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Whenever you roast someone, you'll find there's a line you don't want to cross. If you cross that line, you could seriously offend the person. The problem is, that line is in a different place for every person, so it can be hard to gauge.
Another good source for a roast is interesting interactions you've had with the person. Everyone has days where they're a little off, and how that person acted on an "off" day could be a source for a roast.
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. Figure out where the line is. Whenever you roast someone, you'll find there's a line you don't want to cross.
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.
If one of the jokes you're thinking about making has you feeling uncomfortable, it's likely best to just skip it. Roasting is supposed to be fun, not truly mean.