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I found some answers online, but I don't really understand the nuance.

People seem to say that つまらない is "boring" in the sense that it is uninteresting to you. And 退屈 is "boring" in the sense that you don't have anything else to do. As such, it can often be translated as "bored" or a する verb to "feel bored"

But several examples I see seem to go against that. 退屈な人 isn't uncommon, and seems to often refer to a boring person, not a bored person. And things like 退屈な講義 and 退屈な話 also don't seem to fit.

So what is the actual distinction here?

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    I love when Japanese people say in English, "I am boring". 😄
    – istrasci
    Dec 19, 2022 at 17:18

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As for the meaning, つまらない can mean something different from boring: trivial, nonsensical etc. In the sense of boring, it is mostly interchangeable with 退屈な.

For boring/bored, you'd ultimately need to depend on the context and it should be easier. Roughly つまらない・退屈だ/な are boring in most cases and 退屈する means to feel bored. The latter is after all (in Japanese) a verb in active voice, so there is an agent.

やることがなくて退屈だ/つまらない can be translated as I have nothing to do and feel bored, but it can also be understood (more literally) as I have nothing to do and things are boring.

退屈な人 is always boring person and "person who is bored" is 退屈した人. This is parallel to tiring/tired person = 疲れる人/疲れた人. Note -た connotes with perfective -d.

This kind of difficulty should arise from mismatch of transitivity between Japanese and English, and should be partially handled on case-by-case basis.

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