YOU SAID:
Hello my friend how is funny
INTO JAPANESE
こんにちは、私の友人はどんなに面白いですか?
BACK INTO ENGLISH
Hello, how interesting is my friend?
INTO JAPANESE
こんにちは、私の友人はどれくらい面白いですか?
BACK INTO ENGLISH
Hello, how interesting is my friend?
That didn't even make that much sense in English.