The Witty Comeback Machine

The Witty Comeback Machine

As a former fat kid, I used to have a fairly extensive library of witty comebacks for those charming people who liked to point out that I was, indeed, fat.

Or that they couldn’t ride in a car with me for fear of it tipping over.

Or that I was so big my Polo brand sport shirt had a real horse on it (this one was pretty clever, I’ll admit).

Mind you, I wasn’t really that large—just twenty pounds overweight. At some point, however, I developed one type of comeback that never failed to either shut people up, or bring them to my side through laughter.

Were you also aware that my Polo Sport shirt can be used as a parachute?

You’d better put six extra wheels on your car for me.

Watch out, I’m going to sit on you and suffocate you.

What exactly are these lines composed of, and why are they so effective?

Becoming a witty comeback machine is easier than you think, and it’s one of the best conversational tactics you can learn. This technique doesn’t only rear its head when dealing with insults—it is widely applicable once you learn the framework. If it’s a bad situation, a witty comeback can diffuse the tension and bring emotional levels back to normal. If it’s a good situation, then a witty comeback can make it even better.

Whatever the situation, mastering witty comebacks will earn you the respect of other people for your clever wit. It just takes one line—and the shorter and punchier, the better and more effective. The longer a comeback, the less the punch it carries.

A witty comeback does many things simultaneously. It makes people laugh and disarms them while allowing you to appear smart, insightful, and mentally quick. It also shows people that you’re easygoing and can handle hurdles that come your way. When most people are insulted or made fun of, they either respond with anger or try to play it down. With a witty comeback, you’re showing others that such remarks don’t faze you nearly as much as they would someone else.

Before I get ahead of myself, let me define what a witty comeback is.

Wit is essentially spontaneous creativity. You take a topic or statement and see it from a different angle in a way that is relatable, yet novel. That’s why I kind of enjoyed the aforementioned joke about the Polo Sport shirt, even if it was at my expense.

Witty comebacks can be hurtful, serious, or completely light and harmless. It all depends on you. You can be joking and playing around, or you can wield a sharp sword. You can also do both. If you’re being bullied like I often was, a witty comeback can be both funny, as well as signal to others that they should back off.

What's tricky about wit is that something that may be funny and completely harmless to you can be destructive or hurtful to someone else. You have to know where that fine line is and you have to know how to straddle it. Often, it comes down to the way you respond with a comeback and the words you choose to do so. The same thing said with a serious or smiling expression will be perceived differently. Similarly, some words are more likely than others to flare tension. Delivery matters, and if you can master that, you’ll be less likely to be misunderstood.

There are a few tricks to use so that you always have a witty comeback in your pocket ready for launch—instead of twenty minutes after the encounter.

First, when thinking about a witty comeback, don't think generically.

Don't use, "I know you are, but what am I?" or "So is your mom." People judge a witty comeback based on how original it is—remember, it’s spontaneous creativity. Using something that is both generic and not clever is decidedly neither spontaneous nor creative. Don't just use a template-driven witty retort that you've seen in a movie or something that works better in a different context. And don’t use one of the comebacks you thought were hilarious when you were ten. Those don’t work anymore.

Second, don’t act like you can’t take a joke.

Of course, witty comebacks need an initial statement to “come back” to.

The vast majority of the time, people are indeed joking when they say something negative about you in your presence. In a sense, it’s a compliment because they assume you have a sufficient sense of humor and the emotional resiliency to deal with it. The people who aren’t involved in jokes and good-natured ribbing don’t have many friends.

If you let it show that you are angry or hurt, it spoils the playful tone you could otherwise enhance with your witty comeback. Focus on the intent of the person saying the remark; they likely did not mean to hurt you, even if they accidentally ended up doing that.

For example, if someone made a joke about my fatness, and I got visibly angry, they would likely stop… then walk on eggshells around me for days. When someone is uncomfortable with something, they make others uncomfortable as well. If that happens enough times it becomes clear that I don’t have a sense of humor and I let my insecurity infect my relationships. Know where to draw the line.

