7 First Date Questions That Tell You More Than Small Talk Ever Will, According to a Dating Expert

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Most first date conversations are totally useless for figuring out if you actually like someone. You cover jobs, neighborhoods, how long the commute took, whether you’ve seen that show everyone keeps talking about. An hour in, you know approximately nothing about the person sitting across from you. Jehan Rajendra, founder of Agilis—a London-based dating platform built around actual human connection rather than algorithmic volume—has a theory about why first dates go nowhere. “Many people go into first dates with a checklist, but that rarely leads to understanding who someone truly is,” he told VICE. Change the questions and change what you find out. Here are seven that actually work.“What’s a small thing that recently made you happy?”Joy when something great happens proves nothing. This question is about whether someone can find it when life is just life—no occasion, no milestone, nothing to report. Research in positive psychology finds that people who can do that handle stress better and sustain more stable emotional lives. It’s one of the more telling things you can learn about someone early on.“It highlights what they find fulfilling, which can be very telling,” says Rajendra. Watch the face, not the answer. Someone who lights up over a good cup of coffee or an unexpected act of kindness is telling you how they actually live—not how they want to be seen living.“If you could wake up tomorrow with a new skill, what would it be and why?”The actual skill is almost beside the point. What matters is the reasoning. Someone who wants to learn a language is probably chasing something cultural. Someone who wants to learn to code likely loves solving problems. The answer tells you what drives someone when nobody’s watching.“The ‘why’ is crucial,” Rajendra notes. “It shows their underlying desires—whether it’s for personal growth, helping others, or achieving a specific goal.”“What’s a belief you hold strongly that others might disagree with?”Watch how someone handles this one. Can they say something they actually believe — something that might not land well—without either caving the second you push back or turning it into an argument? Communication research shows emotional maturity surfaces most clearly when someone defends a position under mild pressure.“It’s not about conflict,” Rajendra clarifies, “but about understanding their convictions and their capacity for respectful debate.” Someone who folds immediately or comes out swinging has answered a different question than the one you asked.“What does a perfect Sunday look like for you?”Nobody marries someone because they have the same taste in movies. They stay together—or don’t—because of how they spend a Sunday with nothing on the calendar. That’s what this question is really asking.“It paints a picture of their ideal downtime,” says Rajendra, “which is important for compatibility in the long run.” One person’s perfect Sunday is a farmers market and a long walk. Another’s is horizontal until 2 pm. Both are fine. Incompatible combinations are not.“What’s one thing you’re passionate about, and how did you discover it?”Watch what happens to someone’s face when they talk about something they actually love. Their posture changes. Their voice changes. Social psychology research backs this up—expressed passion produces a measurable pull between people. The origin story of how they found that passion is where the interesting stuff lives, and you didn’t even have to ask for it directly.“Hearing someone talk about their passion is incredibly attractive and reveals their capacity for deep engagement,” Rajendra observes.“What’s the most adventurous thing you’ve ever done?”One person’s adventure is a solo trek through Southeast Asia. Another’s is moving to a city where they knew nobody. What someone reaches for when they hear that word tells you how they’re wired—and how they’ll handle the parts of a relationship that don’t go according to plan.“Adventure doesn’t always mean skydiving,” Rajendra points out. “It could be traveling solo, trying a new cuisine, or starting a business.” How someone defines a leap tells you how they’ll handle the moments in a relationship when there’s no safe option and no guaranteed outcome.“What’s something you’re currently trying to improve about yourself?”This is the one that separates people who are actually working on themselves from people who just say they are. Partners with a growth orientation handle conflict better and adapt more easily when life gets unpredictable. This question makes that visible early.“It shows they are reflective and proactive about growth, which are excellent qualities in a partner,” says Rajendra. A blank stare or a deflection is an answer in its own right.The post 7 First Date Questions That Tell You More Than Small Talk Ever Will, According to a Dating Expert appeared first on VICE.