Charlie arranges a romantic date with Mia in the hopes of consummating their relationship. Alan begins to date Charlie’s most recent ex-girlfriend.

Charlie finds himself in a relationship that is not based on sex.

Charlie sees a therapist to learn how to deal with Alan’s emotional insecurities.

Charlie helps Alan with his obsession of always having to get approval from the women in his life.

Alan starts dating a woman with a Martha Stewart complex. Before long she’s running the house with an obsession for perfection.

One of Charlie’s elderly neighbors tries to seduce Alan, while Charlie tries to stop Jake from giving money to a televangelist.

Charlie tricks Jake into taking ballet lessons, so he can get close to the teacher.

Charlie wakes up with Rose the morning after her birthday party. Her irate father (Martin Sheen), comes to ask Charlie about what the future holds for him and Rose, but…

Ignoring Alan’s warnings, Charlie continues to date Isabella until she threatens to put a curse on his manhood.

Charlie learns he can’t be in a long-lasting relationship, becuase of unresolved issues he has with his mother. Jake asks Charlie for advice about a girl at school.

Berta causes tension between Charlie and Alan, when she temporarily moves in with them

Jake gets suspended from school after drawing an offensive picture of a girl in his class that has large breasts. Meanwhile, Charlie is asked to watch over Alan’s chiropractic office…

Alan has been dating a lot, and Charlie soon finds out that it has been one woman – his ex-wife, Judith. He tries to stop Alan, and even brings Rose,…

After falling off the roof, Alan needs Charlie’s help in looking after Jake, which interferes with Charlie’s social life.

Charlie unknowingly sleeps with an older man’s trophy wife while 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…

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…

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””….

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…

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…

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…

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…

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. When Alan and Charlie ignore her phone calls, to get their attention she ends up…

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…

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,…

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…

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…

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…

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…

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 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,…

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.

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.

A pregnancy scare has Charlie heading to the doctor for a vasectomy.

Charlie tries to sweet talk Judith’s divorcee support-group into letting Jake continue to spend weekends at his place.