- I made them feel like they were the only person in the room.
- I took care of myself.
- I embraced quiet confidence.
- I remembered things.
- I wrote. And I made.
- I gave them enough space.
- I didn’t kiss and tell.
Chapter 34: The Secretary with the Silver Bracelet (Internship)
https://freeimage.host/i/FbdU26b
(AI-generated image of Elise)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
Every man has at least one mistake that becomes a lifelong lesson.
This was one of mine.
⸻
Her name was Elise.
She was the kind of woman who made you forget you were just an intern.
Slim figure, graceful gait, eyes that held stories. Always in a fitted blouse, neutral tones, no-nonsense skirt suits from OG or Metro, and always that silver bracelet, tight around her wrist like a cuff she’d chosen to keep.
She worked as the secretary to Mr. Han, the divisional head: loud, self-important, loved to laugh at his own jokes. She was his opposite: understated, efficient, and somehow magnetic in her restraint.
I never planned to cross that line.
But lust doesn’t care for planning.
⸻
It began in the pantry, at 9:15 p.m., me reheating fried rice, her microwaving fish soup in a plastic container. The cloying scent mixed with the faint bitterness of burnt coffee grounds and the hum of the fluorescent lights.
“You’re still here?” I asked.
She glanced at me with a tired smirk. “Someone’s got to keep the company from falling apart.”
That night, we spoke for real, no office gloss. She shared about her sons, her long MRT rides from Jurong West, her silent husband. I talked about wanting to run away from everything: the corporate future that had already been decided for me.
She laughed softly. “You boys always think the world owes you something.”
The next morning, she placed a 3-in-1 kopi sachet on my desk. I didn’t look up, just smiled.
Then came the notes, Post-its with jokes, her handwriting elegant and confident.
⸻
Then, one evening, I found her waiting in the storeroom. No words. Just heat.
It was clumsy, urgent… her fingers cold from aircon, my hands trembling with adrenaline and guilt. Her back pressed against the shelf of lever-arch files, blouse unbuttoned just enough, her breath hot against my neck.
By the time we stopped, my tie was on the floor and her bra was in her handbag.
The floodgates had opened.
We became a secret orbit: messages scribbled on backdated invoices, brief touches by the copier, glances held too long across the meeting room. Her perfume lingered on my jacket after shared cab rides to Bukit Batok, where she lived.
Then, one Friday, she invited me up.
⸻
Her flat was silent. The fish tank bubbled gently. School bags lay by the shoe rack. “My boys are with their grandma,” she said, locking the door behind her. “And he’s… somewhere else.”
She led me to the living room mat, with no pretense.
Her kisses were slow at first, searching, unsure, then
hungry
, as though she was swallowing the years of being unwanted. I undressed her carefully. The silver bracelet stayed on.
We made love in the dim light, the fan turning lazily above. Her body was warm, scented with rose perfume and citrus shampoo. She moaned softly, burying her face in the cushion, legs curling around me, fingers digging into my lower back.
Later, she lay on her side, the blanket pulled halfway up her bare hip.
“You’re dangerous,” she whispered. “And you make me feel twenty again.”
I reached for her hand. She didn’t stop me.
We did it again,
slower
, on the carpet, with the windows open.
That night, I forgot she was married.
She forgot too.
⸻
But Singapore’s walls are thin, and gossip slips through the cracks like secondhand smoke.
Monday morning, Mr. Han called me in. His office smelled of medicated oil and freshly printed memos.
“I’ll say this once,” he said. “
Don’t shit where you eat.
”
The words hit harder than if he’d shouted.
He didn’t mention Elise by name. He didn’t need to.
“People are watching,” he added. “And I can’t protect you from your own
stupidity
.”
There was no HR follow-up. No memo.
Just a look that told me I had crossed a line no one spoke about, but everyone knew.
Elise avoided me after that… professional, cold.
We never spoke alone again.
I finished the internship with a quiet bow. No farewell lunch. No Polaroids for the noticeboard. Just an MRT ride home, crushed between strangers and my own regrets.
I’ve had many lovers since. Some, I remember clearly. Others, not so much.
But Elise?
I remember her bracelet. The way she said my name. The softness in her voice when the world wasn’t watching.
And I remember Mr. Han’s words.
Never shit where you eat.
Even if it’s the pantry.
Even if she’s lonely.
Even if you think you’re different.
Some fires burn too close to home.
And not every spark is worth the heat.
⸻
[End of Chapter 34]
Mirror Site:
Note from Author
Writing this chapter hits like a slow burn.
Elise was like an office comet… passing once, burning bright, leaving a trail you can’t forget. But play with a comet, and sometimes the meteor hits your career.
