Drew may have to terminate his affair with Lisa or risk job termination when the store bans interoffice dating. His solution? Ask Kate's boyfriend to pretend he's dating Lisa, to throw co-workers off the track.

The guys decide to get their band back together and enter a battle of the bands contest at the Warsaw. Kate wants to be lead vocalist, but no one thinks that this is a very good idea because she is terrible. She forces Oswald to stand up for her, and he begs Drew and Lewis to change their minds. At a meeting about the contest, the gang runs into Herb, a rival from high school. He is certain that his band will win, as they have played together at the Holiday Inn for twenty years. The guys are determined to best him, but know that they cannot win if they let Kate ""sing."" Oswald refuses to ask her to leave, so Drew tells her that she sucks. She quits, and Oswald follows. Drew and Lewis bring in a guy from high school to play keyboards, and make the finals. Kate pries the truth about her singing from Oswald. She feels they should always be honest with each other, but he disagrees. Mimi tries to knock Drew out of the contest by hitting him with a bathroom door, but mistakenly hur

Drew and Lewis are shocked when Oswald announces that he is going to move in with Kate. A jealous Drew feels that it is too soon for them to live together. As Oswald moves out of his apartment, he and Kate get into a shouting match. When Oswald returns a moment later and says that ""it's over,"" Drew assumes that he and Kate have broken up and admits that he thought they were totally wrong for each other. Oswald clarifies that he meant the argument was over, not the relationship. He accuses Drew of pining for Kate. Drew keeps accidentally referring to Kate as his girlfriend instead of Nicki. He claims that he isn't after Kate, but still doesn't think she and Oswald are a good couple. Oswald insists that they are more compatible than Drew and Nicki. They decide to test the relationships by slipping questions from a magazine's compatibility test into the conversation during the couples' Valentine's Day dinner. Oswald and Kate do agree on a few things, while Drew and Nicki seem to

Drew meets a woman at the Warsaw who recommends that he sign up for her dating advice service (for $250). He is reluctant, but finally agrees. She embarrasses him by taking hidden video of his date and using it as a ""teaching aid"" for the class. Drew becomes the laughingstock of the class, despite the fact that most of the students are dorks and losers who have never had sex. Drew seeks the help of the Better Business Bureau to have the service shut down. However, he ends up enlisting tips from the class to get a date with the Better Business Bureau employee. He quickly scares her off with his overeager behavior, and ends up back in the class. Lewis interviews potential new roommates, but Oswald keeps driving them all away. Lewis enjoys the freedom of having the place to himself. Mr. Wick bribes Lewis into letting him use the extra bedroom for a one-night stand. Mimi messes with Oswald's head by trying to convince him that Kate really loves Drew.

Drew lets Darcy dye his hair blonde and grows a goatee so that he will look more like a musician. Larry discovers that someone has been doing cocaine in the men's room at Winfred-Louder. Wick orders Drew and Mimi to collect specimens from every employee for drug testing. Drew does not like invading everyone's privacy. After the men accuse him of being a narc, he throws out all the samples. Wick orders him to give his own sample. Drew refuses and brings in a drug-sniffing dog. Wick becomes furious and fires him. Drew goes into Wick's office and discovers that Wick is the one who is on drugs. He helps him get into rehab. Oswald and Lewis become jealous of Drew's musical success and try to talk him into letting them back into the band. Mimi ends her relationship with Ron after she receives an unpleasant visit from his wife.

Drew's shocked to find his cross-dressing brother sampling Mimi's lipstick--while it's still on her lips.

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.

Drew is finally released from the mental institution. On the day of his release, he runs into Nicki at the Warsaw. She reveals that she is divorced, and feels she made a mistake in letting Drew go. Kate worries that Nicki is going to hurt Drew again. Kate, Lewis and Oswald try to create a distraction to help Drew get away, but he assures them that he is all right. After his friends leave, Drew suddenly proposes to Nicki. She accepts, and they marry in Pennsylvania. Drew's friends cannot find him for several days. Kate admits to Lewis and Oswald that it made her very jealous to see Drew with Nicki. She realizes that she still loves him. She calls Drew on his cell phone and arranges to meet him at a bar near City Hall. Drew returns home with Nicki and announces their marriage. He leaves to meet Kate before Lewis and Oswald can warn him of her intentions. She proposes to Drew, who immediately accepts. Meanwhile, Steve refuses to forgive Mimi for driving his brother insane.

Recurring dreams of Kate force a heartbroken Drew to forego sleep, until Mimi offers him a surefire way to get over being dumped. Meanwhile, Lewis finds some unsettling common ground with Nicki after taking her out on a pity date.