A Few Best Men features David, a central openly gay character whose sexuality is accepted by his friends and family. His identity is treated as a normal aspect of his character, not a source of conflict or ridicule, contributing to a generally affirming portrayal within the film's comedic framework.

The film features Mia, the mother of the bride, whose transsexual identity is revealed as a central plot twist. This revelation is primarily used for comedic shock and the discomfort of other characters, particularly the male leads. The portrayal leans problematic, relying on the perceived unconventionality of her past for humor rather than affirming her dignity or experience.