Jack and Ariel go to New York to represent a famous, ambitious and sexually ambiguous fashion executive who is accused of sexual harassment by a former worker – but Jack is pressured by the clothing firm's board to arrange for a settlement. Back in Washington, D.C., Grant grows jealous of Ariel teaming with Jack, while she ponders the threat of their past intimate e-mails being retrieved and exposed. Elsewhere, Riley feels responsible when he blows off a desperate former classmate whose descent into substance abuse was triggered by an experimental drug.