Breakdown of Ich bedaure den Fehler sehr. Ich hätte dich fragen sollen.
ich
I
sehr
very
fragen
to ask
haben
to have
dich
you (singular, informal)
der Fehler
the mistake
sollen
should / ought to
der
who, which, that (relative pronoun; die, das)
bedauern
to regret (feel pity, find unfortunate)
Questions & Answers about Ich bedaure den Fehler sehr. Ich hätte dich fragen sollen.
Why does the sentence use the infinitive sollen instead of its past participle gesollt?
This is the double infinitive rule! When a modal verb like sollen is used in the perfect tense or the past Konjunktiv II alongside another main verb like fragen, it stays in its infinitive form instead of changing to a past participle. So the correct structure is hätte ... fragen sollen, never hätte ... fragen gesollt.
What is the exact word order for the two infinitives at the end of the sentence?
In a main clause with a double infinitive, the conjugated helper verb (hätte) takes the standard second position. The two infinitives are pushed to the very end of the sentence. The main action verb (fragen) comes first, and the modal verb (sollen) is always placed at the absolute end.
I usually say Es tut mir leid for "I'm sorry". How is bedauern different?
bedauern is a regular verb that specifically means "to regret." It sounds a bit more formal and serious than Es tut mir leid. Grammatically, it also directly takes an accusative object (den Fehler), whereas leid tun uses a dative pronoun and often requires a preposition, such as Es tut mir leid wegen des Fehlers.
Why does fragen use the accusative dich here? Shouldn't asking someone use the dative case?
This is a very common mix-up! While many verbs of communication in German take the dative case (like antworten or sagen), the verb fragen is an exception. The person being asked is always the direct object, meaning it must take the accusative case (dich).
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