Bert and Arnie’s Guide to Friendship

How do unlikable people come to be liked? Jeff Kaplan’s directorial debut, Bert and Arnie’s Guide to Friendship, gives at least one answer to this question. In doing so, it casts a surprisingly humanist light onto an otherwise derisive comedy about two alienated Manhattanites with misogynist tendencies.
Bert Sheering (Matt Oberg) and Arnie Hubert (Stephen Schneider) are different types of jerks: Bert, a self-important novelist, and Arnie, a jaded womanizer. Bert writes quasi-literary historical romances about the sexual conquests of third-century shepherds and Portuguese conquistadors. He takes every opportunity to discuss his literary acumen, even teaching his own books at the university where he works as an adjunct professor. Arnie is a corporate finance analyst. At work, he tyrannizes his employees. At home, he sleeps with women—including Bert’s wife—and then refuses to spoon afterwards.
Bert may be a romance novelist, but he’s no Don Juan. His wife moans the name of her “cooking instructor” (that’s Arnie) in her sleep. When she leaves Bert it spurs him to engage into a frustrated series of interactions with women. These include a botched liaison with a student, hilariously played by Cristin Milioti; a snarly exchange with a prominent reviewer who ridicules his work; and a platonic affair with Arnie’s boss, Sabrina (Anna Chlumsky of My Girl fame).
Sabrina likes spending time with Bert, but doesn’t find him attractive. She is seeing Arnie, too, though for precisely the opposite reason: she sleeps with him but won’t open up emotionally. Bert’s cloying pretension and Arnie’s obnoxious selfishness are somewhat to blame for Sabrina’s reluctance. On their first date, Sabrina tells Bert she wanted to grow up and be a race car driver. He replies, “That’s perfect. Speed. Precision. The world outside is a blur. Forces of gravity beat down upon you. You try to win. You try to be the best. But you go in circles. There’s one thing you can never outrun—yourself.”