There's a pointless flashback to Katy's first day of school. Katy hasn't even been yet and tells her mom she hates it. Dean tells on a classmate who's looking up a girl's dress. Middle school Katie gets bullied by some girl's on Valentine's Day. Jump ahead several years. Katie watches through the auditorium door as the class of 1986, presumably her senior class, graduates without her.
In the Chapel, Fuller assigns Dean and Katie to Roosevelt High (FDR, not Teddy). Dean is insulted because his undercover persona has a C- average; Katie's has all A's and B's. The opening credits reveal that the actors playing Katie and Dean have not received star billing. They're being sent to Roosevelt to investigate a drug ring Tom and Doug thought they shut down. Katie and Dean will be posing as brother and sister.
Dean dumps a stack of school supplies on Katie's desk. She gets irritated, saying she's not trying to make up for everything she didn't learn in high school the first time. I'm pretty sure this show was mandated to have at least one montage per season; this one is boring and consists of Dean and Katie getting ready for school.
Katie stands in her living room, clearly dreading the day ahead. I don't think she should've volunteered for an undercover unit specializing in posing as high school kids. An unidentified man is sleeping on her sofa bed. Dean arrives to pick Katie up, but she won't let him in the apartment. Dean has gotten into his role as a barely average student by not having any school supplies except for a pencil in his back pocket. Most of the hardcore slackers I knew in high school didn't even carry that.
Dean has rented a Trans Am instead of taking his classic car to Roosevelt. He never had a car in high school, so it's a fantasy for him. In English class, Dean makes up crazy occupations for their fictional parents: Dad runs the light boards at Bon Jovi and Springsteen concerts, Mom is a journalist who just got back from an assignment in Europe. The students are given a project: Each student has to find a poem they like and recite it in class.
At Katie's place, she reminds her partner they're supposed to be keeping a low profile, which is hard to do when your parents supposedly interview heads of state and tour with major bands. Dean asks if the shaving kit on the coffee table belongs to Katie's boyfriend. She dodges the question.
Dean doesn't get why she's acting like high school is the last place she wants to be, even though it's literally her job. He tells her to look on the bright side. The worst part of high school was homework and now they aren't expected to turn it in. Dean is excited about partying and is thinking about trying out for basketball. Katie tells Dean she's a dropout.
Meanwhile, Judy has been looking at her dream house. Her eyes pop out of her head when the loan officer at the bank shows her what the mortgage payment would be. The loan officer explains "boo-boos" on her credit report, namely a student loan payment that was made 2 days late...2 years ago. The bank will need a letter from the loan company explaining the delinquency. Judy can't believe this. I know how she feels. Last year, I got the runaround trying to get a car loan while having no credit history whatsoever.
Katie makes a friend on the quad: Lena, a nerdy girl who describes her brother Alan as "the biggest wastoid on campus." Katie asks Lena if she knows where Alex gets his drugs, but Lena has no idea. She suggests to Dean that he get close to Lena to find out more about Alex. Really? After the fit she pitched about using the prostitutes from last episodes for information? Dean thinks Katie should be friendly with Lena; girls tell the girlfriends more than they tell their boyfriends. Katie points out that she's not the one Lena has a crush on.
Dean asks Lena to the homecoming formal and she agrees. A cuter girl, Brooke, calls Dean over and asks him to homecoming. Dean turns her down. Lena says she'll talk to him about coordinating outfits after she finishes volunteering at the animal shelter. Brooke is stunned.
Katie's still unnamed couch surfer mocks her for studying: "I thought you said the only classes that ever taught you anything were driver's ed and sex education. I thought that's why you dropped out in the first place." Kinda reminds me of The Outsiders; Sodapop quit school because he was only passing auto shop and gym. Couch Surfer asks if Katie got pregnant in high school. Katie explains she dropped out because a creepy teacher hit on her. If this detail is supposed to make her character more sympathetic, the actress didn't do a good job delivering the lines or the writer did a bad job on the script or both.
For the English project, Dean recites "Casey at the Bat" and Katie reads one of Shakespeare's sonnets. We jump to Dean looking at a photo of himself, his parents, and a girl who's probably his sister. He told Katie he was an only child! Dean answers the door to find his estranged brother on the other side. I'm officially confused.
