Being Charming

Four principles to make yourself more alluring and persuasive.

2/14/202425 min read

grayscale photo of man making silly face
grayscale photo of man making silly face
Spellbound: An Introduction

Witches. Warlocks. Spellcasters. That’s what they should be called, those people with magnetic personalities who hold our attention in crowded rooms or make us hang on every word in quiet cafés.

They have it. That certain something that makes us feel good about ourselves for being around them. A certain something that compels us to seek them out at parties, at work, and online. But what is it that they have? And how can I get some?

It’s charm.

We hear a lot about charm in pop culture. Cartoon princesses await their Prince Charming. Suave men try to charm the pants off their sexual conquests. Kids are incessantly chasing after that leprechaun’s lucky charms. (OK. Not the same.) What exactly is charm?

To be clear, this isn’t an extended essay about enchanted trinkets or magic. That’s a different kind of “charm.” (Sorry, Potter fans.) It’s a book about disposition and demeanor. In the broadest possible terms, charm is:

Having an alluring personality.

Pretty simple. Let’s all go home and have a beer.

But that doesn’t tell us too much about charm. Digging deeper into the meaning, it’s clear that charm is a particular type of personality. To understand, let’s first look at what charm isn’t.

Charm isn’t “likeableness” which is a kind of personality that inspires simple positivity.

Charm isn’t “charisma” which is a kind of personality that inspires devotion.

Charm isn’t “flirtatiousness” which is a kind of personality that inspires arousal.

You might find these qualities in charming people, but they’re not enough to create a charming personality.

Part of the confusion about charm, I think, comes from the fact that the “pickup artist” community has appropriated the term for their...“philosophy.” Google “how to be charming” and most of the results will feature psychological techniques to pick up women.

I’m not saying these aren’t valuable skills. But I think there’s more to charm than sexual conquest. You can be charming when you’re pursuing sex and relationships or you can be charming in business, with your family, or out with friends. Charm isn’t under the exclusive purview of pickup artistry.

For people looking to be more alluring and persuasive, in the office, social circles, OR the bedroom, I offer a different take on charm.

My definition of charm.

If I were a psychologist, this booklet might be about the neuro-fundamentals of charm. Brainy stuff. If I were a philosopher, I might write a treatise about the “concept” of charm. Different brainy stuff.

But I’m a rhetorician, so I look at the world through rhetor-colored glasses.

“Wait. Isn’t this book about charm?” Absolutely! But I look at charm through the lens of “rhetoric,” so I want to take a moment and define my terms.

Rhetoric, as a term, has a bad reputation nowadays but for a good reason. Few people know what it is. Media refer to politicians’ “empty rhetoric.” You might hear someone’s argument called “mere rhetoric.” But this much-maligned subject is one of the oldest academic disciplines with origins dating back to Mesopotamia. That’s old.

Aristotle defined rhetoric as:

“The faculty of observing, in any given case, the available means of persuasion.”

Modern scholars differ on the scope of rhetoric, but for this essay, I’m sticking with Ari. A "rhetor" is someone who engages in rhetoric, acting consciously and ethically in applying the art. Now, back to the subject at hand...

In rhetorical terms, charm is a matter of ethos, the persuasive appeal to character. Ethos—as opposed to the other appeals of logos (logic) or pathos (emotion)—deals with trustworthiness, expertise, and ethics.

Many rhetoricians, myself included, consider ethos the most important appeal. “More important than logic or emotion,” you ask in shock and awe!? Absolutely.

Your argument might be logically thought out and emotionally compelling, but if your audience thinks you’re a bad person, then it’s over. Finished. Done. They’re not buying what you’re selling.

Charm as a matter of ethos deals not only with how an audience initially perceives you but also the kind of person they think you are after they’ve had time to make an informed judgment.

I consider charm as:

Having an alluring personality driven by a personal character that’s simultaneously trustworthy, empathetic, and fascinating.

