This chapter discusses the symptoms and consequences of the normative assumptions I condensed in the love—friendship paradox (Chapter 5) with specific reference to cross-sex friendship. While we might assume that today intimate relationships are free from social convention, that turns out to be true for cross-sex friendship only to a limited extent. The social construction of different types of intimacy for men and women, and the norm of sexual attraction, impede these friendships. Platonic heterosocial friendships challenge these norms but may also reproduce them. It is under these conditions that "friends with benefits' relationships seem to offer the best of both worlds: casual sex in the context of friendship. But taking the benchmark of intimacy to these relationships shows that they fall short of realizing what they promise. Others construct "erotic friendships' in an attempt to reconcile sex and friendship without partaking in the cultural staging of romance, but without having to forgo to generative potentials of intimacy. The reality of heteronormative barriers regarding what is ostensibly the "freest" of all interpersonal relationships yields insights into the gendered distribution of power in and the gendered constitution of our societies.