Judith is dating Jake's pediatrician, and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.

Charlie tries to save Jake from school suspension for giving his teacher (Missi Pyle) the finger by romancing her, but his several attempts fail every time.

Jake is very impressed and can't stop talking about his mother's new boyfriend, Dr. Melnick, which annoys Alan. While Evelyn borrows Charlie's car to help her impress a Saudi prince, because she wants to sell him real estate. When Charlie gets his car back, he discovers his mother's bra in the backseat. When he finds out why it's there he decides to trade in his car.

Charlie meets his match when he falls for a woman who's better at playing hard to get than he is.

Alan denies having shoplifted a toy as a child and fears he has a dark side, until Charlie admits he planted the toy on Alan to stay out of trouble himself.

Charlie and Alan hire Berta's sister to cater a party their mother has conned them into throwing for her.

Alan meets a woman named Nancy at a grocery store, who fulfills every single one of his desires, forcing Charlie to take care of Jake. After knowing Nancy for a few days Alan decides to ask her to marry him, prompting Charlie to try and talk him out of it, and he even gets help from the brothers' mother.

When Charlie leaves the house to avoid a date that he can't stand, he ends up at a coffee shop, where he meets his old girlfriend Lisa. He finds out that she broke up with her husband, and now has a child. Now he must try to convince Lisa that he's okay with her having a child. While Jake tries to justify to his father why he isn't doing so well in school.

Charlie tries to get Jake's approval on a theme song that he is hired to write for a television show, which is based on a comic book that Jake is a fan. While Alan finds out more about Rose (including how smart she is), when he spends more time with her.

After getting unusually turned down at a bar, Charlie learns that a website has been made dedicated to exposing his lifestyle. Charlie sets out to find who created the site, making amends to all those he stood up, but it's harder than it looks when all the women take the apology better than expected.

Alan is jealous of Charlie when an old classmate, who's now a beautiful woman, seems to be more interested in Charlie.

After an earthquake hits, Judith's house is damaged and she needs a place to stay. So Alan decides to invite her to stay with him and Charlie, without getting Charlie's permission. Charlie isn't happy with this, but accepts it. Alan becomes jealous when Judith goes on a date, and asks Charlie to find him a date, so that he can show Judith that he dates as well.

The brothers throw out their mother, after she insults the way Alan is raising Jake. When Alan and Charlie ignore her phone calls, to get their attention she ends up in the hospital. When Alan and Charlie show up at the hospital they aren't sure if she's faking, and try to call her bluff.

Alan starts to worry about a medical procedure that he is facing, and to get his mind off it, Charlie suggests they go to Las Vegas.

When Judith decides to take a vacation, the brothers have to take care of Jake during the week. Alan finds it challenging, and even forgets to pick up Jake from soccer practice. When Alan finds out that he has to go to the I.R.S. because they're auditing him, he forces Charlie to take care of Jake, and Charlie doesn't do any better then Alan.

After Charlie has back pain, Alan decides to take him to the Hospital. While there Charlie can't stop hitting on the doctor who is examining him. The only problem is that he has a history with her that he can't remember. Berta is feed up with Jake's inability to use the bathroom properly, so she decides to make him clean it until he learns.

Charlie is invited to a party hosted by a gay ad-executive named Eric, so Charlie asks Alan to pretend that he's his life partner. While at the party, Charlie meets Eric's ex-wife Pamela, and tries to sleep with her without Eric finding out.

After Charlie takes Alan to an eye doctor, they end up at cafe where they bump into Charlie's ex-girlfriend, Sherri. While there Alan shows an interest in Sherri, and decides to ask her out. The problem is that Alan can't get over Sherri's relationship with Charlie.

Rose tries to help the brothers sort out their feelings, when Charlie and Alan take their personal frustrations out on each other.

Evelyn reads in the obituaries that her second husband, Harry has died. They all attend the funeral, including Jake who is excited at the opportunity of seeing a ""dead guy"". Charlie is excited by the opportunity of a newly single widow, and Alan is just happy to pay his respects to Harry.

Evelyn buys Alan a new Sports car causing Charlie to claim that his brother has sold his soul to the Devil. The next day, Evelyn extracts payment by insisting that Alan go on a blind, double date with her, her new beau and his daughter. At the restaurant, Alan learns that his mother and boyfriend will not be able to join them because there was a mixup between his heart medication and Viagra and she didn't want to ""waste it"". As a result, Alan is left to deal with the daughter, who is on a weekend pass from a rehab center and still has some loose screws. Alan eventually gets her back to the beach house only to have her drive off in his new sports car and become the object of a televised high-speed car chase.

Evelyn demands Jake spend a night at her place when she finds out he spent Spring Break with Judith's parents. Neither Alan nor Charlie are keen on the idea, but going to a bar after dropping off Jake quickly erases their concerns.

Charlie unknowingly sleeps with an older man's trophy wife while Jake has to read a paper to his class.