Every Wednesday is Tip Day.
This Wednesday: Tips…for making conversation.
Making polite conversation can be tough.
“So where do you live?”
“Chelsea.”
“Really. I live on the upper east side.”
“Great…”
Painful silence.
If, like me, out of shyness or boredom, you sometimes find yourself making several trips to the bathroom during a cocktail party, or desperately wishing that dessert were already cleared away, or searching your mind for anything to say while you’re stuck in a situation with a stranger, here are some strategies to try:
Comment on a topic common to both of you: the food, the room, the occasion, the weather.
Ask open questions that can’t be answered with a single word, and after the person answers, don’t answer the same question about yourself, but follow up on what he or she has said.
Fine, you say, but what are some examples of open questions? Try these:
“What’s keeping you busy these days?” This is a good question if you’re talking to a person who doesn’t have an office job. It’s also helpful because it allows people to choose their focus (work, volunteer, family, hobby)—preferable to the inevitable “How’s work?”
A variant: “What are you working on these days?” This is a useful dodge if you ought to know what the person does for a living, but can’t remember.
“I didn’t get a chance to catch the news today. Did I miss anything interesting?”
“What brings you to this event?” or “How do you know our host?”
“What newspapers and magazines do you subscribe to? What internet sites do you visit regularly?” This question often reveals a hidden passion.
If you ask or are asked “Where are you from?” an interesting and natural follow-up question is, “What would your life be like if you still lived there?”
Personally, I’m annoyed when people automatically steer the conversation to kids. But an interesting question on this topic is “Have you decided to do anything very differently from the way you were raised?”
A friend of mine asks a very provocative question: “Tell me something about yourself that most other people don’t know.” Intriguing, but I’ve never dared to do it.
Now, what to do if the conversation is just not working? Try admitting it! “We’re really working hard, aren’t we?” or “It’s frustrating—I’m sure we have interests in common, but we’re having a hard time finding them.” Clearly this is a desperate measure, but sometimes it works
.
But if I’m bored by a conversation, I admonish myself to try harder by remembering the line from La Rochefoucald: We are always bored by those whom we bore.

