Jin Ping Mei cihua 金瓶梅詞話 (Plum in the Golden Vase) displays an unprecedented interest in breaking apart and reassembling the components of words. This essay asks where the Cihua edition's fascination with character manipulation (a procedure the author refers to as chaibai daozi 拆白道字) comes from and how it relates to literary riddles that precede and follow this landmark sixteenth-century novel. Jin Ping Mei cihua enlarges the presentation and associations of riddles in fiction through its engagement with contemporaneous theatrical literature and the entertainment culture of the brothel. Later commentators, notably Zhang Zhupo 張竹坡 (1670–1698), reorganize the game sequences within which bouts of character manipulation are embedded for the purposes of narrative prolepsis and character development, advocating an approach to reading enigmas as portents that influenced late imperial novelists. In doing so, however, they efface the Cihua's unruly celebration of contingency, the novel's seductive insinuation that it might be written otherwise.