If the target of your joke isn't laughing (if they're upset by it), then it's not a joke, it's bullying. If they _are_ laughing/enjoying it, then it's playful banter. You're right, it very much varies by culture (culture here being as specific as "the specific group of people")
Spent a lot of time in hunting and fishing parties with near constant teasing and in those situations its usually the rudest and most egotistical jerk who doesnt laugh and enjoy. They cross the line repeatedly, everyone takes it in good nature while internally counting the incidents, then eventually someone takes them down a peg and they act like a child.
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In a culture where banter is accepted, sometimes someone will be upset by something.
I think the current tendency to prevent all possibility to upsetting behaviour is overshooting the mark.
Against bullying is a good movement.
Against all possibly upsetting remarks is basically being against banter and killing a part of what makes us human. I hope that free speech remains allowed and to some extend "uncancelable".