Annie Walker (Kristen Wiig) is a single woman in her mid-30s, living in Milwaukee, Wisconsin. After her bakery, Cake Baby, failed, she lost her boyfriend and her savings and now works in a jewelry store. Although her flaky artist mother (Jill Clayburgh) encourages her to return home, Annie shares an apartment with English immigrant Gil (Matt Lucas) and his long-visiting sister, Brynn (Rebel Wilson), who doesn't pay rent and reads Annie's journal. She has a no-strings-attached sexual relationship with the self-absorbed Ted (Jon Hamm) but hopes for something more. Her best friend Lillian Donovan (Maya Rudolph), is virtually her only source of happiness.
Lillian becomes engaged to a wealthy banker living in Chicago and asks Annie to be her maid of honor. At the engagement party, Annie meets her fellow bridesmaids: Lillian's cynical cousin Rita (Wendi McLendon-Covey); idealistic friend Becca (Ellie Kemper); raunchy future sister-in-law Megan (Melissa McCarthy); and Helen Harris III (Rose Byrne), the beautiful but over-the-top wife of Lillian's fiancé's boss. Helen and Annie, each jealous of the other's friendship with Lillian, take an instant dislike to each other, but Lillian persuades them to spend time together. Playing opposite each other in a game of doubles tennis, Annie and Helen deliberately hit each other with their volleys multiple times and scream at their partners if they make a mistake as they are trying to impress the other.
Lillian becomes engaged to a wealthy banker living in Chicago and asks Annie to be her maid of honor. At the engagement party, Annie meets her fellow bridesmaids: Lillian's cynical cousin Rita (Wendi McLendon-Covey); idealistic friend Becca (Ellie Kemper); raunchy future sister-in-law Megan (Melissa McCarthy); and Helen Harris III (Rose Byrne), the beautiful but over-the-top wife of Lillian's fiancé's boss. Helen and Annie, each jealous of the other's friendship with Lillian, take an instant dislike to each other, but Lillian persuades them to spend time together. Playing opposite each other in a game of doubles tennis, Annie and Helen deliberately hit each other with their volleys multiple times and scream at their partners if they make a mistake as they are trying to impress the other.

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