How to Start a Conversation

Speechless? These talking points—courtesy of pros ranging from a humorist to a PR executive—guarantee that you’ll have something to fill every awkward silence. Holiday open houses never sounded so good.

Photo by Shout

Ask What Just Happened

I find the question “What’s your profession?” to be tiresome, because people have jobs that I don’t understand. Or the person answers by saying, “I’m a consultant,” which is just another way of saying, “I’m not going to tell you what I do.” Isn’t it more fun to ask, “What did you do today?” It’s a very intimate question—something you might ask your spouse. Of course, if the person responds, “I worked at my consulting job,” then I guess you’ll have been tricked. But hopefully he’ll say, “I met a friend for lunch,” and then you can ask where they ate and the conversation will go on.

John Hodgman is a Brooklyn-based humorist and the author of a trilogy of satirical almanacs: The Areas of My Expertise ($14,, More Information Than You Require ($15,, and That Is All ($15, He is also a “resident expert” for The Daily Show With Jon Stewart.

Request Permission

Years ago I was talking to someone at a party when this guy just turned up and said, “Hi, can I buy a ticket to this conversation?” He was so ingenuous and direct that he made me smile. And I found the engaging, idiosyncratic manner of his introduction both charming and disarming. The question also works because it’s almost impossible to answer no to—unless you happen to be in the midst of, say, breaking up with someone. By the way, that fellow and I are friends to this day.

Ben Schott is the author of the Schott’s Miscellany and Schott’s Almanac series (from $18, He divides his time between London and New York City.


I started my radio show 28 years ago, right after the birth of my son. Back then, my program director told me I should mention only once or twice on air that I had recently given birth, because “no one is interested.” Lucky for me, he was incorrect: People are very interested. So when a conversation hits a dead end, I bring up personal things. I talk about my children and my hobbies—that I love to ride horses, to cook, to sew. Sharing these tidbits leads the person I’m talking with to chat about her own interests. Too many people are afraid of exposure. But the more transparent you are, the more you give others permission to be open right back.

Delilah is the author of the new book Arms Full of Love ($14, and the host of the call-in radio show Delilah, listened to on weeknights by more than 8 million people across North America. She lives in western Washington.