At a school after dark, Tom and a group of boys are in the principal's office doing drugs and watching hockey on TV. The phone rings. The boys learn that their friend Alan is bringing a new client, Doug Norberg, over.
When a boy in a turquoise shirt arrives, another boy announces that a player nicknamed Iceman just scored another goal. Turquoise Shirt is pleased: "I oughta tell my dad to pay him more." Doug Norberg/Penhall asks, "Your dad owns that team?" Turquoise Shirt introduces Doug to the rest of the group: Tom, Tad, and Troy. Doug wants to buy a half pound of cocaine.
Troy switches the TV to Channel 11 news. Something called Proposition 58 has passed. The boys boo because Prop 58 relates to substance abuse. The infamous Councilman Davis is projected to win the mayoral election again. The boys cheer and chant "4 more years!" Tad snorts another line and says, "This one's for you, Dad." Tom and Doug exchange looks; this case will be a political powderkeg.
Harry pours himself a cup of coffee in the squadroom and states that life would be better if everyone took more time to appreciate its bounties. "Date went well last night, huh?" Cap'n Rufus guesses. The captain tastes the coffee and makes a face.
Tom informs his boss that the mayor's son is a major drug dealer. Cap'n Rufus says, "We bust the mayor's son, the first word outta his mouth will be 'entrapment.'" He tells Tom to make sure the investigation is run by the book. He also warns him to stay away from Tad's house because Councilman Davis has met Tom and Doug.
At Tom's apartment, he and Jackie play some kind of board game. He confides in her about the case. Tom wants to prove to Tad that he isn't above the law.
In the school gym after hours, Doug and Tad play some variation of hockey involving brooms, a large dodgeball, and electric carts they probably stole from the school fieldhouse. They end up crashing the carts into each other. The janitor catches them and turns off the lights. Tad scolds the janitor, "Don't ever do that again!" The janitor leaves and Tad turns the lights back on. He tells Doug he'll have half a pound of cocaine by the next afternoon.
Harry announces to the rest of Jump Street (minus Judy and Booker) that he's in love. He and his new girlfriend "fit together like hand and glove." Doug remarks, "That sounds kinda sexual." Tom says, "That's disgusting." The girl stimulates Harry intellectually. "All night?" asks Rufus. Way to discourage their behavior, Cap.
Harry's girl Bobbie appears. She's pretty and wearing a tight hot-pink shirt and equally tight black skirt. Bobbie invites him to a showing of a French movie at the arthouse theater, cocktails provided, then excuses herself to the ladies' room. "Can I get some fries with that shake?" Doug mutters as she walks away. "A large order," Cap'n Rufus adds. Harry is disgusted with his coworkers: "Just because a woman is shapely, you assume she's not good for anything but sex." I have to agree with him on that point; men have been genuinely surprised that I'm both a size 6 and intelligent.
In class the next day, Tom arranges to make the deal at Tad's car after school. Tom is pulled out of class and into the principal's office. A suit named Chief Deputy Mason tells him that the investigation of Tad has been terminated.
Cap'n Rufus is not happy about the mayor's office intruding on Jump Street's work. Mason assures him that closing the case was not politically motivated. Yeah right. He advises Fuller to let it go.
Cap'n Rufus meets Tom and Doug at a bar. All three are angry about what's happened. Rufus has an idea. They'll use Tad to find out who his street connection is and "if he gets swept up with the rest of the garbage, it's his own fault."
Doug pulls into the school parking lot driving a borrowed red convertible. He asks Tom what happened to the deal. Tom makes an excuse that he was pulled out of school because his mom was sick. Doug now wants a pound of coke. Tad says, "Lemme talk to a guy."
At Harry's apartment, he and Bobbie share a bottle of wine in the candlelight. He starts, "I've never told any woman this before" and is interrupted by Doug's arrival. He's singing opera very poorly at the top of his lungs, which further ruins the moment. Doug apologizes for not realizing it was Tuesday. Bobbie offers to leave so she's not imposing. Doug tells her not to; they can both stay. She and Harry won't even know he's there. Doug soon has the TV blaring and tuned to wrestling, which distracts Bobbie.
Tom and Jackie have breakfast at one of their apartments (can't tell whose). Jackie warns Tom that the mayor will eat him alive if he finds out what's going on.
Meanwhile, Davis is sitting in his home office with the phone off the hook while Tad does some more cocaine in his room. He hides everything when his dad knocks and ditches his shirt. When Tad opens the door, he lies that he was getting ready for bed. Davis knows Tad's school is the target of a drug investigation and the police think Tad's involved. Lying through his teeth like a good politician's kid, Tad swears he doesn't use. Davis tells him good night.
