Love, Rin: My First One Night Stand (Part 1)

It’s no secret that I’m a hopeless romantic. I used to sit in my neighborhood cafe every Sunday morning, scribbling away in my diary while secretly praying the universe would send a tall, dark, handsome stranger over to me. He would begin the conversation by asking if we could share the table, then a cake and eventually our lives. Then we’ll live happily ever after sipping coffees in our quaint Soho cafe every weekend musing over how lucky we are to have found each other.

That still hasn’t happen (yet).

The craziest thing I’ve done for love? I once wrote a 14-page essay to a boy listing all the ways he’d changed my life for the better and how I wished him all the love and joy in the world that he deserves. The crazier part? I wrote it the very same night that he’d dumped me, then I Googled-stalked where his office was, and showed up in a cab the very next morning to hand-deliver it outside his building. Did I win him back with that grand gesture? Unfortunately yes, but that’s another story for another day.

That version of young Rin was both terrifying and impressive for the lengths she used to go to for a semblance of connection. Thankfully for older Rin (and other would-be partners), I’ve mellowed down. Which brings us back to this day – how did this fool for love end up having a body count higher than actual boyfriends? How did I find myself not just advocating for casual sex but teaching a workshop on how to find friends with benefits later this month?

Well it all started with a game of pool, my very first (ex)boyfriend and David Bowie.

It was a cool spring evening in a dive bar in the Lower East Side. My ex and I had broken up six months prior but we were still good friends so I was just hanging out with his usual crew watching them play pool. Then lo and behold, this lanky blonde David Bowie lookalike sauntered over to the table right next to ours and plopped right down with his friend. We locked eyes for a bit and he smiled. Usually, at this point sober Rin would literally freak out and freeze at this beautiful stranger. Then she would shrink herself further in the corner and avoid eye contact the rest of the night. “No way he’s interested in me! He’s too cute and there’s so many prettier girls around!”

Ah but drunk Rin? She’s the fun one. And also the one who’s snarkier and doesn’t have a filter. So I smiled back and figured, ‘Alright, he’s going to come over so I should just stay put.’ Sure enough, in the middle of a loud orchestrated debate between his friend and him, David Bowie turns to me and goes, “So what do you think?”

Fishing lure thrown.

So I smirked and answered, “You want the version you want to hear, or the truth?”

Hook sunk in.

Truth be told, as the words escaped my lips, the half of me who was still semi-sober was appalled at my brashness, and petrified I wouldn’t be able to keep up the cool chick charade. The other half didn’t foresee I was about to follow a random stranger back to his place for the night – especially when my ex-boyfriend and his friends were 5 feet in front of us.

David Bowie laughed and pulled up his chair right next to mine. Clearly this boy was not a newbie. Then the rest of the world kinda melted away as we bantered and flirted into the night. That bit was still romantic – nothing gets me like a good conversationalist who keeps me on my toes. And well, my ex and his friends noticed too as they started nudging each other as they circled around the pool table. I caught my ex’s eye as he raised an eyebrow at me and grinned. I told David Bowie to give me a minute as I walked across to the pool table. My ex whispered in my ear, “I’m going to head off now and give you guys space. Are you good? Or do you want to come with us?” I glanced over at David Bowie as he casually took a chug from his beer and pretended not to notice he’s being given the lookover. A goofy smile plastered itself across my face as I whispered back, “I think I’m going to stay…”

I didn’t know where the night was going but all I knew was this guy made me laugh. I liked him.

When I walked back to David Bowie, he casually gestured at my ex and friends and asked “You’re going off now?”

It was my turn to plop right down next to him. “Nope, I’m all yours.”

It was the first time I saw David Bowie lose his cool veneer for a second as he seemed surprised. It quickly switched back to Mr Smooth – of course I wanted to stay with him. Time to reel it in.

We didn’t stay that long after that and found ourselves outside the bar as drunk happy people streamed past us. David Bowie was smoking a cigarette with a glint in his eyes as he asked “So do you wanna come over to my place?”

I suddenly found myself in the very unfamiliar waltz of “Should I or shouldn’t I?”

Remember how I’d broken up with my ex just 6 months ago?

