Oh What Hope for The Jaded First Date (and the Missing Snake)

by Miles Harrop | Jul 21, 2026 | Uncategorized

It’s a Sunday.
I should be happier.

So there I was. I’m standing in field, in the beautiful Eastern Cape and there is, objectively, a very pretty woman standing very close to me.
I am on a date.

I am also moving rocks around in a derelict patch of bush near the freeway like a confused archaeologist searching for answers in all of the wrong places.

I am, for all intents, an insufferable romantic. Could this be it? A second date with my True Love, written in the stars?

I did not find what I was looking for that day.
I did not find True Love either.

This was a first date and it was getting awkward.

I only found where it wasn’t. I guess sometimes that is all that you are getting.

But I am on a date.
But why am I doing that thing with the rocks in a field?

“Shoulder,” said Igor.

“It’s never the shoulder,” I said.

This was a first date and it was getting awkward.

But I get ahead of myself.

The real question is not whether I found it, whatever “it” is.

The real question is this: What is enough on a first date to avoid abject and voluminous cascades of disheartening disappointment?

Disappointment, in my experience, is usually built on illegitimate expectations. At sixteen I was once told that if you get it all on the first date, there’s not much point in a second date. This wisdom came from my friend Michael, who was, by his own account, an expert on such matters.

At sixteen, having not experienced some of “it”, or any of “it”, let alone “all of it”, I was not entirely sure what he meant.

The Facts of Life

My experience of women had been restricted to an imaginary girlfriend called Slob and the occasional snog with my pillow. Kissing someone other than my mother and having sex with someone other than myself were interesting but vaguely defined parameters.

Many of my friends had brothers and sisters who educated them in the ways of romance. A so-called only child like myself required either good friends or a sit-down with my parents at the appropriate age.

I wanted the former.
I got the latter.

The appropriate age was apparently sixteen, a few days before my first date. The setting was the ten metres between the bottom of our driveway and the top of it. Mother Dearest had clearly drawn the short straw.

“Do you know about love and stuff?” she asked.

I did.
I had fallen in love before.

The first time I fell in love, I knew it was the right person. I had known her for a day and the universe had arranged itself accordingly.

Sex education, the way the British do it: brief, awkward, and delivered as though everyone involved would rather be discussing a damp squib.

She was not perfect-looking. I mean, who is? But I loved her from the top of her strange-shaped headwear to the tips of her cute, slightly oversized hobbit feet.

She could also, according to her, levitate by applying pressure to her nose and ear while whistling. She taught the technique to me. Despite repeated effort, plus several nosebleeds and a mild sense of personal betrayal, I never managed it. She only levitated behind closed doors so that the bad ones wouldn’t see. I never actually saw her do it, but she said she could and that was enough for me.

On reflection, she didn’t know she was my girlfriend. It was complicated.

Jane appeared at Uncle Derek’s farmhouse as if from nowhere and instantly we became friends. We spent our holiday looking for four-leaf clovers, jumping off haystacks, and generally enjoying the sort of pastoral threesome only children can manage without scandal.

On the last day Jane decided to have a birthday, which meant I had to buy her a present using the spending power of a nine-year-old. The village shop offered precious few choices once one removed liquor, cigarettes, gambling and smut. I was left with two realistic options: false-teeth cleanser or crayons and a colouring book.

I chose love.

She caught me wrapping the present and I thought perhaps, now, she might hold my hand or something.

You sicko. I know what you thought. I was nine. I meant the full range of innocent romantic possibility.

“Yeauuuch! Crayons!” she said. “No one uses those any more.”

Then she turned her large hobbit feet and removed herself from my life. And good riddance too. 

Anyway, she was wrong. I still use crayons, although I’m not sure I should be saying that publicly.

By the following week I had forgotten about Jane and fallen in love with somebody else who also never found out. There have been quite a few of those in my life. Small missed opportunities for sexual opera.

Back in the driveway, Mother Dearest pressed on.

“Well, you know how everything works. The birds and the bees. And all of that.”

Why insects and airborne agricultural metaphors needed to be involved in the reason I was carrying a condom in my wallet remains unclear.

“I do,” I said. “And all that.”

“All is good,” she beamed. “You’re a clever little sausage face.”

That was the full extent of my preparation for romance.
Sex education, the way the British do it: brief, awkward, and delivered as though everyone involved would rather be discussing damp wallpaper.

The First Kiss

(Featuring Burglar Bars and a Bull Mastiff)

My first actual date was with a girl I instantly fell in love with and hoped to marry one day.

