Objective: This pilot study tested the efficacy of a brief, novel, theory-driven, self-guided, home-based intervention designed to promote condom use among young men who have sex with men (YMSM). Participants: Thirty YMSM were recruited from a large public US midwestern university during spring of 2012. Methods: The intervention was tested using a repeated measures design with the primary follow-up assessment occurring 6 weeks after enrollment. Results: Forty-five percent of men reported a reduced frequency of unprotected insertive penile-anal intercourse in the past 30 days compared with baseline (p = 0.01). Consistency of condom use improved (p = 0.013), as did motivation to use condoms correctly, condom use self-efficacy, and condom attitudes. All participants indicated that they were glad they participated, would recommend the program, and that overall, they had liked the program. Conclusions: This pilot study supports an expanded trial of this intervention with MSM at high-risk of acquiring human immunodeficiency virus/sexually transmitted infections (HIV/STIs).