Numbers are not simply dry and abstract symbols for arithmetic quantities. Human minds also endow them with rich and complicated personalities. Such personalities can be created and used at a broad cultural level, like the Mayan portrait glyphs used for the numbers 1 through 20. Or they can be found at a highly idiosyncratic level in the form of synaesthesia known as Ordinal Linguistic Personification. Imagining personalities for numbers involves cognitive systems that are linguistic as well as mathematical. Our brains create a space where personal associations and broader social experience can mingle. The paper concludes with three of the author’s poems in which numbers take on personalities that reflect contemporary urban experience.