Which one is correct? 1 makes sense because 得 is describing the extent of how 難過 he is, but 2 also seems to make sense because 地 is just before the verb 哭. So I'm really confused about this. Thanks.
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I've made a few modifications to the sentence to show the differences between the two.
Both work here but are subtly different, in many situations they are not interchangable. (It helps me to remember that in most of chinese they are pronounced completely differently, and the mixing up of the three "de" is completely a modern mandarin problem).
Difference is something like "He is so sad he began to sob." vs "He started very sadly sobbing."
So, in this situation they are almost the same in meaning. They are different structures though (◐‿◑)