How to Break the Ice, by CEO Sam Yagan

Illustration by Steph Davidson

The first time you meet someone, the conversation is sort of on life support. You’re just trying to live another moment in the life of the conversation. I’m an off-the-charts introvert. To me, being around groups of strangers is exhausting. I’ve had to sort of train myself to think about two tactics: finding common ground and invoking humor. With the first part, the No. 1 tip is specificity. If you go up to somebody and say, “Do you like to travel?”—that’s actually a terrible conversation starter. The answer is yes, but it’s so boring. It’s almost like asking, “How do you breathe?” I try to listen carefully for any specific cultural crumb people drop, and I’ll leap on it. “Tennis? I used to play tennis!” Even though I don’t follow tennis anymore. I want to leverage that crumb. Humor is trickier. I wouldn’t say I’ve practiced my sense of humor, but I have become much more confident in using humor as a tool early on, much more willing to try to drop a joke. I just take more risks in those situations than I used to. Standing alone at a party—it’s so life-depleting. I’d rather try and possibly fail.

My work involves online dating, but I believe almost every behavior exhibited online has an offline corollary. Really, the medium doesn’t change human nature. It’s true in all kinds of interactions—even in a job interview, you’re trying to use these same two tactics. On a résumé, the standard advice is to put your interests at the bottom—not to show how well-rounded you are, but because you hope the interviewer says, “You like the Yankees? I was at the game last night.” —As told to Nick Summers

Yagan is CEO of Match and co-founder of OkCupid. 

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