No surprise there. I fell in love the way some people fall down stairs, enthusiastically and with no sense of risk.

The awkwardness of the goodnight kiss was not an issue because we had already kissed. Admittedly, it had been through the burglar bars of her bedroom window at her father’s heavily fortified house, but beggars cannot afford to be connoisseurs.

I had never been kissed and did not know how.

“You stick your tongue in her mouth and wriggle it around,” said Michael, expert counsel on the matter of women.

“Like I’m licking out an ice-cream container?” I asked.

“No,” he said. “Slowly. Let me show you.”

“Hell no,” I replied, choosing fast-moving traffic over Michael’s tongue. Michael’s tongue had been to places tongues should not visit.

An hour later I was on tiptoe at the burglar bars, craning my neck through the iron like a hopeful inmate.

We kissed for what felt like an hour, though it was probably five minutes. It was exhausting. Neck spasms and foot cramps rather denigrate the erotic nature of an occasion.

Sadly, the eroticism had not been lost on Max, the eighty-five-kilogram bull mastiff who had taken a passionate interest in my left leg, while an overexcited parrot sang “She Loves You, Yeah, Yeah, Yeah.”

A week later, at our official first date, my mother asked from the front seat, with the girl already sitting beside me in the car, “Is she your girlfriend?”

“We’re just friends,” said the girl, breaking a piece of my heart.

“Bitch,” I muttered under my breath.

She sort of broke up with me a week later, not before being seen with one of my classmates, who had apparently also discovered the burglar bars, the bull mastiff, and the parrot.

So I learned my first real lesson in romance:

There is no such thing as a fortified house.
There are only rotating appointments.

The Date with Snakewoman

Years later I was working as a doorman at a nightclub, which is basically a postgraduate degree in human behaviour, except the “professors” are drunk, high, angry and sometimes bleed.

I met the odd person who showed interest.
One in particular stood out.

Snakewoman.

Snakewoman, as she was introduced to me, collected venomous snakes.

Which self-respecting young lady doesn’t, I thought, because I was young and stupid and had not yet learned that “quirky” and “predatory” sometimes share a postcode.

During our first date she announced that she had a tattoo somewhere on her body and made us guess where it was.

This was the early 1990s in the backwaters of the Eastern Cape. There was not much to do. So first dates, judgement, and tattoo-location guessing counted as entertainment.

I did not entirely trust the situation, so I brought Igor as a sort of prophylactic measure. Not a condom. A chaperone.

Igor had a karate black belt and a real gun which fired real bullets. He was the kind of friend you bring when a date has boot-knife energy.

“I know her,” he said. “She carries a knife in her boot. She hitchhikes home at four in the morning from the nightclub.”

You see. He was the right person to take!

This seemed reckless. Also exactly like the sort of person who would own snakes for fun.

“Fine,” I told Igor. “Sit in the back. If she reaches for a boot, grab her.”

“She’s a big girl, Miles. What if she’s just scratching her foot?” he asked. “Or lifting her skirt because of your overwhelming carnal magnetism?”

“Good point,” I said. “Just keep an eye on her legs and boots.”

To his credit, he executed the strategy flawlessly. He did not take his eyes off Snakewoman’s legs all evening.

The Matter of the Legs

To ignore the matter of Snakewoman’s legs would be to deny you vital information.

There was a lot of leg.

Her legs began down there and ended up somewhere near her middle bits, where they surrendered to something that could, very generously, be described as a skirt.

The skirt looked as if it had been applied with a very fine paintbrush by someone who ran out of paint halfway through.

I did manage to look at her face once or twice during the evening, which was already more than Igor managed.

There was not much conversation. Mostly guessing, judging, and mild survival planning.

What does one talk about on a first date?

I once read a book about first dates which advised never asking, “How was your day?” I lost the book before chapter two, which was almost certainly where the useful part lived. I have therefore had to make up my own rule set.

Over the years I have developed my own set of first-date questions, which I now offer as a public service:

  1. “What’s your name?”
    A strong opener. Best avoided after ten years of marriage.
  2. “How do you know we’re not related?”
    Particularly relevant in small towns.
  3. “When were you last tested for infectious diseases?”
    Ideally your date should present a clearance certificate, like a roadworthy.

Those are the top three. Here are others that male friends have advised me not to ask.

  • “Didn’t I date your Mother?”
  • “Didn’t I date your Daughter?”
  • “Am I dating your wife?”
  • “Am I dating your husband?”
  • “What’s that smell?”

