Meet Roger Greenberg (Ben Stiller): a dysfunctional 40-year-old at a crossroads in his life. Roger wants to “do nothing” for a while, so he agrees to housesit for his younger and more successful brother, giving him a free place to stay in L.A. While in town, he tries to reconnect with his old friends and band mates but times have changed, and old friends aren’t necessarily still best friends. Greenberg starts spending time with his brother’s personal assistant Florence (Great Gerwig), an aspiring singer and herself something of a lost soul too. During a series of embarrassingly awkward romantic encounters, we sense that perhaps even someone as irascible as Greenberg may have found somebody who is prepared to appreciate him for himself - if he would only stop critiquing Florence’s techniques in bed. Over the course of several weeks, we watch an uncertain and wonderfully vulnerable courtship play out, and learn how funny, and terribly unpredictable, love in the modern world can be.