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Unlike non-restrictive relative clauses, which have long given sole sovereignty to wh-forms, restrictive relative clauses are open to variation between wh-forms, that, and zero. In Present-Day American English, however, restrictive relatives clauses with which have shown a steep decline in usage. The present study aims to shed light on this downward trend of which-relatives by conducting a corpus-based quantitative and qualitative analysis. In an attempt to place the change in the overall evolutionary development of 20th century American English, it is argued with Leech et al. (2009) that which, being the more formal and less colloquial variant, has given way to that (and presumably zero) under the pressures of a larger, prevalent trend of colloquialization. It is further postulated that colloquialization in this case is reinforced by forces of prescriptivism. Though several potential parameters for the distribution of which-relatives are proposed on the basis of the notion of syntactic complexity, the results obtained from the statistical analysis do not offer conclusive evidence of the correlation between the use of which and syntactic complexity. This points to a need for further examination of the phenomenon at hand, perhaps this time from the view of discourse and/or stylistics.