Keep in mind that professional roasts may go a bit farther than you should, depending on your situation. For instance, if you’re roasting your boss, you may need to tone it down a lot.

For example, if the person you’re roasting loves peanut butter and bologna sandwiches, that’s a little outside of the norm and people may find it funny. However, if the person likes to send mean messages to people, that’s not as fun. It goes against the norm, but it also causes emotional harm to people. [3] X Research source

For instance, maybe a person jumped into the pool (fully clothed) at an office party to save a box of donuts. You could use that to tease the person a bit.

For instance, you might turn a mention of the one pair of pants that Joe wears to work that are just a bit too short into a riff on his Steve Urkel-esque fashion sense. But don’t just attack the person’s sense of style without any context, or berate them for wearing clothes that make them look fat.

You could also use stories that have gone around in your social group over the years. For instance, maybe the person is notorious for always burning dinner when guests come over, and so it’s joked about in your group: “Everyone knows Joe’s misadventures around the grill. So when he invites me over for a cookout, I skip a step and bring the fire department with me. OK, honestly I just make up an excuse and get take-out instead. There’s really no punchline here. Joe’s just a terrible, terrible cook. ”

Is the person getting old?: “Larry doesn’t need to go to the theater to see ‘The Mummy’. He was there when they wrapped and buried it. ” Is the person bad with technology?: “Larry is a decent nurse, but terrible with computers. He’s introduced more viruses into the office than the patients have. ” Is the person a spendthrift?: “Larry’s so cheap, the shops in town all had to change the notes on the change dishes by their cash registers to read ‘take a penny, LEAVE A PENNY LARRY!’

“Just look at him over there, slouched in that chair. Let me tell you, my brother is so lazy …” “. . . he can’t even summon the energy to laugh at these hilarious jokes. ” “. . . that when his ex-wife said ‘That’s it — I’m leaving,’ he said ‘Could you grab me a beer on your way out?’” “. . . that no one even bothers to ask him to do anything anymore — oh, wait — i just realized — my brother is a genius!”

For example, say the person has an obsession with tea. You could tell a little story this way: “One time, I saw Charlie lugging a box of like 200 tea bags into the office. I said, ‘Charlie, how can any person drink that much tea?’ He said ‘I’ll tell you a secret — I soak my feet in it under my desk to help with foot odor. ’ And when I asked ‘Then why are your teeth stained brown?’ he answered ‘Well, I’m not going to waste it — this is expensive tea!’”

For example, you could say, “Fred has never been on time for a staff meeting. In fact, when it came time for him to lead one, he thought he was supposed to start it with ‘OK, any questions before we finish?’ And for the ‘continental breakfast’ he brought lukewarm decaf and half an onion bagel for everyone to share. ” While providing detail is good, make sure you don’t waste excessive time getting to the point of the joke. [9] X Research source

Look around the room, and catch people’s eyes. Also, stand up straight, and try not to fidget. Speak in a clear, engaging tone. Practice in the mirror a few times. And remember that you’re putting on an act.

While people who can’t take a joke are often the ones you feel are most deserving of a roast, they’re also usually the worst ones to actually roast. Stick with people who can laugh at themselves. [11] X Research source

Use your own experience with the person to decide which categories are fair game, and which are off limits. For instance, bringing up the eating habits of someone you know has struggled with an eating disorder or body image issues is not a good idea. On the other hand, bringing up eating habits for another person may be perfectly fine, but they may have an issue if you talk about the way they dress.

Pick someone who will be discreet about the material you’re testing. If it does go too far, you don’t want it to get back around to the person.

For instance, the person may have a fake smile plastered on. They may even look upset. They may have their arms or legs crossed, leaning away from you, which is an unhappy position. They may also get restless and move around in their seat a lot.

That said, some people can handle these jokes just fine — maybe even if you were the one in the past relationship with them!

But again, there’s no hard and fast rule here. You have to know your target and your audience.

If you can’t enjoy yourself while telling the jokes, then why bother doing it at all?