Reminds me of that Astronomer CEO who thought he was reaching for the stars, ended up caught with his Head of HR at a Coldplay concert. The music was sweet, but the headlines were louder.
Whether it’s pantry or penthouse, Bukit Batok or boardroom, the rule is the same: never mix your bread and kaya in the same tin. Some sparks warm you; some sparks burn the whole house down.
Admire the moon if you must, but don’t build a ladder from your desk to her bedroom. When the lights come on, you don’t want to be the encore everyone remembers for the wrong reasons.
Author’s note on internship
Internship wasn’t just coffee runs and PowerPoint slides; it was a crash course in navigating temptation when the stakes were more than just a bruised ego. If school was practice, the workplace was the real pitch: same moves, but on a tighter field, with referees who didn’t blow whistles, just raised eyebrows.
Every corridor glance could be harmless… or an opening. Every pantry chat, a harmless laugh… or a loaded one. And every after-hours drink, a coin toss between “
fun memory
” and “
career suicide
.” Elise was proof that sometimes the most dangerous fires are the ones burning right under the fluorescent lights.
You learn fast: beauty doesn’t guarantee kindness, attraction doesn’t guarantee intimacy, and proximity can make fools out of even the cautious. The rule Mr. Han threw at me is indeed the golden rule (
never shit where you eat
) and I no longer feel the need to ever test it. There are enough roads to travel, enough sparks to chase, without setting fire to the floor you stand on. This applies not just to professional life but personal life as well… don’t fuck your in-laws or friends’ partners… as well as your own maid for goodness sake!
At this point, the Casanova isn’t slowing down; but he’s playing smarter. Desire still moves the game forward, but now the thrill comes with the discipline to walk away when the cost is too high. Some lessons you keep for life, especially when they’re learned under fluorescent lights.
Chapter 35: Her Last Month in the Office (First Full-Time Job)
https://freeimage.host/i/Fm1oL92
(AI-generated image of Andrea)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
I started my first full-time job with the memory of Mr. Han’s warning etched into my spine:
“
Don’t shit where you eat.
”
And henceforth, I never did.
Not that there weren’t chances: Singapore in the mid nineties was full of hazy lines and long hours.
There were D&Ds at Neptune, karaoke at K Box, endless office cake celebrations.
There were suggestive jokes over mee siam, lingering handshakes after presentations, and the occasional overfamiliar back-pat from someone in HR after too many rounds of Chivas at a team dinner.
But in the office, I kept my boundaries.
Until her… you’ll see why.
Andrea.
Same age as me, or maybe a year older. She had started her career right after graduating from one of the well-known local university business schools. I, on the other hand, had to finish NS and was two years behind on the corporate clock.
She didn’t act superior. She didn’t need to.
Her presence did the work.
Andrea had grace, the kind of quiet, sharpened grace that came from constantly being underestimated and overdelivering.
Blouses in pastel shades, heels that were just high enough, hair always pulled back in a no-nonsense bun.
Not flashy. Not flirtatious. But undeniably magnetic.
We only crossed paths during inter-departmental meetings.
She listened more than she spoke, and when she did speak, people took notes.
When she smiled, rarely, it came like sunlight cracking through the slats of a blind.
Then came the email:
“
Andrea will be leaving the company at the end of the month. She’ll be clearing her leave starting next week. Wishing her all the best in her new role
.”
Just like that, the line disappeared.
She was no longer part of the daily machinery.
She was out of orbit.
And that made everything feel possible.
I caught her in the pantry that afternoon. She was spooning Milo into a red NTUC mug.
“You won’t miss the kopi here,” I said.
She gave a soft smile. “No. But I might miss the accidental conversations.”
That week, we had lunch at a food court near Amara Hotel.
Then dinner. Then coffee at Coffee Club on a quiet Sunday that turned into a long walk through the Botanic Gardens.
She talked about her new role: regional exposure, better pay, demanding bosses.
“I’m tired of playing it safe,” she said. “It’s time to level up.”
I admired that about her, that she didn’t wait for permission to be ambitious.
That Thursday, she came over.
My flat was a modest rental along Tiong Bahru Road: small, walk-up, no aircon. I’d taken it just to be close enough to walk to work. The furniture was spare, the kitchen stocked with instant noodles, and the mattress sat directly on the floor.
She arrived in jeans and a white cotton blouse, hair tied back, a canvas tote slung over her shoulder.
No makeup… yeah, and no pretense.
We talked for a while, about work, the company, and the people we wouldn’t miss.
And then, somewhere between shared laughter and a refill of cheap red wine, the mood suddenly shifted.
I kissed her tenderly.
And she kissed back.
