The art of contract interpretation involves determining the meaning of an agreement. Often, courts must determine whether a particular term is reasonably susceptible to more than one meaning, and if so, they engage in the process of disambiguating the term. This process involves a subtle dance between the traditional and the modern approaches to contract interpretation: the former looking merely to the “four corners” of the contract and the latter considering extrinsic evidence to establish the intent of the parties. When encountering dissimilar cultural influences in common-law contract ambiguities, the courts apply an objective, “reasonable person” standard, which inevitably dilutes cultural variance into a westernized and often short-sighted contract interpretation. After advocating for a “modern” jurisdictional approach to contract interpretation, this Note will argue that guidelines within both the Uniform Commercial Code (UCC) and the Contracts for the International Sale of Goods (CISG) can provide a salient approach for introducing cultural evidence to tackle cultural conflicts arising during contract interpretation. This Note advocates for the admission of cultural extrinsic evidence to both create ambiguity and resolve ambiguity. The notion of culture advocated for in this Note embraces dismantling the concept’s vagueness into more concrete constituents of social relations. This method of cultural contract interpretation provides the greatest opportunity to recognize cultural conflicts within ambiguous terms and thus avoids blindly engaging in cultural compulsion.