um Rat fragen sollen

should have asked for advice

→ um
phrase Rare #44,229
should have asked for advice Usually used with a form of haben in the subjunctive II, such as „hättest ... sollen“ or „hätte ... sollen“, to express regret or criticism about not asking for advice earlier.
GE: Du hättest deine Eltern um Rat fragen sollen.
EN: You should have asked your parents for advice.

Du hättest Tom um Rat fragen sollen.

You should have asked Tom for advice.

Ich hätte euch um Rat fragen sollen.

I should have asked you for advice.

Ich hätte dich um Rat fragen sollen.

I should have asked you for advice.

Ich hätte Sie um Rat fragen sollen.

I should have asked you for advice.