Her touch was firm, not hesitant. She unbuttoned her blouse slowly, deliberately. I traced my hands along the line of her back, feeling the warmth of skin and the weight of the moment.
We made love on the mattress, under the whir of the standing fan. We kissed again, longer this time, our breaths falling into a shared rhythm. Her blouse slipped from her shoulders with an ease that felt like trust, not haste. The scent of her shampoo, something faintly floral, mingled with the sharper tang of red wine between us.
Her skin was warm under my hands, the muscles of her back tensing and relaxing as I traced the curve of her spine. She pressed closer, her weight settling against me in a way that erased the space between our bodies.
The steady whir of the fan above us seemed to slow, the outside world folding away until there was only the softness of her hair against my cheek and the quiet heat building between us.
Every movement was deliberate, like an almost unspoken negotiation, with her gaze searching mine before each shift, my hands answering with a touch. It wasn’t about taking or giving, just meeting in the same place, at the same pace.
After we both climaxed, neither of us moved for a long while. The fan hummed. Our breathing slowed. She rested her head against my arm, eyes half-closed, as though storing the moment somewhere private before it slipped into memory.
It wasn’t frantic. It wasn’t romantic.
It was measured, unrushed, two adults meeting each other with honesty, if only for a night.
She moved with quiet intention, not searching for love, just presence.
We didn’t say much afterwards.
Just lay side by side in the dim light, the ceiling fan turning shadows across the wall.
“This doesn’t have to mean anything,” she said.
“It doesn’t,” I replied, even though part of me hoped it might.
She left just before midnight. No drama. No lingering.
A few days later, I received a page.
“
Just had dinner at 10pm. Already drowning in decks. Welcome to the rest of my life
.”
I called from a payphone near Golden Mile and left a voicemail.
“You’ll survive. You’ve always looked like you knew where you were going.”
She never replied.
And I didn’t follow up.
Andrea showed that not every silence is cruel; some are simply chosen.
She didn’t vanish to punish.
She disappeared into something bigger than both of us:
ambition
.
She was one of my encounters with restraint.
A reminder that even when the path is open, you don’t always walk down it together.
[End of Chapter 35]
Mirror Site:
Chapter 36: The Art of Being Wanted (Singapore, mid-1990s – Reflections)
https://freeimage.host/i/Fpx53pS
(AI-generated image of the logbook)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
By the time I turned twenty-five, I had not yet reached the halfway mark… not even close.
But the number was already high enough to raise eyebrows in any country, across any culture.
Safe to say, it was now double (
or maybe triple
) the number that most men would count in their lifetimes.
What surprised me more was not how many said yes, but how vividly I still remembered most of them.
The girl from the chalet, the twins in their shared dorm, the half-Ukrainian barista with dry humour and razor sharp wit.
I could recall their voices, their scent, the way they smiled in the quiet after everything. Not all the details, of course. But the essence. The mood of the moment.
I hadn’t started out keeping score… it was never about conquest.
But around this time, I’d begun to write things down.
Just initials. Or a day. Or something I learned.
In the back of a grey-covered school exercise book I kept hidden behind my wardrobe, I began scribbling notes:
“X.Y.: met at University class, taught me what it meant to be tender without strings.”
“S.H.: came over after leaving our shared workplace. Showed me how ambition, pride and loneliness sometimes arrive in the same dress.”
“M.T.: my first with someone who had a child.”
I wasn’t writing for anyone.
Not a memoir. Not a trophy book.
I wasn’t even sure why I was doing it.
Maybe it was guilt.
Maybe it was gratitude.
Maybe it was a slow, unconscious preparation for what this book would eventually become.
I didn’t know then that I’d ever write it.
But I think some part of me always suspected that these moments,
messy, beautiful, fleeting
, would need a place to live.
⸻
And so I began reflecting.
What was it that drew women in, despite me being far from the most handsome or accomplished man in any room?
Here’s what I’ve come to understand, not as bragging, but as a kind of ethnography.
An internal audit of my younger self.
⸻
Not because I said so.
But because I believed it in the moment.
When we were together, whether for a night or a season, they had my
full attention
.
And people feel that.
⸻
Around 24, mid-way in University, I got serious.
Stopped smoking, even casually. Morning jogs. Push-ups. Less prata, more tofu and eggs. I even started doing face masks, secretly, at first.
I didn’t look like a model.
But I looked like someone who gave a damn about his own body and mind. That mattered more than I thought.
⸻
I didn’t flirt loudly. Didn’t crack cheesy pickup lines.
But I made steady eye contact. Let silences linger. Laughed when I meant it.
Confidence without neediness, that was the sweet spot.
The kind that made people lean in, not pull away.
