Does the setting in which a relationship initiation attempt occurs matter to its success? Identical initiations could yield differential success if enacted in different settings. Data from five independent samples highlight the role settings play in the perception of (hypothetical) relationship initiation attempts and (expectations of) their success. Study 1a sourced a wide variety of settings for real-world relationship initiations. A separate sample rated the identified settings on initiation appropriateness (Study 1b). Study 2 tested the appropriateness and associated outcomes of initiation settings while varying aspects of the interpersonal context (initiator attractiveness, Study 2a; initiator familiarity, Study 2b; sexual nature of proposition, Study 2c). Irrespective of initiator attractiveness, familiarity, or type of proposal, perceptions of initiations' success were impacted by the settings' appropriateness. This work is the first to empirically test whether perceptions and outcomes of initiation attempts differ as a function of the setting in which they occur.