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Master the Art of Conversation

“Good conversation is the Swiss Army knife of social skills that anyone can learn to use. Take it with you wherever you go, and you’ll be equipped to turn a seatmate into a confidant, an interviewer into an employer, and an acquaintance into a friend. As an accomplished conversationalist, you’ll be welcomed everywhere; everyone loves good conversation because it is fun.”

—Margaret Shepherd in The Art of Civilized Conversation

In her popular book The Art of Civilized Conversation, Margaret Shepherd offers recommendations for being the kind of person people enjoy being around, the kind of person people look forward to talking to. And for those of us who date, being good conversationalists can make the difference between getting a second date and never hearing from a person again.

The key to good conversation is to get outside of yourself and be aware of other people—who they are, what they care about, what interests them, what they enjoy. We all want to put our best foot forward when we’re getting to know someone new; but you’ll be much more attractive if you focus more on showing interest in the person you’re out with, as opposed to talking only about the things that you care most about. So here are some suggestions for making your part of the conversation less egocentric—which will make you more interesting and attractive.

Do Some Pre-Date Homework

You don’t have to pull an all-nighter or anything, but prepare for your date by coming up with interesting conversation topics. For example, be ready with a couple of funny stories and some thoughts on current events or pop culture. Work these into the conversation naturally.

Also, prepare some questions and thoughts based on what you know about your date. If you’ve visited with the person before, follow up on something from the previous conversation. Get an update on that issue at work or the problem with the landlord. It’s also a good idea to read up on your date’s hobbies or job, simply so you can ask good questions. This will show your interest and make the conversation more meaningful to you as well.

Ask Good Questions

Perhaps the hallmark of any good conversationalist is the ability to ask good questions: initial ones and follow-ups. This communicates your interest in people and gives them the chance to talk about what they care about. But the key is asking good questions that draw people out. For example, yes/no questions (“Do you like Mexican food?”) aren’t nearly as effective as open-ended questions that allow for more discussion (“Where’s the best place you know for tacos?”).

But don’t be too open-ended (“What have you been up to lately?”). Instead, ask specific questions that are easier to answer (“What happened on that job interview you were nervous about?”). What’s most important is that you ask the kinds of questions that generate a ping-pong effect and let a comfortable back-and-forth emerge between you and the person you’re talking with.

Make your Date feel Valued and Interesting

You can demonstrate your interest in someone verbally (like when you ask good questions), but don’t underestimate the importance of the nonverbal messages you send during a conversation. Pay attention to your body language—could your slumping communicate that you’re bored, or could your crossed arms say that you’re not open to what’s being said? And don’t be distracted by other people in the room, by your phone, or by the football game on the TV in the bar. Instead, lean in toward your date (not too close!), smile, and make it clear that you’re really focusing on him or her.

Much of this comes down to simply listening well. Do your best to tune in to what’s being said. Don’t let your mind wander, and don’t plan ahead how you’re going to respond. Just focus on the other person in the moment. After all, we all love to “feel felt” by another person, to sense that someone else is totally in this moment with us, clueing in to what we’re saying, and feeling understood. That’s the kind of person we’re going to feel attracted to.

Be Willing to Share

While you’re working hard to show interest and be a good listener, don’t neglect to share yourself along the way as well. It’s true that you don’t want to monopolize a conversation, but it’s also important to hold up your end of the discussion. As you probably already know, it’s not much fun to spend an hour or two with someone who only asks questions like an interrogator or who won’t fulfill his or her own conversational responsibilities. For example, if someone asks, “Do you have a favorite band?” don’t respond with the one-word answer “Yes.”

There should be a give and take, an exchange of energy and information between you and your date. So do your best to fulfill both of your responsibilities: Show that you’re interested and be interesting. A good conversationalist does both, not just one or the other.

Relax and Don’t try too Hard

Knowing that you’ve prepared for your date and thought through these principles, do your best to relax and simply enjoy yourself. Don’t feel like you have to fill every microsecond of silence or laugh too hard at every joke. What’s most important is that you be yourself and that you make an effort to show who you are and get to know who the other person is as well. Yes, dating can be stressful, but it should also be enjoyable. So once you’ve prepared yourself, try to focus on just having fun while you chat with the person you’re out with.