YOU SAID:
I wish I could maybe ask him out
INTO JAPANESE
多分彼に尋ねることができたらいいのに
BACK INTO ENGLISH
Maybe I wish I could ask him
INTO JAPANESE
多分私は彼に尋ねることができたらいいのに
BACK INTO ENGLISH
Maybe I wish I could ask him
That didn't even make that much sense in English.