Has anybody ever done something that they thought would...

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that they thought would be polite/spare your feelings, only to make you feel worse than you would have otherwise?

I've had people tell me how pretty my hair was or that I'm a very nice lady. I present and identify as Male and I can't afford hormones or surgery. I also go by Male pronouns. As far as I'm concerned, I'm Male.

You mean like a backhanded compliment?

Or things like, "That shirt doesn't look that bad; no one noticed." They're assuming that you know it looks bad and they're trying to make you feel better, but you actually think it looks fine.

I can't think of a specific instance, but little things like that happen now and then.