Community space Stranger Conversations blossoms as ‘library of human stories’ and life experiences

SINGAPORE – She had, in her own words, the “perfect Singaporean life” – a stable job, a Housing Board flat and a long-term relationship. But deep inside, Ms June Tan still felt unfulfilled, and like she was living a life that was not her own.

“It looked good only on paper, not in reality,” said the 33-year-old.

So she decided to make a change. In 2022, she upped and left Singapore after leaving her job as a tutor, ending things with her partner of seven years and returning the flat.

She took the plunge despite not having a concrete plan in mind and, three years on, has travelled to 70 countries – which included eight months backpacking solo in South America, and landing a job as an expedition guide working in Antarctica.

In June 2025, Ms Tan also became an accidental speaker.

Through friends who had attended earlier events, she discovered Stranger Conversations in August 2024, a social mixer series that struck her as a space where open-minded, like-hearted individuals could come together and share their life experiences.

After attending an event, she went on to host two Stranger Conversations sessions, which garnered over 30 attendees each.

Ms Tan said: “Stranger Conversations felt very different from the typical commercial or transactional social spaces we often see in Singapore. (The conversations) weren’t about shopping or catching a movie.”

The platform was created for people who wanted to engage in more “unconventional” exchanges, said its founder Ang Jin Shaun.

“People are so comfortable relating to everyday and simpler topics like applying for a BTO (Build-To-Order) flat or where the next latest cafe is opening,” he said.

“We wanted to have a place for different perspectives to come together and opportunities for cross-pollination.”

In such sessions, participants share real-life experiences of learning and growing through various interests and life periods, such as navigating a nomadic life and isolation, and healing relationships.

Mr Ang, 46, said that the move to create such a space came after he had found himself at a “standstill” and decided to take a career sabbatical, having dabbled in various jobs including those in public service, consulting and small enterprises.

“It was a ‘What now?’ moment for me,” he told The Straits Times in an interview at the quaint second-floor studio space in Chinatown that Stranger Conversations calls home today.

Looking to connect with people with unconventional life paths, he set up Stranger Conversations in 2021. The community has enjoyed steady growth since its first iteration that took place online, with over 250 activities being held in the past year alone.

Updates on the latest and upcoming events are on its Instagram and Telegram platforms.

In June 2025, 28 events were held, with each hosting between 25 and 35 attendees – depending on the type of event.

Stranger Conversations has embarked on its latest major project – a “Summer School for Grown-Ups” programme from July 8 to Sept 27 that saw over 300 applicants.

The programme will have 25 module hosts over three months, and a final cohort of 40 who will be attending the events.

Its attendees hail from a gamut of professions, and range in age from those in their early 20s to those in their 50s, with the oldest hosts in the ongoing Summer School programme in their 70s, said Mr Ang.

He added that Stranger Conversations does not have a target audience, as evidenced by the eclecticism of the topics that have been discussed over the years – from learning how to be a deejay, to learning how to navigate male loneliness and isolation.

Ms Tan said that as a speaker, she steps into a “space of intentional sharing”, adding that she enjoys the freedom to shape her presentation, design her own slides and also integrate interactive moments like journalling prompts.

“I wanted my session to go beyond just storytelling,” she said. “And I wanted to help people reflect on their own lives, too, to engage in both their conscious and subconscious selves.”

Mr Ang said that only three topics are “out of bounds”: those surrounding dating, superstition and politics. Themes that often draw high crowds centre around travel, career breaks and burnout, he added.

Despite Stranger Conversations’ growth, the platform does not make any profit, said Mr Ang.

After initially holding gatherings at parks or other ad hoc rental spaces, it moved into its space in Pearl’s Hill Terrace – which Mr Ang dubs a “public living room” – in May 2024.

It costs him and his team of about 25 volunteers and space minders around $50,000 a year to stay open, a sum that is largely raised through crowdfunding, donations and tickets to events, which are priced from $10.

Some events are free because the host may have provided monetary support for the space and contributed to the rent.

Volunteers and various speakers who host sessions do not receive a salary, nor do they seek one, said Ms Genevieve Ong, who takes on the role of a community builder at Stranger Conversations. There are about 50 such volunteers and speakers.

“Most have other forms of income, and these are people who are at different seasons of their lives,” said Ms Ong.

“We also make it a point to ask them if they are financially well for the month when speakers decide to hold events, but they usually decline a revenue share for the tickets.”

Speakers are discovered organically, added Mr Ang, often through the individuals contacting Stranger Conversations directly to pitch an idea, or after they attend different events and recount snippets of their experiences with fellow attendees.

“It’s rare to find a space that holds this kind of openness,” said Ms Tan.

“It reminded me that there is a growing community of people here who want more than the traditional script – that we’re not alone in seeking depth, authenticity and purpose,” she added.

Mr Ang said: “There will always be something open for someone here (at Stranger Conversations) that will pique their interest; it’s like a library of human stories.”