⸻
Not just their birthdays or favorite songs; though I tried.
But how they liked their kopi. What they were afraid of. Which part of their life they didn’t talk about unless prompted gently.
That kind of remembering made them feel real.
And seen.
⸻
This was the 1990s… no smartphones, no social media.
I wrote letters. Made cassette mixtapes.
Left folded notes in library books.
It was effort.
Effort was
irresistible
.
⸻
I didn’t chased deliberately (
not at this stage
).
I wouldn’t called twice if the first one wasn’t returned, as I wasn’t that needy.
It wasn’t arrogance. It was clarity, that there was more than enough fish in the ocean.
I didn’t want to be seen as a burden.
And somehow, that made them come back more often than not.
⸻
Not once. Not ever.
The world can be small.
Loose lips close doors.
Respect opens legs, hearts, memories.
Sometimes all three.
⸻
I never called it the
“Casanova strategy”
.
It was just…
me
. Tuned. Attuned.
Adjusted by years of trial and error, of heartbreaks and heavy silences, of pleasure laced with consequence.
The funny thing?
All of this, everything I learned, everything I remembered, everything I recorded, sat quietly in a notebook behind a wardrobe in a rented flat near my office.
I paid $500 a month for that one-bedroom walk-up.
No air-con, no microwave. Just a desk, a fan, a mattress, and the smell of old wood.
It was enough.
And in that tiny room, more than once, I lay back with a woman sleeping beside me, and thought:
One day,
this will all mean something
.
I just didn’t know when.
Until now.
⸻
[End of Chapter 36]
Mirror Site:
Author’s note on S-Line:
If you’ve not heard of it yet, S-Line is a recent Korean series where people suddenly develop glowing red lines above their heads that connect them to everyone they’ve ever slept with. These “S-Lines” expose entire sexual histories in public, turning relationships, reputations, and society upside down. More on S-Line here:
https://en.wikipedia.org/wiki/S_Line_(TV_series)
)
If that ever happened in real life… The Casanova of Singapore would be absolute chaos to watch.
Picture the Casanova strolling down Orchard Road with so many glowing threads shooting off in every direction, the skyline would look like it’s been decorated for Chinese New Year.
Chapter 37: The Sisters in Everything but Blood (Singapore & Vietnam, mid nineties – Work Hard, Party Harder)
https://freeimage.host/i/Fy6cVWl
(AI-generated image of Thao)
https://freeimage.host/i/Fy617fV
(AI-generated image of Minh)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
There are nights you plan, and nights you survive.
This was one of the latter.
I had just closed a brutal month at work in Singapore, back-to-back presentations, a client in Hong Kong threatening to jump ship, and enough kopi-O kosong to pickle my stomach lining.
I needed release.
So I booked a flight to Ho Chi Minh City. Cheap, fast, and unfamiliar enough to feel like escape.
It was my second trip to Vietnam that year. The first was for a regional audit. This time, there was no work involved.
I checked into a modest hotel in District 1. Wore my tightest black shirt. Met up with a few other regional colleagues.
And we dived into the city’s neon-lit nightlife, meandered into sticky-floored clubs, heard disco remixes, drank bad vodka, and smelled that scent in the air: a mix of Tiger Balm, motorbike exhaust, and sweat-laced perfume.
That’s where I met Thao and Minh.
Two Vietnamese girls in their early twenties.
Not sisters by blood, but unmistakably close.
They stood out even in the pulsing crowd.
Thao was striking, with porcelain skin with the faintest flush on her cheeks, long black hair pinned into a lazy twist, and an oval face framed by a silk choker.
She had an aloof poise. Slim build, narrow shoulders, and collarbones that caught the light each time she leaned in.
Her voice was low and unhurried, almost amused at the world.
Minh, on the other hand, radiated energy.
Shorter than Thao, rounder in the cheeks, with mischievous eyes that danced when she smiled.
Her skin was the warm golden shade of the Mekong sun, and her figure, petite but curvy, filled her pastel qipao-style dress in all the right places.
She laughed easily, tilted her head when she listened, and smelled like lychee, baby powder, and something faintly floral.
I spoke to Thao first.
She wasn’t flirtatious… just calmly aware of her own allure.
She looked at me like she’d already decided how the night would end.
And so it did.
A few hours later, she was in my hotel room, bare-shouldered, lighting a French cigarette near the open window.
We didn’t talk much.
Her dress slid off easily, a whisper of silk on skin.
She was all sharp angles and soft sighs, arching her back with deliberate control, her fingers barely touching me except when she wanted to adjust our rhythm.
It wasn’t tender. It wasn’t passionate.
It was functional, measured, just this side of clinical.