This definition follows the rhetorical tradition of character-driven ethos. (More on this in a moment.) Each quality—trustworthiness, empathy, being fascinating—informs each of the four basic principles of charm:

Show Interest


Be Appealing


I’m not claiming these are the only principles of charm, but they’re necessary and sufficient to create a charming personality in beginners.

But there’s something else about charm that must be addressed before we delve into these principles: a matter of conduct.

“A good man speaking well.”

Charm, like money, is a neutral tool. Neither is good nor bad in themselves. It’s how you use them that makes them good or bad. You can charm to nefarious ends, or you can charm to proper ends.

All elements of ethos, indeed all elements of rhetoric, are morally neutral. This is what made philosophers like Plato leery of rhetoric and what drives the disdain for rhetoric today. There’s no guarantee that you’re being persuaded of something good. That’s why, as someone interested in charm, you must be particularly mindful of how you use your abilities.

Ancient rhetoricians, we’re talking early Greek and Roman thinkers, thought of rhetoric not just as an art or a science or a practice. They thought of it as a lifestyle.

Rhetoric wasn’t divorced from ethics in their worldview for two reasons, both related to ethos:

Bad people who can persuade are dangerous.

It’s easier to convince someone of what is good if you embody that goodness.

Cicero, a master orator, argued that rhetors must study and understand all the important knowledge there is to learn, insofar as that’s the basic field of rhetorical study: Everything.

But more than Renaissance Men (since the Renaissance hadn’t occurred yet), Cicero wanted rhetors to be virtuous and to understand the power they possessed. To quote him at length:

“Eloquence is one of the supreme virtues, which after compassing a knowledge of facts, gives verbal expression to the thoughts and purposes of the mind in such a manner as to have the power of driving the hearers forward in any direction in which it has applied its weight; and the stronger this faculty is, the more necessary it is for it to be combined with integrity and supreme wisdom, and if we bestow fluency of speech on persons devoid of those virtues, we shall not have made orators of them but shall have put weapons in the hands of madmen.”

Quintilian, another important Roman rhetorician, concerned himself not only with the content of rhetors’ studies but with the content of their character. He argued that orators must take ideas seriously and practice what they preach.

Quintilian’s definition of rhetoric is often boiled down to “a good man speaking well.” He felt so strongly about the necessity of character training that he advocated for a sort of rhetorical boarding school where wise mentors would oversee the development of young orators to make sure they grow up to be morally outstanding men.

While I’m not suggesting that charmers attend moral boot camp, I think Quintilian’s heart was in the right place. Creating a disconnect between tactics and principles creates a vacuum of morality.

Important: The study of charm cannot be separated from the character development of the charmer.

Good charm must be judged not only by its means but also its ends. Let Quintilian inspire you:

“Let us then pursue, with our whole powers, the true dignity of eloquence, nothing better than which has been given to mankind by the immortal gods. Without it, all nature would be mute and all our acts would be deprived alike of present honor and of commemoration among posterity. Therefore, let us aspire to the highest excellence, for by this means, we shall either attain the summit or at least see many below us.”

Inspired by Quintilian and armed with rhetorical know-how, you’re ready to dive into the principles of charm. Can you feel the excitement?

On to the charm!

Principle 1 - Show Interest: Let Them Know You Care

Charming people care. Genuinely. They don’t feign interest or put on a good face during conversations. Charmers make the effort to learn about, understand, and empathize with their audience.

Demonstrate that you’re listening.

We only remember 25% of what we hear. To be clear, that’s not a lot. Showing you’re a good listener, that you can derive something meaningful from what’s being said, is crucial to being charming.

People want to be listened to. That doesn’t mean simple acknowledgment. It means taking in what’s being said, processing it, and demonstrating that you understand.

You can’t passively listen.

Start with names. It’s the easiest way to acknowledge something personal about your audience, and it’s a great show to build rapport. I try to picture a name tag on someone’s shirt. The visual cue helps me remember who I’m talking to. If I must remember someone’s name in the long term, I usually write it down in a notebook or in my Notes app.

