“Why (does) being with a stranger so often mean we (can’t) immediately talk about meaningful things?”

In this piece written for The New York Times’ Modern Love section, Tim Boomer asks the tough questions — and urges us to do the same. Crying for a halt to “the dull droning on about” how warm or wet it is outside, what we do for work, and how long it took us to get there, Boomer calls instead for “conversation about our weightiest beliefs and most potent fears (via) questions that reveal who we are and where we want to go”.

For a question is where it all begins. Before you demur, Boomer will convince you that any question can be elevated “from small talk to big talk with a little tweaking.”

Putting his money where his mouth is, Boomer institutes a “no-small-talk policy” in his dating life and lives to tell the charming tale. He’s not alone: in another New York Times essay, ‘To Fall in Love, Do This,’ Mandy Len Catron also has positive results to show from a romantic experiment asking all the right questions.

The applications of a well-crafted question do not stop there. Need a star employee more than a star lover? Think about what you’re going to ask a candidate — because really, what is an interview but a professional date? (Here are some ideas.)

By adopting, however, in Boomer’s words, “a willingness to dive into conversations that may make us uncomfortable or that many believe to be inappropriate for first encounters,” we are opening ourselves up to more than a well-oiled startup or a once-in-a-lifetime romance. We are giving ourselves the opportunity to come face-to-face with “something beautiful,” the little mercies and miracles of life, with connections that can make a difference. So ask away.

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