As I made my way down the newly minted Winnie Mandela Drive en route to my first ever speed-dating event, the butterflies in my stomach lunged. In those 25 minutes, Ubering from the Parks to Lonehill, the past few years hit me all at once.
How the hell did I get here?
Three years post-separation and divorce, choosing to put myself out there again was a sign of more peace in my life. Still, it felt surreal.
I’m 45 years old, with two wonderful boys, co-parenting working well, and I finally felt that it was the right time to embrace Curated Connection’s 35+ speed-dating event.
Curated Connections is an organisation on a mission to get people off their apps and into real-life experiences – from hikes to padel, drinks mixers to masked balls. And so, in my aloneness, I was heading across the highveld to Lonehill in search of connection, maybe even the hope of meeting someone to journey with.
This brave new world I found myself in – dating apps, swipes, ghosting, gaslighting, narcissism, polyamory, attachment styles, love languages, red and green flags – none of this existed when I got married. It’s a jungle out there.
A jungle in which I was initially eaten alive. “Emma” seemed lovely and chatty. Her first date suggestion? A VIP chef evening. Sounded excellent. Then a perfectly designed ticket arrived in my inbox, and once the EFT was done, she vanished. My phone call to the Houghton Hotel returned a polite: “There is no such event here, sir.” I could only laugh – at the precision of the scam and the numbing sense of being so utterly duped. Naturally, I took myself for a soulful, reflective nine holes of golf. Who needs a VIP chef experience anyway?
The Uber pulled up to the Lonehill restaurant. My adrenaline was through the roof, even after ChatGPT told me: “You’ve got this Nick, and remember – everyone is in the same boat.” My AI comrade had even offered conversation starters and insisted I avoid asking people what they do for a living (apparently a boring and status-loaded question). Instead, I was armed with: “Where do you love to travel?”
Sixteen tables. Sixteen women. Four minutes per conversation. A form to fill in: tick who you’d like to see again, and if the feeling’s mutual, you’ll get matched. Some four-minute dates felt incredibly long. Others, disappointingly short. But I made it through, appropriately tipsy and mentally exhausted; this is big stuff for an ambivert.
The saving grace? A post-event crew gathered at the bar. I toyed with heading home but, of course, I joined the train.
And the train picked up speed. Ten of us ended up at Mr Pants, a charming and eclectic wine bar in Blairgowrie. It turned into a full-blown after-party. Sharing stories of singledom, dating apps, breakups and the wild terrain of modern love. In a moment of inspired madness, I declared: “I have an idea – everyone just come back to my house!”
Not my wisest move.
A Joburg dating circus
At about 11pm on a Wednesday night, my quiet neighbourhood became ground zero for the Joburg dating circus. Music blaring, respectable neighbours likely raising eyebrows: “Wasn’t Nick the sensible one?” My best bottles of wine nonchalantly pulled from the rack. Couples making out on couches. Even my dog Rosie, a gentle collie mix from Woodrock, looked at me like, “What the hell, man?”
By 2.30am, I was gently ushering everyone out.
Somehow, I made it to the office the next morning. Corporate Nick, senior exec, clinging to coffee and online meetings, wondering: what is my life right now?
It was my WhatsApp divorce support group, lovingly titled The Freedom Club, that helped ground me again. Emily in Cape Town, Laurian in London – two fellow travellers navigating the post-divorce landscape. Their voice notes were perfect. Wise, soothing, funny. Reminding me that being human matters. That our messy, imperfect choices are often the very proof that we’re alive.
And maybe, just maybe, inviting ten strangers home on a Wednesday night was exactly what needed to happen.
Rinse and repeat? No, thank you.
But vulnerably throwing myself back out there again? Hell yes.
This story is courtesy of Nick Dunlop (not his real name). He is a Joburg corporate type whose honesty about being back on the dating scene is refreshing, and frankly hilarious.
Top image: Rawpixel / Currency collage.
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Witty and pacy. Very real.
Well written and well liven, thank you Mr Dunlop for your story.