Afterwards, she sat up, wrapped in the thin blanket, and looked down at me.
“Hmm,” she said with a small smirk and gesturing at my manhood. “Before… so big. Now… so small.”
Then she laughed, not cruelly, but not kindly either.
I didn’t laugh.
Not because I was offended.
But because even casual intimacy deserves tact.
And hers had been precise but detached, like solving a puzzle without caring about the picture.
She left with a polite nod.
No kiss. No trace.
An hour passed.
Then came the knock.
Minh.
Same dress. Slightly smudged eyeliner. A light sheen on her collarbone from the humid night.
“I left Thao,” she said. “You still awake?”
I was.
I let her in.
This time, it felt different.
We sat on the bed and talked for almost an hour. She was studying accounting, she said. Missed her cat in Hanoi. Loved French films but hated kissing in public.
She confessed her ex had cheated, and she wasn’t used to men being kind.
When we finally undressed, it was slow, not from awkwardness, but a kind of unspoken gratitude.
Her body was soft and warm, curving into mine with a kind of gentle urgency.
She whispered in Vietnamese sometimes… I didn’t understand the words, but I understood the tone.
When she came, her legs tightened around my waist, fingers digging lightly into my shoulders, eyes wide and wet with something between release and relief.
Afterwards, she curled into my side.
Skin against skin. No tension.
Just warmth.
“You want me to stay?” she asked softly, her hand resting on my chest.
I nodded.
She did.
We woke up past noon.
Ordered pho.
Laughed over bad English translations on the menu.
She kissed me once more before leaving, slow, on the cheek, almost platonic.
I never saw either of them again.
But I still think about them sometimes, not in the way one brags about a wild weekend, but in the way you remember a turning point.
That night made me realise something I hadn’t put words to until then.
I had always found myself drawn to the elegance of Vietnamese women… their quiet grace, delicate movement, and the subtle contrast between modesty and magnetism.
It wasn’t better than Thai or Malay or Singaporean Chinese women… just different. A personal rhythm.
And, just as honestly, while I had many close Indian friends, who are intelligent, loyal, and strong, I had never felt a sexual pull in that direction.
It wasn’t ideology. It wasn’t aversion.
It just… wasn’t there.
Sexuality doesn’t follow reason.
It follows scent. Energy. Timing. The way someone holds your gaze across a noisy room.
That trip taught me that two women from the same place, who call each other sister, can still make you feel entirely different things.
And that sometimes, what you remember most from a long night isn’t the sex…
But the silence that follows it.
⸻
[End of Chapter 37]
Mirror Site:
https://archiveofourown.org/works/68...ters/180398256
Chapter 38: The Rule of Asking Twice (Young, Legal, and Trouble)
https://freeimage.host/i/K9NMRHX
(AI-generated image of Clarissa)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
There are thrills, and then there are aftershocks.
Clarissa was the kind that came with both.
It was the mid-nineties.
I was in my mid-20s, already climbing the corporate ladder, tie always slightly loosened, pager clipped to my belt, and just enough in my POSB account to cover supper at Newton and the occasional splurge on an actual dinner date.
Clarissa had just graduated from junior college,
eighteen
, which I found out much later from her, with the clarity and confidence of someone eager to break out of uniformed rules and curfews.
We met at a friend’s rooftop BBQ in Bukit Timah, the kind of party where the beers were warm, the chicken wings overcooked, and the playlist alternated between Boyz II Men and Mambo Jambo hits from Zouk.
She was petite, bright-eyed, all skinny jeans and a crop top with a cartoon print.
Baby fat still lingered on her cheeks, but her words were sharp, flirtatious, layered with the recklessness of someone discovering the full range of her magnetism for the first time.
“You’re how old?” she asked, eyes wide. “Wah lao, you look like 23… max!”
“I’ll take that as a compliment,” I smiled.
“No, seriously. I thought you were someone’s older brother. Didn’t expect you to be… fun.”
We drank.
Talked.
Laughed a little too much.
We exchanged beeper numbers.
And when I returned home that night, there was already a message waiting… “
Still awake? That BBQ chicken was tragic. You weren’t.
”
We met a few more times, bubble tea near Bugis, a matinee at Lido, a long walk around Marina Bay before it became what it is today.
Then one night, it happened.
She came over to my rented flat, that same cramped, no-frills place near Tiong Bahru.
She took off her sneakers, curled her legs on the couch, and started flipping through my new collection of CDs.
I poured drinks. We played
The Cranberries
.
And somewhere between laughter and her hand resting on my thigh, our lips met.
She kissed with a beginner’s hunger: unsure, curious, a little too fast.