You can also demonstrate that you’re listening by recalling facts from earlier in the conversation or, if possible, previous meetings. Callbacks show you’re integrating the whole conversation instead of just listening piecemeal.

One of the most important elements of listening, though, is proper feedback. People want to know they’re not boring you or that you’re not preoccupied with fantasy football. Make eye contact, nod your head, and show appropriate emotion for the topic. (Now I sound like I’m writing for Sheldon Cooper.)

Charmers listen patiently for a cue to jump in, like a question or a pause. Never interrupt. Even if your audience drones on about the mating habits of the Patagonian mara, wait it out. Interrupting makes you seem eager to stop the other person from talking.

Ask sincere questions.

There are other ways to show interest, of course, and one of the best methods is to ask questions. Be sincere and make sure they’re related to the conversation. No non-sequiturs about Guatemalan cardamom (unless you’re talking to a Central American economist).

The best kinds of questions are the ones that allow people to answer however they’re most comfortable. Don’t ask leading or endless questions:

Non-charmer: “Was it difficult to work on such a controversial movie like FrackNation? Did people send you nasty letters? What did your mom think? Or did she even see it?

How do you answer that!? Be direct and simple:

Charmer: “What was it like working on the FrackNation documentary?”

Audience: “It was a lot of fun! Controversial at times, but I wouldn’t trade the experience for anything. ...[minutes later]... Thanks for asking!”

Circling back to my previous point, acknowledge that you’re listening while your audience responds. Now is not the time to Snap that selfie. (But is there ever really a good time?)

You should also ask questions when you don’t understand something. Know-it-alls aren’t charming. Child-like wonder is. Asking someone to explain a word or point that wasn’t clear boosts your ethos by showing that you’re both honest and humble. DoublePlus Good.

Open-ended questions tend to yield the best results. (As opposed to questions that can be answered “yes or no.”) And don’t be afraid to ask the “big” questions:

Why were you motivated to move to Austin?

How do you balance your personal life and work?

Who are your favorite people in town?

Give compliments. Know how to take a compliment.

It’s a shame that we don’t appreciate enough. I mean we don’t engage in the verb “appreciate” enough. Charmers do. They don’t focus on the negative. They seek out the things they like about other people:

Charmer: “Before I tell you about what I do, I just want to mention that you have great taste in art. Every painting in this house is outstanding.”

Practice complimenting by trying to find some positive attributes of everyone you meet. This can be tough because of something called the “halo effect,” when we make judgments about someone’s entire character based on one thing we know about them. In other words, if I don’t like your pants you must also kick puppies.

The principle here is sincerity. Don’t force compliments and don’t overdo it. Appreciation takes effort, but it will be worth the hard work.

Charmers must know how to take compliments. Neither dismiss the kindness (which can come off as rude) nor play it up (which can come off as braggadocios). There’s a middle ground of acknowledging and moving forward:

Audience: “Loved your talk!”

Charmer: “Thank you. I appreciate it. I’m happy you could attend. How often do you attend conferences like this one?”

Throwing in a question at the end only enhances your charming personality by putting the spotlight back on the audience. You’re acknowledging the nicety but showing that you don’t have to dwell on it.


Embrace debate.

When we think of showing interest, arguing typically isn’t the first thing that comes to mind. But strategic debate done in a way that shows deep respect can be one of the most profound and charming ways of showing interest in your audience.

If someone in your conversation says something you disagree with, speak up. Dedication to values can charm a group of even the most bitter antagonists. Don’t be preachy and condescending—even and especially if your audience is hostile—but instead politely dissent and, if you’re comfortable doing so, express your counter-arguments.

The most important point here is to recognize when a debate will be seen as positive interest and when it will be seen as grandstanding. It’s hard to give a definitive rule for how to tell. You’re going to have to trust your instincts in the moment.

When in doubt, stick by your principles, but always be polite and deferential.

Enthusiasm above all else.

Implicit in every section of this chapter is the notion of enthusiasm. You can only achieve peak charm when you develop an intense, genuine interest in the people, places, and things around you. This isn’t a political enthusiasm that lasts for the length of a handshake. I’m talking about a passionate and unending eagerness to know about the world and its inhabitants.

