Let’s be real. Surface-level chat is like eating plain toast. It fills the void, but it’s not satisfying. When you ask a question that makes someone pause and think, you unlock a whole new dimension of who they are.
It’s also massively relaxing. Why? Because pretenses drop. When you ask, “What made you smile today?” instead of “How was work?,” the other person feels seen. And who doesn’t want to feel seen?
Start With the "Soft" Weirdness
You don’t have to jump into childhood trauma at a coffee shop. Start with playful questions. Ever asked someone, “If your life was a movie, what genre would it be?” It’s goofy, but their answer tells you volumes about how they see their own story.
Or try this classic: “What’s something you believed as a kid that you’re embarrassed now you believed?” Suddenly, you’re sharing laughs about thinking quicksand would be a bigger problem. You’re not just talking—you’re bonding.
