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Winning the Conversation Game

Winning the Conversation Game

EDITOR’S NOTE: The following is the latest installment of The Single Life, a monthly column written specifically for singles.

We interrupt this column to activate the social situation service: a party warning has been issued for the upcoming holiday season. Between now and the New Year, various social events are likely to occur. These settings may require you to take part in actual face-to-face discussions, which may involve using the vocal apparatus known as your mouth as opposed to operating an electronic device with your thumbs. In the event of such a social situation, your ability to text like the wind will be of no help whatsoever. Please be prepared to converse while simultaneously looking at the other part(ies) involved. We now return to your regularly scheduled story.

Consider yourself warned: party season is almost upon us. Now, a social occasion where most (or all) of the guests are your friends is generally not a cause of conversational stress, but what if you find yourself at a work party, church gathering, or other event where you’re obliged to make nice with people you don’t know (or don’t know well)? That’s a little trickier, especially in this digital age when so much “conversation” is done via text, e-mail, and so on.

But don’t fret:  If the thought of actually talking to another person without benefit of technology makes you nervous, just think of conversation as a game. Once you know a few basic ground rules you’ll be able to talk to anyone else who’s willing to play along.

Rule 1: Step Up to the Plate

The first (and often scariest) step is the first one: get out there and play ball. Toss out a conversational pitch and see if someone catches it and lobs it back. One way to do that is to ask an open-ended question: How do you know [party host]? Try to position your question for a positive answer: What one thing are you looking forward to this [week/month/season]? What holiday tradition do you enjoy most?

Once you’ve asked the question—and this is the most important part of the process—shut up and listen to the answer. As in, pay attention to what they’re saying, don’t just wait for them to take a breath so you can jump in with your own story. Next, ask a follow-up question or comment on what they just said. This one simple step will earn you a reputation as a conversational genius. Why? Because (especially in this “here’s-my-latest-post-about-what-I’m-doing-now” obsessed world we live in) just about everybody is talking but almost no one is listening.

If you are willing to step up to the plate as a listener, you will validate the other person’s right to an opinion. (It doesn’t mean you agree with them, just that you are willing to let them have their say.) This is especially helpful if you’re in a room with a bunch of people who outrank you, such as corporate higher-ups. Not only will you come across as an interested, engaged, intelligent person, you might actually learn something.

Rule 2: Take Turns

A well-played conversation is more akin to a tennis match than a football game. You may be able to break through the competition’s conversational line with a long-winded monologue but you won’t score any points that way. I’ve been in conversations where the other party talked so nonstop for so long I was convinced they’d mastered the art of circular breathing. After a while I tuned out and entertained myself placing mental bets on how much longer they’d be able to go before passing out due to lack of oxygen. There’s certainly nothing wrong with sharing an observation or story, just don’t drone on and on. As Walt Disney (or was it P.T. Barnum?) said, “Always leave them wanting more.” Hint: if your audience’s eyes glaze over, it’s probably time to wind up that story and take a breather.

On the other hand, when someone tosses you a conversational ball, do your part to keep it moving. Even if you’re engaged in listening, the talker will appreciate some sign that you’re still awake and alert.

Rule 3: Stay in Bounds

Depending on the situation the old ban on discussing religion or politics may or may not apply, but don’t bring up things that you know will be divisive or hurtful. What’s the point? And tempting though it may be, don’t talk badly about another person, even if they’re an easy mark. While, “the words of a gossip are like tasty bits of food. People like to gobble them up” (Proverbs 18:8), those nuggets of scandal lead to indigestion and infection. Besides, if someone is going say ugly things about another person to you, who knows what they’re going to say about you to the next person?

Rule 4: Play Nice

Remember the things your mother always told you? This is a good time to put them into practice. For example . . .

Don’t interrupt. I’ll just confess right here that this is a personal failing of mine and please, if I’ve ever stepped on your conversational toes, I do apologize. I really do not think my comments are more important than yours, I just get excited and want to chime in. Nevertheless, it’s rude and I’m sorry.

Don’t overshare. In the film 50/50 the main character attempts to pick up girls by playing the sympathy card, but as he quickly learns, beginning a conversation “I have cancer” is a nonstarter. Some things are best saved for your mom, therapist, or BFF. Too much too soon is just awkward for everyone.

Do recognize that no matter what you do, some people aren’t going to play. Most likely it has nothing to do with you. Some people will be rude, possibly even downright offensive. You don’t have to keep talking to them, but try not to respond in kind. It won’t do any good and may do immeasurable harm.

If you have a less-than-positive experience, shake it off and get back in the game. Have fun out there and remember—in the conversation game, everyone can be a winner!


Susan Ellingburg is a natural-born Texan who sings at every opportunity, reads as much as possible, and cherishes every day she gets to spend with friends. She's a serious foodie and not-so-serious gardener who is determined not to let being single stand in the way of living an amazing life. Read Susan's blog at