"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.
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.
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