Nairobi Singles Ditch Dating Apps for Rooftop Matchmaking Nights

Nairobi's social scene is witnessing a shift as singles are increasingly turning to in-person dating events, shunning the perceived superficiality of online dating apps. 

Thursday nights at the 270 rooftop bar in Nairobi have become a focal point for this movement, where urban professionals gather to seek authentic connections beyond curated online personas. The events are orchestrated by ThursdayTM, a London-based company that specialises in organising singles nights in metropolitan areas globally. The Nairobi initiative resonates particularly well with individuals disillusioned by the mechanics of app-based matchmaking. 

In collaboration with Matchbox, a matchmaking software company, ThursdayTM blends technology and interpersonal interaction at these gatherings.

Upon arrival, guests receive name tags and are directed to a QR code check-in. A 16-question survey, designed to uncover values, preferences, and relationship expectations, forms the basis for an algorithm-guided matching process that unfolds throughout the evening. The software identifies potential pairings from the survey responses and reveals "matches" through a tiered countdown system that narrows groups into compatible subsets.

Despite the structured nature of the event, there is room for spontaneity. Attendees can follow the software's suggestions or connect organically with anyone who sparks their interest. Icebreaker questions placed on tables across the venue encourage conversations and ease initial awkwardness. The environment is intended to foster a sense of improvised interaction. Valerie McLaughlin, a 37-year-old Bolivian expatriate who has lived in Kenya for just over a year, describes her attendance as a leap of faith after ending a nine-year relationship. 

"This is my first time doing anything like this," she said. "It's a little daunting to re-enter the dating world, but I came with an open mind." Drawing on past online dating experience, she added, "They're all strangers until they're not."

Cohen Omondi, 28, having recently ended a seven-year relationship and spent six months recalibrating his emotional footing, echoes this sentiment. "The hardest part is adjusting to the absence of that deep familiarity," he explained. "You have to learn to present yourself anew, to be vulnerable again."

Omondi is not exclusively seeking a romantic partner but remains open to friendships and connections. "This is a reset for me," he said, his voice grounded in calm resolve. "I feel like I'm ready." Conversely, 26-year-old Debrah Phoebe approaches the evening with a blend of scepticism and playfulness. "My expectations are low," she admitted, citing past disappointments with dating apps and limited experience in long-term relationships. "But I'm here, and I'm open to meeting real people."

While dating apps have expanded access to potential partners, they often fail to foster genuine interaction. In contrast, events such as these offer a tactile alternative, where participants can gauge tone, body language, and mutual energy in ways that online profiles cannot replicate. Debra Olum, the event host for the Nairobi chapter of ThursdayTM, explains the company's philosophy. "People want a sense of connection that feels grounded," she said. "We're creating spaces where dating is not a chore, but a social, shared experience."

Olum notes that interest in these gatherings spans age groups, with the majority of attendees falling between 25 and 40. A growing number of older singles, drawn by the same desire for authenticity, are also expressing interest. Olum emphasises that the matchmaking element is designed to facilitate connections, not prescribe outcomes. "The survey questions are value-based," she said. "It's about compatibility, not perfection. And if the match isn't right, that's okay---everyone is encouraged to engage freely."

Beyond the romantic prospects, the evening's atmosphere resembles that of a social gathering, where laughter fills the air, carried by the breeze from the open terrace bar. Waiters deftly mix cocktails, while guests engage in relaxed conversations against the backdrop of the Nairobi skyline. This elevated setting symbolises a shift in how individuals choose to approach finding love: with openness and intent rather than filters and swipes.