This one happened at a local Red Lobster. The waitress, while checking on us, glanced at my empty glass and asked "Can I get you anything else besides a diet?"

We all started laughing and the poor girl swore she said it that way every time and never thought twice about it.

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As for myself, once a while back - and in my first year of employment at the company, I walked into my bosses' office (who also happens to be the CEO) while he was sitting there with the VP. He had just gotten his hair cut to look like his young boys summer hair cuts... which meant there wasn't much left - and it didn't look good. I just froze in the doorway saw his hair and said "Oi..." Which probably wouldn't have caused the VP to double-over in laughter except that the CEO is Jewish. I just walked right back out saying "I'll be packing up my desk now..." I don't know what part was worse, insulting his hair or his heritage...