Community space Stranger Conversations blossoms as a ‘library of human stories' and life experiences
'It looked good,' said the 33-year-old, 'only on paper, not in reality.'
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 since travelled to 70 countries – which included spending eight months backpacking solo in South America – and landed a job as an expedition guide working in Antarctica.
In August 2024 , Ms Tan also became an accidental speaker.
Through friends who had attended earlier events, she discovered Stranger Conversations, a social mixer series which struck her as a space where open-minded, like-hearted individuals could come together and share their life experiences.
After attending an event, she has gone on to host two other Stranger Conversations sessions, which have garnered over 30 attendees each, among the highest.
Said Ms Tan: '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 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, isolation and healing relationships.
Mr Ang, 46, said the move to create such a space came after 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 T he Straits Times in an interview at the quaint second-floor studio space in Chinatown that Stranger Conversations calls home today.
Stranger Conversations founder Ang Jin Shaun (far right) in May 2024 after snagging a studio space in Chinatown and converting a hallway into a lounge.
PHOTO: GENEVIEVE ONG
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 which took place online, with over 250 activities being held in the past year alone.
Updates on the latest and upcoming events are done so through their Instagram and Telegram platforms.
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In the month of June 2025, 28 events were held, with each hosting between 25 to 35 attendees - contingent on the type of event. When an activity requires more space, the company seeks space from other tenants, who have now grown to be friends.
The community is currently embarking on its most ambitious project yet – a 'Summer School for Grown-Ups' program from July 8 to Sept 27 that will see 250 speakers and activities, which will see 32 events being conducted across 29 event days.
The community sees attendees from a gamut of professions and in a wide age range - those in their early 20s to 70s, said Mr Ang.
An event called "Burnt out, not broken" having a sharing session, which later evolved into a four-part fortnightly peer support group.
PHOTO: ANGELA KONG
He added that Stranger Conversations does not have a target audience, as evidenced by the eclecticism of topics that have been discussed over the years – from learning how to DJ, to the art of co-existing between birds, humans and urban well-being and 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 enjoyed the freedom to shape her presentation, design her own slides and also integrate interactive moments like journaling 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.
Having initially held gatherings at parks or other ad hoc rental spaces, it moved into its space at 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 funded through crowdfunding, donations and tickets to events, which are priced from $10.
Some events are free of charge because the host may have provided monetary support for the space and contributed to the rent.
Volunteers and various speakers who host sessions – they number about 50 – do not receive a salary, nor do they seek one, said Ms Genevieve Ong, a volunteer who likes to endearingly call her role 'community builder' instead.
' Most have other forms of income, and these are people who are at different seasons of their lives,' shared 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 salary .'
Speakers are discovered organically, added Mr Ang, often times through them contacting Stranger Conversations directly by 'pitching' their idea, or after they attend different events and recount snippets of their experiences with fellow attendees.
Some of these speakers also end up converting into residents of Stranger Conversations, where they hold their signature sessions, like Ms Tan.
'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.'
Added Mr Ang: '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.'
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Photography: Darren Gabriel Leow Fashion direction: CK Grooming: Grego Oh, using Chanel Beauty and Revlon Professional Make-up and hair (for Tan): Nicole Ang, using Chanel Beauty and Kevin Murphy Location: Nathan Home at 8 Baker Street
