Which one is right? "Avrei voluto farlo" or "Vorrei averlo fatto"?

Question

Which of these is correct? When do you use them?

Thanks!

Answer 1

They are both correct, but they mean different things. They are very much not interchangeable.

In "Avrei voluto farlo" the verb volere is itself at the past conditional. Hence it means that the act of wanting is done in the past: it means "I would have wanted to do that" or "I wished to do that", that is at some point in the past I wished to do a certain thing (but I didn't). For example

L'anno scorso avrei voluto farlo, ma non sono riuscito a organizzarlo (Last year I wished to do that, but I couldn't organize it)

Conversely, in "Vorrei averlo fatto", the verb volere is at the present, and it is fare that is in the past tense. Its meaning is "I would want to have done that" or "I wish to have done that". That is I, now, wish I had done it in the past.

Vorrei averlo fatto due settimane fa, ma non si può cambiare il passato (I wish I had done it two weeks ago, but we cannot change the past)

This kind of construction can be done with pretty much every modal verb in Italian. Here is an example with the verb potere, similar examples could be done with any other modal verb (dovere, sapere, etc.):

Potrei averlo già fatto, ma volevo lasciarti riposare (I could have done it already, but I wanted to let you rest)

Avrei potuto farlo, ma decisi di lasciar perdere (I would have been able to do it, but I decided to let it go)

Note that since modal verbs in English lack most tenses, I am forced to use a periphrasis ("to be able to") to translate the second sentence.

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Lest you see it as a dichotomy, let me point out that you can combine the two constructions: you can say "Avrei voluto averlo fatto" to indicate that at some point in the past, the subject wished to have done something earlier. For example

Ieri sera ero depresso: avrei voluto aver abbandonato questa città da anni. (Yesterday evening I was depressed: I wished to have left this city years earlier)