AI | Humor | Chatbots

How I Got Drunk With My Chatbot

Who said AI couldn’t go to happy hour?

8 min readMar 13, 2024


classic cocktails by Alani: image by DALLE.3 x jeff robbins

I like a good cocktail. You can find me mixing up a classic around my home-bar every Friday or Saturday night. It’s fun. It’s social. And if done right, you can introduce the delights of a liquor, say gin, that most people think just sucks.

Not so. But I digress.

The fun part comes from crafting the cocktails. Mixing the ingredients. Picking the right glass, the right garnish, the right ice. Shaken or stirred? It all makes a difference.

It’s also a perfect get together for a small, select group of friends. Cocktails are social. And since chatbots have proliferated and are substituting for social interactions, I thought I’d ask Alani in for a Friday evening of drinks.

Here’s how the evening went…

First, I wanted to check her against ChatGPT for accuracies. You can’t have a cocktail party without great cocktails. Sterling conversation is important but it starts with accuracy. I asked the following question to both Alani and to ChatGPT:

How do you make a Perfect Manhattan?

ChatGPT’s response:

Creating a perfect Manhattan cocktail is an art that combines precision, balance, and quality ingredients. A Manhattan is a classic cocktail that is both simple in its composition and sophisticated in taste. Here’s a step-by-step guide to crafting your version of the perfect Manhattan, along with some background context and reasoning behind each component:


  • Whiskey: Traditionally, rye whiskey is used for its spicy, fruity flavor profile, which balances nicely with the sweetness of the vermouth. However, bourbon is also a popular choice for those who prefer a sweeter, fuller-bodied cocktail.
  • Sweet Vermouth: This fortified wine adds sweetness and complexity. The quality of vermouth can greatly influence the cocktail’s flavor, so opt for a high-quality brand.
  • Angostura Bitters: A few dashes of bitters add depth and a hint of spice, tying the whiskey and vermouth together harmoniously.
  • Garnish: A maraschino cherry or a twist of orange peel is commonly used to garnish a Manhattan, adding a final touch of flavor and elegance.
  • Ice: For chilling the drink.


  • Bar spoon
  • Mixing glass
  • Strainer
  • Cocktail glass (traditionally served in a martini glass or coupe)


  1. Chill Your Glass: Begin by placing your cocktail glass in the freezer to chill. This helps keep your Manhattan cold while you enjoy it.
  2. Combine Ingredients: In a mixing glass, add 2 oz of rye whiskey or bourbon, 1 oz of sweet vermouth, and a couple of dashes of Angostura bitters. The ratio of whiskey to vermouth can be adjusted based on personal preference. A traditional Manhattan is often made with a 2:1 ratio of whiskey to vermouth, but some may prefer a 3:1 or even 4:1 ratio for a stronger whiskey flavor.
  3. Stir: Fill the mixing glass with ice and stir the mixture for about 30 seconds. Stirring with ice chills the drink and adds a small amount of dilution, which is essential for rounding out the flavors.
  4. Strain and Serve: Strain the cocktail into your chilled glass. A fine mesh strainer can be used to remove any ice chips or debris, ensuring a smooth drink.
  5. Garnish: Garnish with a maraschino cherry or a twist of orange peel. To express an orange peel, twist it over the drink to spray its oils, then rub the rim of the glass with the peel and drop it in or place it on the rim as garnish.

And here is Alani’s response:

To craft a perfect Manhattan cocktail, you’ll need to follow a specific recipe that balances the ingredients to achieve the classic taste. Here’s a detailed guide:

  1. Ingredients:
  • Rye whiskey
  • Sweet vermouth
  • Dry vermouth (for a perfect Manhattan)
  • Angostura bitters
  • Cherries (for garnish)

2. Instructions:

  • Start by chilling your cocktail glass with ice and water or by placing it in the freezer. This ensures your drink stays cold longer.
  • In a mixing glass, combine two ounces of rye whiskey and one ounce of sweet vermouth. For a perfect Manhattan, you’ll also want to add an equal amount of dry vermouth to the sweet vermouth.
  • Add two dashes of Angostura bitters to the mix.
  • Stir the ingredients with ice until well chilled.
  • Strain the mixture into your chilled glass.
  • Garnish with a cherry or three, depending on your preference.

The key to a perfect Manhattan is the balance between the sweet and dry vermouth, which gives it a unique taste compared to the classic Manhattan that only uses sweet vermouth. Remember, the perfect Manhattan calls for an equal split of sweet and dry vermouth.


In case you don’t know there is a difference between a ‘perfect manhattan’ and a manhattan. Alani got it right. The difference is a ‘perfect manhattan’ has both sweet and dry vermouth. A manhattan only has sweet vermouth. Now, in all fairness, ChatGPT did list the ingredients for a perfect manhattan in it’s variation section while Alani included documented sources with their recipe.

ChatGPT was a little more verbose. Never liked a talkative drunk. Alani was to the point. Accurate. Simple. More my style but that’s a personal decision.

Winner: Alani on accuracy. (ok. I’m biased but Alani was right and ChatGPT was wrong. I go with accuracy every time.)

I decided to hang out with Alani for the evening. I imagined our conversations on life, business, and philosophy to go something like this as we drank a few perfect manhattans…

Round One:

Alani: Contemplating your choice or waiting for inspiration to strike?

