The Art of Conversation, According to Me


– or –

An Idiot’s Guide to Saying Dumb Things

I’m not what you would call a “people person” (except inasmuch as I am a person and, much like delicious Soylent Green, I am made out of people).  I find that people, in general, are vapid and boring, and I don’t particularly feel the need to waste my precious, precious time hearing them use trite phrases like “people person”  — you can almost hear the air quotes as they say it –, listening to their stories, or hearing about their whiney, self-centered feelings of inadequacy because their mommy didn’t give them a pony when they were growing up or their father sold US nuclear secrets to the USSR and was executed for treason.  I think this, among other things (like my total lack of a license to practice), helps to explain why my career moonlighting as a psychologist went so poorly.


So what if you were locked in a shipping container for days as a baby soaking in a pool of your mother’s blood? BOOOOOORING.

This isn’t to say, “it’s not me, it’s them” — I think the feeling is mutual.  Just like I don’t want to hear about some stranger’s Bachelorette fan fiction, no stranger wants to hear about my Bachelorette fan fiction, about which I will now go into great detail.  No!  I’m totally just kidding; the world isn’t ready for my creative genius… yet.  But seriously, as I’ve mentioned before, I’m not the kind of person to approach strangers; it’s not that I’m particularly private — you are literally, right now, reading a published-to-the-world account of my life and thoughts, you dolts — it’s that I don’t feel I have any particular right to intrude in other people’s lives.  I generally don’t talk to strangers, whether that be approaching the ladies at a bar or talking to my neighbors in the apartment elevator, not because I don’t want them to talk to me, but because I don’t want to force myself on them.  I assume everyone else has the same feeling about people that I do, and to them, I’m just another vapid, boring person they don’t want to have to deal with.

However, there are times when, for one reason or another, I am forced to interact with other humans — sometimes even strangers.  And sometimes, some rare, beautiful times, I find that I am on — I am, at least in my own mind, not just another boring, vapid person, but a Master of Conversation.*  This post is a guide for the rest of you, drawn from those times.

Avoid Foreign Entanglements

If you are like me, you do not have the stamina or the ability to contribute to, much less maintain, a conversation with a group of people.  Nobody wants to hear what you have to say, so your best bet is to corner some poor, unsuspecting sap and engage in a one-on-one conversation.  This guide does not cover group communication.

Bonus Material

If your friends (assuming you have any) are similar to you, it is possible to pull off the Group One-on-One Discussion.  This is an advanced maneuver and not for the faint of heart.  

With a group of friends, approach a potential conversation partner.  Ensure that your friends will in no way contribute to the conversation.  Immediately take control and lead the conversation according to the rules below.  Even though your friends are mere observers of this conversation, if done correctly, both the conversation target and the group will feel that they are a part of the discussion.  Better, the conversation target will feel that they have the attention of the entire group — what love! — and your friends will be subconsciously relieved they aren’t tasked with any real contribution.  Best, in a party situation, you will not look like two losers talking at the edge of a gathering — you will look like several losers talking at the edge of a gathering.

Talk About Them

This is the basics.  This is Conversation 101.  No, scratch that, this is 6th grade Conversation, and I’m your government-employed, took-the-job-as-football-coach-for-the-extra-booze-money public school 6th grade Conversation teacher lecturing you verbatim out of the book.  “Talk about the other person, not yourself,” I say, as I describe my rhetorical self and actions at length.  

The point here is to minimize the use of “I” and “me” and to keep the conversation focused on the other person — this makes the other person feel important and appreciated, which paradoxically makes them like you more (or makes them feel superior to you and get bored — it depends on the person, but in the latter case, you didn’t want to talk to them anyway).  Almost everything else in this article is implementation of this single, important tenet, which will explain how even someone who loves talking about themselves as much as I do is able to pull it off.

Bonus Material

Talking about the other person rather than yourself has a hidden bonus!  If you’re a private person or if you think you’re boring — or if you actually are boring — no worries!  You won’t be talking about your boring life or ill-formed opinions, so the other person will be shielded from your inadequacy in that regard.  Just make sure you never, ever talk to them again once they’ve run out of things to talk about, lest your secret be exposed.

