The first seems reasonable, until the reasoning is given, which reveals the whole message is batshit

Yeah, that’s what I meant. Like, expressing yourself to someone you’re dating, like “This made me uncomfortable,” generally should be ok. This proved to be the exception.

someone getting upset at being told they are lucky to be with the person they are with is kinda full of themselves and reading way too much into it

Well, what if the bartender was being a piece of shit, say someone who has cerebral palsy, saying they’re even lucky to be with someone… Would you still say that person is full of themselves? I think telling anyone they’re “lucky” to be with someone, from an outside perspective, is intentionally demeaning to one of the two people. Now, if someone in a relationship says they feel lucky to have found someone, that’s different. But clearly, it’s open to interpretation. And changes in context.

Little personal story to add, I dated a girl a while back, and ALL her friends and co-workers would say how lucky she was and how good I was for her. We all knew why, she was overweight and I wasn’t. They didn’t even just hint and maybe I read that wrong, they were BLUNT about it. I was doing home cooking for us instead of doing fast food. I worked out, did 5k races, I was in great shape. And I was exposing her to that life and she was noticeably losing weight. But the look on her face when people said “she was lucky”, was defeat.