YOU SAID:
If i had a penny for every time dad smiled, I would be quite poor
INTO JAPANESE
お父さんが微笑むたびにペニーを持っていたら、私はかなり貧しいでしょう
BACK INTO ENGLISH
I would be pretty poor if my dad had a penny every time he smiled
INTO JAPANESE
私の父が微笑むたびにペニーを持っていたら私はかなり貧しいでしょう
BACK INTO ENGLISH
I would be pretty poor if my dad had a penny every time he smiled
That didn't even make that much sense in English.