Business lawyer ALISTAIR (think Joel McHale), who comes from the perfect family and is about to marry the perfect fiancée, but still, he has a dream and he has a secret. His dream is to become DA and he will be as ruthless as need be to achieve that. As for his secret… Inside his closet, inside a box, there are women’s clothes and makeup and shoes. But his coming out as a HETEROSEXUAL TRANSVESTITE is only the beginning of his journey.
Grateful to the LGBT community for their help in his coming out, he hangs out with them and discovers his much his views of the world clash with theirs. He doesn’t think gays should be able to marry nor adopt, he can’t see two men kissing without letting out he weirdest shrieking sound, and he has some deep dark thoughts about immigration.
The irony is that the more he comes to terms with his cross-dressing, helped by his fiancée LOU (think Blake Lively) and his hipstery sister DALIA (think Dylan Gelula), the less he fits into his old world – the conservative, right-wing world of business, power and great views on Central Park.
When PATRICK, his first gay friend (who also happens to be a transgender) asks him to defend him in court, Alistair refuses. A restaurant refused to serve Patrick and his date after seeing them holding hands. CAMILLE, the fierce, fun and loyal bisexual who helped Alistair in the first place, confronts him hard for not taking the case.
Slowly and through comical situations, Alistair will become THE LGBT lawyer in town, while also trying to accomplish his dream of becoming DA, by keeping a foot in the world he comes from.