The Matchmaker's Return: How Nandini Brought Ancient Wisdom to Modern Dating

The first time Nandini tried to set someone up was at her eighth standard social at Cathedral School in Mumbai, 2008. She was barely a teenager, but already she understood something that would take the dating app industry decades to figure out: successful matchmaking is about listening.Sixteen years later, Nandini sits in her company’s office, having just raised $7 million for Sitch, an AI-powered matchmaking service that’s challenging the entire premise of modern dating apps. Her journey from teenage cupid to venture-backed founder reveals a deeper truth about technology: sometimes the most innovative solutions look remarkably like ancient wisdom, updated for modern times.“I always joke that with cofounders, just like in your dating life, you gotta have a few ex-boyfriends before you meet your husband,” Nandini says, referring to her previous startup that failed.

“Same thing with cofounders. You don’t give up. Real founders keep going against all odds.”This philosophy of persistence through failure has defined Nandini’s approach to entrepreneurship. Her first dating app venture ended in a cofounder split and shutdown, despite showing promise. “I had put my heart and soul in it,” she recalls. “To go from saying ‘I'm gonna be a founder’ to ‘I have nothing to show for it’ was really difficult.”

Nandini started building again.The dating app industry seemed like an unlikely place for innovation. Since Hinge and The League gained traction, few new entrants have achieved meaningful scale or attracted serious institutional investment. The market appeared saturated, dominated by Match Group’s portfolio and a handful of established players.But Nandini identified a fundamental shift happening in consumer behavior. “We’re moving towards Concierge-based services,” she explains. “If I’m trying to get in shape, I’m not figuring it out myself; my trainer gives me a workout and I follow it. Why is it that with dating, we’re like ‘you should be swiping through all these people, figuring out if they’re legitimate’?”This insight led to Sitch’s core proposition: instead of endless swiping, users work with matchmakers who conduct 30-minute onboarding sessions and provide personalized matches based on deep compatibility analysis.The difference becomes clear when Nandini describes what traditional apps miss: “Hinge might know you’re South Asian, but it doesn’t know what kind of South Asian you are, whether you were born in the US, whether you want someone who’s Punjabi from the North. On your Hinge profile, you wrote that you love margaritas and Mexican food. How is that helping determine who you’re gonna marry?”Sitch asks different questions entirely. Instead of favorite restaurants, they want to know if going to restaurants is something you enjoy or if you prefer cooking at home.

Whether you’d rather spend money on extravagant holidays or invest in long-term stability. These data points are fundamental to relationship compatibility.“Our secret sauce is the conversation,” Nandini explains. “What is a good matchmaker? A good matchmaker is a good listener.”

This approach has resonated beyond Nandini's expectations. The company launched in 2024 and has already expanded to three cities, with waitlists in twelve more.

They’re planning to cover all major US cities by early next year, then expand internationally.What’s particularly striking is how Sitch represents a cultural moment where Eastern wisdom is gaining traction in Western markets. “The app getting attention on TechCrunch and CNBC is fundamentally an Indian concept,” Nandini notes. “People in New York are suddenly like ‘maybe I should get a matchmaker, maybe they’ve got it right.’”“This is the biggest decision you’re probably gonna make: who you pick as your life partner,” Nandini argues. “Why should you be making it alone? No man is an island.”The technical challenge lies in scaling personal matchmaking. How do you provide individualized attention to millions of users? Nandini’s answer involves what she calls “productizing myself”: building AI that captures her matchmaking intuition and conversation style.“Someone at a16z said they did the onboarding with the AI and heard me speak, and it’s actually the same,” she recounts. “That’s a really interesting philosophical question we’re asking about who we are and what it means to be human.”This scaling challenge reflects broader questions about AI and automation. Unlike dating apps that can easily accommodate unlimited users, Sitch’s model requires maintaining quality relationships with each member.

Success depends on making people feel “seen” and “understood”.The business model also differs fundamentally from existing dating apps. While Match Group profits from keeping users engaged and paying for premium features, Sitch succeeds when people find relationships and leave the platform. This alignment of incentives may prove crucial to long-term sustainability.“Dating apps without institutional funding get bought by Match Group really fast for really cheap, or they never get off the ground,” Nandini observes.

This insight influenced their fundraising strategy, targeting multistage investors committed to long-term growth rather than quick exits.The company’s city-by-city expansion strategy reflects Sitch’s hyperlocal approach. Rather than generic national campaigns, they create marketing tailored to each city’s dating culture. San Francisco gets “ChatGPT can’t find you a girlfriend, but I can.” New York focuses on expensive bad first dates.

The message adapts, but the core promise remains: we understand you, therefore we understand who you’re looking for.“We’re not looking for similar people,” Nandini clarifies. “We're looking for compatibility. Are the things you want compatible with what this person wants? Are the character traits you’re looking for aligned with what this person offers?”As Sitch prepares for rapid expansion, Nandini faces the founder’s eternal question: how fast can we scale without losing what makes us special? With a team of twelve and ambitious goals to help “millions of people across the world,” the pressure to accelerate growth is constant.“I probably spend most of my time thinking about how we can move faster,” she admits. “Everyone deserves to feel loved, and we want to make sure they get that.”Whether ancient matchmaking wisdom can scale to modern technological demands remains to be seen. Nandini’s journey suggests that sometimes the most innovative path forward involves rediscovering what worked before algorithms took over: the simple but profound act of really listening to what people want, then helping them find it.