Dating An Older Man - 17 Secrets You Should Know

By: Carlos Cavallo

If you're thinking of dating an older man, you probably want to know what to expect.

There are a lot of things you need to know in order to date older men. Both positive things - and some challenges you should be aware of.

relationship advice dating an older man Dating An Older Man   17 Secrets You Should Know

You may have a lot of questions, such as:

  • What is dating an older man like?
  • Is it ethical to date an older man?
  • Is it okay to date someone 10 years older?
  • How old is too old?

If you're in your 30s, 40s, 50s -  you need to know how to handle the age difference, no matter how big or small it is.

And if you seen Catherine Zeta Jones and Michael Douglas, you know that it can not only work but look fantastic. As it does with Jay-Z and Beyonce, or Ryan Reynolds and Blake Lively... And many others.

First of all -


Make sure you understand why you're choosing this guy in the first place.  It's always important to ask yourself why the person you're attracted to is so attractive to you.

What you might find is that there is a trigger being pulled. An emotional one.

Very often spontaneous romance happens because your weak spot matches something about him. When it's an age difference of more than a few years, make sure you're not projecting on him.

Yes, there is the old cliché of the " daddy's girl"  and all of the psychological issues that brings with it. But it's a cliché for a reason.

Many women who get involved with older men are looking to connect with something they feel they are missing. As long as you understand why you made the choice, you can go in with your eyes wide open.

REALITY CHECK-IN: Are there others...?

When you date an older man, there's a very distinct possibility that he's been married before. And maybe even has children with another woman.

You're going to have to know for yourself whether or not you want to become an instant mom.  And you have to be aware of all the complications of a relationship with another family.

His first obligation will obviously be to his children. You'll also have to make some kind of relationship with the ex-wife if things go the distance. And you have to understand your priority in that mix.

REALITY CHECK-IN: There's also the money...

Keep in mind that your financial pictures might be distinctly different. One of the most likely places that you will argue is over money.

And yes money can also break up your relationship.

05 Dating An Older Man   17 Secrets You Should Know

Many women do marry for the benefits of extra financial security. If you really do feel an emotional connection and love with him, there's nothing wrong with money as a side benefit.

Just be aware that you may have to have some serious discussions around your contribution possibly not matching his. And even if he says that's not an issue, he does have to approve of your spending and money habits.

On the other hand, if you're the wealthy one, you need to watch out that his intentions are pure as well.

Now, here are a few things you definitely need to know in order to date an older man...

Tip #1: The cool part is, you are always HER...

Have you ever seen a couple where he is the distinguished older guy, and she is the younger woman on his arm?

Let's be perfectly honest here- I'm sure you said some pretty catty things about it. And let's be extra honest and admit you were probably a little bit jealous.

The cool part about dating an older man is that you are always going to look young for his age. And that does wonders for your vanity as well as your feelings about how you look.

It's a great side benefit of being the 'younger woman.'  Live it up!

Tip #2: Beware making him feel like a fossil...

To be sure, one of the things you don't want to do is make this guy feel older than he already is.  Some women make the mistake of trying to make him look older so that she seems younger.

This won't go over very well for him. What he wants to feel is more virile, not like your grandpa.

dating an older man how to build connection Dating An Older Man   17 Secrets You Should Know

The best thing you can do is to point out all of his traits that make him seem:

  •  established
  •  wise
  •  capable
  •  virile
  •  desirable

Hey, if he landed you then he must be doing something right, right?

Tip #3: Give him time to work his magic...

If he's older than 40, then chances are he's going to be pacing himself in the bedroom. So you're going to want to pace yourself as well.

He's not going to rush to the finish line. And the more you can help him make it last, the better.

Ultimately, this is probably one of the reasons you chose an older man in the first place.

Tip #4:  Don't widen the gap...

One mistake that many women make when they date an older man is they tend to overwork the fact that they are younger. Which means they may dress a bit inappropriately.

Or even act inappropriately.

16 Dating An Older Man   17 Secrets You Should Know

You don't want to increase the distance between you and him even more by playing it too young.

It's most likely that he's dating you because he wants you at whatever age you are. Remember that it can also be embarrassing for an older man to date a younger woman who doesn't act her age.

He still needs you to demonstrate your maturity above all else. Never forget that.

Tip #5:  Treat the differences with respect...

Here's a perfect example of this tip in action:

Let's say you're talking about your favorite comedy television shows from when you're a kid. You might want to refer to shows he can relate to first.

