After five years, Debbie now owns a boutique with employees Desi (Megan Fox) and Jodi (Charlyne Yi) working for her. Pete now owns his own record label, with his friends Ronnie (Chris O'Dowd) and Cat (Lena Dunham) working with him. Pete's business is struggling financially, as he is trying to sell an album for Graham Parker (playing himself), but fails after it only sells several hundred copies. The couple also are having to deal with their two daughters Sadie, who is now a young teenager, and Charlotte who is now eight years old. For Debbie's birthday, the couple goes on a romantic weekend to a resort. There they get high off of "special cookies", and ponder about what way they would kill each other if they could. After speaking with her friends Jason (Jason Segel) and Barb (Annie Mumolo), Debbie decides to improve her and Pete's relationship and family by exercising more, and becoming more connected with their parents. Debbie tells Pete that he needs to stop lending his dad, Larry (Albert Brooks), money, because it is hurting them financially. Pete goes to visit him, but is unsuccessful at giving him the news, and still agrees to give him money. Meanwhile, Debbie visits her gynocologist (Tim Bagley), and discovers that she is pregnant. She decides to not tell Pete about this. Later, she yells at a student, Joseph (Ryan Lee), who has been taunting Sadie. She yells at him so much, to the point, where his mother, Catherine (Melissa McCarthy), gets into an argument with Pete. They later have a meeting with the principal, but the couple denies everything that happened. One night, Debbie takes Desi out dancing at a club, believing she has been stealing money from the store, and plans to confront her about it. Afterwards, Debbie drops Desi off at her house, and confronts her about the money. She then says that Jodi has been stealing the money to buy drugs. Desi then reveals that she is able to afford nice things, because she is also an escort. Later, Debbie meets up with Jodi, and she confesses that she stole the money to buy Oxycontin. Debbie then fires her and leaves. Meanwhile, Pete and Debbie are having to deal with Sadie and Charlotte fighting all the time, which results in arguments between the family. Charlotte though, justs wants everyone to stop fighting and for the family to get back to being normal. On the day of the Pete's 40th birthday party, Pete continues to argue with his dad about him asking them for money. Debbie argues with her dad about not spending too much time in her life, and how his is perfect. Oliver then explains that his life is not perfect, and how he has always cared about her and loved her. Later, Pete overhears Debbie talking about her pregnancy, and rides out of the house on his bicycle in anger. Debbie and Larry then go after Pete, trying to find him. Soon, they find that he wrecked after hitting his head on a car door. Pete then gets into an argument with the driver of the car who then punches him in the face. Debbie and Larry take Pete to the hospital, where Larry apologizes for everything, and Debbie forgives him. Debbie and Pete talk later and Pete explains that he is actually thrilled about having a third baby, and that he doesn't feel trapped, so the two reconcile. Sometime later, Pete and Debbie are watching a small concert with Ryan Adams performing. Pete then suggests that they could talk to him about signing on to his record label as they finish watching the show.

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