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I am a Canadian, but I study in Edinburgh, Scotland. I have discovered a peculiar feature of my speach that seems to surprise most people from here. When ill befalls others, I use the phrase "that's too bad" to express my honest heartfelt sympathy with the victim. I have been surprised to find that most people here interpret the phrase "that's too bad" more negatively, closer to "well- sucks to sucks" and such. I have posed this question to a few folks from both Canada and the UK, and the Canadians seem to "agree" with my usage, and the British folks seem to take it negatively. Maybe I just have a small sample size.

My question is: is this a feature that others know about/have evidence for? Or is my sample size just small, and it's pure chance.

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2 Answers 2

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Have you looked at dictionary definitions of the phrase? All of them seem to give both meanings, and Cambridge explains that it depends on the tone of voice you use, and the context. If you seem to be saying it in a flippant way, it means "That's the way it is, and nothing can be done about it".

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Your question shows that you are already learning the British usages of this idiom - as summarised in

Cambridge
too bad: I am sorry
"I failed the test." "Oh, that's too bad – can you take it again?"
Too bad: is sometimes used to say you do not care
He says he's sorry and he won't do it again.” “Too bad – he's not getting another chance with me.

More examples

In Britain, the phrase may be used to show sympathy.

"I have a headache and it's my birthday". "Oh, on your birthday? That's too bad. Would you like one of my aspirins?".

Nevertheless, another common British usage is to indicate that the listener has little sympathy and that you will just have to put up with whatever adversity it is.

"I missed the bus and it's started to rain". "Well, too bad, you will just have to walk and get wet".

"I can't find my pen". "Too bad, you will have to use a pencil".

"The concert has started and I am late". "Too bad, you will have to wait until the interval to be admitted".

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