in this case you would use passé composé in French. If you used the imparfait, it would sound to French ears like "How many times he was dreaming of being her." sounds to English ears. The past continuous form in English doesn't really hit the spot here, just as the imparfait wouldn't in French.
-- Chris (not a native speaker)
But the Imparfait is also "Used to" and "How many times he used to dream of being her" sounds perfectly fine? I don't think I quite understand.
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