YOU SAID:
So to my ex bestfriend I thought I knew to then end sorry I know things aren't going as we planned we really messed up this time
INTO JAPANESE
私の元親友に、私は本当に終わってしまったことを知っていたと思った
BACK INTO ENGLISH
I thought my ex-best friend knew I was really over
INTO JAPANESE
元親友が本当に終わったと知っていたと思った
BACK INTO ENGLISH
I thought I knew my ex-friend was really over
INTO JAPANESE
元友達が本当に終わったと思った
BACK INTO ENGLISH
I thought my old friend was really over
INTO JAPANESE
昔の友達は本当に終わったと思った
BACK INTO ENGLISH
I thought my old friend was really over
That didn't even make that much sense in English.