The night is not just about singles mingling; it has been structured to spark something deeper.
At 7pm, the lift stops on the 18th floor and doors open to an evening breeze of the 270 rooftop bar. Here, single people step freely into the exciting possibility of finding love or, at the very least, a magical evening.
Everyone is here for a reason—maybe a second chance, a fresh start, or just to see what happens when they stop hiding behind dating apps and social media inboxes in their quest for love.
On this particular evening, the people sit in clusters. Some are seated on lounge chairs, others on the edge of flower slabs, while some are standing around high tables, drinks in hand, as the bursts of laughter and banter lace the soft background music.
At their furthest side is an open bar with waiters busy mixing cocktails to enhance the warmth of the night.
On each person’s chest is a white name tag that breaks the ice without needing a clever opener: ‘Brenda’, ‘Joram’, ‘Alfred’, ‘Njeri’, ‘Kevin’.
Valerie McLaughlin, 37, one of the attendees scans the lively groups around her. It’s her first time at an event like this, and it happened spontaneously.
“A friend sent me an invite to the event, and I was like, sure, why not? I think dating can be very challenging nowadays, with people working so much, and the apps sometimes are not the best. Why not try something different and see if it works,” she says.
The Bolivian native, although she’s quick to say, “We are not too many!” has been living in Kenya for about a year. The dating scene, she admits, is like unfamiliar territory. But here she is, surrounded by new faces, sipping her drink, her name tag in place, ready to see how the night unfolds.
“I came with an open mind. You might, you might not [find a match]. I mean, I could have been doing something else this Thursday evening, but why not?”
It’s also a deeply personal step for Valarie “This is my first ever to be at a matching event. I became single quite recently after being in a long-term relationship that lasted nearly nine years. I guess it is a bit daunting to go back into the dating scene,” she says.
She’s not clinging to expectations, nor is she in fear of the unfamiliar. “We are always kick-starting stuff with strangers. My previous boyfriend, I met him online. They are strangers until they are not,” she laughs.
When asked if she would be open to building something with someone new, even tonight, her answer is quick, “Of course! I’m always open to things when the vibe is right.”
She says she has no children and is open to dating a Kenyan man.
Cohen Omondi, 28, stands a little away from the crowd, but he seems fully immersed in the moment. “I am here to find someone who is a partner. I hope to leave here with either a partner, a friend, or just an acquaintance. ”
This is his first time at a singles event. He has been single for six months after ending a long-term relationship that had stretched over seven years.
Cohen came to the event solo, no wingman, and no friend for backup, just him, and the lessons of a previous love and the courage to start over.
“From my experience with the time that I’ve been single, the most challenging part is adjusting to that comfort level of your previous partner, it becomes different with this new person. You have to rediscover yourself to be able to put yourself out there after a long time,” he says and adds,
“I feel that I am ready to do this dating thing again.”
Debrah Phoebe, 26 first shies off from getting interviewed but soon agrees to indulge me a bit. She has equal parts of curiosity and detachment, but she’s here for a reason, just like the others. “For someone coming from the dating apps to find love, my expectations are very low,” she says.
Still, she showed up. Her goal? Keep it real, and keep it interesting. “I’m open to new meets, I just want to have a good time, meet interesting people who, at least I can verify are real, then whether it works or not, it’s still fine.”
Her view of dating is unfiltered. She says she has never been in a fully committed relationship, but she’s not letting that stop her from exploring what’s out there.
“I am open to kick-start things with a stranger,” she adds.
Algorithm of eye contact
The night is not just about singles mingling; it has been structured to spark something deeper.
Debra Olum during an interview at 270° Rooftop in Nairobi on June 12, 2025.
The orchestrator of this event is Debra Olum, and she explains why Thursday Singles nights are gaining momentum in Nairobi.
“ThursdayTM is a global company that hosts singles events around the world. It’s headquartered in London and they have people in different cities around the world who host singles events. It makes dating fun and offers a real-life experience away from the apps,” she says.
For this particular night, she says they have partnered with Matchbox, a matchmaking software that brings tech and chemistry together. On arrival, attendees scan a QR code, fill out a 16-question multiple-choice survey, and then the mingling begins.
“It’s very quick, a multiple-choice situation. Then you proceed to start the mingle,” Ms Olum explains.
As the night wears on, the matching intensifies.
“Once almost every person has interacted, we create a countdown system. You will get one clue where you’ll be grouped into a smaller group. Then comes a second clue where you get into an even smaller group. Afterwards, there will be a 10-second countdown for your match to be revealed, according to the similar feedback we got from the questions.”
The match questions, she adds, are deeply personal.
“They are more value-based; the whole idea is just to match you with someone who is the most compatible. But also, if you get your match and that is not who you feel you are compatible with, you can talk to anyone at the event, it’s not strict.”
There are also printed icebreaker questions on the tables, which Ms Olum explains are perfect for cutting through the awkward.
“There are a bunch of little icebreaker questions all over the tables that usually help get the conversations started and break the initial awkwardness.”
While most attendees are between 25 and 40, Ms Olum says the demand from older age groups has been on the rise.