Demonstrating enthusiasm is a lot like demonstrating charm overall. The best way to show it is to live it.

One way to develop a natural sense of enthusiasm is to determine what you enjoy about people or situations and actively seek that information. Perhaps you enjoy hearing about people’s career paths or their exotic hobbies or their favorite booze. Start with little things and work them into your conversations. Slowly expand on what you find fascinating and create a library of go-to questions where you can demonstrate genuine enthusiasm. Pretty soon you’ll be an enthusiastic, charming person.

ADVANCED TACTIC: Introduce people.

Ready to take your charm to the next level? Try introducing people who you think will either become good friends or have something interesting to discuss. When making introductions, it’s important to keep in mind the context of the people you’re introducing and the setting you’re in. If you’re introducing an employee to a boss at a conference your tactics would be radically different from introducing a friend to a potential date at a block party.

WARNING: Introducing people is harder than it sounds because it’s the ultimate test of your listening skills. You have to know two people so well that you can match up their personalities, interests, or business goals. Succeed and they’ll think of you as the most charming person in their lives. Fail and it’s a long road back up charming mountain.

Principle 2 - Entertain: Dance, Monkey, Dance

Being entertaining doesn’t mean you have to juggle. (Couldn’t hurt.) “Entertaining” from a charming and rhetorical perspective means that people want to be around you. They find you fascinating. There are many ways to create this pull.

Positively positive.

No one likes a Depressing Debbie. And even if they do like her, she’s not charming. We’re attracted to positivity. Not mindless optimism but sensible, upbeat positivity—the kind you get from problem solvers and Apple product launches. Positivity is related to happiness, and humans like happiness. (Duh.)

We’ve already discussed focusing on what you like about your audience as one element of positivity, but beyond that think about the things you like about yourself. I’m not saying you have to brag, but bringing up accomplishments in the right context creates an aura of positivity:

Charmer: I hear you like to run long distance. I’ve been training for my first half marathon. It’s a lot of work, but I’m happy with how it makes me feel. I’m almost ready! Do you have any tips?

Being positive can mean a lot of things, and I won’t try to define them here. Charming people tend to focus on what’s good about the world, the positives in the conversation, and the valuable traits of their audience. Also, smile. (More on this later.)

Make ‘em laugh.

“It’s hard to explain puns to kleptomaniacs because they take things literally.”

Humor is charming. Funny people usually have a personal entourage awaiting their next amusing anecdote or one-liner. It’s a no-brainer to say that people like to laugh.

But being funny doesn’t come naturally to everyone. My best advice is to practice. Like any skill, being funny requires effort and time. Honing the art of comedy isn’t an easy task, but it’s also not impossible.

Foremost you can simply memorize jokes for a given occasion. Just know your audience:

Charmer: “I love attending these liberty dinners. I had the libertarian salad to start. Lettuce alone!”

[Wah, wah, wah, waaaaaah.]

Maybe not the best joke, but I hope you get my point.

If you’re not up for memorizing and want to take your humor to the next level, learn the basics of improv comedy. Improv helps you deal with unexpected context, and it’s a great way to keep conversations moving. Take a class at your local comedy shop or watch a few YouTube videos. (Learn to say, “Yes, and...” a lot.)

Ultimately humor is about observation, about seeing aspects of the world that people don’t notice or give much thought. Jerry Seinfeld puts it nicely:

“I do a lot of material about the chair. I find the chair very funny. That excites me. No one’s really interested in that—but I’m going to get you interested! That, to me, is just a fun game to play. And it’s the entire basis of my career.”

So write down things you see. Make notes about the random thoughts that pop into your head while you’re on a walk or falling asleep or drinking booze. Pretty soon you’ll have a library of material from which to cull your jokes.

Tell epic stories.

For the more serious among us, humor might not be the best option. But being funny isn’t the only path to entertainment. Being able to tell great stories is another charming skill. Drama, especially, can hold a room like nothing else. It’s in our DNA!

