The Conversation Rulebook, Part 1

This is scarier than most actual conversations.

We’ve all been there before – you’re in a place, such as an airplane, an elevator, or even your own office, when you encounter another human being. Perhaps you’ve wondered in these situations, as I often have, What’s my next move? Do I say something to them? If so, what should I say? Wouldn’t it be easier for me to just kill this person?

The answer, obviously, is yes – killing the other person and either successfully hiding the body and deflecting all guilt or being caught, prosecuted, and sent to jail are both far simpler and more pleasant options than having a conversation, but unfortunately neither choice is terribly feasible if you’ve got any other plans for that evening or the rest of your natural life. Sadly, there’s no way around it: You’re going to have to have a conversation.

Now, the vast majority of the conversations you have won’t be terribly enjoyable or interesting for one or even both involved parties. On the rare occasion that a conversation is enjoyable, it’s because both parties have had the proper training.

Right now you may be asking, ”What is this proper conversational training, Truman, and who do I know who’s qualified to give it to me? Is it you? And if so, how are you qualified to give advice of this nature?”

Well, since you asked, I am qualified to train you on how to have a conversation, and my qualifications come from the fact that due to my conservative, clean-cut, highly approachable appearance I am a frequent target for terrible conversationalists, and as such I’ve had ample opportunity to learn from their mistakes.

So sit back, relax, and gratefully absorb the TRUMAN CAPPS DR. PEPPER TEN CONVERSATION RULEBOOK!*

*I sold a sponsorship to make ends meet.


Look, I’m sorry, but you had to find out sometime – please don’t take this the wrong way! It’s not me talking, it’s science. Unless the person you’re talking to is one of your good friends, the 20 minute story you’re telling about your decision to drop out of the biology department at the University of Southern Maine and turn your theater minor into a major is of no interest to them whatsoever.

For what it’s worth, it’s not you – it’s human nature. Why are some movies better than others? Because in the good movies, you can empathize with the characters, so you wind up rooting for them and wanting them to succeed. In bad movies, poorly drawn characters feel like strangers and you don’t give a shit about what happens to them, so as far as you’re concerned, the story has no stakes.

And as usual, what applies to movies applies directly to real life – if the person you’re talking to doesn’t know you very well, they’re not going to be interested in your story because they’re not interested in you. The story of how you changed majors may seem like Animal House meets The Graduate in your head, but depending how well you know the listener, to them it could easily be The Room.

Of course, there are rare occasions when someone can have a story so interesting that it trumps these rules – to clarify, I’ve made the following chart, on which any point south of the Axis Of Lame represents a bored listener and any point north represents an engaged listener.

As you can see, really the only 100% surefire way to tell an interesting story is to have it be about the listener, while literally nobody, including the person with whom you’re romantically engaged, gives a shit about your ski trip.

Before every conversation, take a second to assess what you’re about to say versus how well you know the person you’re talking to. Chances are, they don’t care. What should you talk about, then? Well, that’s easy, because…


Remember how nobody finds your stories interesting? That’s largely because they’re comparing your stories to their stories, and theirs are so much better than the inane shit you’re talking about. Every second that someone is listening to one of your stories that falls below the Axis Of Lame is a second that they’re secretly hating you for not asking them to tell their awesome stories.

Objectively, of course, there’s no way that the other person’s stories are all more interesting than yours unless you’re talking to Teddy Roosevelt.* The other person just thinks their stories are better because they’re wholeheartedly invested in the protagonist and empathize with every single one of his or her actions.

*And if you are having a conversation with Teddy Roosevelt, what the fuck are you doing talking!? Quit flapping your lips and listen. Any given hour of his life is several times as exciting than the entire fourth season of 24.

But if you don’t want to come off as a self absorbed douche, what do you do? You ask the listener questions to elicit their own stories. Yes, of course you don’t care. Of course your stories are better.

Right now, though, you’re playing the long game. The more you listen to the other person, the more likely they are to want to talk to you again, meaning you’ll become better acquaintances, meaning you’ll soon be able to captivate this person with any of your own stories provided they’re not about fucking skiing. Think of your current boredom as an investment in the future excitement of telling this person a story about a dream you had!