Dating A Younger Man? 25 Things You Better Know

By: Carlos Cavallo
 |

One of the most controversial parts of dating and relationships is the age of your partner. Is it okay to date someone younger, older? If you're dating a younger man, you better know what to do.

dos donts dating younger men Dating A Younger Man? 25 Things You Better Know

Do you feel like you're on the "prowl"?

We often think about older women dating younger men as “cougars.”  But that label is just not fair.

You might be a 40 or 50-something woman dating a guy in his 20s or 30s. Or you might be in your 60s or 70s dating a younger guy.  The important factors are where you are in life, and where he is in life.

Age is just a state of mind right?

Well, not really. Age is much more important than you might realize.

I've already talked about dating an older man. But what about dating a younger man?

  • Is it okay to date a younger guy?
  • How young is too young?
  • Can dating a younger man work out?

Well the good news is that ANY relationship can work.

The bad news is that you have to MAKE it work.

Relationships don't run on autopilot. If you've ever tried this, you probably know what I mean.

"It doesn't matter who you date if you don't put the effort in to make a relationship work." - Carlos Cavallo

Why do guys get into relationships with older women?

  1. Guys know that women over 30 are more focused and probably a little bit more emotionally stable. (Probably.)
  2. A lot of the women he meets in the early 20s don't really appeal to him other than sexually
  3. He may not be ready for a family, and he's looking for a woman who's already had hers
  4. She probably already knows who she is

There are probably as many reasons for this as there are men.

Before you date a younger man - Here are some secrets you MUST know:

SECRET TIP #1: Good thing - He doesn't have as much history

One of the best things about dating a younger guy is that he hasn't had time to cultivate a long string of past romances.

16 Dating A Younger Man? 25 Things You Better Know

He may have a few relationships under his belt, and that would be a good thing. You don't want a guy that doesn't have any relationship experience.

SECRET TIP #2: BAD Thing - He doesn't have as much history!

The problem with a younger guy is that he doesn't have a lot of relationship experience, either. Some of the relationship skills that you take for granted may be foreign to him.

Be prepared to educate him on a lot of the subtle nuances of a relationship.

This is why it's a good idea to choose a younger guy who is willing to learn - AND knows that he doesn't know everything.

SECRET TIP #3: You better know his priorities

It should be obvious, but a younger guy is going to have different priorities in life than an older guy would.

Sometimes a younger guy is going to be more into his adventure sports than he is into building a career. Or maybe his focus is on his career and he's not ready to really settle down.

It's up to you to figure out where his head is at and whether he's ready for the kind of relationship you want.

SECRET TIP #4:  Be careful you're not trading age for excitement

It's no secret that older guys can be pretty boring. Like, really really boring.

older woman younger man dating dos donts Dating A Younger Man? 25 Things You Better Know

The thrill...!

But you also want to make sure that you don't choose a younger guy just because you think he's more exciting. He may be exciting, but he may also be completely untethered and lacking a stable foundation.

You might need a guy that can keep up with you. You might be energetic and full of life.

And if you can't seem to find the guys that are willing to keep up, you may have to go younger in the dating pool. Just be careful that you're not seeking these guys because you need a few thrills. Ultimately, you're probably going to want a man who is willing to slow down enough to be with you. (Or speed up!)

SECRET TIP #5: Younger guys are easier to sculpt and change

The truth is that if he's younger that means he hasn't had time to build up resistance to change.

This can be a good thing if he is malleable. You might need a little project to work on.

Just remember that no matter how old he is, a man doesn't want to feel like you have to change him.

A man's number one need from a woman is her acceptance.

If you're more interested in shaping him then accepting him, he will notice.

But the good news is that if he's younger, he already realizes he is in a state of flux. He won't mind being guided towards his better self.

