Larry tries to win back Cheryl over drinks with the New Larry.1 When he mentions the Old Larry hated her sister, it gives Cheryl pause. But for the most part she's impressed that he's trying to change. He invites her to the movies and dinner. Cheryl would love to, but she wants to talk to her therapist Dr. Slavin first.
Larry talks to his therapist, Dr. Bright, about how well the date went with Cheryl. Dr. Bright coaches Larry on exactly what to do on his movie/dinner date with Cheryl2 so as not to come off as a pussy.3
During their movie/dinner date, Marty and Nan Funkhouser run into Cheryl and Larry at the restaurant and Marty asks Larry to sponsor him for a 5-mile walkathon to benefit Alzheimers, which he's doing in honor of Nan's father.4 Larry starts to protest but when Cheryl says it's a good cause, he makes the pledge - once again impressing Cheryl with New Larry. He asks her to move back in and she's touched, but when he gives her a Monday deadline she storms out. Larry chases after her shouting that his therapist told him to give her the ultimatum but she doesn't believe him.
Larry storms into Dr. Bright's office screaming at him for the ultimatum advice.5 He drags Dr. Bright to Cheryl's to set things straight. Larry is impressed with Cheryl's new place on the beach. She explains that her therapist recommended it.6 Dr. Bright explains to Cheryl the ultimatum was his idea, and takes full responsibility for the New Larry. But when Cheryl starts to get the idea that some of the other positive changes weren't Larry's idea she gets confused again and says she needs to talk to her therapist.
Larry, Jeff and Dr. Bright discuss the Cheryl situation. Larry believes that since Cheryl won't make a move without talking to her therapist, Larry needs to meet Dr. Slavin so she can think he's a terrific guy. Larry has an idea and the three head out to explain Larry's scheme to Leon7 who agrees, but has a suggestion to make the plan more effective.8
Loretta and Auntie Rae walk in while they're discussing the fake mugging and tell Leon he can't do it. Loretta suggests that Dr. Bright do it9 and he agrees. Dr. Bright and Larry stage the purse snatching and all goes well until the cops pull up and catch Bright as he runs off while Larry accepts the therapist's gratitude.10 Larry manages to introduce himself and and joins her for a cup of coffee; when she tells him she's a therapist, he confides how sad he is that his wife left him and how she never really appreciated Larry's kind side.
Larry goes to visit Dr. Bright in jail to report that the plan is working well. Dr. Bright says this isn't his top priority at the moment. He is very upset with his accomodations.11 Larry promises he'll get him out but has to cut their session short because he needs to talk to Cheryl who is getting out of therapy. But when he calls Cheryl, she says her therapist told her not to talk to Larry ever again. Larry finds Jeff taking part in the Alzheimer's walkathon to report this news. Jeff says it makes no sense. Larry realizes Dr. Slavin must like him, she wants him for herself. Jeff says Larry is f**ked.12
They pass Marty Funkhouser who's sitting in a cafÃ© along the walk route. Larry demands to know why he's not walking and Marty says he raises money, he doesn't walk. Larry gets an idea while they're arguing about the ethics of this. He meets with Dr. Slavin again and tells her he's been diagnosed with Alzheimer's. She confesses she was interested in him, but now urges him to get back with his wife. They are interrupted by a police detective who needs to get a description of the purse snatcher from Larry. Using Alzheimer's as an excuse, Larry says he can't remember.
Dr. Bright is released and Cheryl and Larry have a date at the carnival that is going extremely well. Meanwhile, Dr. Bright goes to see a therapist - Dr. Slavin - because he's so distraught over the whole jail experience. Just as Cheryl agrees to move back with Larry, she gets an urgent call and listens intently to what Dr. Slavin has to say.