使い分け. The differences between two or more words or phrases and how to select the best one for a given situation.

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How to say “Knowing that I hurt you is breaking my heart”

How does one say: Knowing that I hurt you (your feelings) is breaking my heart. "Breaking my heart" I think I know: 胸が張り裂けています。 but the first part and how to connect the two I'm clueless ...
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What is the most appropriate word for “cry”?

Background: Yes, I have tried typing "cry" into Google Translate. Although, there are so many options, yet no example sentences for each word. In my case, I have been writing a compare & contrast ...