How Keep Conversation Going

Men's Dating

How to Keep the Conversation Going

Nick Slade

Written by: Nick Slade

Nick Slade

Nick spent 20 years in the dating scene before marriage. He has always been the guy friends would come to for advice on relationships, and he developed a knack for giving helpful insights. After college, Nick was a disc jockey for a few years, when the love generation was still alive, so Nick has a lot of relevant experience to draw from when it comes to every aspect of dating, falling in love and screwing things up. He holds Bachelor's degree in humanities and a slew of master’s credits in journalism. Nick is a news junkie and tries to keep up on the latest non-fiction when he has time. He has published two books on how to win at dating and relationships.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Conversation is nothing more than verbal ping pong. One person serves, the other returns and the volley continues. Periodically, a new serve sets the exchange on a new course. Of course, both players need to keep their paddles up and make the effort to send the ball back to the other court.

Meeting new people always presents challenges when it comes to getting the ball rolling — or bouncing. First dates, online chats and just approaching that pretty girl in the coffee shop who smiled at you requires some kind of dialogue.

It doesn’t do much good to start a conversation if you can’t keep it flowing.

Kick it off.

Somebody has to go first. In many circumstances, it’s “ladies first,” but in the art of dating, you are the man and you have to make the first move.

When you sit across the table for the first cup of coffee together, give her something to respond to. You might, very briefly, tell her a little something about yourself — your name, age, where you’re from and what you do, perhaps.

If you’ve already chatted before, have a few topics in mind you know are of interest to her. If she’s not frozen with the jitters, she may take it from there and comment or ask a question, or she may give you a simple smile and a nod.

If she doesn’t give you anything to swing at, just follow up by turning things back to her: “How about you? What brings you here today? Do you live around here? You look familiar, did you go the Lincoln High School?


“There’s no reason for a conversation to be

awkward if you just have a few topics ready.”

Find some common ground.

The biggest conversation killer is one-word answers, because it requires you to come up with a new topic every time and she doesn’t get engaged in the conversation. So you need to find something that will not only give her something to respond to, like “What’s your major” or “What kind of work do you do?” but something you can both delve into with questions and responses.

With a few questions, you may find out you have a friend or a school in common. Maybe you were both at the same rock concert last month. Everybody eats, so maybe you both love that Thai restaurant in the Village.

If all else fails, you can always find a movie, TV show or book you can both relate to.

Any common element you both know something about will give her the opportunity to both answer and then follow up by asking you for your opinion on how you liked the movie, or if you’ve tried a certain appetizer she loves at a restaurant, or whatever it might be.

With the general rule that there’s never more than “six degrees of separation” between you and any other person on the planet, you should be able to find some common ground without much trouble.

Word association.

As long as she responds with something more than a “Yes,” “No” or “Oh, really?” she will be setting you up with something else to say. Just pick up on a word or topic in her answer.

You start with, “My brother came home from Stanford for a visit last weekend.” She says, “Oh, really? My brother looked at Stanford too but decided to go to Berkeley.” Now you can ask about her brother, why he didn’t choose Stanford, what he studies at Berkeley or maybe where she plans to go to college, for instance.

Any word she says will make you think of something to say. Conversation is often just like the word-association game. Pick up on something she says and comment or get her to expand on it.

When you walk, you just have to keep putting one foot in front of the other if you want to get to your destination. Conversations just require a response to each other’s words.

There’s no reason for a conversation to be awkward or clumsy for very long if you just have a few topics ready to serve and keep returning her volleys.

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