Avessi pagato l'assicurazione! Me ne pento veramente.

Breakdown of Avessi pagato l'assicurazione! Me ne pento veramente.

avere
to have
pagare
to pay
veramente
really
pentirsene
to regret it
l'assicurazione
the insurance (f)

Questions & Answers about Avessi pagato l'assicurazione! Me ne pento veramente.

Why does the first sentence start directly with Avessi, without a word like se (if) or magari (if only)?
This is a special structure called the independent exclamative subjunctive. To express a strong regret about a past action, you can drop the se and start the exclamation directly with the past perfect subjunctive (trapassato congiuntivo). It has the exact same meaning as saying Se solo avessi pagato l'assicurazione! (If only I had paid for the insurance!).
Why do we need the past perfect subjunctive (avessi pagato) here instead of the imperfect subjunctive (pagassi)?
The past perfect subjunctive is used because the regret is about a past event that is now impossible to change. If you used the imperfect subjunctive (Pagassi l'assicurazione!), it would express an unfulfilled wish about the present, meaning "If only I paid the insurance!" or "If only I were paying it!".
Where does the me in Me ne pento come from?
The verb is pentirsi (to regret), which is reflexive, meaning "I regret" is normally mi pento. However, whenever the reflexive pronoun mi is immediately followed by another pronoun like ne, the i changes to an e to make pronunciation flow better, resulting in me ne.
Why do we use ne here instead of lo to say "I regret it"?
In Italian, you don't regret something directly as a direct object; you "repent of something." The grammatical structure is pentirsi di qualcosa. Whenever you replace an object that is introduced by the preposition di, you must use the pronoun ne (of it / about it), rather than a direct object pronoun like lo.

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