But her touch was eager, her breath warm against my neck as she undressed, fumbling slightly with the buttons of her blouse. Her body was soft, almost fragile, and she made small, delighted sounds each time I traced a new spot.
We moved to the mattress on the floor.
She straddled me shyly, her eyes closed as I guided her gently, making sure she was comfortable every step of the way.
It wasn’t wild. It was sweet, charged not by experience, but by the novelty of discovery.
Afterwards, she lay beside me, humming softly, her fingers absentmindedly tracing my arm.
“I can’t believe I’m doing this,” she whispered. “My friends would flip.”
I smiled. “They don’t need to know.”
She giggled.
At that moment, it felt harmless.
Beautiful, even.
Until three weeks later, back in the office, a scandal broke.
A
well-publicised sex-for-money case
, with a dozen high-flying men caught with an escort. The twist?
She was underage.
The headlines were everywhere.
Straits Times, Today, even tabloids like
The New Paper
.
Names were redacted. Reputations weren’t.
I read every article, my palms sweating.
Clarissa hadn’t been underage. I had confirmed later with her.
She wasn’t an escort.
There was no exchange of money.
Everything had been legal and consensual.
But the anxiety crept in nonetheless.
Because I realised that before we made love, I hadn’t asked her age with intent.
I had
assumed
she was legal.
Guessed based on appearance, behaviour, confidence.
And in a country like Singapore, where the legal age of consent is 16, but where the consequences of crossing that line, even by accident, can be life-destroying, assumption isn’t enough.
That night, alone in bed, I promised myself:
I would never make that mistake again.
From then on, I developed a subtle habit when making a move on girls: of
asking twice
, discreetly, cleverly, without killing the mood.
“So your classmates are now in NS?”
“A-levels… was that still with those brown answer sheets?”
“Eh, don’t tell me you were born after the Macarena.”
It sounds silly.
But it worked.
Clarissa and I drifted naturally after that: she started university, I took on more regional projects.
There was no fallout. No regret.
But also, no longing to repeat.
She had been light, playful, legal, but dangerously close to a line I never wanted to test again.
And in the years that followed, I gave younger women more pause.
Not because they weren’t attractive.
But because
a few digits too few
could mean the end of everything I’d built professionally.
So here’s what I want to say to any man reading this:
Don’t flirt with the line. Don’t joke about it. Don’t risk it.
Ask. And if there’s even the slightest doubt, just walk away.
Because no thrill, no kiss, no body, however tempting, is worth waking up to a courtroom headline with your name in it.
Be clever. Be careful. Be kind.
Especially to yourself.
⸻
[End of Chapter 38]
Mirror Site:
The Casanova of Singapore — Contents Page
Due to forum limitations, I am unable to edit my older posts anymore and therefore cannot revise the contents page. This will therefore be the new contents page for links to the chapters, until I cannot and a subsequent one will be created.
Chapter 1 -
https://sbf.net.nz/showpo...90&postcount=2
Chapter 2 -
https://sbf.net.nz/showpo...03&postcount=3
Chapter 3 -
https://sbf.net.nz/showpo...12&postcount=4
Chapter 4 -
https://sbf.net.nz/showpo...27&postcount=5
Chapter 5 -
https://sbf.net.nz/showpo...33&postcount=6
Chapter 6 -
https://sbf.net.nz/showpo...4&postcount=11
Chapter 7 -
https://sbf.net.nz/showpo...6&postcount=12
Chapter 8 -
https://sbf.net.nz/showpo...5&postcount=13
Chapter 9 -
https://sbf.net.nz/showpo...0&postcount=14
Chapter 10 -
https://sbf.net.nz/showpo...6&postcount=15
Chapter 11 -
https://sbf.net.nz/showpo...6&postcount=24
Chapter 12 -
https://sbf.net.nz/showpo...2&postcount=25
Chapter 13 -
https://sbf.net.nz/showpo...1&postcount=26
Chapter 14 -