Dean asks his brother how he found him, what he did, and who he's running from. In Supernatural, this conversation is usually the other way around. This scene teaches us nothing of importance, not even the brother's name. God, the writing has gone downhill.
Judy is told by Blowfish that the house needs a new roof. She can't believe the house costs $250,000 if it's in that kind of shape. I agree with her.
Dean visits Lena at the animal shelter. He wants to get to know Alex better since he's taking Lena to homecoming. "You don't have to get in good with him to get to me," says Lena, "My brother's a jerk." He's also a major dealer at Roosevelt. Dean adopts a ginger kitten, names him Iron Mike, and gives him to Katie. Katie is irritated; her last cat almost got her evicted.
Dean asks about Katie's parents. When he was getting his paperwork together to start the police academy, Dean found out he was adopted. He spent a 6-week leave after graduation looking for his birth parents. Dean loves his adoptive parents but wanted to find out where he came from. During his leave of absence, Dean found out his birth father had died and his birth mother had disappeared. He learned he had a brother. "There's a lot of hate about him and there's a lot of hate about me," Dean sums up. Katie agrees to keep the cat, renaming him Cyrano. I liked Iron Mike better.
In the boys' room at Roosevelt, Dean asks to buy some drugs from Alex. Alex thinks Dean is only buying to look cool. I recognize Alex from the episode "Swallowed Alive" as one of the inmates who asked The Hammer to intercede with a problem.
The English teacher asks Katie to stop by his classroom after school. He wants to give Katie a reward for doing so well...when everyone's gone. Yuck!
Dean's brother, who has experience with drug dealers, offers to help Dean catch the dealer by giving Dean pointers on how to act.
Katie barges into the boys' bathroom and tells Alex not to sell anymore drugs to Dean. Their mom spent a lot of money putting Dean in rehab. She goes out to the hall and quietly asks Dean how he came up with the idea to say that.
Dean thanks his brother for his good advice, then goes to Judy's housewarming party. Her furniture hasn't arrived yet, so she sits on a picnic blanket in the living room with Katie, Fuller, Dean, and Blowfish. Dean pours champagne. They tease Dean about having to wear powder blue to homecoming so he'll match Lena. Fuller hated school dances, Judy loved them, and Emo Katie never went to them. They're busting Alex the next day, Katie will be Dean's backup.
Katie stays at Judy's after everyone else goes home. She tells Judy about the creepy English teacher from Roosevelt and the one who victimized her in high school. Katie wants to bust the teacher too; she's waited a long time to set karma right.
After school, the English teacher's surprise is totally innocent. He presents Katie with a thick volume of Shakespeare.
Katie's couch surfer leaves, apparently for good. Elsewhere, Lena breaks up with Dean for buying drugs from Alex. She hopes she didn't hurt his feelings and still wants to be friends.
When Dean arrives at the abandoned school, Katie is kneeling next to a semiconscious Alex. Somebody beat him up and the kid described his attacker as looking like Dean. This is why you don't tell your ne'er-do-well brother about sensitive police operations...
At home, Dean confronts his brother about beating up and robbing Alex. It seems our young dealer always carries decoy bags of baking soda. Dean dumps out his brother's backpack and white powder flies. Dean's brother pulls a gun: "Baking soda or not, just let me leave." He didn't want to rob anybody, but Dean gave him an easy opportunity. Dean's brother can't believe Dean is picking his job over family. "We may be blood, but we ain't family," says Dean.
The two briefly struggle for the gun. Dean's brother proposes a deal: he stays out of Dean's way as long as Dean stays out of his. Dean's brother hurries out of the apartment and runs right into Katie, armed with a gun of her own.
Katie comes out of her room wearing a strapless, floor-length powder blue dress. She calls through the apartment door, telling Dean not to laugh. When she opens the door, Katie laughs hysterically at Dean's powder blue tuxedo. It looks a lot like the one my dad wore to Mom's senior prom, except this one doesn't have a ruffled shirt. Dean even has a corsage. Katie jokes that he looks like a backup singer for Wayne Newton.
"I did this 5 years ago and I still feel stupid," says Dean. Katie says it's not too late to forget the dance. Dean insists on going because Katie never went to her own homecoming. "So the idea is to let me feel stupid?" Katie wants to know. Dean smiles: "Wait 'til we go bowling after the formal." As they leave, he calls, "See ya, Iron Mike!" End of episode.