Dating Over 50? How to Get the Treatment You Deserve.

advice: dating advice: relationship john gray

If you’re a single woman who’s dating over 50, and the men you meet are not bringing enough romance to your dates, this is a post that can help.

The fact is that we all get a little rigid as we age, and that’s natural.

But there is also a biological and psychological explanation that can shed some helpful light on why this occurs and what you can do to inspire more romantic behavior.

In this post, you’ll learn why men may become less romantic on dates as they get older, what they really need to open up to you romantically, and a simple communication tool that can help you get the treatment your heart desires.


Dear John,

I'm a very young acting and healthy, older single woman. 

Contrary to what all the dating experts are saying, mature men do not want to make a female happy. 

Everything has to be their way, and they don't give a single compliment. 

They don't hold your chair out for you nor help you with your coat. 

They don't respect you as a woman, and they want a woman to pay her own way even on the first date. 

What is a single mature woman supposed to do?

– Linda


First of all, I want you to know that this is a very common challenge when you’re dating over 50.

As men get older, we do get more rigid.

Let’s start by getting into WHY this is...


Dating Over 50: Why Men Get More Rigid as They Age


As men age, what happens is a natural decline of testosterone.


And testosterone in men is what creates:

  • Fluidity
  • Flexibility
  • Interest
  • Motivation
  • Generosity of spirit

So when testosterone goes down, their energy levels drop.


In addition to this hormonal shift, many older men (single and otherwise) also have a relationship history that impacts their romantic behavior.

Quite often, they have a track record of doing their best and their best not being good enough, so they stop trying.

To be perfectly frank, they’re not confident that they can make a woman happy.

It's often based on thinking: "I tried this and I tried this and it wasn't enough. So why try?"

In my experience as a marriage counselor for 40 years, what I hear again and again from men if they want to end a relationship is:

"John, no matter what I do, it's never enough to make her happy." 

That feeling of failure is what causes him to stop caring.

What’s interesting is that women rarely realize this because their needs in a relationship or marriage are so different from a man’s.

So they also don't realize the power that they have to open a man up, even when dating over 50.

But understanding this can actually help you get what you want too...


What Men Need That Women Don’t


The typical complaint of a woman who wants a divorce is:

“I give and give and give in this relationship, but I don't get back.”


And what is it that she doesn't get back?

  • Consideration
  • Caring
  • Understanding
  • Affection
  • Warmth
  • Kindness
  • Sincere generosity


You see, men will lose their sincerity when they burn out.

But likewise, women will lose their trust and give up.

So this is another challenge that both men and women have to face when dating over 50.

Women get tired of explaining the same things over and over.

They start to expect a man should just know, without being asked or told.

They think: “He should just do it.”

The problem there is that men don’t know without being asked or told.

However, the good news is that men are trainable. Yes, even as they mature!

There's a saying that goes “You can't teach an old dog new tricks.”

But men are not really dogs. We're only like dogs in that we're teachable.

So we can still learn what makes you happy — even as we mature.

If you let him know what makes you happy and he starts to experience that again and again, he'll actually open up and become a new man because you taught him.

There's an art to this and it's a feminine art.

And with this knowledge, I think you'll be able to put it into practice.

So how do you do that when you’re dating over 50, exactly?

Let’s get into that next...



How to Teach a Man You’re Dating to Make You Happy


So let’s say some man is taking you out on a date, and he's got that rigidity.

He's burned out a little bit from trying to give and not having it be enough for a loving and successful exchange.

So part of him is just like, “Why bother?”

And part of that is common confusion today because the truth is, even when we’re dating over 50, we all want equality between the sexes.

We both want to be contributing to a relationship.

But most people don't understand that the way a man contributes can be different from the way a woman contributes.


What men really need most is NOT...

  • To have a woman open the car door for him, or
  • For a woman to pay for the bill!


What a man needs most is to feel like he makes a difference.


So what you have to do, as a woman dating over 50, is...

  • Go out on a date with a guy, and
  • Just have a conversation to let him know what you think and feel


The purpose of this conversation is NOT to try to…

  • Teach him
  • Ask him
  • Preach to him
  • Show him

It’s simply to share your thoughts and feelings on the subject.

So it can go something like this:


"It's amazing today how people have forgotten what romance is like and that women feel good when a man pays for the meal.

It's not a big deal. It's that gesture of kindness and generosity.

I know for me, I enjoy it.

If a man holds a chair for me or opens a car door for me?

These things make me happy.

Call me old-fashioned, but I really like it.

I think it's a wonderful thing.

And it doesn’t have to be big gestures. There's still equality of giving and receiving.

As a woman, I really like and appreciate those little things.

I'm not demanding at all, but I do like those little things and it makes life fun.

And it certainly makes you more attractive to me. And we'll have more fun together."


These kinds of conversations can soften the whole thing as you indirectly educate him that old-fashioned values are also helpful and can help you two have fun together.

There's no doubt in my mind that a man who’s not doing those little things has done them before and ended up feeling that he wasn't being appreciated for it.

And so he says, "So why even bother?"

By expressing your values and preferences, you will not only more likely get what you need, but you can change his life in a very indirect but fun way.

The key thing is, when he does those things, let him know that you appreciate him.

Let him know what he did that made you happy.

This will inspire him to continue and help him rewrite the story that nothing he ever does is “good enough.”

And that may just be the beginning of a whole new love story for the both of you.


Grow in love,


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