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Becoming Sadly Single At 50 (part two)

What I learned this weekend.

By Ross E Fortune LombardiPublished 2 years ago Updated 2 years ago 9 min read


Becoming Sadly Single At 50 (part two)

What I learned this weekend.



15th July 2022


I met a girl that I liked.


Nah, that’s an oversimplified crap start to an article, and the girl is not what this article is really about.

Not really.

The article is bout an important life lesson I learned this weekend.


Let's backtrack a bit.

You may want to check out the article

Becoming Sadly Single At 50 (part one), at:

To provide some better overall context.


Let’s try that again.


When you decide to try and build your life back, as a divorce older man you have to get yourself organized.

You have to make a list.

For example.


Sort out Council tax

Arrange regular rent payments.

Get a new “Romantic” Partner.

Make a budget

Keep on top of bedsit cleaning


And then try and do everything on the list as quickly as possible,

So you can move on!


But number 3 was giving me some problems.

The list item: Get a new “Romantic” Partner.

Because just like organizing your council tax, or making a budget, it was a grindy job that I did not want to do and it stubbornly refused to get done, so I could cross it off.

Which was annoying.


Sure, I flirted (or my out-of-practice terrible version of flirting)

I joined Tinder and put a very super wide set of parameters that would include almost anyone and everyone.


THIS was NOT desperation.

Each time I got turned down I gave a huge inward sigh of deep relief!

It gave me an excuse to put off and procrastinate an unpleasant job that I felt needed doing.

I really did not want the hassle of a “girlfriend” it was just a list item that needed completing, as part of rebuilding my life.


After all. That is what a proper adult does. Get settled and move on!


So then…

I met a girl that I liked.

I do not mean as a list filler, I mean I REALLY actually liked her.

Unlike the others,

I felt excited to be around her.





Obviously, I am not going to use her real name!

And I will lie about some details on purpose for privacies sake.

We will code name her, “ILE” = “Important Life Experience”


I actually first met “ILE” long before the divorce but after the love for my then-wife had suffocated.

She was fairly scruffy and had this blob of some food on her the side of her upper lip that looked gross.

It looked like some form of pudding.

But even then as I looked into her shiny eyes, all I wanted to do was gently wipe off the blob with the edge of my thumb as I cradled her face and then gently kiss her.

I shook myself internally and thought to myself

“What an odd compulsion to have?!”

Then I shrugged it off and got on with the party.





Time passes,

Divorce starts to happen, I move into a bedsit, and time passes.


This weekend I met codenamed “ILE” again,

I thoroughly enjoyed her company.

I did not want to walk away.


Now I will do a very brief unflattering description here.

Because, fair disclosure, she is 20 years younger than me – and seeing that information you are all instantly jumping to the thought,


“A newly lonely divorce fifty-year-old man falls for a thirty-year-old!

“Same old story told a thousand times by a billion sad older men with ego issues”

I can promise that this is NOT the case.

When I found out her age, during the general conversation I felt a bit gutted that she was so much younger than me.

My attraction felt like a sad cliche rather than genuine.


But I promise you she did NOT look like a pole dancer, or some conventional very dull-looking glimmer “bird” or barbie doll wannabee.

To demonstrate this I will be fairly brutal about how she looked,

Not to be cruel, but to make the important life lesson, the real reason for this article, more valid and make more sense in the end.


She has an unconventional body type – Not the body of a “Victoria’s Secret Model”.

But that…

Made the way she moved and bent over as she laughed and tilted her head enchanting!

She was dressing in baggy layered clothes,

Not in any form of sexualized outfit.

But that…

Did not make me want to kiss her any less!

She has slightly crossed over front teeth,

Which is absolutely adorable and I would never want them changed!

She smoked, while I am a non-smoker who does not like cigarette smoke.

But that…

Just made me think that I wanted to take her for a lunch outside on a park bench.

Not to be cheap!

But so I could also include some cigarettes as part of the alfresco lunch package so she could enjoy a smoke with her food.