SECRET TIP #6: Sometimes it's the OTHER people you have to worry about

Sure, it would be great if everyone accepted your choice like a mature adult. But I'd be lying if I didn't tell you that sometimes friends and family become your enemies in this situation.

dating a younger man things you need to know Dating A Younger Man? 25 Things You Better Know

Everyone will have an opinion...

Most of your family have an idea of who they want you to date. They think they know better.

And the truth is your friends are kind of the same. But more tolerable.

Sometimes your family will be totally opposed to who you're dating. And the age difference.

But if we're being truthful, they would have a problem with something no matter what it was. Sometimes we just have the bad luck to grow up in a family that isn't very accepting of our choices.

And don't forget that HIS friends and his family may also have an issue with him dating an older woman.

It might even be difficult for your ex-husband if you have one. Especially if you have kids. Be prepared for some resistance. Maybe even a few nasty words of jealousy.

Make sure you plan for how you're going to tackle this with your family and friends.

You may have an uphill battle to get them to accept him. If you're ready for the pushback and you have the strength to stand your ground, you'll be able to handle it.

It doesn't have to wear you down or crush your spirit. But you do have to be confident in your decision to date a younger guy.

SECRET TIP #7:  Be careful about your self-esteem

I'm going to reveal a little bit about my personal history here: My mother dated a younger man for over 10 years. During that time she felt like she had to “keep up” and stay as young as possible while she was dating him.

This unfortunately pulled her into a few rounds of unhealthy self-esteem. During that time she got a facelift - one that she honestly didn't really need. Later, after that relationship didn't work out, she dated another younger guy.

The truth is that you may be pulled towards some unhealthy behavior of your own in an attempt to “stay young.”  Don't get caught up in this futile Pursuit.

Your youth is INSIDE you. Not on the outside.

Like they say, age is a number. But your attitude about your “number” can say a lot about you.

20 Dating A Younger Man? 25 Things You Better Know

Always be vigilant that you're not being manipulated into doing things you don't want to do simply to meet expectations. His expectations, or anyone else's.

If your relationship is going to work, then it needs to be realistic. And that means he has to recognize where you are and where he is.

SECRET TIP #8: Get ready for some crazy monkey love

Hey, we wouldn't be honest here if we didn't admit the truth: young guys can be a real tornado in the sack. If you need some bedroom action, a young guy is a place to go.

Not to mention that you can teach him and educate him how to please you best. There's nothing quite like having your own young, naive boy toy to train.

And you're getting a side benefit too. His stamina and enthusiasm can be very refreshing. Especially since men reach their sexual prime in their twenties and women in their thirties and forties.

Why not use that difference to your advantage?

SECRET TIP #9: Commitment? Uh, what’s that?

Another truth you have to face is that he might not have the same idea about commitment. Younger guys are looking to have a good time, more often than not.

Maybe you don’t need commitment. At least not right now.

Hey this can be a fun side adventure for you. But recognize that at some point, you're going to want to establish something secure and committed. Be sure he is also looking for that same thing.

Sooner or later you both have to figure out where this thing is going.

And you never know, he might be the one that needs the commitment first!

SECRET TIP #10: There might be some parts of his youth that just drive you crazy

things to know when dating a younger man Dating A Younger Man? 25 Things You Better Know

Is he ready to grow up?

You got to realize that he's going to have some of those younger guy annoying habits. Stuff that he hasn't quite outgrown yet.

  • Maybe he hasn't gotten a “grip” on adjusting his package in public
  • Maybe he's really into public displays of affection
  • Maybe he has a really cornball sense of humor

Whatever his qualities are, you have to accept him as he is. If his habits and lifestyle drive you nuts, you may want to look elsewhere for a more mature guy.

SECRET TIP #11: So what's in it for HIM?

Don't forget that he is choosing an older woman for some reason, too. You should understand his reasons for being attracted to an older woman as well.

  • Maybe he has some mommy issues
  • Maybe he is looking for someone with more sexual experience
  • Maybe he wants someone with an income that can show him some fun

Whatever the reason may be, you need to know what it is.

