Go Beyond The Literal

If this chapter has one lesson so far, it’s to stop taking every statement, question, or quip at face value. Stop taking them literally, and you’ll find yourself in interesting conversation far more often. This means that you should be able to find multiple meanings behind a simple statement or question, but it requires going into a conversation with a completely different mindset.

It’s a mindset of playing, exploration, and initiating jokes and humor. Most conversations you’ll find yourself in on a daily basis are merely exchanges of information—these are face-value conversations that are mostly boring and don’t build rapport very well.

I know this might still across as abstract, but here’s what it looks like when someone is stuck in literal mode, and can’t look beyond face value in a statement or question. Note that these are four separate examples, and the bolded statements are following the literal path.

“So I spent a fortune at the Apple store today.”

“How much?”

“He plays guitar like a deity.”

“What song did he play?”

“Last night’s dinner made my taste buds cry.”

“Where did you eat?”

“I quite enjoyed that speech.”

“Me too, it was so informative.”

These might seem like natural follow-up questions, and they are, but there are multiple ways of answering these remarks. The comments above happen to be ones that are very literal and taking the topic at face value. Again, that’s going to strand you in boring small talk city.

When someone makes a statement like that, it’s a subtle invitation to engage on something interesting, and it’s also a sign that they don’t necessarily want to talk about the literal topic itself. They want to talk about the emotions involved, and they are open to engaging in a joke on it. Once you’ve identified this emotion, make a remark that either misconstrues it to an absurd degree, or use a story that involves you and exaggerates that emotion. They’ve initiated a joke with you, and whether or not you take a literal stance on it, you do have the option to continue the joke.

When you stay literal, you miss opportunities for witty banter all day. People subconsciously initiate jokes with you, and you can initiate jokes with people in the same way. With some practice, you’ll get better at not only recognizing good openings for banter, but creating ones out of seemingly ordinary statements.

How might we reply to those statements in a way that steps into a joke or humorous context? All you’re doing is following the other person’s lead and going with the flow.

“So I spent a fortune at the Apple store today.”

“It’s so expensive there I had to sell a kidney to buy my new phone.”

“He plays guitar like a deity.”

“More Buddha style, or would you say Ganesha style?”

“Last night’s dinner made my taste buds cry.”

“At least you didn’t have to eat your own cooking. I made that mistake once.”

“I quite enjoyed that speech.” [Suppose that the speech’s topic was horse breeding.]

“Me too, seems like the money is in horses, isn’t it? What would we name our horse?”

So what did we do there to make those responses flow and become an entry to witty banter? We just gave responses that weren’t literal, and that stayed 100 percent with the tone and flow of the statements made.

Our comments weren’t forced and didn’t appear like making a joke outright, and that’s a small but important difference here. We took an invitation to a joke and initiated it, versus actually making a joke.

Jokes have strict structures—setup, context, punch line, and laughter. It’s usually pretty obvious when someone is telling a joke, even in normal conversation. That means there’s normally a specific time for you to laugh—which is hard to do if the joke isn’t funny. Initiating and inviting someone to a joke doesn’t create that problem.

All you have to do is practice thinking outside of the box. A key skill underlying this is the art of misconstruing.

The Art of Misconstruing

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Some of the funniest situations I’ve seen in both movies and real life have come from simple misunderstandings.

Bob misunderstood what a proctologist did and scheduled four appointments, or Jenny misunderstood that the generic name for a painkiller is an analgesic, and is not pronounced nor administered the way she thought it was. Which one of those was from real life and which was from a movie? Well, both were from real life.

Those are instances of lightning caught in a bottle. Wouldn’t it be great to create those moments when you want? You can take the lead instead of waiting for an opportunity to arise and essentially relying upon luck.

Misunderstanding and misinterpretation are great sources of humor because you play with two sets of expectations and operate in the gray area between them. Generally, the thing being misconstrued is fairly mundane, and the other person is most likely expecting a dry reply to their statement. Instead, what they’re offered is something they hadn’t considered, which piques their curiosity and makes them appreciate your wit.

Sometimes you have to be intentional about setting up these misunderstandings yourself, and that is the Art of Misconstruing: misunderstanding people in an intentional manner to bring about a comical situation.

In other words, playing dumb or confused and taking an entirely different meaning from what someone has said on purpose. It’s one of the easiest and quickest ways to bring the conversation to a playful nature and break the mold of small talk.

Think of it as a transition from a boring topic into a more engaging conversation. Whatever perspective you take, it’s simply a shift toward both parties enjoying themselves more.

The misconstruing tactic requires you to stay in character for a split second while you do it. Strangely and counter-intuitively, this requires people to believe for a split second that you truly mean what you say. Otherwise, you convey mixed messages, and your words don’t match up with the rest of your non-verbal or verbal delivery.

