YOU SAID:
Although they annoyed him but he preferred to be with them rather than alone.
INTO JAPANESE
彼らは彼を苛立たせましたが、彼は一人ではなく彼らと一緒にいることを好みました。
BACK INTO ENGLISH
They annoyed him, but he preferred to be with them rather than alone.
INTO JAPANESE
彼らは彼を苛立たせたが、彼は一人ではなく彼らと一緒にいることを好んだ。
BACK INTO ENGLISH
They annoyed him, but he preferred to be with them rather than alone.
That didn't even make that much sense in English.