“[Humans] can’t help telling stories, and that they turn things that aren’t really stories into stories because they like narratives so much. Everything—faith, science, love—needs a story for people to find it plausible. No story, no sale.” – Adam Gopnik explaining the thesis of “The Storytelling Animal”

Telling great stories means two things:

Having great stories to tell.

Being able to deliver them in a compelling manner.

If you’re not the Most Interesting Man in the World, you might not have a plethora of great stories from your life to draw on. But who says the stories have to be about you? Read about interesting people, listen to podcasters (modern storytellers), and retell other people’s stories. Become a collector of history.

As far as presentation, it’s much like humor. You just have to practice. My blog has tips for being a persuasive and elegant presenter, but there are thousands of great resources on the Interwebs. Or you might join a local Toastmasters.

Bring the conversation around.

OK, so you’re telling jokes and making people weep with stories of yore. Now it’s time to step back and bring it around to the other folks in the room. Charming people make the conversations about their audience.

Once there’s a suitable opening in the conversation, start asking questions again or observe someone else in the audience. Better yet, integrate them into the story! Don’t keep the focus on you for longer than the length of an amusing tale.

Master a skill.

I brought up juggling in the introduction earlier because I think mastering a skill is an important element of charm. A flawless performance is fascinating.

Of course, you could learn something deeply artistic like singing, playing an instrument, or painting. But those aren’t great skills for the kind of situations where you’re trying to charm. I’m thinking, instead, about portable skills:



Reciting poetry

Magic (with caution)

You wouldn’t want to take any of these skills to the extreme. If it takes more than a minute to set up or it requires a costume change, then it’s likely not going to be charming.

Peak charm, though, comes when you can integrate the skill with a story or joke.

ADVANCED TACTIC: Talk to the loners.

Charming people often find themselves the center of attention, even though charm increases the more the charmer puts the focus on others. That’s why the ultimate charming move is to shine the spotlight on the person who has had the least attention.

WARNING: To pull this off requires an ethos of unquestionable sincerity. That is, you can’t be seen as trying to make fun of the person you’re spotlighting. Don’t attempt to engage a loner if you’re known for being sarcastic. That can only hurt your charm.

Start by talking to a loner one-on-one. Unlike a general audience where charmers can create smooth conversation by asking questions of other people, it’s best to start by talking about something general or yourself. Allow the loner to warm up to you before you ask them to participate.

Once you have a rapport going, start introducing people into the conversation slowly. One at a time. And make sure to keep bringing the loner back into the discussion. Pretty soon the conversation will run itself.

SIDEBAR: Learn from Improv (Yes, And...)

Anyone familiar with improv comedy knows that the quickest way to kill a scene is the word “no.”

In rhetoric, too, a fast way to kill the argument and inflame emotions is to continually say negative things to your opponent. Not many people like to be told “no”—especially in a debate.

But why do we have to use the word at all? Of course, you should acknowledge if you disagree with something, but avoid the word “no.” Replace it with “yes.”

“Yes” is the verbal equivalent of a head nod. It’s a type of agreement but not necessarily with the point at hand. When your opponent makes a point that you strongly disagree with, follow it with, “Yes, and….” Then make your point. (Another helpful improv phrase is, “Not only that, but also….”)

You might be surprised how cordial your opponent will become when you use this technique, a favorite of improv artists around the world. It keeps the conversation flowing, helps you emit an amicable aura, and keeps tension down by perpetuating a positive mood. Why, yes, it’s one of my favorite rhetorical tactics.

Principle 3 - Be Appealing: Dress Up, Stand Straight, Smell Nice, and Smile

Where charm and flirtation have the most overlap is in the value of appeal in appearance and demeanor. Charm requires an alluring personality, so charmers need to present themselves in a way that people want to stick around.

Be a snappy dresser.

Study after study has shown that we judge people based on how they look, and an outfit is a significant part of the visual. You don’t have to throw on a bow tie or raid Don Draper’s closet, but dressing with class will aid your charming personality. When we look good we feel good, and feeling good (read: confident) is a big part of charm. Coordinating colors/patterns/stripes helps, too.

