Annie Walker (Kristen Wiig) is a single woman in her mid-thirties, living in Milwaukee. Her bakery failed due to the recession, wiping out her savings, and her boyfriend left her thereafter. Having lost her passion for baking, she works at a jewelry store and shares an apartment with eccentric English immigrant siblings Gil (Matt Lucas) and Brynn (Rebel Wilson). Annie has a casual sexual relationship with the rude and self-absorbed Ted (Jon Hamm), but hopes for something more from him. The only positive presence in her life is her lifelong best friend Lillian (Maya Rudolph). When Lillian becomes engaged to her boyfriend Doug (Tim Heidecker), she asks Annie to be her maid of honor.