This chapter explores the background, ethics, and design of “Dating Games.” It explores how Dating Games differ from other forms of serious games and how designers can both get dating and Dating Games wrong if poorly designed. The chapter does this through the lens of the author’s non-digital Dating Game, Fellowship of Fools: The (Romance) Game and Fellowship of Fools: The (Sexuality) Game. The chapter also examines the role that friendship plays in romantic and sexual relationships and thus also uses the author’s game, Fellowship of Fools: The (Friendship) Game. Dating Games, not unlike dating generally, are a “fraught” field. Players bring with them a great deal of cultural assumptions that require a great deal of thought and care on the part of designers.