Roger Greenberg (Ben Stiller) is single, fortyish and deliberately doing nothing. In search of a place to restart his life, he agrees to housesit for his brother in LA and tries to reconnect with his former bandmate (Rhys Ifans) and ex-girlfriend (Jennifer Jason Leigh), but soon finds himself forging a connection with his brother's personal assistant, Florence (Greta Gerwig). As Greenberg discovers there is only so much "nothing" you can do, the awkward beauty he builds with Florence starts to look more and more like a reason to be happy.