Talking about past experiences isn’t just “sharing stories”—it’s a great chance to understand someone’s values and ways of handling things. Don’t stop at surface-level questions like “Where have you traveled?” Instead, ask about the choices and feelings behind their experiences to quickly build closeness and get to know the real them.​If they say, “I took a solo trip last year,” don’t just say “That’s brave.” Try: “Solo travel must have been really special—when something unexpected happened, like getting lost or not having a hotel booking, did you panic first or figure it out right away? Last time I traveled alone, my first move was to find a café to calm down. I really admire people who can solve problems instantly.” Asking about how they handle situations reveals if they’re calm or flexible, and sharing your own small experience can also spark connection.​When they mention, “I led a team project before,” don’t just say “Impressive.” You could ask: “When working in a team, if someone had a different idea from yours, would you be more likely to convince them or listen to their reasons first? I had a similar situation before and found that understanding their perspective first led to a much better plan.” Using work or project experiences helps you learn about their communication style and teamwork mindset—important things to know for future interactions.​If they talk about, “I learned an instrument as a kid but quit later,” don’t just respond “That’s a shame.” Try: “Sticking with an instrument takes a lot of effort—did you quit because it was too hard, or because you found something else you liked more? I took painting lessons as a kid but stopped because I got into reading novels. I still regret it sometimes.” Asking why they quit shows their attitude toward “persistence” and “making choices,” and sharing your own little regret makes the conversation feel more genuine.​Even if they say, “I had a pet before but had to give it away,” don’t just say “That’s sad.” You could ask: “When you were with your pet, was there a small moment that felt really warm? Like how it would stay with you when you were sad? The cat I used to have would always lie on my keyboard when I worked overtime—I still think it’s healing to remember that.” Focusing on emotional details in their experience helps you see what warm moments they care about, and whether they’re sensitive and caring.​The key point: Talking about the past isn’t an “interrogation”—it’s about being curious about their choices and feelings. When you ask, “Why did you do that?” or “How did you feel then?” and respond with your own real experiences, they’ll feel like you’re not just listening to their story, but actually trying to understand them. This kind of deep interaction is far more likely to make them want to keep talking to you than small talk.