Cap'n Rufus has a review board hearing about why Tad is still under police surveillance. The board finds him guilty of misusing police resources for personal reasons and suspends him without pay for 30 days. Once word gets back to the Chapel, everyone is upset; they know Rufus is taking the heat for them.
Tad and his friends have another nighttime get-together in the principal's office. Tad heard Tom was kicked out of school because he was a narc. He wants to throw a party to celebrate while his parents are out of town. Doug wants to contribute a pound of coke. Tad promises to call his supplier, Jack.
When Doug gets home, Harry is channel surfing. Doug's bags are packed and waiting by the door. Harry is blunt: "If you stay here another night, there's a good chance I might strangle you in your sleep. I don't wanna do that." Doug is hurt but doesn't want to show it. He hands over his key and tells Harry not to worry; he has plenty of places to stay.
Montage time! Doug walks through a downtown neighborhood with his luggage. He sees a hotel advertising rooms for $11/night. I'm sure that was a fleabag rate even in the late '80s. A hooker propositions him on the street. He shakes his head and goes into a bar.
The next morning, Doug wakes up under a black-and-white patterned comforter in an unfamiliar bed. He's startled to hear a man's voice say, "Good morning." A guy in a suit, Randy, is standing next to the bed holding a loaded breakfast tray; there's even a single rose in a vase. Doug scans his surroundings: "This looks like my old place. Is this 1518 Cedar Place?" Randy confirms and adds, "That explains why you were pounding on my door at 3:30 A.M. yelling, 'I'm home.'"
Doug seems to be realizing something and peeks at himself under the covers. He must be naked because he stammers, "Randy, did we--What exactly happened last night?" "Nothing," Randy assures him, "You were such a mess I slept on the couch." He offers coffee and takes a step closer with the tray. Doug likes what Randy's done with his old place. He's still uncomfortable about the situation (as he should be) and asks if they can have breakfast at the table.
Moments later, Doug is eating grapefruit in a bathrobe that presumably belongs to his host. Randy asks Doug how he wound up here. Doug clutches at the neck of the robe and puts on a high-pitched voice: "I've always depended on the kindness of strangers." Randy chuckles, "You'd make an interesting Blanche Dubois." Doug explains about his breakup with Dorothy and living on Harry's couch; he misses Dorothy. Randy says, "It sounds like two people who love each other but can't communicate." He suggests that Doug go see Dorothy.
Jackie is upset that Tom didn't come over the night before as planned. Tom tells her about Fuller's suspension and asks if she told anyone about Tad; Jackie admits to telling her boss. Now Tom is upset because she betrayed his confidence. Jackie argues she was trying to keep Tom from ruining his career. Tom won't play political games.
Doug is visibly nervous to be in Tad's house because Davis knows him. He, Tad, Troy, and the other guys go up to Tad's room for some drugs and alcohol. Doug asks for more beer. Tad tells him where the kitchen is and also to bring some sandwich supplies back with him. Downstairs in the kitchen, Davis almost catches Doug raiding his refrigerator; Doug has to hide in the pantry to avoid him. Back in Tad's room, Doug claims that they're out of beer and sandwich stuff and offers to make a food run.
Cap'n Rufus is surprised Doug and Tom are still going after Tad. He wants them to drop the case before their careers are ruined too.
Tad's party is in full swing. A friend goes looking for Tad in the palatial master bedroom/master bath, but doesn't find him. That's because Tad is currently overdosing in a corner of a smaller upstairs bathroom.
Davis drops by Cap'n Rufus's house. Rufus expresses sympathy for the mayor's loss. Davis says, "I want the man who killed my son." Rufus tells him as gently as possible that nobody killed Tad; it was an overdose. Davis can't live with the fact that Tad might still be alive if he had let Jump Street bust him; he wants the dealer caught. Rufus agrees to do all he can. In the school parking lot, Tom and Doug flash their badges at Troy, who claims not to know who Jack is, but eventually cooperates.
Doug and Troy go to a rundown building and get buzzed into the dealer's apartment. Outside, marked police cars park on the street and officers start getting out. Jack's junkie assistant pats Doug down because he doesn't trust anyone under 30; Jack looks like he's on the wrong side of 40 himself. He sells Doug a pound of cocaine. Cap'n Rufus gives the other cops the signal to make the bust and catches Jack before he can escape.
Jackie visits Tom in the squadroom. Tom isn't returning her calls. She knows telling her boss about Tad was wrong and asks for forgiveness. Tom can't. She leaves. Thank goodness. Tom's love interests are always annoying characters; at least Dorothy's fights with Doug were good for some giggles. Fuller enters and Doug starts a round of applause for his return.
Doug rides his motorcycle to the house he'd been living in with Dorothy. When he arrives, there's a large FOR RENT sign on the lawn. He peeks in the living room window and sees that all the furniture is gone. Looks like he won't be making up with Dorothy. End of episode.