How to Come Across As Devilishly Clever
  • “If you want to come across as devilishly clever,” said the beautiful English professor, “all the degrees and all the accolades in the world pale in comparison to this one thing: learn to use ‘who’ and ‘whom’ correctly.”

    This, she said, will signal intelligence more than anything.

    Failing that, I say, don’t use “whom” at all but stick exclusively with “who.”


    Because nothing makes you sound less clever than misusing the word “whom.”

    “Our server,” somebody once wrote, in a letter of complaint, when I was bartending, “whom never gave us her name …”

    Uh, okay. How will you ever take that letter seriously?

    Here are several more methods by which you can increase your cleverness:

    Cultivate wordplay.

    Because your words are your thoughts verbalized, it is largely your words that make you clever. Seek, therefore, to describe things in a colorful and unorthodox manner:

    “Hey, bartender, what’s that mint-green bottle that stands out so clearly among the multicolored glass?”

    You see?

    That’s good language.

    Be persuasive.


    Learn facts and remember them.

    Learn also to speak clearly and concisely, and always avoid jargon. This, without any doubt, is among the most persuasive and universal signs of cleverness there is:

    The more clearly you present something, the more persuasive you are, and those who speak well speak briefly.

    Learn quips, quotes, and anecdotes.

    Learn many of them. Memorize them. Develop a deep well from which to draw so that you’re not just recycling the same three or four or five and sounding like a broken record.

    Don’t use stale anecdotes.

    It always delights a person when she or he hears a new story from an old friend.

    Don’t use stale cliches:

    “My heart was beating like a drum, and when the moment finally came it cut like a knife.”

    Certain cliches, however, are colorful and even encouraged:

    “Sharks? Well that’s a different kettle of fish entirely….”

    This sort of cliche you should embrace and enthusiastically use.

    Think of conversation as a stroll.

    Small talk isn’t about content. It’s about commiseration.

    It’s about making people feel relaxed.

    When you ask someone for the time and you’re told how to build a clock, you’ll not easily move forward.

    When, upon the other hand, you ask for the time, and you’re told:

    “I don’t know. The battery in my phone died — and it is a sad pass indeed when a man like me can’t tell the time without his phone, don’t you agree?” — you’ll likely be put more at ease.

    Small talk, I repeat, isn’t about content. It’s about mood.

    Make your interlocutor relaxed and comfortable, and you’ve gotten off on the correct foot.

    Never make a joke at someone else’s expense for the sake of a laugh.

    “Hey, baldie! Can you turn your head? The glare coming off you is blinding me.”

    It’s tacky, it’s amateurish, and, worst of all, it’s fiercely unfunny.

    Don’t ever ask “What do you do?”

    Instead, say something like:

    “What in life brings you bliss?”

    (“God,” she answered. “I spend virtually all my time at work, and so I’m afraid there’s little time for bliss.” At which point, almost magically, many conversational options have suddenly opened up before you, among which is the fact that you are now — only now — at liberty to ask what it is that occupies her time so.)

    Don’t use big or biggish words that you only partially understand.

    Do cultivate a bigger vocabulary.

    This is easier than you might think. Begin by learning fresher, less common words for standard things.

    Instead of saying, for instance, “You look beautiful tonight,” try:

    “You look particularly radiant this evening.”

    Which, incidentally, I once heard a very kind and clever fellow say to a middle-age woman he knew, though only a little, who had just sat down next to him at the bar, and this woman, I swear to you, was walking on sunshine all night long from that one compliment alone.

    Observe clever people and try to understand precisely what you find clever about them — and then copy that principle.

    The most important thing of all:

    Believe that you can become more clever.

    Because you can.

    Because it’s not how smart or clever you are.

    It’s how smart and clever you want to be.