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adj. sleepy; tired; difficult, hard
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Why does this character "困" mean “sleepy”?How do we explain its structure?

Let's dig a little into the etymology of this character.

困 exists in《说文》. Its original definition and explanation in 《说文解字》(a Chinese dictionary made in the Han Dynasty) is “故廬也。从木在囗中。” "从木在囗中" describes the structure of the character. Its original meaning: 树干被砌石圈死,生长受阻 (a frame of stones form around the trunk of the tree so its growth is obstructed). This meaning disappeared a long time ago.

睏 (the traditional form of 困 "sleepy") does not exist in 《说文解字》 which means it didn't exist back then when the dictionary was made. But we can find 目, "人眼。象形。重童子也。", meaning "eye". This means that at some point in the histroy, 目 and 困 were combined to form a new character with a new meaning -- 睏 (sleepy). This is easy to explain: eyes are obstructed, trapped, limited, cannot open, thus "sleepy". Because when you feel sleepy you have a difficult time opening your eyes.

Now back to trainchinese dictionary. We have two entries of 困 in our dictionary. Please note that their traditional forms and meanings are different. As always, the character before "/" is the simplified form, and after "/" is the traditional form:

Simpl. / Trad.
1. 困 / 睏 [kun4] , (adj) sleepy; tired; difficult, hard
2. 困 / 困 [kun4] , (v) to trap, to surround; be stranded; (dialect) to sleep

As you probably know, traditional characters preserve more of the original structures and meanings of characters, and they are closer to the traditional categories of Chinese character classification.

Examples: 鸟/鳥 (bird), 只/隻 (single, one), 双/雙 (double, pair), etc. As you can see 鳥 looks more like a bird than its simplified version 鸟. And looking at the simplified forms, you might not be able to link 只 and 双, coz they look so different! But their traditional forms are closed linked: 隻 and 雙. There is a reason behind many Chinese characters are formed in a certain way, and you can find out more of the reason by observing and analyzing the traditional forms.

On the other hand, Simplified characters are more artificial and man-made in a sense. But they have certain highlights, e.g. it saves time to learn them and to write them. In traditional characters, both 困 and 睏 exist with different meanings.

Back in the 50's, when the Chinese in ma
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