Tax accountant Elliot Sherman (Michael Showalter) has been left at the proverbial altar more times than once. From high school to college to business school, Elliot always finds himself on the losing end of the love triangle. After a swearing-off of relationships once and for all, Elliot decides to take the plunge one last time when he meets his dream woman, beautiful magazine editor Caroline Swann (Elizabeth Banks). But just as he's about to hear wedding bells, her hunky, long-lost high school sweetheart Bradley Lake turns up, out of the blue, triggering Elliot's fears of yet another colossal dumping. As Elliot feels his life spinning into a downward spiral, things begin to change when he encounters Cecil Mills (Michelle Williams), an adorable office temp and aspiring singer, just off the bus from Fergus Falls, Minnesota. As Elliot struggles to assert himself for the first time, a series of escalating comic events are set in motion, until finally, with Cecil's help, he learns how to step into centre stage in his own life and leave Baxter-hood behind forever.