Present-day Dutch shows an alternation reflecting a transition from the use of the comparative particle dan ‘than’ toward the particle als ‘as’ in comparisons of inequality. We argue that this transition—as well as the replacement of denn/dann by als in Early New High German, and als ‘as’ by wie ‘how’ in present-day German—results from a conflict between two competing principles, Economy and Iconicity. The conflict between these two constraints in German and Dutch gives rise to a cycle, in which having two particles—one for each construction—and having one particle for both, comparatives and equatives, alternate over time.*