You should always be aware of what the occasion calls for in terms of dress. A tux and tails won’t add to your charm at a beach party, for instance. As a general rule, charming people are slightly overdressed compared to the general audience.

But even if you choose simply to fit in with the dress around you, there are other considerations. To start, make sure that your clothes are clean, pressed, and flattering for your body—no matter its type. It also helps to be fashionable, but that doesn’t necessarily mean brand-laden. It simply means understanding what look is “in” or “classic” and wearing it well.

Finally, you might consider a piece of flair, something that accentuates your personality without detracting from it. That might be something as innocuous as a pocket square or as outrageous as a Tokyoflash watch.

Whatever it is, make sure it has personal meaning or a cool story.

Body language matters.

Charm, like any presentation of yourself, is multi-faceted. It’s not all words and fancy suites. Your body language, too, can make an impact on how people perceive you. If you stand with your arms crossed, are you coming off as defensive or angry? Will someone get weirded out if stand too close? Should you be jumping up and down right now? All things to consider with body language. Let’s start with posture.

People with great posture look (and feel) like they’re in command. It boosts your confidence. Standing tall, strong, and proud is a surefire way to add to your charm. And sitting up straight in a chair, even away from the back slightly, is the seated counterpart.

But posture isn’t the only important aspect of body language. Positioning can boost or diminish your charm. If you’re having an intimate conversation with someone, standing face-to-face and making eye contact is appealing, but if it’s more casual then standing shoulder-to-shoulder might be better. Knowing how far to stand from someone is also important. The general rule is that closer means more intimate and further away means less intimate.

Mirroring the audience’s posture and position is a good way to establish rapport. If your audience is leaning on a table, then you might want to lean on the table. If their arms are crossed, you should try crossing your arms. This is, admittedly, a bit of pop psychology, and mirroring doesn’t guarantee a connection. As with every bit of advice in this booklet, you should be aware of the context and act accordingly.

Smell like you mean it.

This one might be obvious. Don’t stink. Sure, charmers might enjoy interesting hobbies like cliff diving or antique car repair, but that’s no excuse for smelling like sweat and motor oil. Charmers wash behind their ears.

A smell can be a powerful emotional trigger. One researcher explains:

"The association of fragrance and emotion is not an invention of poets or perfume-makers. Our olfactory receptors are directly connected to the limbic system, the most ancient and primitive part of the brain, which is thought to be the seat of emotion.”

This means it might behoove you to invest in a casual cologne. Not something you would wear to a nightclub but a pleasant, less intrusive scent, please. And whatever it is, don’t shower in it. A little will take you far in the charm department.

Smile your face off.

“Your smile is a messenger of your goodwill. Your smile brightens the lives of all who see it. To someone who has seen a dozen people frown, scowl, or turn their faces away, your smile is like the sun breaking through the clouds.” – Dale Carnegie from “How to Win Friends and Influence People”

Who doesn’t love a smile? It’s benevolent and caring and a sign of respectful positivity. You cannot be a charmer without a smile.

But exactly how important is smiling? In his book Brainfluence, Roger Dooley writes about a University of California study that showed how bar patrons exposed to pictures of smiles, even briefly, were more likely to drink more and pay more (double!) than patrons exposed to frowning faces. Happiness indeed.

That being said, there’s little worse than a forced smile and teeth that betray uncomfortable muscle tension. If it’s not genuine, don’t do it. But like most things, practice makes perfect. That’s right. You should practice your smile in the mirror. Practice smiles have the added benefit of giving you a psychological pick-me-up every time you pass a mirror. Win-win.

Don’t be easily offended.

An important, non-physical element of appeal is personality. It’s difficult to say if there’s one particular personality that’s more appealing than others, but a consistent personality trait among charmers is that they’re not easily offended.

