The acquisition of needed resources is a necessary part of human activity. Persuasion is a tool that can be used to acquire commodities. However, because of obligations inherent in intimate relationships, the necessity of elaborated persuasive messages is lessened Furthermore, when an intimate's request is rejected, negative responses and counterpersuasion are likely. This article presents the results of a study in which three measures of intimacy are related to the obligation to grant requests for resources, the obligation to offer resources in a time of need, characteristics of requests for resources, and characteristics of responses to rejection. Although not all three measures yielded identical results, increasing intimacy with a potential helper increased obligations to grant requests for resources, and obligation to offer resources in a time of need. Moreover, increasing intimacy was negatively associated with request elaboration, frequency of explanations, and inducements. When responding to rejection, increasing intimacy was negatively related to forgiving statements and positively related to counterpersuasion. Finally, after rejection, intimates composed messages, judged to be less polite than those that contained their initial request. The politeness of postrejection messages created by nonintimates was not perceived to differ from that of their initial requests.