https://sbf.net.nz/showpo...4&postcount=27
Chapter 15 -
https://sbf.net.nz/showpo...8&postcount=28
Chapter 16 -
https://sbf.net.nz/showpo...5&postcount=38
Chapter 17 -
https://sbf.net.nz/showpo...3&postcount=39
Chapter 18 -
https://sbf.net.nz/showpo...8&postcount=40
Chapter 19 -
https://sbf.net.nz/showpo...5&postcount=49
Chapter 20 -
https://sbf.net.nz/showpo...6&postcount=50
Chapter 21 -
https://sbf.net.nz/showpo...5&postcount=51
Chapter 22 -
https://sbf.net.nz/showpo...2&postcount=53
Chapter 23 -
https://sbf.net.nz/showpo...2&postcount=54
Chapter 24 -
https://sbf.net.nz/showpo...8&postcount=55
Chapter 25 -
https://sbf.net.nz/showpo...8&postcount=58
Chapter 26 -
https://sbf.net.nz/showpo...1&postcount=60
Chapter 27 -
https://sbf.net.nz/showpo...9&postcount=63
Chapter 28 -
https://sbf.net.nz/showpo...7&postcount=67
Chapter 29 -
https://sbf.net.nz/showpo...7&postcount=69
Chapter 30 -
https://sbf.net.nz/showpo...1&postcount=70
Chapter 31 -
https://sbf.net.nz/showpo...0&postcount=74
Chapter 32 -
https://sbf.net.nz/showpo...1&postcount=77
Chapter 33 -
https://sbf.net.nz/showpo...0&postcount=78
Chapter 34 -
https://sbf.net.nz/showpo...4&postcount=82
Chapter 35 -
https://sbf.net.nz/showpo...8&postcount=88
Chapter 36 -
https://sbf.net.nz/showpo...1&postcount=89
Chapter 37 -
https://sbf.net.nz/showpo...1&postcount=91
Chapter 38 -
https://sbf.net.nz/showpo...3&postcount=92
Chapter 39 -
https://sbf.net.nz/showpo...0&postcount=94
Chapter 40 -
https://sbf.net.nz/showpo...8&postcount=99
Chapter 41 -
https://sbf.net.nz/showpo...&postcount=101
Chapter 42 -
https://sbf.net.nz/showpo...&postcount=102
Chapter 43 -
https://sbf.net.nz/showpo...&postcount=103
Chapter 44 -
https://sbf.net.nz/showpo...&postcount=110
Chapter 45 -
https://sbf.net.nz/showpo...&postcount=111
Chapter 46 -
https://sbf.net.nz/showpo...&postcount=112
Chapter 47 -
https://sbf.net.nz/showpo...&postcount=116
Chapter 48 -
https://sbf.net.nz/showpost.php?...&postcount=117
Chapter 49 -
https://sbf.net.nz/showpo...&postcount=118
Chapter 50 -
https://sbf.net.nz/showpo...&postcount=119
Chapter 51 -
https://sbf.net.nz/showpo...&postcount=121
Chapter 52 -
https://sbf.net.nz/showpo...&postcount=123
Chapter 53 -
Chapter 54 -
Chapter 55 -
Chapter 56 -
Chapter 57 -
Chapter 58 -
Chapter 59 -
Chapter 60 -
Chapter 61 -
Chapter 62 -
Chapter 63 -
Chapter 64 -
Chapter 65 -
Chapter 66 -
Chapter 67 -
Chapter 68 -
Chapter 69 -
Chapter 70 -
Chapter 71 -
Chapter 72 -
Chapter 73 -
Chapter 74 -
Chapter 75 -
Chapter 76 -
Chapter 77 -
Chapter 78 -
Chapter 79 -
Chapter 80 -
Chapter 81 -
Chapter 82 -
Chapter 83 -
Chapter 84 -
Chapter 85 -
Chapter 86 -
Chapter 87 -
Chapter 88 -
Chapter 89 -
Chapter 90 -
Chapter 91 -
Chapter 92 -
Chapter 93 -
Chapter 94 -
Chapter 95 -
Chapter 96 -
Chapter 97 -
Chapter 98 -
Chapter 99 -
Chapter 100 -
Chapter 101 -
Chapter 102 -
Chapter 103 -
Chapter 104 -
Chapter 105 -
Chapter 106 -
Chapter 107 -
Chapter 108 -
Chapter 109 -
Chapter 110 -
Chapter 111 -
Chapter 112 -
Chapter 113 -
Chapter 114 -
Chapter 115 -
Chapter 116 -
Chapter 117 -
Chapter 118 -
Chapter 119 -
Chapter 120 -
Chapter 121 -
Chapter 122 -
Chapter 123 -
Chapter 124 -
Chapter 125 -
Chapter 126 -
Chapter 127 -
Chapter 128 -
Chapter 129 -
Chapter 130 -
Chapter 131 -
Chapter 132 -
Chapter 133 -
Chapter 134 -
Chapter 135 -
Chapter 136 -
Chapter 137 -
Chapter 138 -
Chapter 139 -
Chapter 140 -
Chapter 141 -
Chapter 142 -
Chapter 143 -
Chapter 144 -
Chapter 145 -
Chapter 146 -
Chapter 147 -
Chapter 148 -
Chapter 149 -
Chapter 150 -
Chapter 39: The Woman Who Needed a Different Kind of Love
https://freeimage.host/i/KHYNVg1
(AI-generated image of Elaine)
Disclaimer: All names, characters, and events in this chapter are fictional, although inspired by the lived experiences and memories of the protagonist. Any resemblance to actual persons, living or dead, is purely coincidental. Settings and timelines have been adapted for narrative purposes.
