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 (IACI) and co-founder of OkCupid.