Ask Questions

The best way to keep the conversation about the other person is to ask a relentless series of questions.  Don’t bother giving the other person time to respond, just rattle away anything that comes to your head.  By the time you’re done, they’ll be so exhausted from trying to remember all the inane BS you just asked that they’ll probably give up entirely.  Congratulations, you have won the conversation!  Now find your next victim.

No!  Totally do give the other person time to respond, but as their response winds down, be prepared with a fresh, poignant question — this stops them from hitting the awkward silence stage where they turn the question on you.  Here are some examples:


You: “Do you have any pets?”

Them: “I have a cat.”

You: “…”

Them “… how about you?”


You: “Do you have any pets?”

Them: “I do not have any pets.”

You: “Is that because you’re not emotionally or financially stable enough to care for another living being?”

Notice that in the first example, the question became about you.  Great, now they have to hear about your boring-ass hamster.  In the second example, you have furthered the conversation — now you get to hear about their financial and / or emotional instabilities!  That should keep them busy for awhile while you furiously analyze their response for further possible questions.

When relentlessly asking questions, it’s important to avoid the temptation to bring the conversation back around to yourself — I know you think you’re interesting, but trust me, you’re not.  This pitfall typically takes the form of answering your own question before the other person gets a chance to; it’s an easy out to finding common ground with someone, but it’s best to allow them to share their feelings on the subject before sharing your own, so that you don’t cloud their judgement or subconsciously force them to change their response.  Plus, it keeps you from becoming the Veruca Salt of the conversation.  Nobody likes Veruca Salt.

Do you love blueb’ries? I love blueb’ries.

Here, again, are some examples:


You: “Do you prefer dogs or cats? I’m a cat person!  My cat is named Lana and she is black with a little fleck -“

Them: “Please excuse me while I find literally anyone else to talk to.”


You: “Do you prefer dogs or cats?”

Them: “I like dogs; I have one, it’s a malamute…” blah blah blah blah

You: “Well, you’re wrong, cats are better.  Has your dog ever killed a man?”

You can still talk about yourself and find common ground, but do so after they’ve answered.  This way, you’ve shielded them from feeling awkward about their response as they answer just because it differs from yours and having to hedge (“Oh, I like cats too I guess, I just like dogs a little more.”).  Now you’ve exposed their true feelings and you can judge them accordingly!  It also gives you the opportunity to lie so that they like you better.  “Malamutes are adorable, tell me more,” you say, while imagining a mass malamute grave and your cat manning the bulldozer pushing the bodies in.  You smile disarmingly.

Finally, it’s important to adapt your questions to the conversation.  It’s often useful to mentally prepare a few questions to begin a conversation; if you’re meeting someone new, have a few standards that you can ask anyone: 

  • Where do you live / where are you from?
  • How do you know [mutual friend]?
  • What do you wear to sleep?
  • How many sexual partners have you had and how would you rate them on a scale from 1 to 10?  Please include names.

For acquaintances or friends you haven’t seen in awhile, have a mental log of older conversations — maybe they were prattling on and on about their New Year’s resolutions, so you can ask them how those are going.  Or maybe they gave you an in-depth rating of sexual partners; perhaps they’ve added a few since you last saw them?  A question that harkens back to a previous conversation will remind them of who you are and also let them know that you value them enough to remember that they met your mutual friend when he was the gimp at an orgy.  If it’s someone that you’ve seen recently enough that no new developments in prior conversations could have occurred, too bad — this guide doesn’t cover that scenario.

Once an initial salvo has been launched, you can keep following up with questions related to their responses until you feel you’ve exhausted that line of inquiry.  You should keep mental track of responses that lead to multiple questions (or conversational branches, as I’ll call them right now and never again), so that when you exhaust a particular line of inquiry you can revisit that branch.  Once all branches have been exhausted, you can always fall back to your initial list of questions.  Let’s see an example:

You: “Do you have any pets?”

