Bob Muldoon and Ruth Guthrie, an impassioned young outlaw couple on an extended crime spree, are finally apprehended by lawmen after a shootout in the Texas hills. Although Ruth wounds a local officer, Bob takes the blame. But four years later, Bob escapes from prison and sets out to find Ruth and their daughter, born during his incarceration.
Young writer Sam has a crush on Birdie, the cute and quirky barista at his local coffee shop. When his conventional attempts to woo her crash and burn, he takes his efforts online, creating an Internet profile embellished with all of the details that would make him Birdie’s dream guy. When the harebrained scheme is a surprise success and Birdie falls for his exaggerated alter ego, Sam must keep up the act or lose his dream girl forever.
The film centers on a hooker-turned-Broadway-thespian (Imogen Poots) and follows the "recurring intersection between these two facets of her life". A Broadway director (Owen Wilson) pays for her escort services despite being married to the star (Kathryn Hahn) of his new play A Grecian Evening.