Here’s How to Craft the Perfect Comeback

“My dear, you are ugly. But tomorrow I shall be sober and you will still be ugly.”

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In a 1997 episode of Seinfeld called “The Comeback,” George Costanza is merrily stuffing himself with free shrimp at a meeting. His coworker mocks him: “Hey, George, the ocean called. They’re running out of shrimp.” George sits there humiliated as laughter fills the room, his mind searching frantically for the perfect riposte. It’s only later, on the drive home, that he thinks of the comeback. But the moment has passed. (That may have been a good thing, since George’s epiphany was, predictably, mediocre: “Well, the jerk store called and they’re running out of you!”)

The disappointing experience of thinking of the perfect response too late—l’esprit de l’escalier, or “staircase wit”—was identified by French philosopher Denis Diderot. He was so overwhelmed by an argument at a party that he could think clearly again only once he’d gotten to the bottom of the stairs.

We’ve all been there, envying those who are quicker on their feet. So we decided to ask people who rely on witty rejoinders for a living—improv performers, freestyle rappers, and others—how anyone might seize the opportunity for clever retorts in everyday life. Here are their insights.

Don’t think too much

In improv, the funniest responses occur on the spur of the moment, says Douglas Widick, a performer who trained with Chicago’s Upright Citizens Brigade. Don’t worry about crafting the perfect reply. “It’s about letting go of the need to judge ourselves,” says Belina Raffy, CEO of the ­Berlin-based company Maffick, which uses improv skills in business. “Especially if we are operating from the desire to make each other look good—a key tenet of improvisation.” Not every riposte will be a gem, but some will hit their mark.

Listen before you leap

Still, spend some time considering the argument that your sparring partner is laying out. Your retort may be more accurate and therefore more successful, says Jim Tosone, a business technology executive turned improv coach who developed the Improv Means Business program.

Put a few in the bank

Some of history’s most skilled comeback artists stored witticisms for later use and were able to pull them out of their memory at the critical time. Winston Churchill was known for his comebacks, but Tim Riley, director and chief curator at the National Churchill Museum in Fulton, Missouri, says that many of his burns were borrowed.

One of his most famous lines was in response to a jab from politician Bessie Braddock: “Winston, you are drunk.” The prime minister replied, “Bessie, my dear, you are ugly. But tomorrow I shall be sober and you will still be ugly.”

Riley says a line similar to the above was actually copied from a W. C. Fields movie (which likely lifted it from a dig made by a House of Commons member). Nevertheless, it took quick thinking to pull it out at the right moment. “It was an off-the-cuff recall of something he had synthesized, composed earlier, and that he was waiting to perform,” Riley says.

Don’t obsess over a misfire

The high you get from spearing your opponent with a verbal thrust can be shadowed by its opposite: the low that comes from blurting out a lame response.

If it doesn’t go your way, the rapper iLLspokinn advises brushing off your missed opportunity rather than dwelling on your error: “It can be toxic to hold on to it,” he says.

Delays can be fatal

When you are conversing via text or social media, you get a few extra minutes to think through your responses. That could improve the quality of your zinger, but don’t deliberate for too long. Replies lose their punch after a day or so. “Speed is integral to wit, whether in real life or screen life,” says Scott Talan, a social media expert at American University.

In fact, some companies have learned to deploy quick-witted social media retorts as a marketing strategy. Wendy’s Twitter account has become so well-known for its sassy replies that some users try to intentionally provoke it, almost like a battle of the wits. “Bet you won’t follow me @Wendys,” a user challenged. “You won that bet,” Wendy’s immediately shot back.

George Costanza also learned that he who hesitates often loses in the comeback game. He meets his shrimp nemesis again at a business meeting and takes the opportunity to use his old “the jerk store called and they’re running out of you” line. Too late! The guy already has a comeback for the comeback: “What’s the difference?” he asks with a smile. “You’re their all-time bestseller.” Now, check out some of Shakespeare’s best insults that still sting today.

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Originally Published in Reader's Digest