Following Traugott’s (2007, 2008a,b) research on the grammaticalization of English degree modifiers, this paper explores the history of a family of very similar quantifier/degree-modifier constructions in German. In particular, we present a detailed diachronic analysis of ein bisschen (‘a bitDIM’) and ein wenig (‘a little’). On the basis of data from the German Text Archive (Deutsches Textarchiv) and the historical archive of the German Reference Corpus (Deutsches Referenzkorpus), we examine to what extent these constructions followed a grammaticalization path comparable to the one Traugott observed for their English counterparts. Quantitative analyses on the gradual context expansion of ein wenig and ein bisschen are combined with qualitative analyses on potential bridging contexts allowing for reanalysis to occur. Diachronically, there is a reduction in individual formal variation as the constructions converge in their behaviour. Their combined histories suggest that the older German modifiers may have served as attractor sets for an increasingly strengthened mid-level quantifier/degree-modifier schema, promoting the emergence of younger modifiers such as ein Quäntchen (‘a quantumDIM’) and ein Tick (‘a tick’) via analogy. These observations stress the crucial role that network links between constructions can play in grammaticalization.