Technically I’d only slept with 2 people at that point (there was a rebound fling a month after we broke up but the sex was terrible and I never saw him again). But I’ve never imagined myself as someone who would have a One Night Stand, especially when I was starting to sober up in the cold outside. Despite being young, wild and free in New York, the pragmatic Singaporean in me was hissing in my ear, “OMG HE’S GOING TO KILL YOU AND THEY’LL NEVER FIND YOUR BODY BECAUSE NO ONE KNOWS YOU WENT HOME WITH HIM”

I told him the truth, “Mmm.. I don’t know if I should.”I was still being coy but I’m sure he sensed the actual hesitance in my voice. He shrugged coolly and smiled, “Let’s walk until you make up your mind..”

I lived 15 minutes away from the bar so I shrugged back, “Why not?”

As he finished his cigarette and tossed it away, I started to be vividly aware of the little things. How much taller he was next to me. How icy blue his eyes were. The smell of his cologne wafting as he stood next to me. How he sauntered like a cat, weaving in and out while ‘bumping’ into me. The way my heart was beating fast from the thrill. How one corner of his lips curled up first before the other when he laughed.

All this while we’re still chattering away and my inner self was being put on trial.

“Rin, this is a complete stranger. You should have gone back earlier with the guys.”

“Awww… but I like him. He’s nice!”

“He’s too smooth! He’s done this a million times!”

“So what? He picked me tonight! Maybe it’ll be different…”

“Yeah, you’re being too easy… even if he doesn’t kill you, what if you catch something from him?”

“You’re being paranoid, why can’t I have fun too?”

“If he really likes you, he would respect you and want to see you again. Then you know he’s serious.”

“If he really likes me, he’ll see me again even if I did go home with him the first night.”

“This is not you!”

“Maybe that’s why I should… if not now, when?”

“Did you really just use ‘if not now, when’ to justify your horniness??”

That’s when David Bowie stopped me in the streets, pulled my waist towards him and kissed me deeply. He tasted like ice cold menthol with a hint of cigarettes.

Then my inner trial ended. I looked up at him and dreamily smiled, “You win…”

Of course when I went back with him, I didn’t think it’ll be a one night stand. I was imagining this is the origin story of how I met the future father of my kids. How cheeky, how bold – what a wonderful night led by destiny!

Reality-wise? I actually forgot how the sex was that night. Chalk it up to old age or the eventual tally of flings, but I don’t remember anything else about it. Just how peaceful he looked in the morning with his blonde curls against the white pillowcase. And how awkward I felt as I kept my eyes closed, pretending to still be asleep while trying really really hard to hold in a fart. (What can I say? I’m gassy in the mornings…)

It was the first time I spent the night at a stranger’s. I could hear the rest of his housemates stirring to life outside the bedroom. The sounds of the bathroom, the clattering of plates in the kitchen, the hushed voices in the living room. Meanwhile David Bowie was still blissfully asleep right next to me. What does one do next?

And this, dear Reader, is where I’ll leave you for now. So does David Bowie end up staying a ONS, never to be seen again, or does it end up being more? Stay tuned for Part 2.

And now time for the shameless plug, I’m running the updated Friends With Benefits workshop in person at!

Thurs 26 May, 6.30 – 8p.m. SGT

Location: Showroom @ 994 Bendemeer Road

This session is open to all genders

Amidst the perils of dating and relationships, sometimes all you really want is just good old fashion frisky fun. Ever wondered how to have casual sex and still be safe and not catch feelings? Join me for all you need to know to keep it casual, safe and fun (and yes how to find one…)

Some of the topics covered:

• Why casual sex doesn’t mean easy sex

• The difference between ONS, fuck buddies and FWB

• How to keep feelings and sex separate

• How to stay safe and protect yourself

• NEW: Where and how to find one (and what not to say)

Whether you’re trying to find out if casual sex is right for you or already have some experience, you’ll get the essentials to be confident in your hook-ups and get your questions answered in this intimate and informal session. All participants will receive a Sexy Fun Kit goodie bag worth $37! What’s a Sexy Fun Kit? Why everything you would need for a ‘sleepover’ of course (which I wish I had that first night!)

Take 15% OFF with the promo code: SCHORNY15

Have questions about the workshop? Drop me an email and I’ll be happy to answer them!