Me preguntó si me gustaba aquella ciudad.

Questions & Answers about Me preguntó si me gustaba aquella ciudad.

Why do we use the imperfect tense (gustaba) here instead of the preterite (gustó)?
The preterite (preguntó) is used for the action of asking because it was a single, completed event. The imperfect (gustaba) is used for liking the city because it describes an ongoing state or feeling at the time he asked, not an action with a clear start and end.
Why does the sentence use aquella instead of esa to mean that?
In Spanish reported speech, when you shift a conversation into the past, the spatial and temporal distance increases. The original direct question likely used esta to mean this. When reporting it later, esta often becomes aquella to show that the city is now distant in both time and space from the speaker's current reality.
Does the word si ever trigger the subjunctive mood in an indirect question like this?
No, in indirect questions, si is always followed by the indicative mood. Even though learners often associate the subjunctive with doubt or unknown outcomes, expressing whether or not with si in this specific structure strictly requires the indicative (gustaba).
Are the two instances of the pronoun me functioning in the exact same way?
They are both indirect object pronouns, but they relate to their verbs differently. The first me tells us who received the question. The second me works with the verb gustar to show who is doing the liking, because structurally the sentence translates to the city being pleasing to me.

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