Lillian becomes engaged to a wealthy banker living in Chicago and asks Annie to be her maid of honor. Only her friendship with Lillian Donovan ( Maya Rudolph) keeps her sane. She has a sexual no-strings-attached relationship with the self-absorbed Ted ( Jon Hamm) but hopes for something more. Although her flaky mother ( Jill Clayburgh) encourages her to return home, Annie rents a bedroom from British immigrant Gil ( Matt Lucas) and his lazy overweight sister Brynn ( Rebel Wilson). After her bakery failed, she lost her boyfriend and all of her savings, and now works in a jewelers store selling engagement rings. Annie Walker ( Kristen Wiig) is a single woman in her mid 30s, living in Milwaukee, Wisconsin.The synopsis below may give away important plot points. As Annie seems to be losing Lillian's friendship to perfect Helen, only truly understanding what each wants will bring all the parties closer together. Officer Rhodes might only be able to take so much before giving up on Annie. As Annie seems to be losing the competition at every turn, another bright light enters her life in the form of police officer Nathan Rhodes, although she tries to hold him off because of the other failures in her life. Immediately, Annie and Helen are in open competition not only to organize Lillian's bridal festivities, but to be Lillian's BFF. At the engagement party, Annie meets the other bridesmaids for the first time: Lillian's marriage-cynical cousin Rita, Lillian's idealistic newlywed friend Becca, Doug's brash sister Megan, and Doug's boss' seemingly-perfect and wealthy wife Helen. The only bright light in her life is that her BFF Lillian has announced that she's getting married to her boyfriend Doug and asked Annie to be her maid of honor. And she is in a dysfunctional relationship with misogynistic Ted, who treats her solely as a third-string sex partner whenever it suits his mood. She is forced to share an apartment with socially-inept siblings Gil and Brynn, who don't respect her personal boundaries. By strings pulled by her mother, she now works in a low-paying job as a jewelry-store clerk, which she hates. Despite her baking acumen, her retail cake store, Cake Baby, failed leaving her finances in rough shape. In Milwaukee, thirtysomething Annie Walker's life is falling apart.
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