YOU SAID:

im so bored to the point where im trying to have a conversation with this...

INTO JAPANESE

私はこれと会話をしようとするところまで退屈しています...

BACK INTO ENGLISH

I'm bored to the point of trying to have a conversation with this...

INTO JAPANESE

こいつと会話しようとするくらい退屈だ…

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It's boring enough to try to have a conversation with this guy...

INTO JAPANESE

こいつと会話しようとしてもつまらない…

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It's boring to try to talk to this guy...

INTO JAPANESE

こいつと話そうとしてもつまらない…

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It's boring to try to talk to him...

INTO JAPANESE

彼と話そうとするのは退屈だ...

BACK INTO ENGLISH

It's boring trying to talk to him...

INTO JAPANESE

彼と話そうとするのは退屈だ...

BACK INTO ENGLISH

It's boring trying to talk to him...