A madrasta esperava que tu tivesses prosseguido a carreira familiar.

Questions & Answers about A madrasta esperava que tu tivesses prosseguido a carreira familiar.

Why do we use tivesses prosseguido (Past Perfect Subjunctive) here instead of just prosseguisses (Imperfect Subjunctive)?
The main verb esperava (hoped) is in the past tense and expresses an emotion or desire, which triggers the subjunctive. We use the compound Past Perfect Subjunctive (tivesses prosseguido) because the action of pursuing the career happened before, or was supposed to be completed by, the time the stepmother was hoping. If we used prosseguisses, it would mean she hoped you would pursue it at that same time or in the future.
I often mix up these verb forms. Why is it tivesses and not tivestes?
Tivesses is the imperfect subjunctive for tu, which always features that double-s ending. Tivestes is the past simple (Pretérito Perfeito) for vós. We need a subjunctive form here because of the trigger esperava que, and we are addressing tu, so tivesses is the correct auxiliary verb.
Is familiar used here just like the English word "familiar"?
No, this is a classic false friend! In Portuguese, the adjective familiar directly translates to "family" or "pertaining to the family", which is why a carreira familiar means "the family career". If you want to say something is "familiar" in the English sense of being recognizable to you, you would usually use conhecido.
The verb is prosseguir. Does it have an irregular past participle?
No, prosseguir is completely regular in its past participle form. Like most verbs ending in -ir, you simply drop the ending and add -ido, resulting in prosseguido.

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