For Jillin’ It founder Jill Dunn, matchmaking was never about algorithms or checklists, it was about people. The idea for her now-thriving matchmaking practice took shape after her divorce, when she found herself navigating modern dating as a single mom with two young children and very little free time. Dating apps felt transactional and exhausting. What she craved and what she quickly realized others craved too was real connection.
Searching for in-person singles events in Fairfield County, Jill came up empty. So she did what natural connectors do: she created one herself. That first event in her hometown of Norwalk sold out, filled the room, and sparked something immediate. Guests lingered, conversations flowed, and the question she heard all night was simple: When is the next one? Within weeks, Jill hosted another event, then another. As she met more singles, she instinctively began seeing who might be a fit for someone else even if they hadn’t attended the same gathering. What started organically soon evolved into a deeply intentional practice.
Eight years later, Jillin’ It has led to marriages, long-term partnerships, and countless meaningful relationships. Yet Jill’s philosophy remains refreshingly human. “Dating, reimagined” means pulling people out of swipe culture and back into grounded, intentional connection. Jill often critiques what she calls “Amazon Prime dating” the illusion that you can filter for the perfect partner and have them delivered instantly. Instead, her work centers on values, emotional alignment, and curiosity over judgment.
Jill’s own experiences shape everything she does. She’s open about dating after divorce, the vulnerability it requires, and the emotional highs and lows along the way. That honesty resonates deeply with clients. She doesn’t approach matchmaking from a pedestal, but from lived understanding. Her role goes far beyond making introductions; she becomes a guide, helping clients stay hopeful, reflective, and confident without losing themselves in the process.
Every potential match is carefully vetted. Jill personally video chats with everyone, verifies key details, and conducts background checks. “In a way, I go on the first date for them,” she explains. By the time two people meet, the fundamentals already align. The first date isn’t an interview, it’s simply a chance to see if there’s openness for a second. That shift alone removes enormous pressure.
What truly sets Jill apart is her commitment to transformation, not just outcomes. Clients learn to see dating as information rather than rejection. They stop dating from scarcity and start dating with clarity. Many of the strongest relationships Jill has helped create began with uncertainty and proof that connection often unfolds quietly, over time.
As Jillin’ It grows, so does its impact. With expanded offerings like the Jillin’ It Love Club, a growing team, and more in-person experiences planned, Jill remains focused on what matters most: helping people feel seen, supported, and open to love again. For anyone who’s felt discouraged by modern dating, her message is clear, don’t put your life on pause. Come as you are. Connection is closer than you think.
Every date is information, not rejection and none of it is wasted.
Dating isn’t about instant chemistry or perfection. It’s about curiosity, alignment, and staying open long enough for connection to unfold because some of the best relationships start with ‘I wasn’t sure at first.’