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 gang decides to get the old band back together for a battle of the bands contest at the Warsaw. Kate desperately wants to be lead vocalist but the guys are hesitant because she's an awful singer. The guys run into Herb, an old high school rival, who is confident his band will crush Drew's in the contest. The gang is determined to win but the guys know they won't if they let Kate sing.

Oswald announces his plans to move in with Kate. Drew's jealousy gets the best of him and he ends up in an argument with Kate. Oswald accuses Drew of pining for Kate and then insists he and Kate are more compatible than Drew and Nicki. The guys decide to test their relationships by slipping in questions from a magazine compatibility test during their Valentine's Day double date.

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 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.