Tips from a comedian and a journalist on the art of going from small talk to big ideas — all summer long.

Imagine almost any situation where two or more people are gathered—a wedding reception, a job interview, two off-duty cops hanging out in a Jacuzzi.

What do these situations have in common? Almost all of them involve people trying to talk with each other. But in these very moments where a conversation would enhance an encounter, we often fall short. We can’t think of a thing to say.

Or worse, we do a passable job at talking. We stagger through our romantic, professional and social worlds with the goal merely of not crashing, never considering that we might soar. We go home sweaty and puffy, and eat birthday cake in the shower.

We stagger through our romantic, professional and social worlds with the goal merely of not crashing, never considering…