How to Start a Captivating Conversation—Even If You're Shy

Recently, I was at a party and I noticed myself obsessively checking my phone, wondering if the entire evening would be a bore, when I saw a silver fox eyeing me from across the room. When I glided over and said hello, he responded with a four-word question that made me cringe: “What do you do?” Suddenly, I realized why I was feeling bored and down—I had spent the last hour and a half having the same conversation over and over again. The last five people had all asked me what I did for a living and I ended up repeating my spiel (“I’m a writer, personal chef, and event planner!”) over and over again.

Because I believe that meeting new people at a party shouldn’t feel like a job interview, I’ve simply stopped asking people what they do. If this idea seems foreign and scary, keep reading. Here’s how to start up a provocative conversation with an unknown at a party.