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Dating Advice: How to Hold a Conversation

Dean Nelson, author of Talk to Me, reveals the foolproof ways to have an interesting, engaging chat with your date

By Sarah Pfledderer

“People think you’re funny. Make me laugh.” That was one of the brasher warm-up queries Dean Nelson has fielded on a first date. That woman’s bold move paid off, though—they’ve been married now for 46 years.

Nelson, an award-winning reporter and founder of PLNU’s journalism program, has also used those 46 years to hone his conversation skills, interviewing professional athletes, poets, and politicians. In the process he’s learned a thing or two about the art of asking the right questions.

“In any conversation, whether it’s a formal interview or a date, you need warm-up questions. Start easy and, as the conversation goes on, get increasingly complex.”

Assuming it’s not a blind date, do your research on the person ahead of time (hallelujah, social media!) to bring open-ended questions to the table that steer your date toward topics you want to learn more about. “Questions beginning with ‘why’ and ‘how’ are always better than ‘when’ or ‘what.’” Consider “How much do you love dogs?”, not “Do you have any pets?”—since you should know from your research whether they own pets. The latter elicits a one-word response, while the former “brings the person back to telling a story. The early stage of dating is trying to figure out someone’s story, and deciding if you want to continue with this story.”

As for the more taboo topics, like politics and religion? Don’t be afraid to pry—”Finding out the answer on a first date might save you a lot of time”—but above all be conscious of nonverbal cues. Crossed arms or looking away sends different signals than leaning on the table or smiling. “If a person isn’t showing any curiosity, I think that answers whether you want to go out with them again.”

Finally, always set a time limit on any initial conversation. That gives you a preexistent reason to leave, or the opportunity to acknowledge that time’s up but you still want to get to know them longer—in that sitting or at another time, even as soon as “tomorrow,” which is just what Nelson proposed to his future wife at the end of their first date.

“And the conversation hasn’t stopped since.”

Dating Advice: How to Hold a Conversation

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