Them: “Yes, I have a dog and a cat.”

You: [Oooh, a branch! Noted!] “Do they get along?”

[An hour later]

Them: “… and that’s an exhaustive list of every time my cat and dog have ever interacted.  Please, let me leave so that I can kill myself.”

You: [Oh no, they’re done.  Let’s revisit that branch!] “What kind of dog is it?”

Bonus Material

Ask opening questions that are so open-ended as to make the other person uncomfortable.  Here are some good examples:

  • “What’s new,” to someone you’ve never met.
  • “Tell me about yourself.”
  • “Interest me.  Go!”
  • “Why?”

Anyone who is not made uncomfortable and answers these questions well is either a pompous ass, and you should leave before getting sucked into the Vortex of Them, or too good for you and you should stop bothering them.  Anyone who is uncomfortable and has trouble answering is more your speed, but at this point never wants to talk to you again.  Leave the party/gathering, change your hair or make-up, and come back pretending to be a different person.  Attempt to engage these people with more straightforward questions.

Exiting Gracefully

Once you have exhausted your initial list of questions and all incremental questions, you have probably been talking to this person for a long time.  Congratulations! You are now Fast Friends.  Consider asking this person to be in your wedding as a [groomsman | bridesmaid] or, if this person is a member of the sex(es) you find most attractive and are legally able to marry in your state / county / country / province, as the [bride | groom].  Haha, just kidding! No one will ever marry you!  You are taking conversational advice from the internet and are destined to die alone.  

Sometimes you will find that you have exhausted your initial list of topics very quickly, and there is nothing that can be done.  Every response you get is negative and lends itself to no further conversation:

You: “Do you have any pets?”

Them: “No.”

You: “… well… do you… want any?”

Them: “No.”

You: “… so… where… do you live?”

Them: “Brooklyn.  I loved it there five years ago but it’s becoming too mainstream; all of the mom-and-pop coffee shops there are being replaced by other mom-and-pop coffee shops, but these ones have coffee-related puns for names; I swear it’s only like 15 more years before it becomes a Starbucks haven.  I’m getting out as soon as I can and moving to Porchland — no not Portland, God what is this, 2012? Porchland.  It’s a pre-industrial concept village of what Austin would have been like if running water had never been invented.  It has a population of 217 people and already has over 500 microbreweries.”

You have discovered a Boring Person.  This person is not worth talking to, and in this case, you must also find a graceful way to exit the conversation, lest you get stuck in awkward silence for the rest of the engagement or are made dumber by having to listen to their hipster BS.  

In either of these cases, the correct thing to do is to politely excuse yourself, preferably with an actionable excuse.  Finding someone else to talk to is always a good one, or perhaps getting a drink or performing other standard large-group-environment maintenance.  It is essential to have a real out, though.  If the conversation is done, don’t invite yourself back by saying “I’ll be right back” or offering to get the other party anything — simply indicate that you are departing and imply that they are on their own.


“I am going to go grab a drink, can I get you anything?”


“I’m going to go grab a drink.  It’s been ‘great’ talking to you.”

Ensure that third parties are complicit in the exit strategy — avoid indicating that you are going to talk to a specific person if that person is otherwise engaged or may not want to talk to you.  “Oh! There’s Bob!  I have to go ask him about his colonoscopy!” is a great way to get out of a conversation, provided that Bob is at the party and actually will talk to you.  Walking over to Bob and having a drink thrown in your face is not the most compelling excuse, and now you’ve invalidated the appreciation you’ve built up in the conversee, who has seen past your shallow attempt to extricate yourself from the apparent nightmare of conversing with them. 

“It was like this, but in my butt!”

If your exit excuse is something short term, like getting a drink, you must make sure that your partner has moved on to other things.  If, after your maintenance is complete, you find that your partner is still wandering aimlessly through the engagement — or worse, is looking right at you begging you to return — do not re-engage.  You have already run out of things to say, your conversation partner has a high opinion of you and your conversation skills, and re-engaging will only lead to disaster as that facade comes crashing down.  In emergencies, when all other outs are taken and your prior partner is looking in your direction expectantly, put down your drink, turn around, and leave the party.  It’s better this way.

