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Today, Singapore Tourism Board launched a highly unique ‘Aunties, Not Algorithms’ raffle that could see you win a free trip to the country for the first date of a lifetime. But there’s a twist…
Instead of randomly pairing you with the other winner, two applicants will be selected specifically based on their compatibility. The goal? Fly you to Singapore, where you’ll meet the love of your life.
Here’s what you need to know about how to apply, what the contest entails, and what you could win.
Inside Singapore’s ‘Aunties, Not Algorithms’ first date offer

The contest title of ‘Aunties, Not Algorithms’ is based on local culture in Singapore, where Aunties always know best—especially when it comes to love. The contest will see two famous celebrities and a pro matchmaker work together to match the perfect lovebirds.
These celebs include Kheng Hua from Crazy Rich Asians, along with comedian Atsuko Okatsuka and celebrity astrologer Aliza Kelly.
Hua will take on the role of ‘the wise Auntie’ who’s lived it all and seen it all. Okatsuka is ‘the modern Auntie’ who will say what everyone is thinking. And Kelly is the official Matchmaker, who will analyze her ‘big three’ to find a great match: personalities, patterns, and energies that most people miss.
To apply, head to FirstDateInSingapore.com. You have until March 13, 2026, to submit your application.
Here’s what two lucky lovebirds will win:
- Round-trip flights to Singapore
- Lodging at a centrally located, standout hotel
- An ‘Auntie-approved’ first date with Michelin-starred Chef Malcolm Lee
- An ‘Auntie-approved’ itinerary that showcases the city’s culture
- A spending stipend that lets you keep exploring
