The article proposes an interpretation of Dante’s «montanina» song as a polysemic text, in which the literal meaning, the description of a late falling in love and the passion that ensues, overlaps with further meanings of a doctrinal and above all political nature. The new falling in love that the text presents could be the representation of the beginning of a new personal and political phase, which sees the abandonment of the municipal ideal and the adherence to the ideal of universal monarchy. This interpretation, which also involves the Ep. IV to Moroello Malaspina, commonly regarded as the razo of the song, leads one to situate the two texts in the period of Dante’s sojourn in Casentino documented by five other letters (Ep. VI-X).