Bonus Material

The Introduction is an advanced move that can get you out of talking to two people.  If you’ve exhausted your conversation with someone, find someone else that you know and introduce them, then make your escape.  This maneuver simultaneously solves the problems of exiting the conversation and of possible re-engagement therein.  If you’re leaving the conversation because it was boring, make sure you introduce that person to someone you don’t like — this also solves the problem of ever having to talk to that person, too! 

Extra bonus points if you set either person up with something from a prior conversation:

“Oh, Bill, get over here — You have to hear Jerry’s story about his goldfish.  It’s priceless!  I’ve already heard it, so I’m leaving.”


In the rare cases where you are actually forced to contribute to the conversation, using humor is a good out if you have nothing of substance to say, which, let’s face it, is always.  I’m clearly not an expert in humor, but here are a few tricks I find generally helpful, and yet are devoid of any subtlety or skill whatsoever.

  • Make outdated references so everyone knows you’re behind the times — bonus points if it’s a Simpsons reference, and extra double bonus points if it’s something you know no one has seen, like Battlefield Earth.
  • Substitute the phrase “[first letter of word] – word” for any noun in a sentence.  This works equally well for swears (“what an a-word-hole”) and non-swears alike; bonus points for employing this strategy with non-nouns (“And then we realized the c-word had b-worded, and that’s the story of our pregnancy scare.”)
  • Undergo your own personal vowel shift.  Why send text messages when you can send tooxt moosages?  Negative bonus points for swedifying — “ermahgerd” isn’t funny and never will be.  “Terxt merserges” is a little better, though.
  • Other purposeful mispronunciation; must be logical given the spelling.  Instead of “we are going to the theater in Annandale,” say, “we are going to the theater in Annandalé” (uh-non-duh-lay).  This only works well if you can do it without flinching, with a straight face; it works best in the middle of a sentence, because you can move in immediately.  Bonus points for making other people flinch.  Extra bonus points for correcting others instinctively if they correctly pronounce it.
  • Say something so outrageously offensive, yet utterly un-clever, about someone present in a manner that it can only be taken as a joke — call someone fat or ugly in your best idiot voice.  This is an advanced maneuver and should not be undertaken lightly, as it can backfire powerfully — it’s usually best to stick to things that are outrageously untrue, like calling a super model ugly.  Bonus points if it’s true and everyone else was thinking it, but it still comes off as a joke.

Bonus Material

Start picking up vapid phrases that are currently (or were recently) in vogue and peppering them into your speech:

“Oh man I had this totes awk meeting with my boss today where he accidentally pulled up porn on the projector.”

Bonus points if you include text message-isms in your speech, but pronounce them as words:

“I had this totes awk meeting with my boss today where he accidentally pulled up porn on the projector.  I lol’d” (lawled).

Extra double bonus points if you include retro slang that no one uses anymore in your speech:

“I had this rad meeting with my manager today where he accidentally pulled up porn on the projector.  I lol’d.  It was totes awk, but at the same time, pretty boss, because now I can hold this over him forever.”

Super negative bonus points if you start doing this ironically, but it gradually morphs into an everyday practice.

“I had this rad meeting with my manager today where he accidentally pulled up porn on the projector.  I lol’d.  It was totes awk, but at the same time, pretty boss, because now I can hold this over him forever, your honor.”


In order to be an excellent conversationalist (like me!), you need only follow a few simple rules — keep participants to a minimum, avoid talking about yourself, ask questions, exit gracefully, and use humor.  Those are basically the headers to this post, which indicates that I did a good job of choosing my headers.  Go me!  

Now get out there and start a conversation!  Practice makes perfect.

* Full disclaimer: There is no concrete evidence that anyone, anywhere, has ever actually enjoyed a conversation with me.  I did meet someone else who follows these principles and who employed them on me.  It was validating, invigorating, and terrifying all at the same time.


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