Breaking Up with the Boss' Son is the 8th episode of the series. It aired on December 5, 2004, in Canada on Teletoon and on November 3, 2008, in the United States on Cartoon Network.
Jen's new crush turns out to be Coach Halder's son, Cory Halder, but he still wants to go out with her. As it turns out, he's a horrible date, but because Jen doesn't want to be fired, she'll have to find a way to get him to break up with her. Meanwhile, Jonesy gets work at Stereo Shack under Darth, a nerd he bullied repeatedly in the past.
Jonesy is in Jen's workplace, looking to purchase a football, when a cute guy arrives and grabs her attention. Jen is instantly smitten with him, and things only get better when she learns that he's going to be her new co-worker. Because of this, she starts to give him tips on the job, with the most important being that the boss is a giant bonehead. As she's telling him what he'll need to know, the giant bonehead arrives and lets slip that the new guy is his son, Cory Halder.
Later, the friends are gathered by the Big Squeeze, listening to Jen vent about how she can't believe Coach Halder has a wonderful son. Her friends aren't that interested in her complaints, however, mainly because they center around her worries about how her boss will also be her boyfriend's father if Cory goes out with her. However, by talking her way through her worries, Jen makes them seem less important, and ends up coming to the conclusion that she might as well ask him out.
When she does ask him out, he agrees quickly. However, their date is a total flop. Cory is incredibly self-absorbed, and spends his time either talking about himself or watching sports. When he takes a break to use the bathroom and Jen gets a call from Caitlin asking how the date is going, Jen has an easy answer: it's the worst date she's ever been on.
Naturally, when she talks to her friends, she wants to break up with him, even though she accidentally agreed to another date. However, her friends warn her that this may not be a good idea, as Cory is her boss' son, and may use his pull with his father to get her fired. This worries Jen, as she doesn't want to be stuck with him forever, but Caitlin has a suggestion to get her out of a bad relationship: simply turn into a horrible girlfriend. To do this, Jen asks the guys what they would suggest, and they give her a laundry list of ideas, including getting matching outfits, being clingy, and using an overcomplicated pet name for her boyfriend.
When the date actually comes, it initially seems as if the plan is working. However, it soon turns out that instead of hating everything that Jen is doing, Cory actually enjoys how she's acting, and is to some extent reciprocating. Jen excuses herself to call Caitlin, and when Caitlin insinuates that she might not be able to lose Cory, Jen decides to instead crank the act up to even higher levels. To further this, she takes Cory to Frilly and Pink, but instead of being disgusted by the girliness of the store, he's instead fascinated by the softness of a pashmina. In fact, he likes the store so much that he buys Jen a bunch of stuff from it.
Jen is not happy, and she decides to let Cory know how she really feels. Unfortunately, when she does this, she's right next to the microphone at Stick It, and an electrical short caused by Nikki causes it to come on and blast through the mall's personal address system, letting the entire mall know exactly how she feels about Cory. However, Cory isn't offended by this confession, as it turns out that he wanted to dump her as well but his father told him not to because she could conceivably sue the store for harassment. He and Jen then go their separate ways with a clear understanding that they're not dating anymore.
The next day, the gang has gathered by the Big Squeeze. Jen reveals that Cory transferred to a different location, so things aren't weird at the Penalty Box, and Nikki reveals that she got the tape of Jonesy's humiliation by paying off Jonesy's debt. Jonesy has humiliation of his own, though: a picture of Nikki dancing in first grade. He shows it to the gang, then takes off with it as Nikki chases after him, demanding that he give it to her.
Sub-Plot: Working for Darth
Wyatt is in Stereo Shack, looking for electronic equipment, when Jonesy puts a lightsaber through an expensive speaker while playing with it. At first the store's manager, Darth, wants to call mall security on him, but Wyatt has a better, cheaper idea for the both of them. Soon, Jonesy is working at Stereo Shack to pay the store back for the equipment he broke.
Unfortunately for Jonesy, Darth is somebody he picked on through most of middle school, and while Jonesy may not remember, Darth certainly does. His employment there soon turns to a lightsaber duel with Darth, one that Darth handily wins and caps off with a wedgie. Initially, Jonesy is relieved that nobody saw him get humiliated by a nerd, but it turns out that the security camera caught the entire battle, and if Jonesy doesn't want the video to get out, he'll have to do whatever Darth says.
What follows for Jonesy is an immense amount of hard work. By the end of it, he's exhausted, but his brain has been at work along with his body, and he suggests a deal to Darth, knowing that there must be something Darth would take in trade. Darth does indeed have something he wants: a date with Nikki. Jonesy, who knows what Nikki's like, believes that this is going to be hard to pull off, and when his friends show up at the store and make fun of him, he knows it's going to be hard.
