YOU SAID:
Jake is parking his car while his friends wait him
INTO JAPANESE
ジェイクは彼の友人が彼を待っている間に彼の車を駐車しています
BACK INTO ENGLISH
Jake parks his car while his friend is waiting for him
INTO JAPANESE
ジェイクは彼の友人が彼を待っている間に彼の車を駐車します
BACK INTO ENGLISH
Jake parks his car while his friend is waiting for him
That didn't even make that much sense in English.