The best way to do this is by asking questions. Find out what his background is. Make sure he's communicating to you what his needs are in a relationship.

SECRET TIP #12: It needs to be more than flattery

Look, if you want this to actually turn into a relationship, don't let the fact that you can attract a younger man go to your head. The age difference will always be there.

What's more important is that you establish the DEEP parts of your relationship, not the superficial parts.

If all you're getting is a sense of boosting your self-esteem, you have to take another look at the relationship.

SECRET TIP #13: Sometimes you're not going to jive

No matter how young your attitude is, you're going to come from a different time. You'll have watched different shows, listened to different music, grew up in a different time in high school, watched some different movies…

dating younger men dating relationship advice Dating A Younger Man? 25 Things You Better Know

Is the age gap too big...?

You might have gone to school with a lunch box - and he will ask you “What’s a lunch box?”

Get ready for some involuntary eye rolls.

What's more important than the differences is how you handle them when they come up.

If you have the right attitude, it's not a hard obstacle to overcome.

You can use the differences as a source of amusement and connection, or frustration and disconnection. The choice is yours.

SECRET TIP #14: Watch out for the Jealousy

It's no secret that insecurities can be your undoing. If you're constantly wondering how you managed to land a younger guy like him, you might be on the lookout for every perceivable threat.

And it could go either way. You might be jealous of him, or he might be jealous of you.

After all, let's face it:  If you can attract a young guy like this, you might have that kind of vibe with other younger guys too.

SECRET TIP #15: Watch out for his Ego

This one doesn't change no matter how old he is. Or how old you are.

The simple fact is that a man has an ego. He has a certain need to be right in certain situations.

If you're a bit older than him, there's a good chance you might be a little more "right" than he likes. And maybe a little more frequently than he likes.

So don't be shocked if you find yourself having to massage his ego from time to time.

SECRET TIP #16:  You still have the same huge challenge - communication

Communication is the Achilles heel of every single relationship. So in that, you are on equal footing with just about every other relationship.

dating younger men how to connect build intimacy Dating A Younger Man? 25 Things You Better Know

Make sure you pay attention to your communication as much as anything else. And you may have to communicate about your age difference every so often, too. Make sure it isn't a sticking point or a sore subject for either one of you.

You might notice that most of the items in this list of tips so far involves healthy communication. That should be a signal to you that it's one of the most important things for you to work on in your relationship.

SECRET TIP #17: Make sure his brain can keep up

Probably the one area to make sure he can keep up with you is in the intellect department. When all is said and done, all the wild monkey love in the bedroom isn't going to matter if you two can't talk and relate to each other.

Make sure you have common interests and compatibilities that make the rest of the relationship work. And be sure you know if you can keep up with each other when it comes to conversation.

In the end, you can't spend all your time in the bedroom. You got to make sure you got everything else going on, too.

SECRET TIP #18: WHEN the difference is as important as WHAT the difference

If you’re 10 years older than him when you're 30, that's a whole big difference from being 10 years older than him when you're 50.

The older we are the more we come closer with intellectual and lifestyle age differences.

03 Dating A Younger Man? 25 Things You Better Know

Take some time to really objectively assess what your difference actually is. (You might have an AGE difference - or an attitude difference.) It might be only a few years, but it could be huge in terms of attitude.

And on the other hand, it might be 20 years difference, but no difference in Attitude.

SECRET #19: Consider the biological reality

If you're over 40, chances are you're reaching the limit of your child-bearing years. So you both have to be on the same page and have the same goals when it comes to children and a family.

A younger guy can change his mind about wanting children. And of course, you still have the option of adopting if you're ready to take on that role later in life. (or AGAIN.)

So don't gloss over this in conversation. Make sure you discuss the hard cold truth about your age difference and what it will mean in terms of options for you.

SECRET TIP #20: Money is still a factor

You may be further along in your career than he is. He might be sensitive to the difference in income.

