For those of you that are not aware of the now colloquial term “cougar” in the context of dating, I think Urbandictionary has a definition that describes it best:

“An “older,” experienced woman who happens to find herself in a sexual relationship (committed or not) with a younger man. She is not necessarily a slut, nor is she desperate. She offers sexual expertise and is open to new experiences. She simply wants to have fun. Though older, she may actually look younger than her “hook-up.” She is attractive, confident, and just wants to have fun. She will not attempt to trap her mate into marriage, children or even an?exclusive relationship. She is not interested in drama or games, as that would?interfere?with the pleasure she enjoys. Eg: My friend says I’m a?cougar?because I’m having sex with a?younger?guy, but I didn’t?hunt?him down – he approached ME!

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My experience being a cougar:

So being a cougar… I honestly didn?t mean to be one. In fact, I always dated older men.

Even when I was 18, my first boyfriend was a 33-year-old-bodyboarding champion, (I only dated him to get revenge on the guy I lost my virginity to, who was also a champion body boarder).dating in your 40s, dating younger men, single, cougar, midlife

But after my first real relationship in New York at the fresh age of 22, lasting for five years with someone my own age, somehow I ended up dating men who were significantly older again.

Possibly daddy issues, who knows? It became a pattern and I was actually more comfortable with silver foxes than men who were my age.

Eventually, I was attracting much younger potentials and strangely attracted to them as well.

Evidently, I was getting too old for the silver foxes who no longer saw me as a symbol of their phantom youth. And possibly, by attracting and being attracted to younger men, I was also trying to reclaim the last bastion of youth in me, before I turned 40!


So I just turned 44 years old and my current boyfriend is 27. I still have to calculate to make sure that it?s really 16 years difference. (Well he?s turning 28 this year. God I hope he?s telling the truth).

It?s a very fresh three-month-relationship. And I?m dealing with a lot of major communication breakdowns, veganism and oat bloody lattes!

This is by far the youngest I?ve ever dated, and possibly the most challenging.

David is a very complicated millennial, who claims to be 53 mentally, a slight introvert, and possibly on the spectrum.

I actually asked him if he was on our first date, after he asked for my credit score if I was renting or buying?

And if I?ve had a recent std/aids test? (All within the first ten minutes).

On top of that, his best friend is his ex-girlfriend, who he also lives with and has been living with for six years, which is the whole time he?s lived in New York. I know, reading this, I also ask myself what am I doing?

?I’m too old for this sh*t.?

I honestly don?t know? Well, he?s incredibly handsome, 6?3 and honestly fun to be with. That?s the problem, only when I?m with him is it fun. But as soon as we?re separated, it?s an utter disappointment.

Dealing with radio silence, teaching him to be considerate, having to explain how a relationship works and just how to be a man.

This, ladies and gentlemen is the problem with being a cougar. You have to teach them. My friend says it?s the best part. You get to mold them, shape them…NO! As Danny Glover says ?I?m too old for this shit.?

Currently, David is out of town for work and I?m actually quite I guess..that says it all. He?s a very specific case.

However, my last millennial Chripher, who was 12 years younger, wasn?t any better.

He was just a straight-up alcoholic bartender who also lacked communication skills and eventually became a booty call I fell in love with…Dammit.

It?s me! It?s me…IT?S ME! I am attracting this and therefore there?s something in me I have to face.

Possibly, I could be afraid to have a real relationship.

As a result, I surround myself with men much younger than myself with inevitable disappointments to justify my fear of relationships or my fear of being with someone who?s capable of having one.

Am I expecting too much?

What did I expect, he?s 27 years old, single, living in New York, why would he want to settle down? Because that?s what he said. David is loving me the best way he can.

I shouldn?t have any expectations at all, except to have fun! (Even still, I have to teach these young ones what to do in bed).

Each time I try to break up with him, he starts crying and I?m a sucker for that. Oh wow, this is such a revelation for me! I?m honestly at a loss. I thought, being a cougar, would be fun!

Having control, being more experienced and not caring about it so much. I wonder if the silver foxes deal with the same issues?

I?m not sure, since, men can easily detach and compartmentalize. I for one, thought by this age I could! I guess I?m still a hopeless romantic at heart who?s just so eager to sabotage.

Clearly, it?s not them (the boys I?m dating), and they?re clearly not to blame since we?re at such different stages in life. I remember when I was 27, I was having the time of my life and nowhere near settling down…but that?s me.

Expect nothing and accept everything.

I think I?ve come to the conclusion that being on the same page is what matters, regardless of age. I may be 44 and I obviously have some issues to deal with…but who doesn?t!?

I think if the person is worth fighting for and doesn?t give you anxiety and makes you smile when you think of them and you feel they care about you genuinely, without prying out their teeth for them to express that…then go for it…regardless of age!

My friend gave me a quote from Anthony Hopkins. ?It?s none of my business what people say of me and think of me. I am what I am, and I do what I do.

I expect nothing and accept everything.

And it makes life so much easier.? I feel, being a cougar, that?s the best advice to uphold!

I?m not sure what will happen between David and I. Regardless of all his youthful, sweet shortcomings, he?s sincerely a good and loving person.

One thing I know is that the circumstances and people in your life mirror what?s going on inside you. I evidently have major communication issues and maybe, I have no idea how a relationship works since my last real one was when I was 22!

Ever been challenged by the dating age gap? Comment below and feel free to share your experiences 🙂

K.D. Brighton

Author of 40 SINGLE NYC: The Gold Notebook

For those of you that have been following our journey, K. D Brighton is a frequent contributor to Check out her other articles and feel free to have a look at her book with 5-star reviews, “40 single NYC; The Gold Notebook” now available on Amazon. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to As an Amazon Associate I earn from qualifying purchases.

4 thoughts on “Accidental cougar: My experience dating younger men

  1. I’m sorry.  I just had to read this after reading the title.

    It’s really a can of worms.  Are you a slut?  No.  Are you trying to reclaim your youth?  I don’t think so.  There’s nothing wrong with liking others that are not so close to your age range (older or younger).  As long as you stick to the understanding that “under 18 will get you 20” you should be fine, LOL.

    My attractions are all over the place.  For me, it’s initially looks (especially if they’re just cute, not necessarily drop-dead gorgeous).  After that, it quickly becomes about personality.  If we don’t click, it’s off to the next one.

    Now, take my words with a grain of salt.  I’ve been with my husband now for 22 years (married for 4 – it’s just paperwork at that point).  Still, I totally get where you’re coming from.

    When you date younger men, you’re going to have to educate them a bit, as they don’t have the relationship history to refer to like you do.  Still, even if they were older, there’s the learning period of finding out what you like about them what they like about you and the annoyances as well.

    Now, as for the whole best friend/roommate ex thing….that’s just odd to me and I don’t know how I’d handle that one.

    I’m sorry I don’t have words of advice that really help you but I do want to thank you for sharing this experience.


    1. Thank you Scott for your comments. No I don’t consider myself a slut and yes you are absolutely right that the heart wants what the heart wants. It’s not like I have a radar to explicitly target younger men, it just happens that way I guess. Ladies like J-Lo and Lisa Bonet are true trailblazers in this department and I admire them. Thank you so much for taking the time to comment. All the best to you.

  2. Dating Older men is not an issue but rather what determines a long lasted relationship is trust, to promote trust in relationship that would lead to marriage then both of you dating must refrain from sexual relation, this attitude of avoidance of sex would motivate the guy who is dating to pay your bride price. Thanks for experience and how you manage to cope.

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