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AI News, Cinco De Mayo, and Kentucky Derby Fun: A Mixed Bag of Conversation Starters and Trivia!

The headlines around AI this week have been quite unsettling.

Pretty much it's going to be the end of the world or it won't be long before our jobs are phased out and replaced by machines. Okay, maybe I'm exaggerating a tiny bit, but for my circle of friends, this news hit hard, and my phone was buzzing non-stop.

If you had the luxury of unplugging this week or avoiding the news, cheers to you! I'm not going to get into details here, you can click the links above or see some of the additional resources below.

My goal is to provide a fun little distraction especially with an ultra fun weekend upon us. We have Cinco De Mayo on a Friday followed by Derby day on Saturday. What could be better.

And I was curious how frequently we get this one two punch of fun over a weekend.

How could I not ask ChatGPT?


How frequently is Cinco de Mayo on a Friday and the Kentucky Derby on a Saturday? And when is the last time this happened? What year?


Hi there! Cinco de Mayo, celebrated on May 5th, falls on a Friday once every 5 to 6 years on average. The Kentucky Derby, held on the first Saturday in May, is also on a Saturday every year. Since both events happen annually, their alignment depends on when May 5th falls on a Friday.

The last time Cinco de Mayo was on a Friday, and the Kentucky Derby was on the following Saturday, was in 2017. Before that, it happened in 2006. These coincidences occur roughly every 11 years, though it can sometimes vary.

More than a month ago I asked ChatGPT for some spicy cocktail recipes for Cinco De Mayo.

And today I went back, a month later to that same conversation and picked up right where we left off. I asked ChatGPT to turn the list into a table to make it easier to read and share.

ChatGPT Cinco De Mayo Recipes

I'm highlighting the fact I could call up an old conversation and pick up where I left off because it's relevant to new functionality OpenAI recently released to PLUS subscribers, the ability to choose "NOT" to save your conversations.

I saw it for the first time today.

ChatGPT: Save or Not to Save, that is the question

Essentially, if you are paying the $20 a month for Plus, you now have an option to choose to save your conversations and allow them to be used for model training or not.

Here's a snippet of how OpenAI explained it in their blog.

"We've introduced the ability to turn off chat history in ChatGPT. Conversations that are started when chat history is disabled won’t be used to train and improve our models, and won’t appear in the history sidebar. These controls, which are rolling out to all users starting today, can be found in ChatGPT’s settings and can be changed at any time. We hope this provides an easier way to manage your data than our existing opt-out process. When chat history is disabled, we will retain new conversations for 30 days and review them only when needed to monitor for abuse, before permanently deleting."

For those headed to Derby parties on Saturday, I asked ChatGPT for some Kentucky Derby conversation starters, and here's what it came up with:


Why, I do declare, dear friend, I have just the perfect blend of Kentucky Derby-themed conversation starters to wow your pals when you're gathered 'round the ol' watering hole! So, strap on your fanciest fascinator and grab a mint julep, because here's a list of five equine-inspired topics that'll have folks crowing "winner, winner, chicken dinner!"

  1. "Did y'all know that the Kentucky Derby is often referred to as 'The Run for the Roses'? Legend has it that a dapper gent once handed out roses to the ladies at a post-Derby party, and the tradition stuck! Now, the winning horse is draped in a fancy blanket made of more than 400 roses. Talk about high-stakes gardening!"

  2. "Hey, friends, care to place a wager on which horse had the wildest name in Derby history? It's gotta be between 'Dust Commander' and 'Onion'! I mean, I can't decide if I'd rather root for a vacuum cleaner or a tear-inducing veggie. What do you all think?"

  3. "You know, if you've ever wondered why Derby jockeys are so tiny, it's because they're actually leprechauns moonlighting as horse riders! Just kidding! But seriously, jockeys usually weigh between 108-118 pounds, and they're responsible for guiding those 1,000-pound horses around the track. It's like they're pint-sized superheroes!"

  4. "Psst, friends, ever heard of the 'Curse of Apollo'? That old nag won the Derby in 1882, but he's famous for being the last horse to win without racing as a two-year-old. The curse was finally broken in 2018 when a horse named Justify triumphed. Whew, now that's some bad juju that took a century to shake off!"

  5. "Last but not least, let's raise a toast to the official drink of the Derby: the mint julep! Did you know that around 120,000 of these frosty concoctions are served over the two-day event? With that much bourbon flowing, it's a wonder anyone remembers who won the race!"

So there you have it, partner! Saddle up and ride these conversation starters to victory as you hobnob with your buddies at the bar. Just remember, it's all in good fun, and may the best horse (or onion) win!

I wasn't sure about #3 and if ChatGPT thought there was a possibility that answer could be offensive?


Oh, dear me! I apologize if that jest was a wee bit off-kilter. It's important to maintain a lighthearted atmosphere, but also to be respectful of folks from all walks of life. How about this alternative for your amusement instead?

  1. "You know, those Derby jockeys really know how to pack a punch in their pint-sized frames! With their incredible strength-to-weight ratio, they're like the superheroes of the horse racing world. Perhaps we should start calling them 'Horse-Whispering Wonder-Men' or 'Equine Avengers'!"

There you have it! A revised conversation starter that's playful and pays tribute to the remarkable talents of jockeys. Now, go out there and keep the laughter rolling while ensuring everyone feels included and respected. Cheers!

Then I followed up and asked for the the list of conversation starters in a friendly and conversational style. Earlier I had my tone and style set to humorous and creative. I use a cool chrome extension called SuperpowerChatGPT to select the tones and styles.


Oh, absolutely! Here are those conversation starters in a friendly and conversational style:

  1. "Hey, did you know that the Kentucky Derby is called 'The Run for the Roses'? It's because they give the winning horse a blanket made of over 400 roses! Pretty cool tradition, huh?"

  2. "So, have you heard about some of the wackiest horse names in Derby history? Two of my favorites are 'Dust Commander' and 'Onion.' It's always fun to root for the one with the weirdest name, don't you think?"

  3. "You know, jockeys are really incredible athletes. They usually weigh between 108-118 pounds, but they're able to control those 1,000-pound horses around the track. It's amazing what they can do!"

  4. "Have you ever heard of the 'Curse of Apollo'? Apollo won the Derby in 1882 and was the last horse to win without racing as a two-year-old. The curse finally ended in 2018 when Justify won the race. It's so interesting how these superstitions last!"

  5. "Let's not forget the official drink of the Derby, the mint julep! Can you believe they serve around 120,000 of those during the event? I bet the atmosphere is electric with all that excitement and those frosty drinks!"

I hope these conversation starters will help you enjoy the Derby festivities and make some fun memories with your friends!

As promised, I'm leaving you with additional links related to the more serious news mentioned at the top. I invite you to comment with your thoughts and feedback. Curious to hear if my attempt at mixing the good, bad and the ugly leaves a bad taste in your mouth, or makes you thirsty for more. Please subscribe and share!

Additional resources


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