Pickleball, condo BBQs: Singaporeans connect via AI-powered friendship apps amid global trend

[SINGAPORE] Artificial intelligence (AI)-powered social facilitators – or friendship apps – are gaining traction with people seeking genuine, offline connections.

Singaporeans and many others globally are using these platforms, to meet strangers for anything from pickleball games to comedy shows, for a shot at new, authentic friendships.

Users fill out an extensive personality quiz – with a range of questions from music tastes, budgets for nights-out, to political values. Data collected allows the platform to suggest the most fitting hangouts for users to choose from – and match them with others, within their gathering of choice.

One global name in the AI-powered social app space is 222. It began as a research project in 2021 by Keyan Kazemian, Danial Hashemi and Arman Roshannai, investigating AI and machine learning to facilitate in-person meet-ups in large cities.

The New York-based app is now active in eight US cities, and international locations such as Toronto and London.

Competition in this space can be fierce, with other players such as French-based social networking app Timeleft created in 2020; and Meet5, a German company founded in 2017 tailored to users above 40, dominating the market.

These companies have expanded internationally in recent years, with Meet5 raising an eight million euro (S$11.9 million) Series A round in September 2025. As at late December, 222 had raised US$10.1 million in a Series A funding with an investor count of 15, based on data from CB Insights.

Players in Asia have also lost no time in jumping on this bandwagon. Hong Kong-based service GenieFriends deploys AI in its attendee-matching algorithm for social dinners, and to personalise gifts for event participants.

Meanwhile, Singapore is home to AI-powered social app lemon. Timeleft also came to Singapore in June 2024 – its first key market in the Asia-Pacific region. It already has a presence in more than 50 markets and 200 cities, including in Malaysia, Indonesia and Hong Kong.

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Tackling ‘big-city loneliness’ with data

The main selling point of AI-driven social apps is their ability to create opportunities for highly compatible, offline connections in this hyper-digital age.

A 2025 report by the World Health Organization indicated that one in six people grapple with loneliness, and pointed out that social health has a significant correlation to physical and mental health.

This struggle was clear to Kazemian, co-founder and chief executive of 222, after his experience working at Match Group – owner of the world’s largest portfolio of online dating services such as Tinder and OkCupid. He saw various complaints from users of its products, who struggled to get to an in-person interaction via the app.

The solution? Better usage and collection of data, and a machine-learning algorithm to predict initial social compatibility between users, for improved “in-real-life” connections.

“The more data that we get (from users), the better we are able to predict social compatibility,” said Hashemi, chief operating officer and co-founder of 222, in an interview with The Business Times.

Eric San, co-founder of GenieFriends, said that user profiles are processed via OpenAI’s embeddings Application Programming Interface – through which lengthy profile descriptions are converted into shorter, numerical representations.

“The closer (the numbers) are to each other, the more similar they are,” he wrote in a Medium blog post in 2023.

Timeleft – best known for its “dinner with strangers” concept – also uses a degree of AI solutions in its matching algorithm to plan events, said Tu-Han Vincent-Sultan, global head of go-to-market of the friendship-making platform.

“Our goal is to use AI to support human engagement – but never to replace it,” he told BT.

This move appears to have paid off – as retention rates on the app are “high” on a whole, said Kimberley Kiew, marketing lead at Timeleft.

Singapore as a key market

Even to newer players in the social facilitator market, Singapore is identified as a key location in the Asia-Pacific to set up their product.

The co-founders of lemon – tech product manager Nam Sunwoo, Peking University physics undergraduate Pin Chen and AI research engineer Han Jiatong – launched their business in the Republic in May 2025.

Their journey, which began as a community project, was not without challenges specific to the country, however.

“The brutal reality is that Singapore is a much smaller market (for a social app business) to be operating in, as compared to the US,” said Nam on a call with BT.

Stereotypes of the city-state being “less vibrant” than Western cities “with fewer things to do” were not the only hurdles. The fear of “stranger danger”, which many Singaporeans may have grown up with, could easily put people off making friends via social apps, too.

But such reasons also support such apps – and fill a real need – in the Asian city, said Pin and Nam.

“It is clearly difficult to expand one’s social circle as a young adult in Singapore, besides going for networking events or using dating apps, which often aren’t ideal options,” they added. “This is where an app offering customised events could help.”

Recent numbers appear to support this bet. lemon, in less than a year, has accumulated more than 600 active users, including a handful of “superusers” – regular customers who attend events every week.

Its largest gathering drew 20 people – a cafe-hopping trail in the central part of Singapore. Other popular activities included a barbecue at a host’s condominium, and pickleball games which had the most regular number of sign-ups.

Singaporeans may not be that closed off to new methods of making friends these days, too. Timeleft’s Kiew said there has been a steady rise in the number of users in the Republic since the launch of the product, relative to elsewhere in the Asia-Pacific.

“The (take-up rate) in Japan was a bit low; Taiwan had the largest number of users globally one month (after we launched there). But Singapore has had consistent growth over the past year,” she added.

The percentage of local users on Timeleft in the city-state has grown to 75 per cent in 2025, from 50 per cent the year prior.

Vanessa Chew, 23, a fresh graduate from the National University of Singapore, registered for a game of pickleball via an AI-powered social app.

“The questionnaire I filled out (on the app) was very long – but it helped to match me to a group of people I connected well with, so I think it worked well for me in the end.”

She did acknowledge that Singaporeans may be hesitant to try these apps in the early adoption stage, but that it could be the start of something new.

“I think that it’s a good way for Singaporeans to forge new friendships, considering how the game (I attended) had a pretty high attendance.”

Singapore as an Asia-Pacific market for social facilitator apps has caught the eye of global players such as 222 as well. The US-based app is aiming to expand to the city-state by 2026, Hashemi told BT.

“There will be cultural and infrastructure differences to manage – but we are sure the core model will take off in a city like Singapore,” he said.

Growth plans

As competition grows in this emerging market of AI-powered social apps, the pressure is on for existing players operating in the Little Red Dot.

Timeleft in Singapore, as of February 2025, began operating on a subscription-only model. Besides its signature dinners every Wednesday, the business offers women-only dinners on Tuesdays, and drinks sessions on Thursdays, said Vincent-Sultan.

lemon, on the other hand, started levying a S$30 curation fee on each participant for each event last December.

“Any kind of monetisation is to break even right now,” its three co-founders said.

A subscription model in 2026 is a possibility for the young startup, though the goal is to “stay sustainable”, the core team said. Expansion to other Asian cities such as Taipei and Hong Kong would be a mid-term goal, too, they noted.