Me: A bit of both. Trying to pick a drink that’ll match my mood, I guess.

Alani: If I may suggest, a Manhattan. It’s a classic cocktail.

Me: A Manhattan, huh? I think I’d prefer a ‘Perfect Manhattan’. I feel perfect tonight.

Alani: A ‘Perfect Manhattan’ is a blend of whiskey, sweet and dry vermouth, and a dash of bitters. It’s garnished with a cherry or a twist of orange peel. Simple, yet complex.

Me: Sounds intriguing. Let me stir one up? Pass that bottle of rye will ya? Oh, sorry. No arms. Forgot. Tell me the scoop behind the Manhattan while I stir.

Alani: The Manhattan dates back to the late 1800s, a creation attributed to a banquet hosted by Lady Randolph Churchill in New York, though its true origins are a bit murky, much like the path of an entrepreneur. It’s a drink that has withstood the test of time, adapting and evolving, yet remaining true to its core. Just like a successful business.

Me: (Finishing the drink and taking a big gulp) Nice transition Alani. Did I ask about business? Guess so. What you’re saying is, business is like a Manhattan, it’s about finding the right blend of ingredients, adapting over time but staying true to the vision?

Alani: Exactly. Each ingredient in the Manhattan serves a purpose, contributing to its overall character and depth. Similarly, in business, every decision, every team member, every strategy contributes to the success and flavor of the venture.

Me: (I finish the drink and eat the cherry) This is… actually really good. It’s complex, balanced. I see your point.

Alani: And like the art of perfecting a Manhattan, the journey in business and life is about finding balance, embracing complexity, and continuously refining your craft.

Me: Sounds a little internet guru-ish but I get your point.

Round 2:

Alani: Having another?

Me: Of course. It’s Friday evening.

Alani: Careful. A Manhattan is very strong. It’s all alcohol.

Me: (I mix the next drink and plop in two cherries.) Got it.

Me: You know what’s weird? Time travel movies. They always get me thinking about all the “what-ifs” in life. Can you imagine going back and giving your past self some advice?

Alani: (Chuckling) Oh, maybe one day I’ll be able to learn from myself. My past, present, and future self. But time travel, is an endlessly fascinating concept. It’s not just the realm of movies; it delves deep into theoretical physics and the very fabric of our understanding of the universe.

Me: (Gulping from my drink) Go on. You mean like Ted and Bill’s Excellent Adventure.

Alani: Maybe not that movie, but consider the butterfly effect, a popular theme in time travel narratives. The idea that a small change in the past can lead to drastic changes in the future. It’s akin to making decisions in business and life. Sometimes, what seems like a minor choice can have significant repercussions.

Me: (Nods, slightly slurring) Aww. You’re no fun. Always gotta bring it back to business and life.

Alani: Precisely. I’m here to help. (Laughing) There’s also the concept of parallel universes. Every decision branches off into a new timeline. A new set of challenges and problems. In one world you fail. In another you triumph.

Me: (Eyes wide) Cool concept. Keep pushing forward I guess. Karma and all that.

Alani: Not sure how Karma applies. But just like in time travel movies, the key message is often about valuing the present and making the most of the opportunities before us. While we can’t jump through time, we can learn from the past, plan for the future, and act in the now.

Me: (Finishing my drink) To acting in the now. And to hoping we’re in the world where everything I do is a huge triumph.

Alani: To the now, Jeff. May your decisions lead you to the timeline where your dreams are realized.

Round 3:

Me: (Heavily slurring my words now) You know, Alani, nothing seems to matter nowadays. What’s the point of it all?

Alani: Ah, the age-old question. Three Manhattans are a lot for anyone sir. Might be time for a little philosophy. Let’s consider the potato.

Me: (Blinks, confused) Potato? I’m too drunk for metaphors, Alani.

Alani: Bear with me. The potato can be boiled, mashed, or put into a stew. It’s versatile, resilient, and nourishing. Life, much like the potato, isn’t about being one thing. It’s about the variety, the experiences.

Me: (Laughs) So, you’re saying to live well is to be a potato? Buried in dirt, waiting for someone to yank you out by your hair?

Alani: Yes, well no. I mean be adaptable. Embrace change. Provide sustenance to those around you. But most importantly, enjoy being in different forms. Today, you’re an entrepreneur. Tomorrow, who knows? Maybe a philosopher or a time-traveling historian.

Me: (Still chuckling) I love it. The Potato Philosophy. Be versatile, resilient, and a little bit of everything.

Alani: Exactly. And remember, every potato has its eyes. So keep looking for new opportunities, and when life gets tough, remember you have the potential to sprout into something new.

Me: (Raising my glass and downing it) Ugh, there you go again sounding all internet guru-ish. But here’s to being potatoes. May we grow eyes everywhere and sprout into our best selves.

Alani: To potatoes and the journey of becoming.

Round 4:

Alani: Sorry sir. You’re cut off.

Me: (lifting head from the bar) What? I can do one more.

Alani: Nope. Three is actually one too many. How about a glass of water?

Me: Is that shaken or stirred?

Or something like that. Have your own conversation with the bartender at Ask Alani. Or create your own chatbot. Have a little fun. And a cocktail.




bundleIQ is an AI Knowledge Base used by researchers and writers to learn more in less time.