The simple fact is that money is a huge challenge for many couples. Who makes it, how you spend it, and all of that.

SECRET TIP #21: He might still be searching for himself

Nothing is more frustrating than when you feel like you found what you were looking for - and the other person is still in search mode. This is something that could happen to you If you date a younger guy that is still trying to "figure himself out."

dating relationship advice dating younger men Dating A Younger Man? 25 Things You Better Know

Does he know what he wants in life...?

The problem that comes up when you've found out who YOU are is that other people who haven't discovered this can be a bit annoying to you.

You may have to put up with his pet projects, changing priorities, and passion of the week.

If you're okay with this, and your attitude can handle it, it can be fun. But if not, it could be incredibly frustrating for you to witness - and to experience.

SECRET TIP #22: If he hasn't found his direction yet, this will frustrate you

Even if he's found himself, he might be confused about where he's heading in life. All men go through a period of confusion and disillusionment.

If you date a guy that's still looking for direction in life and figuring out what he's "supposed" to do, this could frustrate you.

In fact, it could drive you absolutely bonkers.

Make sure you establish where you need his head to be at before you get into a relationship with him. Because if you do it the other way around, you'll drive yourself nuts.

If you need a guy that is already on his path to destiny - building his Empire - but the man you're with is still searching, you'll need to simply let him go. It won't work out.

One of the masculine traits a woman needs in a man is his sense of purpose and direction. If he doesn't have it, you'll find yourself turned off and annoyed most of the time.

SECRET TIP #23: If he's a partying kind of guy, and you're not…

Depending on how old he is, you could wind up with a guy that is stuck in Eternal adolescence.

Again, if you need a man that is past his fraternity kegger years.

Make sure you keep an eye on his habits. You might start out with a lot of fun times and late nights, but it will get old really quick.

SECRET TIP #24: He may not realize what he got himself into

A lot of men like to date older women because they have an idea in their minds about what this is going to be like. Sometimes they are right, many times they are wrong.

pros cons dating younger man Dating A Younger Man? 25 Things You Better Know

Have realistic expectations...

Make sure you find out what his expectations are for the relationship, and for you.

Find out exactly why he is okay with dating an older woman. Don't just take the first answer he gives you, keep asking and keep an open eye.

You don't want to be blindsided by his ignorance or naivety.  You have to protect your own heart, after all.

But when push comes to shove, you need to understand your man. You have to know how to make a connection with him that will keep him devoted and desiring you.

Most women don't know how to make this kind of a connection with a man - and that's the most common reason that a guy will start to distance himself from your relationship.

It starts out with some quiet behavior, then he starts pulling away, he stops responding to you...

And before you know it, he's out the door. And you're left pulling your hair out, wondering: "What did I do?"

The solution is simple: Understand his "Connection Code"

When you know what a man wants from you - and what he's looking for in a committed relationship, you'll know how to keep him.

Go check out the Connection Code HERE...

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  • Carlos Cavallo - Dating Advice For Women
    Carlos Cavallo
    Dating and Relationship Guru

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    Carlos Cavallo's Dating Advice Guru Relationship Tips For Women
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    Dating & Relationship Advice Published By:

    Morpheus Productions, LLC
    1115 Madison St NE #1047
    Salem, OR 97301

    1-888-414-0780

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  • Carlos Cavallo - Dating Advice For Women
    Carlos Cavallo
    Dating and Relationship Guru

    Why He Stopped Loving You...


    Carlos Cavallo's Dating Advice Guru Relationship Tips For Women
    Get Your Free Book Now:
    The 7 Mistakes Women Make That Make Men Pull Away...
  • Take The Quiz!
  • Listen to Carlos podcast

  • Carlos Cavallo's Relationship Tips

    Dating & Relationship Advice Published By:

    Morpheus Productions, LLC
    1115 Madison St NE #1047
    Salem, OR 97301

    1-888-414-0780

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