|Zoe Kazan||Tammy Greenwood|
|Judah Friedlander||Dan O'Finn|
|Rachel Dratch||Kathy Jeemy|
|Jay O. Sanders||Tim the Delivery Guy|
Genevieve, a florist, and Greg, a restaurateur, are relationship-challenged. Genevieve avoids the pain of a broken heart by never going out with a man more than five times, and Greg has a string of disastrous relationships behind him. Though Greg agrees to Genevieve's five-date rule, neither he nor Genevieve can predict the romantic sparks that fly when they get together.