Based on ethnographic fieldwork, we explore how boys use jocular play to perform romantic relationships in their peer culture and construction of masculinities. The analysis combines an ethnomethodological approach to doing gender with poststructuralist-influenced studies on masculinity and boyhood. We demonstrate how the boys – through game-playing, teasing, humorous narration, and ritual insults – do gender while they explore potentially embarrassing romantic experiences. The boys police and produce acceptable heterosexual masculinities while having fun and doing friendship, demonstrating the dynamic and entertaining potentials of performing romantic relationships in jocular peer play.