Chicago Postal Employee and would-be novelist Gary is in a job he hates and in neutral in his love life.  His co-worker eats rice through a straw, his parents openly discuss the money they wasted on his liberal arts degree, and his sports-memorabilia-salesmen brother Tony, who has the perfect fiancé, keeps setting him up with seventeen year olds.  Gary and Tony spend hours at the local blues bar watching harmonica legend Sugar Blue and discussing Gary’s continual fixation on his ex, Kirsten.  Gary can’t even focus on his writing, spending hours toiling on his blog, readership 15.  Then two random events change everything.  At a bagel shop, he steps in-between an arguing couple, coming to the rescue of the beautiful stranger Ginny.  Then, a mislabeled package falls into his hands, a delivery for the independent publisher Gary has been semi-stalking for months.

When Gary goes to deliver the package, he is surprised when Ginny opens the door.  Forgetting she is the daughter of the most important ‘book man’ in Chicago, he asks Ginny out.  Tony and his fiancé Danni offer Gary advice on his first real date in years, and the evening is alternately victorious and disastrous.  Gary strings together elaborate lie after lie when Ginny tells him she’s sworn off dating writers, and a case of mistaken identity nearly leads to a brutal thrashing at the hands of Sugar Blue.  But Gary and Ginny have a true connection (based on lies) and as they get closer, Gary struggles for a way to tell her about his writing without making her think he’s using her to get to her father.  And Kirsten, of course, has decided that since Gary is no longer pursuing her, she wants him back.  Her interference spoils Gary’s secret and Ginny assumes the worst.