This article responds to encouragement to remember the wonder in gender and sexualities education. Specifically, it addresses gender and sexuality in a variety of contexts, from mediated forms to how gendered sexual expectations are socially constructed and conveyed through cultural scripts, particularly in heterosexual contexts. According to traditional sexual scripts, men are encouraged to be sexually active and privilege personal sexual pleasure (e.g., arousal, orgasm), whereas women are often conditioned to be sexually passive, reactive, dismissive and reputationally protective. Exploring gender, conditioning and education as they relate to sexuality and pleasure, this article combines scholarly research with play in its approach. Findings acknowledge both the continuation of traditional sexual expectations and practices as related to sex and gender as well as the value of more contemporary, sexual nuance such as those found in PlayLabs, educational workshops addressing sex and mentoring as related to sex and pleasure.