Humor serves many purposes, according to Glinert, who teaches “From Genesis to Seinfeld: Jewish Humor and Its Roots.” A good joke makes us smile, laugh, and create and release tension. It also allows people to play with words, safely refer to taboo topics, and even disparage others. But jokesters beware. “Telling a joke is a risk,” notes Glinert. “You’ve got to take precautions. One of the worst things that can happen is when a joke falls flat. I’d rather be thrown into a fiery furnace.” (His favorite joke: How many Jewish mothers does it take to change a light bulb? None, because if you ask her, she’ll reply, “I’ll just sit in the dark.”) Here are Glinert’s serious tips on how to succeed at joking around.

Tailor your joke to the setting.
“A set-piece joke to break the ice during an after-dinner speech has a different goal from one told hanging around with friends.”

Find the right moment.
“The best opportunity comes when people are waiting for someone to say something. I’ve been at memorial services where people were so uncomfortable—they were just waiting for someone to say something humorous.”

Be sure the audience is listening.
“You have to monitor its reactions as you go along. Be alert. What matters is watching your audience to see whether the topic has caught its interest or seems to amuse. A good talker has to be a good listener. Otherwise, you might become that dreaded creature: the bore.”

Pace yourself.
“The way you tell a joke is like playing jazz. You must have perfect timing. It pays to practice—particularly the punch line.”

Know your audience.
“If you’re trying to use humor to make an impression on a prospective boyfriend or girlfriend, think twice. Your self-confidence could be mistaken for insecurity. Other times people tell jokes as a way of competing for attention. If your boss tells a joke, be sure to laugh. Don’t joke about politics or sensitive issues unless you’re sure of your audience.”

Be Chill.
“Avoid being overly dramatic. Be low-key. You might even start talking in a low-pitched voice or even a monotone to draw in your audience so it takes you seriously.”

End naturally.
“Don’t end the joke with a big emotional display. If the joke doesn’t go over well, you won’t lose face. And never laugh at your own jokes if you can help it.”