Lady friends have also had input into topics not to be discussed at the first date including:

  • You think that your parents are aliens.
  • Venereal disease
  • Symptoms of venereal disease
  • Your favourite venereal disease.
  • Why they are single (Anyway, may have been covered by the topics above)
  • Why are you single (dont got there).

The skirt looked as if it had been applied with a very fine paintbrush by someone who ran out of paint halfway through.

“It can’t be on your legs,” I said, returning to the tattoo. “I can see them from right from the top all the way to the bottom.”

“Bottom,” murmured Igor dreamily into my ear. “It is certainly not on her bottom.”

Later, during the debrief, Igor explained how he had become so certain. Snakewoman had bent down to pick something up off the floor, exposing what he described as an almost libellous display of bits.

“I wish I could show you,” he said.

“Well, unless you have a cellphone camera ten years before one is invented, then no, you bloody can’t,” I said.

I was grumpy. Igor had enjoyed the Grand Canyon tour of Snakewoman’s lower geography. I got a polite peck on the cheek.

The myth of the guaranteed first-date favours were, in my experience, not entirely reliable.

And yet I made a mental note to arrange a second date.

Because apparently my brain learns nothing.

The Second Date

Snakewoman invited me to go snake-hunting on Sunday. No other option.I could either see her again on Sunday, or not see her again.

I wanted to see those legs again.

So I agreed.

Igor refused to come, but he did buy me a book titled Common Eastern Cape Snakes and How to Treat Their Bites.

“Are you scared of a snake bite,” he asked, “or a Snakewoman bite? Did you see the size of her incisors? She could suck a tennis ball through a tennis racket”

“Why would anyone want to suck a tennis ball through a tennis racket?” I asked.

Igor ignored me, which was one of his more useful gifts.

“Anyway, one man’s oyster is another man’s mucous” I said sagely to Igor.

“We have walked this road before”, he said. “I give it one more date. You will just get distracted by someone or something else”

“No”, I wailed through gnashed teeth, “this could be the one”

It wasn’t.

Which is why I said “So there I was”.

I did say that. Right at the beginning, when I thought that I knew where I was going with this story. Go and look.

“Anyway, one man’s oyster is another man’s mucous” I said sagely to Igor.

On a Sunday.
In bush near the freeway.
Rolling rocks around like a man searching for answers in the wrong place.

Just me and the legs.

We found no snakes.
Not one.

The entire dangerous-hobby premise collapsed, and with it the only thing making the date remotely interesting.

Snakewoman had dressed practically this time, which felt deeply unkind.

The conversation failed in that overly polite way conversations fail when you have nothing in common except the mutual desire not to be alone. By then, we no longer even shared that.

There was still no tattoo.

And I felt something quietly useful click into place.

Not romance.
Not certainty.
Something better.

The Useful Thing: Knowing What You Don’t Know

I once read that known unknowns are infinitely more valuable than unknown unknowns.

This is the trap on first dates, in business, in friendships, in life:

We think we need to know everything.
If they’re the one.
If they’ll wreck our life.
If they’ll save it.

The real skill Knowing what you don’t know. And making peace with that.

We think that if we gather enough data, the universe will hand us a guarantee.

But you never have enough information.

You don’t even have enough information about yourself.

You have patterns.
Biases.
Old injuries dressed up as preferences.

You have red flags, and the equal and opposite problem, the flags you refuse to see because the legs arrived.

And the real skill, the one nobody teaches properly, is not “open your heart” or “manifest your soulmate”.

The real skill Knowing what you don’t know. And making peace with that.

Because sometimes the only thing you discover on a first date is:

Where the tattoo isn’t,
Where the snakes aren’t,
and where you shouldn’t go again.

Which, if you think about it, is already progress.

The Close

“Why did you go out with her again?” Igor asked later. “You strike me as an intellectual. The sort who needs good conversation. Not just a leg, man.”

He had a point.

Why did I go out with a knife-wielding quasi-snake-catching woman with a tattoo in a wretchedly mysterious location?

But we never found the tattoo.
We never found a snake.
We never found enough conversation to justify the walking.

Because I thought certainty lived one date ahead.
Because I wanted the universe to answer me in a clean sentence.
Because I wanted to know everything. And I really wanted to meet my one true love.

But we never found the tattoo.
We never found a snake.
We never found enough conversation to justify the walking.

And I didn't find my one true love

I only found where it wasn’t.

And sometimes that just has to be enough.

Written By Miles Harrop

I write about the mess, the absurdity, and the dark comedy of being human.

I live in South Africa, talk to a plant called Mr. Head, and have survived everything I've written about so far. So far.