How to be more eloquent & witty.

Is anything more irresistible than a razor-sharp wit?

Well … maybe a razor-sharp wit paired with piercing, steel-gray eyes. (But I digress!)

I’ve always admired writers, speakers and entertainers who are able to churn out delightful bon mots, at the drop of a hat.

I aspire to be one of those people, too.

And while I’m a pretty handy wordsmith, I’m not exactly the reincarnated spirit of Oscar Wilde. (Alas!)

Still, when it comes to being sharp, eloquent and witty on command, I’ve got a couple of go-to dance moves.

If you’ve ever wondered how your favorite writers and bloggers keep words flowing like warm honey … perpetually plucking the perfect phrase out of thin air … merrily frolicking through a daisy field of dashes and quotation marks without missing a beat …

… here are a few tantalizing tricks of the trade:


What? Yes. When I’m feeling uninspired, I saturate my brain with zippily-written TV shows — anything with exceptionally-crafted dialogue and unmistakable voices.

My current must-watch list? Mad Men, Scandal and Lost Girl.

I also fill my brain-tank with podcasts, galore — especially comedy shows with hysterical, fast-paced banter. Judge John Hodgman, My Brother, My Brother and Me and Stop Podcasting Yourself are three new favorites.

Does watching (and listening to) witty people make you wittier, too? Absolutely. Expressing yourself in a rushing waterfall of witticisms is like mastering a foreign language. And when it comes to learning new languages, experts agree that immersion is key.


According to the BBC, most people know about 35,000 words. But we only use about 3,000 words on a regular basis. The rest fall into our “passive vocabulary” — inert and all-but-forgotten. Tragic!

To expand my active vocabulary, I visit, and The Online Etymology Dictionary multiple times a day.

If I want to write a piece about a particular concept (say, “teaching” or “escape” or “readiness”) I almost always begin by researching the root meaning of the word — its etymological history. And the rest, as they say … is history.


Oscar Wilde once said, “Quotation is a serviceable substitute for wit.”

(See what I did there?)

Being able to recite a perfectly-timed quote — correct citation and all! — is downright dashing.

An entire poem? Even better.

In my younger days, I used to write Victorian sonnets onto gigantic scrolls of butcher paper, and hang them on my bedroom walls. I’d rehearse them over and over, till I could rattle them off, at will.

A foolhardy waste of time? Perhaps.

But it did make me prrretty popular with the ladies …


“Brevity is the soul of wit,” according to some guy named William Shakespeare.

People who express themselves using the fewest possible words are often perceived as “wittier” than their verbose and long-winded contemporaries.

Fair? Just? True? Perhaps not.

But why take ten pages (or ten hours) to convey what might be expressed in a single breath?


When a jazz musician improvises a dazzling piece of music on the spot, she’s not performing in a vacuum — she’s working within the framework of the jazz tradition. Blue notes, polyrhythms, syncopation, call-and-response. There’s a method to her madness.

Writing is just the same. Most professional writers use scripts, prompts, templates and frameworks to help structure their thoughts. (Remember your sixth grade English teacher, prattling on and on about the importance of the “Five-Paragraph Essay?” She was onto something…)

I love creating scripts and frameworks for myself — and for you — because they serve as “training wheels” for witty, persuasive self-expression.

My stance? Frameworks are not “evil,” and they’re not “cheating.” They’re an efficient foundation for on-the-fly improvisation.


When I need to come up with a memorable tagline, headline or subtitle in two shakes of lamb’s tail, I leap to The Free Idiom Dictionary.

Let’s say I wanted to create a tagline for a publishing company that prints books about legal issues.

I might type “law” into The Free Idiom Dictionary, and behold! The phrase “word is law” pops up.

The tagline practically writes itself: “When it comes to publishing, our word is law.”

Presto! Puns, to the rescue!


To quote Stephen King: “If you want to be a writer, you must do two things above all others: read a lot and write a lot. There is no way around these two things that I am aware of, no shortcut.”

I’d estimate that I spend 35 hours a week writing — blog posts, emails-emails-emails, website content for my clients, notes and exercises for my workshops, script packs and wee-books, grocery lists, love notes, thank you cards, text messages, tweets, words-words-words up the wazoo.

Do anything for 5 hours a day, 7 days a week, year after year, and you’re bound to become reasonably good at it.



: My girl Melissa Cassera created a new class for business owners who want to write online content that’s more addictive than a Game Of Thrones couch-marathon. (The first session just ended, so get on her waiting list for round two.)

: Sarah Von Bargen is a veritable fountain of tips ‘n advice for writers who want to be wittier. (Do not miss: How To Blog If You Don’t Like Writing.)

: Gala Darling is a digital seductress who knows how to woo and charm an audience, like no one else! Read all of her insights on storytelling and blogging.

: Susan Harrow created a free audio-class on how to speak in sound bites. (A skill I’m still striving to master!)

: Stephen Fry’s memoirs — The Fry Chronicles and Moab Is My Washpot — are basically a crash-course in world-class witticism.
Ditto for anything written by Bill Bryson.

: Last but not least: this wiki article on “How To Be Wittier” is awfully charming.

Who is the wittiest person you know? (Living or dead, fictional or fabulously real?)