It’s difficult to have a prolonged conversation with someone, let alone a friendship, if everything you say offends them. This doesn’t mean, of course, that to be charming you must become a sociopath or moral relativist. It simply means that charmers are mature about how they deal with what they find offensive. They think before they react.

There is a vast difference, for instance, between someone telling you they’re a member of the Ku Klux Klan (go ahead and walk away) and someone telling you they voted for a candidate you don’t support (go ahead and stay put).

If your goal is to charm, manage your reactions. Feel free to disagree, but don’t turn your disagreement into righteous indignation—especially if your long-term goal is to use your charm to be more persuasive.

Occasionally being offended shows that you have strong principles, but being offended by every story, sentence, or word uttered by your audience is not only uncharming. It’s immature.


We’re sensory beings: sight, sound, smell, taste, and of course touch. Sometimes touch can be the most evocative of the senses in a social context. Touch helps build bonds between people, likely because touch can cause the release of oxytocin, the chemical in our brain that helps us assess if a person is trustworthy.

Also, we’re not a touchy-feely culture, so when someone touches you, it’s bound to cause a reaction. To be clear, I’m talking about appropriate, social kinds of touch: touching an arm, putting your arm around shoulders, hugging, etc. Nothing creepy, creeper.

WARNING: It’s difficult to know if your touch is going to be well received. People are finicky about this issue, and if there’s any doubt, simply keep your hands off.

If you’ve just shared an emotional moment with someone, touching their arm might deepen their positive feelings. A hug can release stress and make someone feel at ease. Touch can be a powerful way to increase your charm. Start with a handshake (firm but not crushing) and go from there.

Principle 4 - Timing: Know When to Charm and When to Run

It’s hard to sell volcano insurance in Rhode Island, and it’s just as hard to charm in inappropriate situations. Nothing kills charm faster than bad timing. Kairos is the rhetorical concept of knowing the supreme moment for persuasion. Understanding kairos can make you a better charmer.

The right setting.

The physical setting can make a huge difference in whether or not it’s appropriate to be charming. Just as proposing marriage in the total darkness of Crystal Cave will likely get you a “no” (and a swift kick you won’t see coming), trying to be charming in the wrong place can hurt your reputation.

It’s impossible to list the objectively best places to charm because it’s integrated with the next point (time). Charming in a bar, for instance, is likely fine...unless you’re there to help a buddy discuss his relationship problems. Turning on the charm at a social gathering is likely great...unless it’s a funeral.

Be mindful of your immediate surroundings, too. You might look like a fool and not a charmer if you’re telling a serious story standing next to an “I’m With Stupid” poster. The principle of a charming setting is one where your efforts don’t distract from something more important and where your surroundings don’t distract from you.

The right time.

“Observe due measure, for right timing is in all things the most important factor.” – Hesiod, Greek poet

You might describe the best time for charm as social and casual. It’s a context where you’re free to be the center of attention but can put the focus on someone else if need be. But that doesn’t mean you should charge ahead at all parties or bar outings.

Indeed, part of what makes someone charming is that the moment seems to call them into the position of a charmer. It’s neither forced nor contrived. Charmers don’t come off as charmers, at least not initially. It’s a reputation built on a foundation that, like physical foundations, no one notices.

The key here is understanding context. This can be difficult in a social situation where you’re entering without prior knowledge.

If you walk up to a group and tell a joke, for instance, it’s not going to go over well if they were just talking about Susie’s medical scare.

When in doubt, ask! Remember that admitting you don’t know something isn’t a sign of weakness. It’s charming. And it will help you with timing.

An important element of kairos, both setting and timing, is observation. Don’t jump into charming “routines.” Take in your surroundings and make conscious decisions about what you should do. Adapt if necessary or forgo the charm altogether.

Signed, Sealed, Delivered.

Timing isn’t only important on the macro level. It’s equally important on the micro level. How you deliver specific words to an audience can make a profound impact—positively or negatively.

Comedians spend as much time perfecting timing as they do writing jokes. Emphasis A will get result B, delay C will get result D, etc. Like every aspect of charm, delivery takes practice and repetition. The core elements of delivery are emphasis, time, volume, and physicality.

