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When does a joke go too far in close relationships?

I’ve always believed humor helps people bond, but what happens when jokes start making someone uncomfortable, especially within a family-like relationship? I’m asking because I’ve seen situations where teasing crossed a line and completely changed the dynamic. How do you recognize that moment before things spiral out of control, and is there a way to fix the relationship afterward without making it even more awkward?

From my personal experience, the line is crossed the moment humor stops being mutual. If only one person is laughing, it’s time to pause and reflect. Honest apologies and acknowledging boundaries can repair a lot of damage if done early. Stories like prank goes wrong manga on Honeytoon really highlight how quickly playful jokes can turn into emotional chaos. Reading it reminded me how important respect is, especially in close relationships, and why intentions don’t always matter as much as impact.