It’s okay to be the butt of jokes sometimes, but if repeated remarks about an insecurity genuinely bother you, don’t use witty comebacks to undermine your self-esteem. Though it might diffuse any tension, it will make you feel like a doormat. That’s where discussion of boundaries comes into play, and banter is no longer appropriate. But that’s a subject for another book.

Generally, handle the initial negative statement with a wry smirk and with the knowledge that you are about to crush them.

Third, use the right tone.

The best witty comebacks are delivered with 50 percent indifference. When you deliver one with 100 percent excitement and 0 percent indifference, guess what happens? You blow it and the comeback falls flat. Indifference is the correct tone because comebacks are about your attitude—pretend that you are James Bond delivering a witty retort after a failed murder attempt by a villain. Fifty percent indifference also ensures that you aren’t being aggressive or spiteful. It’s far too easy for a bit of bitterness and negativity to slip into your tone.

A witty comeback is the verbal equivalent of judo or aikido—using an opponent’s words against them. If you take that analogy, you need a certain amount of cool to effectively counteract your rival. Witty comebacks take the power away from the insult hurled. However, saying something too excitedly or with the wrong tone betrays that you were affected by the remark, making it harder to appear cool or indifferent.

There are three main types of witty comebacks. None are better than the other. You just need to pick the type you're most comfortable with.

Type #1: Pick apart their words.

Think about the other person’s word choice and quickly analyze whether there is another angle or meaning to those words. An easy approach is to interpret their words as overly literal or outlandish. The key is to interpret them in a way that is favorable to you to make it seem as if they complimented you instead of put you down.

Bob: You are working as slow as a glacier. Pick it up!

You: [focusing on the word glacier] You mean I’m strong and cool under pressure? True.

Your job is made considerably easier when someone uses a simile like Bob did, but in the absence of one, you can focus on the thing they’re putting you down about. To take the same example, let's say Bob said, “You’re working too slowly. Pick it up!”

One way you can respond is by thinking of the benefits of working slowly, leading to a comeback like, “The tortoise always wins the race!” Not only are you calling yourself a tortoise in a playful way, but assuring Bob that your rate of work will have benefits that he would appreciate.

Type #2: Agree and amplify.

For this tactic, take your cue from the way the cartoon character SpongeBob SquarePants handled Mr. Krabs’ mocking words, “That hat makes you look like a girl.” Instead of feeling hurt and handing over the hat like Mr. Krabs would like, SpongeBob batted his eyelashes and said in a sweet voice, “Am I a pretty girl?”

The idea here is to agree with whatever the insult was, and then add to it in an absurd way. You amplify the initial sentiment to a degree that is ridiculous. This was my go-to technique to deflect jokes about my weight.

If you forgot from earlier in this chapter:

Were you also aware that my Polo Sport shirt can be used as a parachute?

You’d better put six extra wheels on your car for me!

For another example:

Bob: Your cooking was pretty terrible last time.

You: You’re lucky you didn’t stay until the end of the night, we all got our stomachs pumped. Dinner at my place later tonight?

Type #3: Use an outlandish comparison.

Actually, this is related to the prior point, and it brings the conversation into a different sphere and makes both people laugh at the weird, outlandish imagery. What makes this work is that the comparison, although extreme, is still somewhat realistic. To use the same framework, you’re amplifying (to yourself or the other person) with an analogy here.

Bob: Your cooking was pretty terrible last time.

You: True, I should have used the eggs as hockey pucks, right?

Witty comebacks are the lifeblood of witty banter, which is being able to take an element of what was said and attack it from a different angle without missing a beat. You should be able to see how this can play out. They are instant retorts that aren’t hostile or combative, while addressing something gracefully. And this is a skill that you can use in many ways, as you are about to read in the next section.

Word of caution: Fight the temptation to rattle your comebacks off one after the other. Again, you have to remember that your goal is to get people to like you. You're not trying to prove a point or protect your pride.

You're just trying to keep your conversation from hitting awkward spots and dying a premature death. Firing off one comeback after another can kill whatever level of comfort you've managed to create because you will appear insecure, defensive, and full of bluster.