Roger Greenberg (Ben Stiller), single, fortyish and at a crossroads in his life, finds himself in Los Angeles, house-sitting for six weeks for his more successful/married-with-children brother. In search of a place to restart his life, Greenberg tries to reconnect with old friends including his former bandmate Ivan (Rhys Ifans). But old friends aren’t necessarily still best friends, and Greenberg soon finds himself spending more and more time with his brother’s personal assistant Florence (Greta Gerwig), an aspiring singer and also something of a lost soul. Despite his best attempts not to be drawn in, Greenberg and Florence manage to forge a connection, and Greenberg realizes he may at last have found a reason to be happy.