For example, if he is a 1970s kid, he probably watched "The Brady Bunch." If you want to connect with him better, bring up that show. And then later on you can talk about your 1980s shows like "Saved by the bell."

Tip #6:  It's not the gap, it's the bridge...

Some women worry about how old is TOO old.

dating older men secrets you should know Dating An Older Man   17 Secrets You Should Know

The truth is, it really doesn't matter as long as you both get along and can relate to each other on a deeper level. As I like to say, it's not the size of the canyon -  it's the strength of the bridge.

As long as you remember that the connection is still the most important thing that he's looking for, you'll do fine.

Tip #7: Let him be your white knight...

An older man is going to be much more concerned about chivalry and playing the masculine part.  It's something he will age into.  It's a natural process for guys who get a little older.

So you have to be willing to let him do more things for you. Let him open the door, pull out your chair, and let him do those little things that make him feel like he's the man.

It's a great side benefit and one that you should indulge in.

Tip #8: Mind the gap...

Of course an age difference is much more pronounced when you're in your 20s then when you're in your 40s. Since I typically advise women in their late 30s and up, of course I'm actually talking about the age where the difference isn't that much of a difference.

dos donts of dating older men Dating An Older Man   17 Secrets You Should Know

Let's face it, if you're in your 20s and dating a man in his 40s, most people are going to scream "daddy issues!" even if that's your taste. The fact is that you only have 20-ish years of life experience, and he has about twice as much.

And those are big differences when you're that age.

But when you're older, he can be older and it really doesn't make that much of a difference. As long as - as they say -  you're both young at heart. In terms of life experience, you are probably both fairly equal.

And let's be perfectly honest, there's a reason for it being more acceptable when the woman is younger than the man - which I'll explain in the next tip:

Tip #9:  It's more acceptable if it's HIM...

One of the most common double standards is older man/younger woman. It also happens to be one of the more acceptable combinations for most people.

The reason is because an older man implies more resources, more wisdom, more willingness to commit. He's sown his wild oats. He doesn't need to be a wild Playboy.

20 Dating An Older Man   17 Secrets You Should Know

This is almost always been true in the past. The age difference between the man and woman was usually necessary so that both were at the same maturity level.

Studies have shown that the average difference in ages when you're in your 20s is about 2 to 3 years. When you're in your 40s, that age difference is usually around seven years or more.

It does have its roots in science. Again, older men = more ability to provide for his wife.

Tip #10:  Accept your relationship - and him...

Don't let other people's prejudices affect your acceptance of him or the relationship.  Once you made a decision to have a relationship with an age difference, you must accept all that comes with it.

relationship tips advice dating an older man Dating An Older Man   17 Secrets You Should Know

If you know that you have a solid connection with him,  and your relationship is good, don't let other people's opinions or prejudices impact your feelings.

In our age of the Internet and social media culture, it's common to see shaming and other bullying tactics online used as a way for other people to make themselves feel important.

Make a personal declaration to declare your relationship bulletproof from the opinions of others. It's probably the single best thing you can do to weather the storms.

Tip #11:  He knows...

One of the top reasons you would want to date an older man is because of his being more clear about what he wants in a relationship. Let's be real here -  younger guys just want to have fun for as long as it lasts. Older guys are ready for more. They've outgrown that.

Chances are he knows exactly what he wants in a relationship with you. And that will feel like a fresh breath of air.

He's probably ready to communicate more, and pay more attention to your needs. Mostly because he doesn't need to attend to his own as much.

Tip #12:  And if he doesn't know...

And on the other hand, if you meet a guy who is still stuck in his younger "party wild" years, you know you have to avoid that relationship right away.

Something else that can help you is noticing how much this guy actually does know about what he wants.

dating older men relationship advice you need to know Dating An Older Man   17 Secrets You Should Know

If this older guy is still a bit clueless about your relationship and his needs as well as yours, you should be quicker to cut him loose. Chances are he's not getting any better the longer you keep him.

As you date older men, you should notice more immediately if he has matured well - like a fine wine - or he's turned into vinegar. Being able to spot his maturity level will make it much easier for you to see if he's The One for you.

Tip #13:  Set your sights on similar experience...

In reality, the best compatibility between two people is when they share similar experiences of life.

  • Sometimes this is in childhood...
  • Sometimes it's having a common ethnic background...
  • Sometimes it's having similar political beliefs...

But ultimately the glue that holds you together will be the experiences you share.

Which means if he is retired and doing his own thing, and you are still in the workforce, you may have some challenges ahead.

