nicht so behandeln dürfen

shouldn't have treated someone like that

→ nicht
phrase Rare #37,284
shouldn't have treated someone like that Used with hätte or hätten to express regret or criticism about how someone was treated in the past. The person being treated appears between nicht and so behandeln or before the phrase.
GE: Du hättest deine Schwester nicht so behandeln dürfen.
EN: You shouldn't have treated your sister like that.

Ich hätte euch nicht so behandeln dürfen.

I shouldn't have treated you that way.

Sie hätten Tom nicht so behandeln dürfen.

You shouldn't have treated Tom that way.

Ich hätte dich nicht so behandeln dürfen.

I shouldn't have treated you like that.

— Rote Laterne (1991)

Ich hätte Sie nicht so behandeln dürfen.

I shouldn't have treated you that way.

Du hättest Tom nicht so behandeln dürfen.

You shouldn’t have treated Tom that way.

Ihr hättet Tom nicht so behandeln dürfen.

You shouldn't have treated Tom that way.