block: sexually, financially, career-wise, and in love. They’re not timid about sharing their opinions. They carry themselves with a cocksure attitude that you find appealing.

If you’ve dated younger guys that were wimpy and lacked confidence, it’s understandable you’d consider dating an older man. That take-charge attitude and the desire to take care of his woman is plenty appealing.

4. Jealousy Takes a Backseat

Younger guys tend to be jealous at the drop of a hat.

“Dude. That bank teller was totally checking you out. WTF?”

It’s yawn-inducing, I know. But how nice is it to be with a man who knows that, from time to time, another man will admire his lady…and not freak out about it?

It goes back to that confidence thing. He’s assured of what he has (including you) and isn’t threatened by another man.

5. His Status is Appealing

Some critics of women dating older men say they do so because they have “daddy issues,” but a recent study proved otherwise.

Here’s what it said:

“…it is evolutionarily beneficial for women to seek older mates, and that there will be no significant difference in attachment styles between women in age-gap versus similar-age relationships.”

What this means is that it’s an evolutionary pattern that women are drawn to older men, in part because of their status and resources.

Think about it. If you were pumping gas and a gorgeous Lamborghini/Tesla/Porsche pulled up next to you with a good-looking older man in it, wouldn’t you do a double-take?

Don’t you find photos of men speaking on stage on dating apps appealing?

When you find out a guy you just met is a doctor, doesn’t your mouth water?

These are all status indicators, and they’re part of the attraction factor. It’s completely natural for you to be drawn to a man because of his status. It subtly communicates to you that he can take care of you, and that life with him would be fun!

6. He’s Mature

While most of the above benefits of dating an older man fall under the “he’s just more mature” category, it’s worth pointing out additional perks of dating a mature man.

He has his sh*t together, first and foremost. He’s likely been in at least one long-term relationship, so he knows how to give to his partner and compromise when necessary. A mature man isn’t in the middle of an identity crisis. He knows who he is and what he wants, and he isn’t shy about communicating that.

7. Communication Comes Easily

Speaking of communication, there’s a better chance that an older guy will be a better communicator than a younger one. Again, if he’s been in at least one long-term relationship, the subject of communication more than likely came up, so hopefully, he’s learned how to express himself in constructive ways that will make him a good partner.

Dating an older man may surprise you: he may be a better listener than anyone younger that you’ve been with. And if you prefer talking on the phone to texting, there’s a good chance he does too.

8. Baby Time May Be Over

If you’ve already had kids in your past relationship or don’t want any in the future, dating an older man is a good path for you, because it’s less likely that he’s interested in having (more) kids. He may even have grown children, which may be easier to deal with if you get serious and end up living together or married (you’re not the wicked stepmother to small children).

Having a relationship with an older man without the focus being on raising children gives you the ability to really bond and connect with no distractions.

Cons to Dating an Older Man

Every man is different, regardless of his age. But these are a few things to be aware of if you consider dating an older man.

1. He Might Be a Bit Controlling

Because older men usually know what they want, they can have a strong need to control a situation…and also you.

The older we get, the more set in our ways we are. It goes both ways. But you’ve both got to be able to compromise in order to make a relationship work.

If, when you start dating an older guy, you immediately get the sense that he’s controlling, walk away. You need a man who will let you be you and won’t try to change you.

2. Life May Be Less Exciting

The last guy you dated took you to parties. You went out for dinner or drinks often.

This older guy wants to stay home every night of the week.

He’s already had his party years. He’s done going out and being social. So you’re left…yawning.

While it depends on the person, you may find that an older man prefers his routines and may not be as keen to go out. If it’s important to you to have an active social life, dating an older man may not be for you.

3. He Might Want To Settle Down Too Fast

Like I said in the pro section: older men know what they want. If this one is looking for a long-term relationship, he might move a little fast for your tastes.

If…

…on the first date, he asks your ring size…

…he starts shopping for a house for the two of you early on…

…he tells you he loves you after only a few dates…

…you need to pump the breaks. You likely want a serious relationship too, but you know you can’t rush it. If it’s meant to be with this guy, it will happen. Speeding into becoming an established couple never works.

4. People Think You Have Daddy Issues

Here’s an interesting fact: 20% of men getting married the second time around marry someone who is 10 years or more younger than them. If the age difference between you two is significant, expect some raised eyebrows and negative opinions.

