A Reflection on Wit, Wisdom, and the Art of Second Guesses: October Competition Recap

This month’s “What I Said/What I Should Have Said” competition brought a flood of clever, thought-provoking, and laugh-out-loud entries. Over 150 submissions poured in, demonstrating that hindsight truly is a comedian’s best friend. As always, we saw a mix of longtime participants and fresh faces, which made narrowing down the winners a delightful challenge.

The entries were as diverse as they were humorous. Some perfectly captured the spirit of the prompt, while others subtly shifted toward a different but equally entertaining category: “What I Said/What I Meant.” These entries were so well-written and relatable that we couldn’t ignore them—but we also realized they were not quite what the prompt had in mind. For this reason, we’ll revisit this concept sometime next year with a dedicated “What I Said/What I Meant” prompt, so keep those brilliant ideas brewing.

Let’s dive into the best of the best, along with a few honorable mentions.

The Winners

First Place ($100): Brent Donnelly

• What I said: “Sorry I misplaced your book about Quantum Theory.”
  What I should have said: “Fortunately, there are many timelines in which I will return your book about Quantum Theory. Unfortunately, this is not one of them.”

Brent’s entry was a masterclass in blending intellectual wit with universal relatability. By invoking the multiverse, he elevated a simple apology into a moment of cosmic humor. This line wasn’t just funny—it was smart, memorable, and downright brilliant.

Second Place ($50): Zeena Hine

• What I said: “Oh, great. A pollster. I’m sorry, but I don’t give out my candidate preferences over the phone.”
  What I should have said: “How nice to hear from you. I’m voting straight write-in candidates. Do you have pen and paper handy?”

Zeena’s knack for sharp political satire was on full display here. Her entry managed to transform a routine phone call into a biting commentary on modern elections. She remains one of our most consistent contributors for a reason—her wit is unmatched.

Third Place ($25): Kayla Kiczek (Age 10)

• What I said: “Trick or Treat!”
  What I should have said: “Let’s be real here. I have no interest in tricks. I’m all about the treats. So, we can do this the easy way, or we can do this the hard way.”

Kayla’s entry delighted us with its bold, confident humor. At just ten years old, she proved that wit knows no age limit. We expect to see more from her in future competitions!

Honorable Mentions

While the winners took the top spots, several entries deserve a spotlight for their creativity and charm:

Dennis & Ruth

• What I said: “Oooh, a book club that meets monthly? That sounds lovely. It will encourage me to read more.”
  What I should have said: “30 days? What was I thinking?! Week one was a bust, but I’ll just listen to the audiobook while I exercise. Shoot, that didn’t go well. Okay, are CliffNotes still a thing?”

This entry hit close to home for anyone who’s ever overestimated their time management skills. It was equal parts humorous and painfully relatable.

Andrea Kiczek

• What I said: “No thanks, I’m not hungry.”
  What I should have said: “Just to be safe, order an extra appetizer. Anything you want. No, not that one. Not that one, either. Wings, just get wings. And I’m eating half your fries.”

Andrea’s entry nailed the fine art of “not being hungry” while still commandeering someone else’s meal. It’s a universal truth wrapped in humor.

Erica Blair

• What I said: “Thank you for my birthday present.”
  What I should have said: “Thank you for sending me a fourth copy of your book. My collection was missing one with your autograph stamped in it.”

Erica’s entry was a clever poke at over-gifting and vanity, delivered with subtle politeness that made it all the more effective.

The “What I Meant” Phenomenon

As we combed through the entries, we noticed a surprising trend: many submissions leaned more toward “What I Said/What I Meant” rather than “What I Should Have Said.” These entries were sharp, insightful, and often hilarious, but they reflected a slightly different perspective on the theme.

For instance, “I’m going outside to play” versus “I’m going on a secret F.B.I. mission. See you Thursday” captured what the speaker meant but didn’t intend to say aloud. This was a delightful angle we hadn’t anticipated, and we loved it so much that we plan to revisit this as a standalone prompt in 2025. So if this was your favorite approach, keep your notes handy—we’ll want to hear more!

Next Month’s Challenge

Title: “Modern Etiquette for the Digital Age”

Prompt: Write a witty, tongue-in-cheek guide to navigating modern dilemmas in the digital world. Entries should focus on new “rules” for social media, online dating, or Zoom meetings.

Examples:

• “If you start a group text, you are required to moderate it for eternity. This includes resolving disputes, clarifying emojis, and providing tech support to that one friend still on Android.”
• “On a Zoom call, your cat may attend as a silent observer. Your dog, however, must refrain from barking at the Amazon delivery person.”
• “When liking your ex’s post, you are allowed one accidental click—but only if you unlike it within 30 seconds and never, ever mention it again.”

Deadline: Saturday, November 30, 2024. The winner receives $100 and publication in the Sentinel!

Thank you to everyone who participated in October’s competition. Your creativity, humor, and ability to find levity in life’s awkward moments continue to impress us. We can’t wait to see how you navigate the digital world in next month’s challenge!