Ben Stiller stars as the single, 40-ish Roger Greenberg, who’s at a crossroads in his life after a couple of failed careers and finds himself house-sitting in Los Angeles for his more successful/married-with-children brother (Chris Messina). In an effort to restart his life, Greenberg tries to reconnect with old friends including his former bandmate Ivan (Rhys Ifans) and one-time girlfriend Beth (co-writer Jennifer Jason Leigh). 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...