Flow Like a River

You know those people who always have something clever or witty to say? Ever wonder how they cultivated this seemingly magical quality? If you have, know that being witty is much easier than you might think, and you don’t have to be born with the gift of gab. By following certain tricks and techniques, you can develop the same persona yourself. The first element to tackle is conversational flow and keeping a back and forth going.

The first trick is to never speak in absolutes. Eliminate questions and statements involving words like favorite, absolute, only, worst, etc., from your vocabulary. If you ask someone “what’s your absolute favorite movie?”, you are actually asking a pressurized question that introduces pause and destroys flow. Instead, always generalize your questions by putting boundaries and constraints on them. This doesn’t require as much thought from your conversational partner, allowing them to simply answer a question with a range of responses instead of being caught looking for the one “right” answer.

Flow Like a River

When I was growing up, my favorite television show wasn’t one of the conventional cartoons like G.I. Joe or X-Men.

People tend to assume I had a sad childhood when I say this, but it’s not that I was deprived of cartoons by draconian parents.

Cartoons typically aired early on weekend mornings, which meant you had to go to bed early the night before to get up in time for the shows. I always overslept, so I never saw the cartoons. But why was I oversleeping?

Because I always stayed up late to watch David Letterman, the host of The Late Show with David Letterman for over thirty years.

I didn’t know it at the time, but of all the late-night television hosts, David Letterman was one of the most legendary. I just watched because I thought his Top Ten Lists were funny in an adult way that I couldn’t quite understand. He would talk about economics, and though I didn’t quite grasp the specifics, I knew the general feeling he was trying to convey and would laugh when my older brother laughed. I didn’t get many of the digs and jabs he would take at guests, but I saw a specific tone and facial expression and went along with it.

It wasn’t until I grew older that I started to really notice the subtle tactics Letterman used to energize boring guests and turn dull segments into funny ones.

In particular, it was his ability to banter wittily with his band leader, guests, and even himself in a self-deferential way that was the engine of the show. Letterman was like Teflon—he was so smooth and slick, he could always go with the flow, nothing ever seemed to faze him, and he was never without a witty quip or two.

It seemed as if he could joke about anything, and his jokes never seemed forced or out of place. It didn’t work as well for me when I tried emulating Letterman the next day at school, but it did get me thinking about what constituted a person who was conversationally so slick and smooth, so able to let anything negative roll right off of them, that they were Teflon.

How can you not just always have something to say, but always have something witty and clever to say? Witty banter is many things at once—disarming, charming, intelligent, and quick. It almost sounds impossible when you think about the effects it has on others.

But banter is a skill just like pitching a baseball or underwater basket weaving. Once you know the patterns and building blocks, you can practice and improve them. And once you practice enough, they become instinct and habit that come easily to you because they are second nature.

This book is going to be one of your best tools for becoming adept at the kind of witty banter that will help you succeed in social situations.

You’ll learn what makes a statement clever, how to deliver it quickly, and how it all comes together to make you someone of note and worth talking to. We’ll start with techniques for flowing conversation. You can’t achieve wit if you’re caught in awkward silence!

Never Speak in Absolutes

Don’t mind the irony in the section title (using the word “never” to warn against using the word “never”). But I stand by it.

One of the most common ways to kill any kind of conversational flow, regardless of how interesting the topic might be, is when one of the speakers reduces their questions to absolutes. Absolutes are tough to answer and sometimes even to contemplate, as you’re about to read.

I was once set upon with absolute questions by a cousin at a family gathering. He was eight at the time, so it was excusable, but I’ll never forget how it felt when someone kept talking to me in absolutes.

He asked me what my favorite ice cream flavor in the entire world was. I thought for a while and said rocky road. He started howling that I had horrible taste and demanding to know how I could forget Neapolitan. Next, he asked me what my favorite television show of all time was, and so on. It was a tortuous conversation full of long pauses and subsequent judgment of my tastes and opinions.

Years later, he would discover that he was lactose intolerant, so the joke was ultimately on him.

There are more common absolute questions that you’ll come across in your daily life, but the point is that they are difficult to answer off the cuff, because doing so requires some indexing, thought, and decision-making. That’s a lot to ask within the flow of a casual conversation. Whatever train of thought you previously had must first be derailed in order to answer this question. And then where does that leave you?

Absolute questions usually appear very innocent. For example, “What’s your number-one favorite movie of all time?” That’s a pretty innocuous question on its face, but it is an absolute question. It puts people on the spot and usually leads them to answer with, “Oh, I’m not sure, let me think about that,” then never finish their thought, which of course then derails your conversation. You might as well ask them to solve an arithmetic problem. For instance:

“What’s your favorite band?”

• "I don't know, let me think about that." 
• "Hmm... I'm not sure. What's yours?"
•  “I’ll get back to you on that. I have no idea!”

The problem here is that you’re asking an absolute question, which begs for an absolute answer. When you do that, you offer the other person no wiggle room and, worse, you’ve given them the difficult task of coming up with a definitive answer to your question. What is my favorite movie?

Your question will fail, the conversation will stall, and you may never get back on track. Most people like to tell the truth, and if they are tasked with something that requires them to really dig deep and come up with an honest answer to an absolute question, they will try to complete this difficult task. A small percentage of people will be able to come up with something quickly, and another small percentage of people will give a response that vaguely satisfies your question. About 1 percent of people will have these things on the tip of their tongues for whatever reason, and the rest won’t know how to respond.

The bottom line: it sounds simplistic and unimportant, but using absolute statements, answers, and questions makes conversation difficult and leads to premature death. (Of the conversation, not the people involved.)