After that split second has passed, it will become obvious through your words and your delivery that you are making a joke. A wide, mischievous smile is the best giveaway for banter.

Here’s a simplified example of misconstruing: when someone says “I like cats,” you might reply with, “To EAT?” Pair your words with a shocked look on your face and eyes wide open. That’s the character you are trying to convey.

You’ve misconstrued the other person by not picking up on their context or intent. Imagine how a foreigner might interpret those words because of a weak grasp of the English language. Where does the conversation go from there?

They’ll likely join the banter with you and agree, such as “Yeah, but only stray cats. The domesticated ones are too fat.”

Here’s another example of how one of my friends used intentional misconstruing in a conversation. One time during a camping trip, I was amazed at a peculiar insect that had landed on my leg and I exclaimed, “What is this? I’ve never seen anything like this before.” My friend leaned in closer to inspect what I was examining, then declared, “Yeah, that’s a leg.” My other friends who witnessed the scenario then also started examining their hands, arms, and feet while acting amazed as they uttered, “Ooh, what is this? I’ve never seen anything like this, have you?”

My friends misconstrued my fascination with the unique insect on purpose and reacted as if I had declared sudden astonishment of my true subject’s backdrop, i.e. a boring, regular leg.

Misconstruing is one of the most common ways of creating a humorous situation. It is the basis of many jokes because it’s easy to take a situation and steer it in whatever direction you want. It allows you to initiate a joke with in most social situations.

It also helps you break out of typical, boring topics. By simply choosing to misconstrue, you can inject whatever perspective you want into a conversation at any point.

This technique is freeing and empowering! It doesn’t get old and it can go a long way in adding life to otherwise generic or boring conversations.

What are some ways to misconstrue in a funny way?

Exaggerated Conclusion

This is where you misconstrue what someone says and take it to the extreme conclusion.

You exaggerate what they say to an exponential degree. If someone actually said X, you would pretend that they said X multiplied by one hundred and react accordingly.

For example, when someone says “I love my television,” you might reply, “So do your parents know that you guys are living together before marriage?”

Instead of saying “I agree,” or coming up with a statement in the same vein, or at the same intensity as the original statement, take the original statement, blow it out of proportion and put it in a different context.

If somebody says a politician has a good point, a really funny exaggeration would be "Yes, he is the epitome of this country’s political evolution, let’s use him for breeding.” Notice that the way this statement is delivered will make a huge difference to the way it’s received. Even a minimally mocking tone makes this line appear like an overly extreme reaction. But a playful demeanor will earn you a much more positive response. Though it might be tempting to stay away from jokes about controversial topics like politics, they are often the ones that have the most impact.

To summarize, misconstruing is all about blowing up somebody’s statement to an absurd and exaggerated form.

Here are some more examples:

Say someone comments, “That coffee was terrible!” You could reply, “I agree, my car’s battery water is tastier.”

When somebody laments, “My handwriting is horrible,” you can poke fun on the person by responding “Yes, deciphering hieroglyphs would be an easier task than trying to make out your script.”

In reply to the line, “I’ll call you when I get home,” you can say, “I didn’t know it’s possible to make a phone call from Mars, but okay.”

What makes this form of misconstruing powerful is the absurdity of your exaggeration. It should be so absurd that it is no longer believable. That’s where the humor comes from. A lot of people screw up this technique when they don’t exaggerate enough. They fall somewhere in between the truly funny exaggerated form and the generic statement.

Say someone declares, “I’m so hungry, I’m for sure gonna eat a lot in this meal.” If you reply with “Yeah, it’s no doubt you can finish off this whole pie by yourself once you get to it. Don’t worry, the rest of us can find something else to eat,” you’re not exaggerating enough to make your quip hilarious. What’s worse, if that person is actually able to eat the pie by themselves, then you will have created an awkward situation likely to make the other party feel conscious about how much they actually eat.

Here’s another bad example. Imagine someone comments, “I haven’t had time to shop for new clothes recently.” If you respond by saying, “Oh, that’s why you’ve been dressing so shabbily lately,” that person is not likely to take your criticism as good-natured ribbing, even if that was your original intention. The problem here is that you haven’t exaggerated your response enough to make it obvious you’re both supposed to be laughing, and not that you’re the only one laughing at them.

Instead of packing in a punch, the above replies fall flat and are likely to elicit raised eyebrows at best or insulted feelings at worst. So if you want to use this technique, make sure you really blow it up and make it out of this world. That way, it’s obvious to the other person that you are making fun and they can laugh along.

Imagine if for the above bad scenarios, you would instead respond with, “Yes, I know it was really you who finished off the gingerbread house in Hansel and Gretel” and “Oh, that’s why you’ve been looking like a homeless person these days.” Those sound easier to laugh to with the other person, don’t they? Nevertheless, remember to refrain from picking things to exaggerate that the other person might genuinely care about.