In short.

I had a crush on HER, on who she is! Not just on what she looked like!


We giggled, we laughed, and I did not want to tear myself away.

Obviously, eventually, I had to.


I packed the experience away as just a nice random moment in time and then tried to keep it in proper proportional context.

After all – she is twenty years younger than me.

If I had only been 5 years younger while she had been only 5 years older, then maybe it might have been worth pursuing.

10 years would have been ok,

But a 20-year difference was just sad and delusional of me.


So, I try and put it to the back of my mind, and I go for a night out at a local comedy event.

I do my usual “try and tick off item 3” on my list thing.

Some friends come back to the flat,

We chat lots,

People, go home.

I am tired and try to go to bed.

I watch an NCIS episode and then settle down to sleep.

Except that I do not sleep.


Instead by midnight I have sent codenamed “ILE”

This text.


“I Ross here.”

“We met at <blah blah location> on Thursday –

I do not know if you are attracted to men.

I do not know if you are single or not-

And I DO know that there is 20 year age gap, so there is no realistic future for us as a couple.

But I would always wonder if I never asked,

- So, would you like to go on a date with me?

I think you are simply adorable and quirky in the best possible way, and I feel we could laugh and talk for hours, constantly giggling together.

- If not, then I would happily live in your friend zone with no complaints.”


The next morning

I waited unable to do any dish washing or flat cleaning, just waiting for a reply.

Demanding of myself that I wait until at least 3 pm before trying a live phone call.

By noon I had left a very clumsy message asking her to get in touch.

And she did not.

And unlike all the other various women I had tried to be romantic with,

Instead of being relieved that “ILE” did not get back to me, instead I felt – Sad!


As I said,

This article is NOT about “ILE”, not really.

It is instead about what I learned.

A lesson that I felt was so important that I write this, risking personal humiliation, embarrassment, and ridicule to make it.

Because as always, the message is always more important than the messenger!


I honestly thought that I would never be excited by someone again.

That the best I could wish for was someone equally lonely.

Just means to an end to cross off my dull adult, “rebuilding my life” list.

That I could just settle for in comfort and consider myself lucky.


I no longer want that.

Now I know that feeling excited and nervous about someone is still possible,

I want that REAL feeling again.

I no longer see a future so-called “romantic partner” as just a job to cross off a list.

Now I want to, actually, really, fall in love.

And feel again like I did when I met “ILE”

I am no longer wanting to settle for mere comfort now that I know that such strong passion is still possible.




I want to heed this vital life lesson!

I am writing this for YOU! (not for me)

YOU, Out There! Reading this NOW!


To help make the world a slightly better place.

If I can feel excited and able to want real romance again, THEN SO CAN YOU!

Do not settle!

Do not just try to cross off a list item!

Do not do that to yourself!

You can feel shy and nervous again.

You can feel vulnerable again and enjoy it.

You can feel alive again!

You can Feel it again!



I will no longer be chasing potential partners at every opportunity to get “a job done”

Instead, I am going to chill and wait for something real to spontaneously happen!

Like it did this weekend.

Even if, it might never happen ever again!

Because NOW, I know that it CAN!

And that feeling is worth the wait!




You may ask,

If you really felt this way, then why let codenamed “ILE” get away?!

BECAUSE DUMB ARSE: Life is not a rom-com!


One text and one live message are enough!

I do not want to be “Stalker-ish” or “Creepy” or make “ILE” uncomfortable!

Unlike some douche bag INCEL, I both like and respect her enough to not want to scare her.

We live in a terrifying world already crammed full of too many nasty nightmare predatory men with no immortal soul.

So, yes, I did let her “get away”, which is also known as being a “decent human being!”

It IS deeply, ice cold, enraging that I should even have to explain that to anyone!




About the Creator

Ross E Fortune Lombardi

Writer. Gamer, Goth

A (Constantly Failing To Be Funny) satirist!

[email protected]

Mutare non est meum

Cantus moriar


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