Many people feel that women who date significantly older men are looking for a substitute for their father. Maybe they had a bad relationship with their dads or maybe he was absent while they grew up. Even if this isn’t the case for you, realize that there are a lot of opinions out there about women who date much older men (far fewer opinions about the men in those relationships, which is totally unfair), so be prepared to deal with it.

5. You May Feel Immature

Among your friends, you are the mature one. They turn to you for advice, and you’ve got a level head on your shoulders.

But when you date a much older guy, you may feel like a baby. He’s lived so much more life than you. He’s had more experiences. And if he makes you feel that way, you’ll struggle all the more.

You want a man you can learn from, regardless of his age. Just make sure he’s not taking on the role of your teacher without you wanting him to be.

6. You May Not Get Along with His Friends

This man may be head over heels for you, so he’s willing to compromise on the differences that your ages create. But his friends are another story altogether. They may not understand why he’s dating you and may give you the cold shoulder. It may be challenging to get them to take you seriously. If he’s worth it, you’ll put in the effort, but realize they may never accept you fully.

7. He May Not Be in Shape

Certainly, there are many older men who take care of their bodies, but if you’ve only dated younger men, you may not even know what an older guy’s body looks like. It may, quite honestly, turn you off.

You may have a meeting of the minds with this man, but are you physically attracted to him as well? It takes both for a well-rounded relationship.

Advice on Dating an Older Man

If you do decide to date an older guy, realize that the experience will be different from any past relationship. But 56% of women (who prefer dating older men) clearly have figured out how to get the most out of a relationship with an older guy, so take the following advice to heart to make this relationship successful.

Be Prepared for a Bumpy Road with Friends and Family

I touched on this a minute ago, but things may be challenging as he introduces you to the people who matter to him. They may assume he’s just having a fling with a younger woman, and may not be ready to accept that you two are long-term.

Be patient. It will take time for his friends and family to accept you. Be gracious when you’re with them, and do your best to engage them in conversations to show that you’re interested in developing a relationship with them.

Don’t Be a Trophy

While this isn’t necessarily going to happen to you, realize that some men date younger women as a sort of trophy. It makes them feel powerful and desired if they can snag a much younger woman.

You don’t want to be part of that. If you date an older guy, it’s not because he’s older that you’re attracted to him, but because he’s got a great personality, etc.

If he starts parading you around like food on a platter, that’s a red flag that he’s not into you because of who you are.

If He Has Children, Love Them

Maybe you never planned to have kids and now you’re with an older man who has them. If you’re serious about him, the kids are part of the package, so it will serve your relationship well if you put effort into getting to know them and having a relationship with them.

Depending on the kids’ ages and personalities, they may take a while to warm up to you. Give it time. Don’t try to be a second mother to them, but a friend. Find opportunities to spend time with them on your own and do things they’re interested in. He’ll take notice and fall even harder for you!

Don’t Make Jokes About His Age

Just like you don’t like being called a baby because you’re younger, this man doesn’t like it when you make jokes about him being an old man. It’s not cool. If age really doesn’t matter to you, you won’t make an issue of it.

Ask your friends not to make jokes either.

Respect His Past

An older man more than likely has a past that involves at least one major relationship. If he has kids, his ex may still be in his life.

Don’t make things worse by acting jealous or bringing up past relationships. You’re with him now; what’s past is past. You want the same mindset from him.

Be Open to What He Can Teach You

A man who’s been around the block a few extra times has a lot to give. He may have hobbies that you’ve never even considered taking up (sailing, anyone?), so if you’re open, you might find new things that you discover you love to do.

He may also have wisdom gleaned from past relationships that can help you be a better partner. So listen and see what you can learn.

Conclusion:

If you’re sick of dating younger guys, it may be time for something different. Dating an older man will at least give you a new perspective on men and relationships. You may find that you’re different with an older man versus a younger one. Maybe you’re the one who needs control in a relationship with a younger guy, but you find that you really like being taken care of with an older man.

Bottom line is: it doesn’t matter how old the guy you fall for is. He just needs to have the qualities you’re seeking in a partner. He should be kind and loving and meet you in the middle in terms of effort put into a relationship. He should make you feel like a queen.

What’s your experience dating an older man? Love it or hate it? Share your tips in the comments below.

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