They're definitely not laughing with you, and you've lost a lot more than the room
Leave the comedy to the professionals, or you will regret it.

Humor tells us a lot about people. Not every joke is a personality test, but listen to what somebody jokes about and you learn something. Do they make fun of themselves? Do they use humor to bring people together? Or does somebody else always have to be the target?
This is where things get complicated, and instead of laughter all you hear is silence. Often, that's your reputation and narrative going down in flames.
We live in a time when people are more aware of language, identity, mental health, race, religion and personal boundaries. Some people call that “woke.” Fine. There is a useful side to that word: paying attention to things we once ignored.
But there is also a darker side.
Outrage travels extremely well.
Research into social media has found that moral and emotional language spreads more rapidly online, while other research has shown that social feedback can reinforce expressions of moral outrage. In other words, outrage isn't just something people feel. Online, it can become something people learn to perform.
Suddenly, a joke isn't just a joke.
Justine Sacco learned that in 2013 when a provocative tweet she posted before boarding a flight went viral while she was in the air. By the time she landed, her employer had fired her.
Roseanne Barr learned it in 2018. Her racist tweet about Valerie Jarrett was followed within hours by the cancellation of her highly successful television show. Barr later called it a bad joke, but ABC wasn't interested in the explanation.
Kevin Hart learned that old jokes can have a very long shelf life when past tweets resurfaced just after he was named Oscars host. He stepped down from the job and apologized.
Here's the other side.
Not every controversial joke is harassment. Not everybody who is offended is automatically correct. The EEOC makes clear that workplace law doesn't prohibit every offhand comment or isolated incident. Context matters, as does severity, frequency and whether protected characteristics are involved.
You see, professional comedians are a different animal altogether. I know dozens of excellent comics who've been plowing the clubs for decades, honing their craft. I've worked closely with a number of them, and learned the single most important lesson possible.
Stop trying to one-up the professionals. It's their craft. You're just a fool who thinks they can be funny.
George Carlin is, in my humble estimation, the greatest stand-up comic who ever lived. He built a career challenging the boundaries of language, and forced people to face some very uncomfortable truths. Lenny Bruce was arrested for testing those same boundaries. Anthony Jeselnik has made an art form out of making audiences wonder whether they should laugh. Dave Chappelle has willingly and deliberately walked into some of the most controversial subjects in modern culture.
That's their job. Your job isn't comedy.
So don't borrow a comedian's joke and drop it into a corporate conference room because you thought it worked on television. Chances are it won't, and you're left uncomfortably holding the bag.
When it comes to your reputation, your brnad, that narrative you are so carefully protecting, write this one on the inside of your eyelids so you never forget it.
Know your audience.
Even better, know the relationship between you and your audience.
Take the time and know the power dynamic of that audience.
Maybe most importantly, know when the joke isn't worth it.
I've been the butt of plenty of jokes over the years. My profession, my interviews, mistakes I've made, being a “white boy,” being called a “toxic male", whatever. Fine. Sometimes I laughed. Sometimes I fired something back. That's part of being around people and understanding the audience.
Also keep in mind there is a difference between being funny and being cruel. “Hey, I was just joking” is not a magic eraser. If the joke requires somebody else's humiliation, personal pain, mental health, private life or identity to work, maybe the problem isn't that everybody else is too sensitive.
Maybe the joke just wasn't very good. Likely you overstepped yourself because the mouth was in motion before the brain was in gear.
So, laugh. Have fun. Be entertaining. Just remember that every word you say is part of your professional narrative. And once somebody else gets to write that narrative for you, fixing it can take a hell of a lot longer than telling the joke did.
They most definitely will not be laughing with you.
Be dangerously intelligent. Control the Narrative™.