YOU SAID:
When I was in high school I was really dorky.
INTO JAPANESE
私が高校に通っていたとき、私は本当にdorkyでした。
BACK INTO ENGLISH
When I was in high school, I was really dorky.
INTO JAPANESE
私が高校に通っていたとき、私は本当に馬鹿だった。
it is unlikely that this phrase will ever reach equilibrium