YOU SAID:
I went to the park with my freinds
INTO JAPANESE
私は私のfreindsと公園に行きました
BACK INTO ENGLISH
I went to the park with my friends
INTO JAPANESE
私は友人と公園に行きました
BACK INTO ENGLISH
I went to the park with a friend
INTO JAPANESE
私は友人と公園に行きました
BACK INTO ENGLISH
I went to the park with my friend
INTO JAPANESE
私の友人と公園に行きました
BACK INTO ENGLISH
I went to the park with my friends
INTO JAPANESE
私は友人と公園に行きました
BACK INTO ENGLISH
I went to the park with my friend
INTO JAPANESE
私の友人と公園に行きました
BACK INTO ENGLISH
I went to the park with my friends
it is unlikely that this phrase will ever reach equilibrium