Drew finally meets "Miss Right," only to discover she's also just right for a job he's trying to fill. Meanwhile, Mimi's back--and this time, it's personal: she's been hired as personal assistant to Drew's boss.

The store's owner asks Drew to be her personal assistant, but his new position soon turns compromising when her interest extends into his private life.

Things look ho-ho-hopeless for Drew when the store's employees--including Kate--go on strike during the holiday rush, and he's forced to hire scabs to replace them.

The good news: Drew's dream of getting a personal assistant comes true. The bad news: Mimi is it.

Drew starts his own beermaking business after learning there's trouble brewing at the store and that he could be getting canned.

Drew serves as acting store manager while also fulfilling his regular duties. He is outraged when the store declines to make him the permanent manager, instead hiring Nigel Wick, an Englishman who makes it clear that he would rather be anywhere but Cleveland. Wick makes a stamp of Drew's signature and makes it appear as though Drew is responsible for cost-cutting measures such as the elimination of employee discounts. He coaxes Drew into agreeing to be the ""bad guy"" by offering him a promotion to assistant manager and a new desk. However, Drew draws the line after Wick tries to fire all of the employees with seniority right before their pensions kick in. He claims that the employees are staging a revolt, and Wick wins the staff's approval by eliminating all of ""Drew's"" cutbacks. Oswald and Lewis search for a way to fill a large order of Buzz Beer, which is due in just a few days. They put the neighborhood children to work bottling and delivering beer, much to Drew's horror.

Drew catches the eye of an attractive stranger at the Warsaw. The woman, Bonnie, agrees to come back to his house to see his brewery. After she learns that he does not have a permit, she reveals that she is a zoning inspector and says that she must report him. Mimi (for a fee) suggests a way that Drew might get out of the situation. She says that the gang could organize a party and sell maps to the location, then give away the appropriate amount of beer. Bonnie comes to Winfred-Louder to apologize to Drew, and agrees to attend his party. She brings a policewoman friend to the gathering. Unfortunately, she threatens to arrest Drew and his friends for soliciting to sell alcohol unless they shut down the party and return everyone's money. Bonnie and Drew sleep together. She feels bad about causing him so many problems. She recommends that he get signatures on a petition and appear before the city council to request a change in the zoning laws for his neighborhood. The council h

Kate alerts the guys to the fact that a hurricane has struck the near the neighborhood where Drew's parents live in Florida. As they watch the news report, Drew's parents suddenly show up at his house in their Winnebago. They have been on the road since losing their house for failure to make payments. They finally admit that Beulah lost their life savings in a land development scam. The Careys plan to stay with Drew for a few weeks until they receive their claim in a class-action lawsuit. Unfortunately, they lose the case. George and Beulah take over the house and prevent Drew from having any privacy. After his parents spoil a date, he begins spending all of his time at the store. He finally resolves to ask his parents to leave by laying a guilt trip on them. They prove too tough to crack, and Drew ends up staying with Lewis and Oswald.

Drew decides to turn over a new leaf by becoming more assertive. He taps into the boardroom to see the footage of his meeting and hear his evaluation. Drew ends up getting more than he bargained for when he and Mimi see Larry and Mrs. Louder having sex in the boardroom. Meanwhile, Mimi still has a confused Mr. Wick living at her house and Kate and Oswald begin secretly dating.

Drew and Nicki plan to videotape themselves having sex. The next morning, Drew's parents come to town to celebrate his engagement. Drew tries to tell his mother about a problem with his relationship but is constantly interrupted. Drew eventually tells Beulah he has called off the wedding. She begs Drew to go through with the bachelor party and break the news to George afterward because of how depressed he's been.

Drew meets a woman at the Warsaw who recommends he attend her dating advice service. He agrees only to be publicly embarrassed when the instructor shows a videotape of Drew's date as "a teaching aid". Drew is the laughingstock of the class despite the fact that most of them are career losers who are still virgins. Drew seeks the help of the Better Business Bureau to shut down the advice center but ends up needing class advice when he scores a date with a Bureau employee.

