This article looks at theories of melancholia to analyze “bromantic” comedies of the kind often associated with film producer, director, and writer Judd Apatow. Taking its title from the references to the film An Affair to Remember (dir. Leo McCarey, US, 1957) that run through the classic romantic comedy Sleepless in Seattle (dir. Nora Ephron, US, 1993), this article suggests that in fact romantic comedy may itself be considered a melancholy genre. Insofar as the heterosexual coupling that typically ends romantic comedies forecloses same-sex desire, the foreclosed objects exist, in the words of Judith Butler, as “ungrievable and unacknowledged losses.” Same-sex desire becomes “an affair to forget.” In the bromance Superbad (dir. Greg Mottola, US, 2007), however, homosexual possibility comes to the fore, so that melancholia actually turns into mourning for the lost male object of the protagonist's desire. In Knocked Up (dir. Judd Apatow, US, 2007), the film's visuals and its staging of visuality work against the rom-com conventions that the film draws upon, resisting the plot's forward movement into heteronormativity. The article ends by examining The Hangover (dir. Todd Phillips, US, 2009) and considering the psychic consequences of forgetting that relate to a repudiation of, and simultaneously disavowed identification with, the feminine that characterizes the heterosexual male's melancholia. A coda examines Bridesmaids (dir. Paul Feig, US, 2011), a film about female-female relations that was produced by Apatow and designed to cash in on the popularity of The Hangover. While Bridesmaids, like Superbad, strikes a note of mourning, the devalued status of women prevents them from achieving the grandeur of melancholics, a grandeur that accrues to men even in low comedic forms.