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답답하다 : Be in state of not going forward, because he is in his logic pond.

너 답답하다 You are in trouble state or you are pitiful.

답 is an answer so that 답답하다 means that even though there is an answer, we do not know the answer (This is someone's joke). This is an origin of 답답하다 ?

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    One of the earliest, if not the earliest, appearance of that word is found in 救急方諺解 published in 1466. – droooze Jan 6 at 15:44
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답답하다 has two meanings so that there are two origins (cf. First one may be in droooze's link)

1) There is no way to proceed :

There is a vocabulary "첩첩산중", whose meaning is 답답한 상태(no way out of it). But the direct translation is "surrounded by many mountains".

In ancestor-language of Korean, a mountain is "thaba" so that its pronunciation is changed into 답.

2) It describes "state surrounded by things" :

When we wear a swimming uniform, then the suit gets stuck to (들러 붙다) our body so that we are stuffy (답답한)

Here pronunciation of 들러 붙다 is changed into 답답 하다.

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