1. When you need someone to open up about something, have them drive you somewhere.
People are at ease behind the wheel because they are in charge of their surroundings. Their attention is also primarily on the road and secondarily on the conversation you’re having, so if you catch them off guard they’ll feel both comfortable and surprised enough to give you an honest answer. Also, sitting side by side with someone during a difficult conversation is less intimidating than staring each other in the eyes.
2. When you want to establish a connection with someone, ask them about their family.
Inevitably they will say something sad at which point you can rub their arm and say “that must be hard for you.” Okay, I stole this trick from Friends, but it totally works. Well, one time the guy started crying, but all the other times it has led…
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