When I start to believe that the last bits of my Gin are sticking to the ice cubes, I officially have the killer instinct of a security guard when it comes to wit and humor.

• Honest and serious can be funny: This is a good drink, but you already know that. (optional smolder for emphasis)
• Funny is sometimes funny: Please make this drink a little stronger. Unfortunately, English is my first language. (optional glance at date, then eye contact with server)
• Trying to be funny is never funny unless everyone is already laughing: Those drinks were so good, I’d date myself. (you are the only one laughing, but keep laughing and say the next thing that comes to you)

Being funny is like dancing. Telling a story is like walking. I’m not sure how to explain it, but you might know what I mean.

I grew up in a small town in the midwest where conversation is often inspired by the following three topics:

1. Weather
   Person 1: Man it’s hot today.
   Person 2: Sure is. (insert story) Tomorrow is supposed to be the same.
2. Roads
   Person 1: Did you see they paved 65?
   Person 2: Yeah, it’s about time. How long they been working on it? Terrible pot holes. (insert story) Glad it’s done.
3. Other People
   Person 1: I thought I saw x the other day in town.
   Person 2: Yeah, x’s son/daughter is headed to college at x. (insert story) Anyways, I heard they got a scholarship. I sure hope my kid does.

While the topics may seem boring or the conversations may start out dull, the conversation is expected to include something funny and/or something interesting. Reality may not always deliver these things so we sometimes have to get a little creative with “wouldn’t it be funny if” or “what if” situations. Using our imagination during these conversations trains us to tell long jokes.

The key to telling a long joke is in the details. Build tension. Make it real and relatable.

The best long jokes I know set-up a situation that sounds plausible and then tell about a situation where something unexpected happens. Everything in between can be changed to suit your audience. Improvise to your audience to keep them hooked—you might even get in a shot or two directed at them during the course of the joke which is an added plus.

Another thing to learn from midwest conversation: Do not correct yourself if you got a detail wrong—just add another layer. If I said I saw someone in town and someone said the person was out of town or somewhere else, I’d just say it must’ve been another day because x happened and get on with the point. Neither of us care about the details, we’re waiting for the interesting part or the funny thing.