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I was gaming with a friend at his house, and his grandfather told me this phrase which I don't understand.

The friend explained that 少壮不努力 means I don't study hard when I'm young, and he explained that 老大徒伤悲 means that a gang leader would be sad about me.

Obviously I know he's joking about 老大 being a gang leader, but he didn't want to tell me the real meaning, and I couldn't find what 老大 officially means. According to Wikipedia, 老大 could mean

The honorific title to the elder brother .
Respect for the boss .
Respect for the leader .
The name for the gang leader.
Respectful title for chiefs and superiors .
The honorific title for "older people".
Common name for "the number one person".

What is the correct meaning for this context?

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老大 here is not the noun 'leader/ boss'

It is an adjectives phrase

老 = old; 大 = grown (in age)

'老大' in '老大徒伤悲' means "old"

Detail break down of this expression:

  • 少壮 - young and in your prime

  • 不努力 - not work hard

  • 老大 - grown and old

  • 徒伤悲 - only have sadness

少壮不努力, 老大徒伤悲 means "If you don't work hard when you are young, there will only be sadness for you when you get old"

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    I would add that this particular reading of 老大 comes from the mirror construction with 少壮, that makes it clearer why in this case it doesn't mean “boss" as in other common usages.
    – blackgreen
    Commented Aug 5, 2020 at 9:33

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