Emphasis is simply the act of distinguishing which points should stand out and which shouldn’t. In writing, we can show emphasis by making certain words stand out. The visual clue gives readers a sense of what’s important and how to read the text.

When speaking, emphasis comes from any number of clues but one of the most charming is pronunciation. Make a word stand out by saying it with effect and your audience’s ears will perk up with pleasure.

Time, too, is a crucial element of delivery. Never underestimate the power ... ... of the pause. A well-timed pause will have your audience waiting with bated breath for your next syllable. It’s most effective, of course, during moments of drama. But don’t take the pause for granted in moments of comedy as well. We all know a friend who rushes into the punch line of a joke. Not funny, Brad.

It should go without saying, but no one will know if you’re charming if they can’t hear you. Conversely, it’s rarely charming to scream. (Though Gilbert Gottfried gave it his best.) Volume is an underappreciated element of delivery that can affect how you’re perceived.

A good volume is one that’s appropriate for the setting. Amplify or tone down as necessary, but consider using volume strategically. Loud doesn’t have to equal “important.” Soft-spoken rhetors usually find themselves in a position of having the audience’s undivided, if physically strained attention.

As a final note on delivery, I would suggest paying a lot of attention to your hands and arms. Watch carefully how you gesticulate. Compare yourself to great rhetors.

Do you flail wildly like a flightless bird? Or do you use your hands with purpose to amplify important points?

We talked about physicality a bit in Principle 3 when we talked about body language and smiling. That advice applies here, too. The idea is: Move like you mean it.


At the intersection of setting and time, there’s an action that might be the epitome of charm in our age of informality: the toast. When done with tact and eloquence, a toast can feed the spirit and make you an unforgettable charmer.

WARNING: By its nature, a toast makes you the center of attention. Even though you’re likely toasting someone else, the primary focus will be on you—your demeanor, dress, expressions, words, etc. Toasting requires not only that you understand the context of your immediate surroundings but of the greater “room.” Raise your glass with caution.

There are a few principles that apply to just about every toast:

Keep it short.

Make the message simple.

Don’t read it.

End with sincerity.

Don’t forget to drink.

I could write another essay about toasting in various contexts. (Hmmm...) But there are many resources out there for the would-be toaster.

SIDEBAR: Frame of Mind Matters

Your audience must be in the right frame of mind to receive your argument. Again, this correlates with ethos. You seem inconsiderate or rude if your argument occurs when your audience doesn’t expect it, or if your argument seems out of place.

For instance, if you have a great idea for a product, pitching your idea at a company happy hour after a gallon of margaritas probably isn’t the best idea. Better to wait until the next morning’s staff meeting.

Bring Aspirin.

Conclusion: All Good Things

Being charming doesn’t have to be difficult, but it will require practice and dedication—and the realization that genuine charm isn’t a disguise, an act, or even an attitude. It’s an essential part of your character, of your moral self.

Being good is doing good.

If you remember nothing else from this booklet, let your one takeaway be that ethos, your character, above all else, is the essential element of charm and persuasion. The now-unfortunately-cliché quote, “Be the change you want to see in the world,” strikes the correct chord. By being good you’re doing good.

People are more easily convinced by what you do than what you say. If you demand that people cut back on their fossil fuel consumption to save the planet while traversing from country to country on a private jet, you look silly. Even if people agree, they won’t take you seriously. But if you make drastic reductions in your personal fuel use, it’s harder to dismiss your argument.

In regards to charm, the principle of ethos applies just as much. A charmer isn’t charming with friends and a jerk with family. A charmer doesn’t “pour on the charm” in a business deal and give the cold shoulder to employees. A charmer doesn’t praise ego-strokers or belittle people who disagree.

Don’t act charming. Be charming.

Not only will you, the charmer, know the difference, but discerning audiences will punish you for trying to pull one over on them. In the long run, it’s in your self-interest to integrate the principles of charm into your character as a permanent fixture.

Happy charming!