He attempts to get Nikki to do a blind date, however, and eventually wears her down into one date. She shows up at the food court at the appropriate time, but when she sees who her date is, immediately moves to leave. Darth is saddened by this, but accepts that Jonesy only did it because of the videotape. This piques Nikki's interest, and within minutes she and Darth are at Stereo Shack, setting up a humiliation for Jonesy. Darth starts to have second thoughts midway through, but Nikki reminds him that Jonesy didn't exactly keep his end of the bargain, and this convinces Darth to go through with it.
In the middle of Darth's work, Nikki grabs a stray wire, and this sends a short through the electrical system, causing the microphone at Stick It to turn on and broadcast Jen's breakup through the entire mall. Darth fixes the problem, and soon the video is being broadcast on the mall's jumboscreen. To make matters worse for Jonesy, not only does the entire mall see his humiliation, but the girl he's on a date with sees it too, and she walks away from him while laughing at his humiliation.
Coach Halder: Masterson! You've let down your defense! Jockstraps need reorganizing, aisle 9! Pronto! And don't forget to stock the extra-large ones this time!
Jen:(to Cory) The first thing you should know, is the boss is a bonehead. We're talking first-class moron. Coach Halder: Ah! There you are, Masterson. I see you've met our newest employee. Jen: Definitely. Coach Halder: Cory here's following in my footsteps, and I couldn't be prouder. Isn't that right, son. Cory: That's right, Dad. (Coach Halder leaves.) Jen: The coach is your father? Cory: That's right. Jonesy:(cough) Way to go. (cough) Jen: Oh. When I said bonehead, I meant it in a really nice way.
Wyatt: Jonesy, be careful. Look don't touch, remember? Jonesy: Would you relax? It's just a stupid toy. (He puts the lightsaber through a speaker.) Darth: Okay, option one, you pay a hundred bucks for the speaker. Option two, I call mall security. Jonesy: Hmmm... (He empties his pockets and finds just a nickel and a button.) Darth: Gee, a nickel AND a button? Jonesy: Yeah...but that's a rare antique button. Darth: Yep, mall security it is.
Darth: Shall we start you off with a lightsaber? All of my employees are trained Jedi. Jonesy:(looking at it) Well I don't want this one! It's small! Darth: SILENCE APPRENTICE! You don't remember me? Jonesy: Nope. Can't say I do. Darth: Atomic wedgies ring a bell? Jonesy: Hmm... Darth: How about pantsing me in front of the whole sixth grade? Jonesy:(chuckling) That was you? Man, that wedgie must have hurt! We pulled it over your shoulders! Darth: Oh yes. But now you're mine. Yes mine! YES MI-HI-Ha-hoo-hoockh– (He begins to cough uncontrollably.)
Jonesy: I'm the top scorer on the varsity hockey team. I think I can handle a toy sword. Darth: Prove it. (They proceed to duel. Jonesy, losing the battle, plays dirty, twisting Darth's helmet around.) Jonesy: I rule! (Darth angrily rights his helmet and comes after Jonesy. He proceeds to knock Jonesy's lightsaber out of his hand and give his employee a wedgie.) Jonesy: Ouch! Darth: Ah, you begin to understand the error of your ways. Jonesy: I can't believe I got my butt whipped by a nerd! Good thing no one cool was here to see it. Darth: Oh, so you wouldn't want the security tape released then?
Darth: Don't worry. I'll keep the videotape safe as long as you do what I say. Jonesy: So you're saying I'm screwed. Darth: Like a lightbulb.
Nikki: You look so sweet, but it's like there's this inner cow just dying to get out. I like it. Caitlin: Thanks! You're a total cow too!
Jen: Oh, I have the touch. I've turned off tons of guys before.
Darth: I'm having second thoughts. Jonesy and I had a deal, and a Jedi master is nothing without honor. Nikki: Did Jonesy live up to his side of the bargain? He set you up with a girl who thinks you're a freak. Darth: Cool. I'm over it. Thanks.
(The video of Jonesy getting beaten by Darth is playing on the jumboscreen while Jonesy tries to pick up the nerdy girl from the Stereo Shack.) Jonesy: So then I scored the winning goal in overtime–it was awesome. (The girl starts to laugh.) I can see you're impressed. (She gets up and walks away, laughing.) Here's my number. What happened? What'd I do? (He notices the video.) NOOOOOOOOOOOOOOOOOOOOOOOOOO!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
Goof: In the part where Jonesy froze in mid-battle pose with the lightsaber and just before the rest of the gang spot him, his arms are switched (his left arm is his right and his right is his left).
Goof: Jonesy says that he has a picture of Nikki tap-dancing in first grade, but the picture actually makes it look like she's doing ballet.
Jonesy's job: assistant at Stereo Shack Reason for firing: Nikki paid off his debt, so Darth got rid of him.
Cory Halder's voice actor is the same as Geoff from the Total Drama series.