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Questions & Answers about O que pretendes dizer com isso?
Why is pretendes translated as 'do you mean'? Doesn't pretender mean 'to pretend'?
No, pretender is a classic false friend! In Portuguese, it means 'to intend', 'to wish', or 'to aim'. If you actually want to say 'to pretend', you should use the verb fingir. The phrase pretendes dizer literally translates to 'do you intend to say', which is a standard way Portuguese expresses 'do you mean'.
Could I say O que queres dizer com isso? instead?
English uses the preposition 'by' in 'mean by that'. Why does Portuguese use com (with)?
Could I use aquilo instead of isso for 'that' at the end of the sentence?
Isso is the most natural choice here because it refers directly to something the person you are talking to has just said. In Portuguese, isso relates to the listener's 'space' or recent words. You would use aquilo only if you were both referring to a more distant statement or event that neither of you had just brought up.