A primary rule of thumb for conversation is to make it easy for the other person, which of course makes it easy for you. Moreover, it’s obvious that no one wants to carry the burden of a conversation. No one wants to fill in all the blanks, prevent all the silences, and direct the entire discussion. If your line of questioning ends up putting the burden on the other person as if it were a job interview, that other person is either going to disengage quickly, or bounce everything back to you with a “What about you?” response. Then you’re going to have to deal with the mess you’ve created.

When you ask somebody “What’s your absolute favorite (fill in the blank)?” you’re putting them on the spot. You’re really asking them to dig down and think, and worse, to commit to something they may not have strong feelings about. They’ll likely just say the first name that pops up in their mind and pass it off as their favorite because they don’t want to take too long to respond. This might be fine once or twice, but imagine how they will feel after a while if every question you ask is along similar lines.

They will start to feel as if they’re at a job interview or in an interrogation instead of a pleasant social interaction. They will feel as if they’re being put in a position of carrying the burden of the conversation—a responsibility they don’t particularly want. It’s very tiring.

So what’s the solution here? Let’s see how we can modify those absolute questions into questions that are far easier to answer and won’t stymie people or stall the exchange.

Put boundaries around the question and make it non-absolute and people will be able to answer the question far more easily.

A common absolute question might be “What’s your favorite movie?” Transform this question into:

• What are your top few movies?
• What are some good movies you’ve seen recently? 
• Any movies you can recommend? 
• Do you prefer to watch television or movies?

These questions go from more specific to broader and easier to answer. By doing this, you’re not tying somebody into an absolute commitment or an absolute statement. There are several qualifiers here based on number or time, and when people don’t feel pressured to come up with an absolute answer, they can relax and answer just about anything.

Moreover, open-ended questions like these give you enough material to respond well. If someone names a movie as their favorite, but you haven’t seen it, you’re likely headed for an awkward dead-end in the conversation. On the other hand, if someone names several movies, it gives you a better chance of being able to connect at least one of them to your own favorites and move forward with the conversation.

Here’s another example. Imagine asking someone, “What’s your ultimate dream vacation?” This question would likely put the person in a conundrum as to how they should answer. Do they decide based on how appealing the destination is? Do they put more weight on the place’s sites or its culture? Do they need to mention time of the year, travel companions, budget considerations?

The point is, that single question touches several matters at once and would easily overwhelm the person you’re talking with, especially if you’re only aiming to achieve an easy, casual conversation. A key point to keep in mind is that if your question branches out to smaller points, it would do better posed in terms of its “branches” rather than imposed as an entire “tree.”

So instead of expecting someone to decide on their ultimate dream vacation on the spot, consider moving your conversation along with the following more manageable prompts:
• What cool vacation places have you looked up recently?
• Any beach destinations you would recommend for a summer trip?
• Would you prefer to travel with friends or with your family?
• Would you rather go on a cruise or a road trip?

As you can see, putting boundaries around a question helps ease the pressure of giving out the “best” response among a multitude of possibilities when faced with an absolute question. Each qualifier and boundary makes the question easier to answer, and also stirs the responder’s thought process to provide a more interesting and nuanced answer.

There’s an additional benefit to asking people easier, more general questions. It allows them to hedge their statements in a way that makes them feel safe. There isn’t an opportunity to judge taste or opinion. Some of us may never think about this, while others of us are constantly consumed by avoiding judgment.

If I were to say, “I think Forrest Gump is the greatest movie of all time,” I imagine someone could judge me for my taste. It’s a fairly black and white statement, so either you agree or disagree. It’s a stance, and with each stance, there is an anti-stance.

However, if instead you said, “I saw Forrest Gump recently and it was pretty good,” you still contribute to the topic of movies with substance, yet it’s unlikely anyone will judge you unless they truly hate Tom Hanks and feel-good movies. Again, this avoidance of judgment may seem unimportant, but it is assuredly not to some people, especially those who suffer from types of social anxiety.

A good conversationalist’s talent is making sure the other person is comfortable. With comfort comes openness, then comes rapport, then comes an environment ripe for witty banter. We can do this by remembering to ask broader questions that aren’t looking for a right or wrong answer.

Who knows what the best movie is? This is never the point. The best questions are subjective, and your goal should be to keep conversational flow and create an environment of comfort and familiarity.

Avoiding absolute questions means sharpening your question-asking skills. It forces you to stand in the other person’s shoes and see things from their (conversational) perspective. You have to take into consideration how the conversation feels from their side and not just throw out a question that happens to be stuck in your head, that ends up being extremely difficult to answer. Flow doesn’t happen on accident.

Now, what if you find yourself on the receiving end of an absolute question? Should that signal the death of the conversation?

Not necessarily. You can also learn how to answer absolute questions that you’re asked. We know now that absolute questions can be difficult to navigate, so you should be able to answer them more generally in a way that can contribute to flow.

Say someone asks you that question about your ultimate dream vacation. Instead of getting stumped, recall that such a question has different facets and you don’t need to cover all of them in your response. You may choose to answer just one specific aspect of it, for instance by responding:
• I haven’t really thought of it, but I’ve seen a feature on Bora Bora and it looks pretty interesting.
• Well, for this winter, some of those ski resorts seem inviting.
• Anywhere with my two best friends would be a blast!

Remember, place boundaries on your answers, and this often means answering a slightly different question than was asked. It’s all too easy when you understand that people aren’t seeking an accurate answer or stance, they just want to move things along.