Megan reflects on her faltering career as a writer after her college friend, Caryn, pays Megan a visit and shares the news of her promotion at The New Yorker. Meanwhile, Sage and Rose get a performing gig at a Miami nightclub thanks to their publicist, where they meet Perez Hilton. Also, Megan strains her relationship with Will after he invites her and Caryn to a tennis match he is photographing.