If you grew up in a particular religious structure that you hold to even now, and he does not, it will create a divide between you. You need some common experience threads to strengthen the relationship connection you share.

And connected to this is...

Tip #14:  Having a similar horizon...

This just means you both share common direction in life. The same goals, hopes, and dreams. You have to have similar visions of what you want your future to be together.

how to build connection intimacy dating older man Dating An Older Man   17 Secrets You Should Know

You might not be planning your wedding quite yet, but you should still have an eye out for things that will get in the way of a longer relationship. And you have to start looking at this right at the very start.

It may seem a little bit unromantic, but if you really do want a long-term relationship, you have to be looking at the big picture. And if it doesn't match up with your goals, then you have to be willing to end it to move on to find the right one.

And this may be tricky if you're in your 30s and he's in his late 40s and the topic of children comes up. The truth is you do have a clock, and he doesn't.

So be sure you know what you want from him and the relationship before you find yourself committed too far.

Tip #15:  Watch out for the P word...

There's an even trickier part to relationships with an older guy that comes up more as a conflict later in life. And that is politics.

The fact is that a man in his 30s, 40s, 50s is going to have a fairly set political stance - if he has one at all.  You have to acknowledge that you may be dealing with a guy who might believe "you can't teach an old dog new tricks."

Watch out for your need to change him to match your idea of the relationship also. A man in his 20s might be a little more flexible, but ultimately there isn't any man that wants to be changed by the woman in his life.

We want to be supported and accepted for who we are more than anything else.  The same way you would want that from him.

Tip #16:  Older guys have more time...

The fact is as a man ages, he doesn't need as much time to himself anymore. He may  still be working on his kingdom, but he won't have to give as much time to other extracurricular activities.

tips for dating older men Dating An Older Man   17 Secrets You Should Know

Such as going over his buddies house for late-night video game festivals.

Or going out to his buddies wild house party...

If he has any maturity, he has already outgrown some of these younger guy hobbies.

Which means he should have more time for you now that he is more settled into himself.

When a man is younger, he needs to attend to his sense of exploration and adventure. But when he's older, that should fade a bit. Leaving more room for you and your relationship.

But this can also work in the opposite direction too.  There are many older men that are in the prime of their empire building.

He may be committed to an executive lifestyle. Or a business he is growing. Or a new business he is starting.

I have coached many women who -  for whatever reason -  get involved with a man who doesn't really have the time for them, and then spends every waking moment trying to desperately squeeze more from him.

As the saying goes, you can't squeeze blood from a stone. If he hasn't got it to give then you may have to accept what time you do have with him.

As always, make sure you know how much you really need from him before you get involved. Because it's always much more difficult to walk away once you've gotten involved.

Tip #17:  Ultimately, it's not about the number...

In the end what it comes down to is a pure and abiding love for each other and who you are. The number attached to that really doesn't make a difference.

It really is just a number. When the two people can find common ground and love regardless of that number, then it becomes about the relationship. Not the mathematics of dating an older man.

11 Dating An Older Man   17 Secrets You Should Know

In reality, a good relationship probably won't even make you aware of the age difference. It might only come up in defending it to your mom, or to others who don't understand.

Keep your focus on the fact that you two are simply human beings. If the age difference doesn't come up in your mind or his frequently, then just experience your relationship. Forget about the numbers, when the rest takes care of itself.

But wait... I have one more thing for you to think about -

Do you know how to build that bridge...?

Earlier I mentioned that you need to be able to build a bridge of connection across whatever age gap you might have.

The reality is that most women don't know how to do this right. They don't know how to make a real connection with a man.

Many women assume that they have good communication ability from their friendships with other women. But the reality is that connecting to a man is a very different kind of communication.

  • Do you know how to forge a bond with a man so that he will be loyal to you and your relationship?
  • Do you know how to open his heart so that he lets you in?
  • Do you know what signals he wants to see from you in order to fall in love with you?

Here's a secret: Most women do not know how to do these!

Some women think they know how to connect with men, at least for the first few dates. But what they don't realize is that he's looking for a secret signal to move forward with you.

If he doesn't see it, he will lose interest. And he may even ghost you.

how do I find love dating in modern world Dating An Older Man   17 Secrets You Should Know

To discover what the signals are that he's looking for, go read this article now...

Carlos Cavallo's Dating Advice Guru Relationship Tips For Women
Carlos Cavallo - Dating Advice For Women

Carlos Cavallo Dating and Relationship Guru

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