Drew entertains a group of investors from Vietnam who are considering opening a store in Hanoi. They have drinks at the Airport Ramada Inn. When the house band goes on break, Drew and the guys fulfill the investors' request for music by taking the stage for a song. The manager feels that they are better than the regular band and asks them to play for a week. Drew fears that this would be too much of a distraction and wants to focus on his new job. He changes his mind after a groupie hits on him in the parking lot. The guys audition guitar players, and hire a free-spirited guy named Ed. Kate becomes dissatisfied with her job and tries to get fired. Drew agrees to let her go, but promises to re-hire her if she can't find a better job in a week. She doesn't have any luck, but Drew backs out of the deal because he wants her to find the kind of happiness he now has with his band. Drew blows off a party at Mrs. Louder's house, and later skips work to fool around with Darcy. The ho

A flashback show that features clips of some of the series' music-video segments.

Drew suspects that his mother and his barber may have carried on a long-term affair.

Steve objects to Mimi's plans for a wild bachelorette party at a strip club. They decide to hold their bachelor and bachelorette parties simultaneously at Drew's house. After Drew mentions that he might start dating again, Kate tells Lewis that she is going to make her move. Drew overhears her say that she is going to tell someone she loves him during the party, but doesn't know that she is talking about him. Drew plots to keep Kate away from the guy. He ignores her obvious attempts to talk to him (as well as Lewis's hints) and makes a complete fool of himself. They both decide not to confess their feelings yet.

The cast and special guests perform comedy sketches with a ""back to school"" theme. Teenage Drew visits a doctor and learns about his ""changing body."" A wood shop teacher conducts class, despite the fact that he is just a decapitated head. A sketch parodies the accelerated aging process seen in commercials for milk. Oswald and Lewis try to convince SHeDAISY to hire them as backup singers. Two girls at a slumber party decide to practice kissing on each other. Christa Miller and Jenny McCarthy question the purpose of the sketch after noticing that Drew, John Carroll Lynch and a bunch of pervert crew members are gawking at them. They retaliate by making a sketch in which a buff Abraham Lincoln becomes a stripper and dances for Drew. Oswald tries to impress Jenny with a story about a painful football injury, but the flashback reveals that he was actually a cheerleader. Mimi warns musical guest Smash Mouth not to steal her idea for a speed metal version of Gordon Lightfoot's ""The Wr

Drew hosts a film about the dangers of cooties. Another film shows girls how cheerleading can help them later in life. Mimi bothers Uncle Kracker for help with a crossword puzzle. A clueless police officer goes undercover while still wearing his uniform. Peter Frampton recalls his past romance with Mimi. A talking zit gives a young man questionable dating advice. Mimi tries to convince Sugar Ray to stay over at her place after the show. Drew compliments teachers, with the exception of his elementary school teacher, Ms. Freeman. He boasts that math isn't necessary in life, only to miss out on a party because Mark McGrath of Sugar Ray tells him the location in the form of a story problem.

Oswald, Lewis and Steve are shocked to learn that Drew is married to both Nicki and Kate. Drew intends to clear up the situation immediately, but puts it off for two weeks. He alternates between wives, telling each woman that he is away in Toledo on business when he isn't with her. Unfortunately for Drew, Mimi finds out what is going on. Drew begs her not to rat on him. He tells her that he loves both women and is abstaining from sex until he can narrow it down to just one wife. Mimi still feels that his behavior is sleazy, and tries to set him up for a fall. Kate calls while Drew is with Nicki, and he ends up having to agree to a dinner with both of them. He tells Nicki that Kate has gone crazy and thinks that she is married to him. He then tells Kate that Nicki has gotten hooked on anti-depressants. He manages to keep them at bay until Kate finds wedding cake in the freezer that says ""Drew and Nicki."" Oswald and Lewis decide to look for a house because women are turned off

As Drew prepares to marry Lily, his mother notes how upset Kellie seems and realizes that she has strong feelings for Drew. She believes that Drew feels the same way about Kellie. Drew and Lily go through with the wedding, but the union proves to be a brief one when they realize that they really are not right for each other. Drew winds up sharing a dance with Kellie.

Kellie finally agrees to marry Drew, but their wedding plans are thrown into disarray when she goes into labor.