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

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.

When Evelyn buys Alan a sports car, Charlie warns she'll expect payback, which she gets by forcing Alan to agree to accompany her on a blind double-date.

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.

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

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.

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, but then meets Eric's gorgeous ex-wife.

After Charlie has back pain, Alan decides to take him to the hospital, where he keeps hitting on his doctor, unaware he's dated her before; Berta is fed up with Jake's inability to use the bathroom properly

When Judith decides to take a vacation, Alan has to take care of Jake during the week and finds it more taxing than he imagined. When his IRS audit forces Charlie to take care of Jake, Charlie doesn't fare much better.

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.

The brothers throw out their mother after she insults the way Alan is raising Jake, and when she lands in the hospital they're not sure if it's genuine or a ploy to get back their affection.

Alan invites Judith to stay at Charlie's place after an earthquake, but soon feels jealous when she has a date and begs Charlie to find him one, too.

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

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.

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. Meanwhile, Alan finds out more about Rose when he spends more time with her.

When Charlie leaves the house to avoid a date that he can't stand, he ends up at a coffee shop, where he reconnects with his old girlfriend Lisa, now a divorcée with a child; Jake tries to justify to his father why he isn't doing so well in school

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.

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

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

Jake is very impressed with his mother's new boyfriend, which annoys Alan. Meanwhile, Evelyn borrows Charlie's car to help her impress a Saudi prince she's trying to sell a house to.

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

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

Alan learns that Charlie belongs to an exclusive men's group, and he begs his brother to let him join.