This article examines how different groups of men negotiate and produce distinct masculinities in actual encounters. The article studies the establishment of the United Jewish Appeal (UJA) during the 1940s and focuses on how American and Israeli Jews interacted in fund-raising events. It identifies the threats to the masculine faces of these groups that arose in this setting and examines the organizational practices that were developed in order to allow these groups to cooperate and coproduce their distinct models of masculinity. Exploring masculinities in interaction highlights the importance of concrete organizational practices and monetary transactions, in particular, for the construction of masculinities. Specific discursive and organizational arrangements allow actors to act in a masculine manner and receive affirmation for their masculine claims. In the case examined here, specific discursive practices and the temporal and spatial organization of fund-raising events eased the tensions between two distinct groups of men and allowed them to maintain their distinct and potentially conflicting masculinities.