In the present article, we studied approximating pairs of numbers (a, b) that were used to estimate quantity in a single phrase ("two, three years ago"). Pollmann and Jansen (1996) found that only a few of the many possible pairs are actually used, suggesting an interaction between the ways in which people estimate quantity and their use of quantitative phrases in colloquial speech. They proposed a set of rules that describe which approximating pairs are used in Dutch phrases. We revisited this issue in an analysis of Swedish and American language corpora and in a series of three experiments in which Swedish and American adults rated the acceptability of various approximating pairs and created approximating pairs of their own in response to various estimation tasks. We found evidence for Pollmann and Jansen's rules in both Swedish and English phrases, but we also identified additional rules and substantial individual and cross-language variation. We will discuss implications for the origin of this loose "grammar" of approximating pairs.