YOU SAID:

I hate it when I break a nail.

INTO JAPANESE

私は爪を壊すとき、私はそれが嫌いです。

BACK INTO ENGLISH

I hate it when I break my nails.

INTO JAPANESE

爪を折ると嫌い。

BACK INTO ENGLISH

I hate breaking nails.

INTO JAPANESE

私は爪を壊すのが嫌いです。

BACK INTO ENGLISH

I hate breaking nails.