Advantages and Disadvantages of Dating a Younger Man (Part 2)

Advantages and Disadvantages of Dating a Younger Man is the entertaining story of a personal encounter. A true experience. The story, first published on The Nude Truth, became a chapter of my memoir, The Gypsy Saw Two Lives (

Since it was published, the post on dating younger men was read hundreds of times and often I wondered if the readers expected more or a different story. I asked myself if the content provided them with needed information.

I don’t have the answer, but I do know the story continues to be popular.

With mixed emotions of guilt on one hand, because the first post didn’t offer what the readers expected, but on the other hand, with the thought that probably it provide useful information, since it continues to be read by hundreds, I decided to write PART 2 and address the general topic of dating younger men. Precisely one scenario.

To avoid potential disappointment, I clarify that this post does not address the simplistic scenario of the so called “cougars” and their “toy -boys.” If someone has a lot of money and wishes to entertain herself with a younger man, this post doesn’t address cougars and toy-boys. In today’s world, if it’s acceptable for a man to date or simply have sexual encounters with much younger women, the women may do the same, and it’s equally acceptable… or not? Cougars and their younger toys do not make the topic of this post.

The goal of this article is to raise and attempt to answer a few questions regarding more complex relationships between older women and younger men.

What is the definition of a real relationship? Given that everything is a personal perception, my definition is a more complex involvement on several levels, both emotional and sexual. What is your definition of a relationship? Is it different than mine? Similar?

Let’s take a scenario:

For many ” chronological age” is only in “our minds,” it is a matter of attitude.

If you and your partner are truly in this category, read no further! You are safe:) and more importantly, happy!

If, however, there are any doubts or curiosity, you might wish to read on.

What is your definition of “younger?”

For many, 8-10 years is not defined as younger, and as a result is not a concern.

For the sake of the argument, let’s say 15 years is an age difference which might be a concern.

Why and when?

Yes, WHEN???

Let’s say, a 40- year woman, who ages well, starts dating a 25-year old hunk!

For the sake of having a vivid picture which includes, but is NOT limited to physical attraction only, let’s say the woman is a college professor and the 25-year old man just finished a graduate degree. It is irrelevant whether they had any sexual attraction while she was teaching him. They didn’t act on it. However, after his graduation, their relationship blossomed… First as a friendship, as they had much in common and conversation was never boring. Slowly, they both became aware that there was more than friendship.
What does that mean? How does one discover that a friendship is more? Perhaps during a conversation about poetry, about the eternal topic of love, that impossible to define, which could only be felt: desire? What we call chemistry? They thought about each other more and more often and had a need to share the littlest of things.

If the scenario were reverse, and a 40-year old professor, whose hair was grey, giving him an appearance of “distinguished,” fell in love with a 25-year old woman, no one would think twice, but the situation is reversed, so we pay more attention to it. This is not politically correct, but it is the reality.

Let’s say that the 40-year old college professor, the woman who ages well, and the 25-year old graduate fall in love so deeply, they get married. They have so much in common. They read the same books, like to experiment with foods and even take cooking lessons together. He likes to hike and so does she! Not to mention their intimate encounters, as she brings 15-years of experience into their love life! The relationship is Heavenly!

Come to think of it, statistically, women live longer than men…In fact, it would be logical for younger men to marry older women!
Why isn’t this the standard?
Hmm… on the other hand…

I forgot to mention, the 40-year old professor is divorced. She has two teenage children at a difficult age. They dislike the younger boyfriend, or later husband. Their friends make fun of them. “Mom you’re crazy!” one of them dares say.

She, the older woman is DONE with children! He, the younger man, blinded by love, didn’t think of it for the first few years…
When he turns 40, and looks around, he sees all his friends married and pushing strollers. Hmm… his beautiful wife… well now she is 55 and menopause hit her, with all the hormonal changes and the loss of estrogen and progesterone and as a result the change in libido. Oh! Let’s stop looking in that mirror to see the fine lines around the mouth. No, not the expression ones, because she smiled too much!

This is when WHEN becomes a stepping stone: When she is 55 years-old and he is 40!

Time is an interesting concept. A couple seemed perfect when he was 25 and she was 40, but the same people at 40 and 55 are in two different life stages, each with their specific requirements and needs.

Would such a couple continue to be happy and what would it take?

Please share your thoughts.
We welcome your comments.