Dating Older Men In Singapore

*Names were changed to protect identities

In my second year of Junior College, hooking up with guys on Tinder was my hobby to keep my mind off my ex, and relieve A-level stress.

But after meeting an endless string of 20-year-old F-boys got boring, I decided to explore Tinder’s other territory—men who were 40 and above.

Amidst the sad, divorced men desperate for a new wife, and married businessmen looking for a companion, I matched with Dan*.

Dan was 40 years old and had moved to Singapore alone for work. While he wasn’t incredibly charming, he had a self-deprecating humour I liked.

Initially, I couldn’t imagine dating Dan because our 22-year age gap felt weird, and he was old enough to be my father. But when I prepositioned for him to meet me for S$175 an hour, he agreed.

Going on a date with Dan

On our first date, we met at a fancy restaurant in Buona Vista. I wore my most boujee-looking dress, a velvet bodycon number. Still, I felt like Julia Roberts in Pretty Woman; dressing the part but still not fitting in with the upper class.

Also, I was nervous about running into people I knew and what onlookers would think. A young woman having a romantic dinner with a much older man? Scandalous.

But Dan assured me, “It’s normal. Many men like me do this, the people here probably see it all the time.”

As we made small talk over dinner, I noticed how oddly confident I sounded. Usually on first dates, I’d be embarrassingly shy. I’d trip over words and have trouble keeping eye contact.

But with Dan, I played footsie under the table and laughed at his jokes even if they weren’t funny. And in the elevator, I found myself initiating a hot-and-heavy make-out session, which made him murmur, “Do you want to go back to my place?”

We stumbled back to his apartment and I led him to the bed as if I’d done it a million times.

Midway through sex, I had an out-of-body moment. As I saw myself naked in bed with Dan, my mind wandered to the time I lost my virginity. I remembered how I swore to keep sex for someone I loved, and thought, “How the hell did I get here?”

When we were done, we cuddled in bed and talked. When I asked if he planned to settle down, he brushed off my question by saying he’d had plenty of hook-ups, but I was his first ‘hook-er’.

And suddenly, I grimaced. I got out of bed, hopped into the shower and got dressed quickly. Probably realising he’d offended me, Dan left and placed three hours worth of sugar money (S$525) on the kitchen counter.

After a moment of hesitation, I pocketed the money and left.

The train ride home

As I sat in the train home, I thought about Dan and what I’d do with the S$525. I thought about buying new makeup and clothes, or a new DSLR, but spending the money didn’t feel right.

Throughout the course of the evening, I felt an overwhelming sense of pity and guilt about making money off a lonely man. By his kind treatment towards me, I could tell he hadn’t had someone to cherish in a long time.

Then, it dawned on me why I was so offended by Dan’s ‘hooker’ joke.

Somewhere between the deep conversations and bad puns, I forgot we weren’t on a real date. He wasn’t paying for the meal as an act of chivalry, but for my time.

By placing a direct monetary value on my body, I had been essentially prostituting myself, which explained my sense of unease and the uneven power balance between Dan and I.

I felt like I had to ‘perform’ for him, and let him kiss and grope me even if I didn’t want to. Because I felt like I owed him, I agreed to go home with him.

During the hours we spent in bed, I didn’t own my body, Dan did. And it made me feel trapped and aware of how exchanging sex for cash was so unnatural.

Despite initially convincing myself sex didn’t mean anything and knowing it was easy money, I realised I couldn’t do it.

That night, I realised I valued my body too much to put monetary value on it. I still held sex as sacred and decided to never sell my body again.

Being A Sugar Baby

The next time Dan texted me, I told him I’d only meet him to return the money. He declined, and suggested remaining friends instead.

While we still follow each other on Instagram, I can’t imagine being around him again without feeling cheap.

While I acknowledge how some women make a living from exerting their sexual autonomy, I know I can’t do it.

And even if the sugar baby community is growing, I encourage girls to check themselves before they wreck themselves because every choice is always easier said than done.

Till today, the S$525 still sits in my bank account, unable to be spent.

Cover image: Source