How to Be a Good Conversationalist

One of the most common complaints we get from guys starting out in our programs is that they “don’t know what to say.” But I have a question for you. Do you run out of things to say when you’re with you’re nine-year old niece, cousin, or best friend? Why not? It’s because you’re not worried about impressing them.

People feel constrained when they feel like they’re being judged. But in order to feel judged, they have to feel like another person has leverage over them.

What do your boss, your boss’s boss, or a girl that you’re attracted to have in common? You might feel that their rejection has consequences. When you’re talking to your boss or an attractive woman, you might not think that what you have to say is interesting enough, so you don’t say anything at all.

But you shouldn’t stress about what to say in social situations because unlike at business meetings, conversations at parties aren’t usually logical. Instead, they’re about connecting with other people through sharing experiences and emotions. This is a hard concept for some men to get.

One shortcut is to switch from closed-ended questions to open-ended questions. Closed-ended questions require a “yes” or “no” answer, and will usually cause the conversation to die out quickly.

Man: “Do you come here often?”

Woman: “Yes.”

Man: “Do you like it?”

Woman: “Yes.”

Man: “Do you live in New York?”

Woman: “I have to go to the bathroom.”

Open-ended questions require a more lengthy explanation, and allow for more of a give and take in the conversation.

Man: “You have an accent. Where are you from?”

Woman: “Bulgaria.”

Man: “That’s awesome. What’s the biggest difference between Bulgaria and New York?”

Woman: “Well, I think that people in Bulgaria are more open about their emotions. New Yorkers tend to be much more closed and always seem to have an ulterior motive…”

Can you hear the difference? This is a dramatic example, but the structure opens up conversational opportunities. They can talk about what she’s done in New York, how Bulgarians perceive Americans, how Americans perceive Eastern Europe, what it’s like to live in New York as a foreigner, and a wide range of other topics.

My point is that open-ended questions get a woman to invest in the conversation and give you information to work with, while closed-ended questions kill the conversational energy and force you to constantly think of new things to say. This strategy also holds true when approaching groups.