말았어야 했어

shouldn't have

→ 말다
phrase Uncommon #5,350
shouldn't have Used to express regret that something was done. It follows a verb stem, as in 하지 말았어야 했어, meaning “I shouldn't have done it.”
KO: 그렇게 화내지 말았어야 했어.
EN: I shouldn't have gotten so angry.

너 한테 말하지 말았어야 했어.

I shouldn't have told you.

오지 말았어야 했어

I shouldn't have come.

— 레베카 (1940)

고향을 떠나지 말았어야 했어

I shouldn't have left my hometown.

— 반지의 제왕: 두 개의 탑 (2002)

그러지 말았어야 했어

I shouldn't have done that.

— 다이 하드 (1988)

난 그걸 먹지 말았어야 했어.

I shouldn't have eaten that.