She wasn’t the kind of woman I usually pursued.
No visible tattoos. No clubbing stories. No smoky glances across a bar.
Elaine was a secondary school math teacher, in her late 30s, always in modest floral blouses and calf-length skirts, the kind of woman who wore sensible shoes and carried a canvas tote with worksheets and water bottles inside.
We met at a volunteer event in Bedok, tutoring underprivileged kids.
I was there on a friend’s suggestion, expecting to clock a few hours and leave.
She was there every week, every time, rain or shine.
She had the kind of quiet presence that didn’t chase attention, but settled into you like secondhand perfume.
And over the weeks, we began talking, first about lesson plans, then about HDB resale grants, and eventually… about loneliness.
Elaine had never married.
“Not for lack of suitors,” she said with a dry laugh. “Just none I wanted to marry.”
I believed her.
She was attractive in a reserved, cerebral way: almond-shaped eyes behind square glasses, a graceful posture that came from years of discipline, and a voice that never needed to be loud to be heard.
But she carried something else too… a subtle melancholy, the kind that hides in smiles that hold for half a second too long.
Over teh at the hawker centre one evening, she confessed:
“You know, Lee Kuan Yew once said that women like me, graduate women, especially teachers, would end up alone if we were too fussy. I was barely 20 and already worried I’d prove him right.”
I didn’t know what to say at first.
He had said it, back in the ’80s, lamenting how too many intelligent, educated women weren’t marrying, and how Singapore’s birth rate would collapse if they didn’t.
Elaine chuckled. “He wasn’t wrong, you know. My colleagues… most of them are still single too. It’s hard to meet people when your whole life is school halls, staff rooms, and marking until midnight.”
I nodded. I’d heard it before.
Teachers, especially female teachers, often found it hard to meet people outside their profession.
They were respected, but not necessarily pursued.
Surrounded by students and fellow educators, their world became a well-worn circle.
And yet, Elaine was no spinster.
She was sensual beneath the discipline: observant, self-aware, and full of unspoken heat.
That night, after dinner, we ended up at my flat.
It surprised even me… I hadn’t expected to invite her, and she hadn’t expected to say yes.
But we were adults. And the loneliness in both of us met at a gentle equilibrium.
She undressed slowly, almost ritualistically, folding her blouse and skirt before placing them on a chair.
Her body was soft, lived-in, beautiful in a way untouched by performance or vanity.
I kissed her neck.
She closed her eyes, exhaling lightly, fingers running through my hair like she was rediscovering how to feel.
We made love like people with nothing to prove.
It was slow. Deep. Muted.
Her breathing grew heavier with each motion, her legs wrapping around my waist, her nails dragging softly down my back.
No moans. No theatrics.
Just presence. Just warmth.
Afterwards, she curled into my chest, sighing.
“This doesn’t have to be more,” she said, “but thank you for reminding me that it still matters.”
We continued seeing each other for a while.
Coffee after her CCA duty.
Dinner after my late meetings.
We even went to the Philharmonic once, her treat.
But I sensed she wanted more than I could give.
Not in a demanding way, just in the soft weight of expectation that began to settle into our conversations.
And so, I did something rare.
I introduced her to Daniel, an old friend from university.
Also a teacher, but on a different subject in another school, a couple years older than me but younger than Elaine. Widowed young due to unfortunate circumstances.
He was a patient, kind man, and a good listener.
They hit it off.
She drifted from my life with a thank-you note, handwritten on recycled paper, folded neatly into my mailbox.
I wasn’t sad.
Just quietly proud that I’d been a bridge, not a detour.
Elaine reminded me of a truth I’ve come to believe more strongly with time:
Not every woman you connect with is meant to be yours.
Some are meant to remind you what depth looks like.
And for those who feel stuck in closed-off professions, like teachers, healthcare workers, anyone whose life is wrapped in routine, here’s my advice:
• Volunteer. Step into a space where you’re not defined by your job title.
• Join hobby groups. Literature clubs, hiking meetups, even chess.
• Ask your friends. Let them play matchmaker. You’ll be surprised.
• Talk to strangers. Not in clubs, but in coffee queues, book fairs, community classes.
• Stop assuming everyone you meet needs to be “The One.” Sometimes connection precedes chemistry.
Because love doesn’t always arrive in a classroom.
Sometimes, it waits outside.
⸻
[End of Chapter 39]
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