It has been proposed that people cope with the embarrassment of acquiring condoms using a variety of tactics, such as buying from a sales clerk of the same gender or buying additional products. However, the actual use and efficacy of these coping mechanisms have not been rigorously evaluated. This research investigates three specific questions related to coping with embarrassment: (R1) Do people prefer cashiers of the same gender when buying condoms because it helps them cope with embarrassment or because of the similarity‐attraction effect? (R2) When multiple coping mechanisms are available, do people use more than one at a time? And (R3) Do men and women prefer different coping tactics? Using an experimental design, Study 1 investigates R1 and finds support for both explanations. Studies 2 and 3 use field and lab experiments, respectively, to investigate R2 and R3. The findings indicate that people only use one coping tactic at a time and that men and women have a different preference for coping tactics. Women prefer coping tactics that mask condom acquisition, while men prefer social–emotional support tactics. Furthermore, discrepancies between the field experiment and lab experiments indicate that people underestimate the influence of embarrassment on their actual behavior.