Have you ever had a friend be secretly offended/hurt by a comment you meant as a joke?

In this situation now. I made what I thought to be an innocent comment on a hat they were wearing. Someone else shared with me that they felt offended by what I said, like I was trying to make fun of them or be rude. This was not my intention at all and now I feel like I’m walking on eggshells.

Have you ever had a friend be secretly offended/hurt by a comment you meant as a joke?
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