The movie starts out with our heroine Annie (Kristen Wiig) having sex with her on-again, off-again, sort of, kind of, but not really, boyfriend Ted (Jon Ham). Ted is trying to get Annie to have fast and rough ‘fun’ sex, while Annie tries to get him to have nice and slow ‘meaningful’ sex. Annie‘s boyfriend is a charmer. She caves, and has sex his way.
It’s the next morning. Annie wakes up earlier than Ted and freshens up in the bathroom. She sneaks into bed. Ted wakes up sees Annie and kisses her. He tells her bluntly that he really wants her to leave, but doesn’t want her to think he’s a jerk. We see Annie, fully dressed, walking towards the gate. She can’t find a button to open it from the inside and decides to climb the gate. Once she reaches the top of the gate, the gate begins to open, and we see Annie move with as Ted’s maid watches on.
Annie then meets with her best friend Lillian (Maya Rudolph). They distantly participate in an outdoor workout, but when the instructor sees them working out for free, they run off. In a diner, they chat about how they don’t see each other that often anymore because of Lillian working in another city. They leave the diner and walk down the street to see a closed down bakery, where we learn this was once Annie’s bakery. We see Annie in her current job at a small jewelry store. She tries to sell a piece to a young, happy couple only to tell them their love won’t last. The boss comes over to Annie and tells her that she only has this job because her mother is the boss’ AA sponsor.
Annie and Lillian meet up and Lillian tells her boyfriend proposed. Lillian then asks Annie to be her maid of honor and attend her engagement party to which Annie accepts. Annie drives her crummy car to an upper-class house where Lillian introduces her to all her bridesmaids. Her cousin Rita (Wendy McLendon-Covey), her coworker Becca (Ellie Kemper), her fiancé’s sister Megan (Melissa McCarthy) and her fiance’s boss’s wife and friend Helen (Rose Bryne). At the party after the best man gives a small speech Annie feels obliged to and gives a small heartfelt speech. Helen then gives a speech which makes Annie a little jealous and the two keep giving speeches about their relationship with Lillian after each other until they both end up singing. Later that night Annie drives home where she is pulled over by a cop, Officer Rhodes (Chris O‘Dowd) because of her tail lights. He lets her go and gives her a card for an auto repair shop.
Annie gathers Lillian and the bridesmaids together, and they have lunch at a sketchy restaurant before the bridal fitting. Helen refuses to eat meat before the fitting while everyone digs in. While Lillian excuses herself the girls talk about the bridal shower, but Annie (who‘s broke) wants to wait and think about it more. They go to a high class wedding boutique which Annie thought they could just walk into, but they need an appointment. Helen talks to the women, who we realize she knows, and they gain instant access. Helen points the girls to an expensive bridesmaids gown while Annie shows them something on the cheaper side. Lillian gushes to the girl that Helen got her a dress made by a famous French bridal gown designer. All the girls suddenly begin to get sick except for Helen. Helen claims it was the food at the restaurant, while Annie claims it’s all a coincidence. Megan and Rita run to the bathroom, where Rita throws up in the toilet, and Megan sits on the sink and begins to use the sink as a toiler. Becca runs in after them and throws up on top of Rita’s hair. Lillian also needs to use the restroom and tries to make it to a bathroom across the street, but she begins to slow down and use the street as her toilet. Driving in the car with Lillian Annie promises to make it up to her. Later that night Annie is in a convenience store and sees Officer Rhodes. They talk outside while sitting on the hood of his car and start to become closer to one another. Rhodes realizes he used to go to her bakery and thinks she should try to open up another bakery, but she doesn’t think so.
Annie attempts to get back into Lillians’ good graces by throwing an awesome bachelorette party. She gets some ideas from the ladies pushing her idea for a Parisian theme bridal party, but Helen’s idea of a Vegas night out is voted as the best. On the plane, everyone sits in first class except for Annie who sits in coach next to a person who dreamed the plane crashed and saw Annie in her dream. Annie, who is scared of planes, rushes up to first class to talk to Lillian. Helen gives Annie some prescription pills and her glass of rum to take with it. Meanwhile, Rita and Becca are talking about their life and sexual experiences and end up kissing. Megan sits next to a guy she thinks is an air marshal, but keeps trying to explain to her that he is not. Annie takes the pills and starts to walk about the plane. She keeps trying to get into first class despite the persistence of a male flight attendant to keep her away. Annie, hallucinating on the mixture of drugs and alcohol, gets on the microphone and says that she sees a person on the wings of the plane. This causes the plane to be grounded in somewhere in middle America. Annie is driving Lillian home. Lillian breaks the silence by telling her that she’d prefer for Helen to take over maid of honor duties. Later that night, Annie passes by Rhodes in his car, and they hang out in the bar. They talk, become close, and then back at his house they sleep together.
The next morning, Rhodes tries to surprise Annie with baking materials so that they can bake together, but overwhelmed she quickly leaves his house. She gets an extravagant invitation to Lillian’s bridal party that’s has a Parisian theme. At the party, Annie breaks down. She fights with Lillian, and decides not to go to the wedding after all. Driving from the party her car breaks down and she is stopped by Rhodes. He gets a tow truck, and Ted comes by to pick her up. Rhodes tells Annie that she needs to get her tail light fixed and leaves. She gets in the car with Ted only to get out after a few minutes of being in the car with him and walks home. There, she starts to put her life together, she begins baking again and moves in with her mom.
It’s the day of Lillian’s wedding. Helen comes to Annie’s door and tells her Lillian’s missing. Annie takes her to someone she thinks can help. In the car, Helen admits that she was trying to overstep just so she can feel what it’s like to be appreciated. They make up and make a truce. Annie drives to the interstate to find Rhodes, but he doesn’t pay her any attention. She drives recklessly, pretends to drink while driving, pretends to text while driving, etc. but nothing gets his attention. She finally bumps into his car and tells him she needs his help and tracks Lillian to her apartment.
Annie goes to Lillian’s apartment where they make up, and Annie becomes Lillian’s maid of honor once again. At the wedding Annie is by Lillian’s side and the bridal party is seen having a good time. After Lillian and her husband depart for their honeymoon, Helen tells Annie she has a surprise for her. Annie sees Rhodes waiting by his cop car. Rhodes guides Annie in the back sit of the car and tells her that she didn’t think he would get away with reckless driving. They drive off into the night.
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