Gentleman Scholar

How to Rescue a Boring Conversation

Alternatives to the deadly “What do you do?”

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When you’re trying to have a conversation with someone you just met, and the conversation is not getting off the ground, what’s a good topic or question to bring up to try to get some momentum going? Sometimes I find myself talking to people and simply not knowing what to say next, after the usual small-talk topics have been exhausted.

Troy Patterson.
Troy Patterson.

Photo by Christina Paige

Thank you for your question.

When next you find yourself in this awkward spot, try a time-tested line: “I’m going to refresh my drink. May I get you anything?” Never fails. Making your way to or from the bar or the fridge, you can allow yourself to get swept up by a warmer current of chitchat and then simply drop off your interlocutor’s drink without picking up the thread. This is how to ditch a bore while earning his appreciation. And if you strike out—if your ploy doesn’t yield an upgrade—at least you and your new acquaintance will have something better to do with your mouths than to timidly grouse about the weather.

I don’t mean to issue a blanket condemnation of meteorological murmurings. One good reason to talk about the weather is that weather is sometimes bad: Shared hatred and mutual disgust make excellent crucibles of connection, as any good demagogue will tell you. Another good reason to shoot the breeze about the breeze is to take the temperature of a stranger’s temperament and to place his station by working through a classically noncontroversial topic. The early stages of a conversation are, consciously and otherwise, about determining your interlocutor’s rank and asserting your own. This is human nature, as you will recognize if you learned the least bit of anthropology in college, whether by listening to lectures, studying your peers at room parties, or eavesdropping on visiting professors’ intrigues while working a job at the faculty club.

Entering a conversation with a stranger, one’s first impulse is to speak in a way that maximizes the potential for romantic enchantment, career advancement, status enhancement, so on. Fears and desires are evident in grammar, diction, vocabulary, and elocution, as Paul Fussell discussed in 1983’s Class: A Guide Through the American Status System. Dismissing Alexis de Tocqueville’s naive belief that this country’s political organization “would largely efface social distinctions in language and verbal style,” Fussell wrote:

Actually, just because the country’s a democracy, class distinctions have developed with greater rigor than elsewhere, and language, far from coalescing into one great central mass without social distinctions, has developed even more egregious class signals than anyone could have expected. There’s really no confusion in either language or society, as ordinary people here are quite aware. Interviewed by sociologists, they indicate that speech is the main way they estimate a stranger’s social class when they first encounter him.

I am going on this detour to mimic the swerve of an engaging conversationalist on a provocative tangent—and also to say that the sooner you consciously acknowledge this truth of casual conversation, the sooner you’ll make peace with it; to remind you that there are steep odds against adults carrying on certain kinds of conversations across class lines; and to remark that it is amusing, when chatting with members of the petite bourgeoisie, to stay on the lookout for the euphemisms and Europeanisms and aspirational ennoblements that distinguish what Fussell calls “the middle-class quest for grandeur and gentility.” What’s the difference between a lawyer and an attorney? The latter, introducing himself as such, believes that the extra syllable confers an extra degree of fancy-schmanciness.

May I trace a reciprocal of the tangent? (As I say—as the Encyclopédie Moderne said—“Conversation is not a regular attack on any particular point, but a ramble at hazard through a spacious garden.”)* “What do you do?” is not a great question. We all resort to it, granted, and it is no longer widely considered crass and vulgar, but it’s a bit dull, and it has a way of taking the bloom off the roses in the garden. “What do you do?” points toward an old sin of American talk. One throughline of Stephen Miller’s 2006 book Conversation: A History of a Declining Art concerns the dreariness of talking about work. In the middle, Miller studies Charles Dickens’ remark that the U.S. “is a place where the pleasures of conversations are rare, mainly because the ‘love of trade’ makes Americans narrowly self-interested” and also quotes Gustave de Beaumont, Tocqueville’s road-trip buddy, noting that “American men are occupied with but one single thing, their business.” Near the end, Miller observes that American advice on conversation has frequently proceeded from the careerist example of Dale Carnegie’s How to Win Friends and Influence People: “Carnegie thinks of conversation as instrumental. The title of the book is misleading. The book is not about winning friends.”

To win a friend—or, at the very least, to gather data that will enrich your appreciation of the human comedy—you should ask something like “What are you excited about?”—which is nice and wide and cheerful. Just thinking about tomorrow clears away the cobwebs, you know. To say, “What are you looking forward to this fall?” invites the other party to remark on enthusiasms and travel plans and hopes and dreams, and it allows him his choice of a momentous or delightfully trivial answer. He looks into the future while you look into his eyes. It will be your duty, in this joint improvisation, to ask good follow-up questions. It will be your pleasure to reveal something of yourself—the slant of your curiosity, the cast of your mind—by drawing him out and encouraging a self-portrait.

Remember: Within many a superficially boring person, there is an interesting person waiting, all too patiently, to get out. Sometimes, to access the inner person, you have to probe as much as tact will allow—or even to prod, in the manner of a reporter or a shrink or a hiker poking a forest-dwelling furball with a stick to see if it’s alive. But if you do this, you will have become an active, attractive listener. Cultivate the rare talent for “eloquent silence” described, in 1842, by one Orlando Sabertash, author of one of the countless guides titled The Art of Conversation:

[The] man who listens with easy attention to the saddest prosing,—who delights the speaker with the impression his words seem to produce: this man, who only throws in an assenting smile, puts a single, well-timed question, or expresses a doubt, certain of being easily removed,—is the man of real genius, a sort of nonpareil in fact, and the rarest of all apparitions in modern society.

*Correction, Aug. 7, 2014: This article originally misspelled Encyclopédie Moderne. (Return.)