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I was watching this video (pretty funny by the way) and the title stuck out to me.

ダルい上司の打ち合わせ回避する方法考えた

Typically, ダルい would mean that you feel very tired/lethargic. However, in this case the boss is actually a little too energetic and instead seems to be causing his subordinates to become だるい as opposed to being だるい himself. Surprisingly, the jisho definition 2 seems correct:

  • bothersome; tiresome; pain-in-the-ass​

but I can't find any Japanese language sources for this.

  • 大辞林 : ①疲れていて,からだに力がない。動くのがおっくうである。 「熱があるのか体が-・い」
  • デジタル大辞泉 : 疲れや病気などで、からだを動かすのがおっくうである。かったるい。

Can anyone provide a Japanese language source for this usage?

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ダルい can indeed mean both "tired" and "tiresome" depending on the context. However, the same thing is true with many other i-adjectives related to emotion, and monolingual dictionaries may not distinguish them explicitly as English speakers might expect. For example, 楽しい means both "is having fun" and "makes you have fun", but デジタル大辞泉 has only one definition that vaguely covers both of these two meanings in English.

ダルい上司 usually refers to an annoying boss who often makes you tired, not a boss who is tired. Likewise, ダルい打ち合わせ refers to a tiresome meeting. (I don't know whether ダルい in your title modifies 上司 only or 上司の打ち合わせ as a whole. It's not important in this context.) Also note that this usage of ダルい meaning "tiresome" is slangy, which may be another reason why it's not explicitly explained in monolingual dictionaries (yet).

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  • If you wanted to use ダルい, how would you make clear that it's a boss who is lethargic as opposed to an annoying boss?
    – Ringil
    Sep 9, 2020 at 12:09
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    @Ringil ダルそうな上司 tends to mean that, and ダルそうにしている上司 is unambiguous. (Or 気怠げな上司 , 気怠そうにしている上司...)
    – naruto
    Sep 9, 2020 at 12:30

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