Quem me dera que o meu chefe tivesse sido compreensivo em vez de mostrar arrogância.

Questions & Answers about Quem me dera que o meu chefe tivesse sido compreensivo em vez de mostrar arrogância.

Why do we use "tivesse sido" (Pluperfect Subjunctive) here instead of "fosse" (Imperfect Subjunctive)?
Because the sentence expresses a regret about something that already happened in the past ("had been"). The phrase Quem me dera que always triggers the subjunctive. If you were wishing for a different present or future reality, you would use the Imperfect Subjunctive (Quem me dera que o meu chefe fosse compreensivo - I wish my boss were understanding). But since this is a past regret that cannot be changed, you must use the Pluperfect Subjunctive (tivesse sido).
What is the literal translation of the idiom "Quem me dera que"?
It literally translates to "Who to me had given that". The verb dera is the simple pluperfect indicative (Mais-Que-Perfeito Simples) form of dar (to give), though in this fixed expression it acts more like a conditional ("Who would give me that"). It is a very common idiom used to express a strong, heartfelt desire or regret, equivalent to "I really wish" or "If only" in English.
Could I use "Oxalá" instead of "Quem me dera que" to express this past regret?
Yes, you could say Oxalá o meu chefe tivesse sido compreensivo. Both expressions trigger the subjunctive and express strong past regret when paired with the Pluperfect Subjunctive. However, Quem me dera que feels slightly more personal and focused on the speaker's own yearning, whereas Oxalá stems from an Arabic expression meaning "God willing" and translates closer to "If only". Note that Oxalá does not require the word que after it.
Why is "mostrar" in the uninflected infinitive here rather than being conjugated to match the boss?
Because it directly follows the prepositional phrase em vez de (instead of). In Portuguese, as a general rule, whenever a verb is immediately governed by a preposition (such as de, para, por, or sem), it is used in the infinitive form. Since the subject remains the same (the boss), the standard impersonal infinitive works perfectly here.

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