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Five Steps to Telling an Entertaining Story

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Whether the audience is a boisterous horde of buddies perched over a pub table or a blind date seated across from you at a candlelit Italian trattoria, telling a story is the most effective way to entertain your listeners while conveying your personality and background. Although everyone has a canon of anecdotes worth reciting, not all stories are created equal. So, how can you ensure your personal narrative rivals the bards and not the barbarians? Just keep these five simple pointers in mind the next time you’re inspired by the muse of banter.

Begin at the End

walk-about: The StorytellersWhether it’s a pickup line or a salesman’s pitch, anyone who has ever baited a potential lover/buyer has relied on an “introduction hook”. Thus, while you may only be vying for attention, introducing your story with a hook piques curiosity and focuses the spotlight on you and your story. To find your hook, locate the moment of suspense right before the climax of your story. Such a hook can be as simple as an extended story title, for example: “Let me tell you about the time my friend Eddie mooned a pre-prom party and we almost got mauled by a mob of high school kids.” While this hook effectively creates interest and intrigue, I could really drum up suspense by peppering my hook with tactile details, such as: “Let me tell you about this late afternoon in May, when I found myself sprinting alongside my friend Eddie as we forged our getaway from a pre-prom party that Eddie had just given a Full Monty showing of his pale ass after he dropped his jeans and mooned them!” Vivid details not only make your hook sparkle, but can add riveting sensations to your whole story by following the next step…

Paint a Word Picture

Guide listeners on an emotional journey by jazzing up descriptions with colorful, evocative details throughout your anecdote. Many barroom storytellers (especially men) are creatively deficient in this area and recite stories as if they’re telling a joke, which means they omit sensory details and simply relate expository facts in order to deliver a punch line. Remember: Stories exist in the reality created by the storyteller, therefore adorn every sentence with a specific sound, smell, sight, or sensation. The high school kids chasing my friend Eddie and I weren’t simply mad; they were maniacally red-faced and foaming at the mouth.

Create Compelling Characters

While hooks and details are storytelling lubricants that ensure stories are exciting and easy to follow, characters are what listeners
. Just think about your favorite movie or novel. The first thing that probably comes to mind is a captivating character. And all great characters have one common attribute: they all want something, desperately. Would Moby Dick or Rambo be the same if Captain Ahab or John Rambo only half-heartedly wanted to slaughter white whales and enemies of America? Apply the same thinking to your anecdotes. Explicitly state what motivates the protagonist of your story – even if the protagonist is you. So, for my story, after painting a word picture of my friend Eddie as “a wildman with a suggestive smile tattooed across his face and the jovial disposition of the Lucky Charms leprecon”, I define his motivations as “wanting to wreck the magic of a picturesque pre-prom party ever since he’d been stood up by his prom date back when we were seniors in high school.”

Build Conflict

Conflict is the engine that drives your story forward. If a compelling character immediately gets whatever he or she desperately wants, the story is (literally) over before it begins. Therefore, make your character work and sweat for their goal. Once you understand your character’s motivations, conflict is easy to identify and build. Because your hook established the climatic moment of your character’s goal, the listener is anticipating the outcome, giving you an opportunity to keep them on the edge of their seat. Enthrall your audience with the obstacles that precede the climatic conclusion. Returning to my story, before Eddie discovered the pre-prom party he was so desperately hunting, I vibrantly relate our suburban-street journey as “each block we turned down, Eddie frantically surveyed for anything resembling a tux or flowing evening gown.”

Add a Twist

66/365 A picture tells a thousand words
Your twist doesn’t have to rival M. Night Shyamalan, but it should provide enough stimulation to give your story a second wind. Your twist always follows the climatic moment, right after your listener’s laugher or shock has subsided. By adding a twist, you make it’s clear you’re telling a story and not a joke. So, to finish my example with Eddie, a twist could be as simple as his disappointment in learning that, after mooning those acne-faced high schoolers, he’s still haunted by the bad memories of getting stood up. Don’t go overboard, but a good twist simply keeps your story unpredictable and intriguing by adding an unforeseen element.

In conclusion, tweaking the details of a personal narrative isn’t lying – it’s storytelling. Rather than just spitting words, take time to reorganize and invigorate the details and pace of your story using the tips above and prepare for an encore from your listeners!

About Rob J.

Rob J. is a writer and dating instructor in New York City. Themes that resonate in both his teaching and writing are masculinity, genuineness, rational self-interest, and general awesomeness.

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5 Comments

  1. youngman33

    August 6, 2009 at 1:33 am

    I enjoyed this article a lot. A technique I like to use sometimes, as I am not the greatest natural storyteller but am a decent good writer — I will write down any story I might want to tell, which allows me to enhance it greatly, making it much funnier when I end up telling it.

    • Bobby Rio

      August 6, 2009 at 5:03 pm

      That actually pretty a good tip youngman… it is also good to write them down, and sort of have a collection of them.. just to read through occasionally and remind yourself about them.

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