Entré al cuarto de puntillas sin que mi hermano me escuchara.

Questions & Answers about Entré al cuarto de puntillas sin que mi hermano me escuchara.

Why do we use sin que followed by a conjugated verb here instead of just using sin + infinitive?
We use sin que + subjunctive because there are two different subjects in the sentence. The person entering the room is you (yo), but the person listening is your brother (mi hermano). If the subject were the same for both actions (like 'I entered without making a sound'), you would drop the que and use the infinitive: Entré al cuarto sin hacer ruido.
Why is the verb escuchara in the past (imperfect) subjunctive instead of the present subjunctive?
The tense in the sin que clause must align with the timeframe of the main sentence. Because the main action happened in the past (Entré, the preterite tense), it forces the subjunctive verb into the past tense too (escuchara). If you were describing a present habit like 'I always enter without him hearing me', you would use the present subjunctive: Entro al cuarto sin que me escuche.
I notice the phrase de puntillas translates to 'on tiptoe'. Is this a fixed expression?
Yes, de puntillas is an idiomatic expression that means 'on tiptoe' or 'tiptoeing'. In many parts of Latin America, you will also frequently hear en puntillas or the diminutive de puntitas. They are all completely interchangeable.
Why is it Entré al cuarto rather than Entré el cuarto? Doesn't the verb already imply entering 'into' a place?
Unlike the English verb 'enter', the Spanish verb entrar usually requires a preposition to show where you are going. In Latin America, the preposition a is the most common choice for entering a physical space, so entrar a + el cuarto combines to form entrar al cuarto. You cannot follow entrar directly with the location noun.

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