More enervating than it is ambitious, Jake Squared is partly a romantic comedy and mostly a pseudo-philosophical apology for self-absorption. Creatively blocked indie-filmmaker Jake Klein (Elias Koteas) examines his failings as a lover by making a film within the film, starring a younger, hornier version of himself (Mike Vogel). While Vogel's Jake flirts with every woman he meets, Koteas's Jake directly addresses Jake Squared's viewers through a series of fourth wall–demolishing speeches and aphorisms, including pompous quotations from Federico Fellini, DailyOm.com, and Sonny and Cher.
The film's meta-narrative spins out of control after three more versions of Jake, two played by Koteas, inexplicably appear, and force him to see sides of himself he'd sooner ignore. Writer/director Howard Goldberg is so in love with his narrative's ensuing disjointedness that he never examines Jake's most endearingly eccentric observations, like when Jake Prime baits a bikini-clad ditz into admitting she thinks Jews control the world. Even the most introspective scenes, like the one in which Koteas's Jake Prime talks to an actress playing his mother (Meredith Salenger), try to foster intimacy through unproductively alienating confrontations. Jake sobs into his mom's arms, telling her that he wishes he was as happy as she and her husband of 55 years were. Goldberg shows Koteas, a versatile and charming performer, crying in an extreme close-up, then quickly cuts away, dumbly undercutting his performer's expressive body language. In spite of Goldberg's abundant chutzpah, Jake Squared isn't quite 8 1/2 for Rumi-quoting narcissists.