When Jude walks into work with a girl hanging off of him, Jonesy remarks on his predicament, and as soon as she's gone, Jude admits that he wants to break up but doesn't know how to do it. Jonesy then decides to teach Jude how to do it, but Jude has a different idea, and offers Jonesy five dollars to break up with Rita for him. Jonesy quickly agrees, and he soon meets Rita at Grind Me for Jude's scheduled coffee date. There, he breaks up with Rita and then makes his way over to his friends, who are sitting at another table.
Jen thinks that Jonesy was too harsh, but Jonesy defends himself by claiming that what he did was just business. When he says it, an idea forms in his mind: he'll set up a business to tell people bad news. His friends think that this is a bit of an odd idea, but they're used to Jonesy's scams. Caitlin then checks her phone, sees that a new type of makeup is going on sale soon, and leaves to get some.
Jonesy proceeds to set up a table in the mall and announce his service: for just five dollars, he'll tell people things that others want them to know but don't want to tell them. To advertise, he gets a bullhorn and a giant rooster hat, and business quickly starts pouring in. His first new customer is Wayne, who gets Jonesy to tell Jude to get back to work. Eventually, Jonesy has a stack of cards with bad news to give out, and he's ready to get to work on them, even if at the moment he's annoyed by the presence of Nikki's new boyfriend.
Jonesy then proceeds to go on a bad news-giving spree. His first victim is Kai, who has been fired by Ron for being a "girly little excuse for a maggot." After that, he proceeds to tell a girl that her boyfriend dumped her, and he does this with so much sensitivity that he scores a date. His next victim is a guy with a mullet, which he cuts off, and the follow-up is Wayne, whose fries he stills under the orders of Wayne's mother. The grand finale is Jason and Joanie, whose constant kissing gets broken up; for this last act, he receives a round of applause from the entire mall.
Later, at Underground Video, Jonesy tells Wyatt and Jude that his breaking bad news service is the best job he's ever had. He's scored four rebound chicks and is making tons of money from it. When Wyatt worries that Jonesy might make a lot of enemies, Jonesy defends himself by saying that he's just the messenger. Wayne arrives at that point, simmering with rage over having his fries stolen, and begins to chase Jonesy for retribution. Seeing this, Wyatt notes that they always shoot the messenger.
Eventually, Jonesy manages to lose Wayne, and as soon as he does he sees Stone walk by, talking on the phone. He tails Stone, but when Stone finishes his conversation, he turns around and runs into Jonesy. Recognizing Jonesy as the bearer of bad news, he makes Jonesy an offer: five dollars to break up with Nikki for him. Jonesy takes the money, but is worried that he won't be able to go through with it and puts off doing it. However, he finds that with his worry about dumping Nikki hanging over his head, neither his money nor the broken-hearted girls throwing themselves at him can bring him joy.
Wyatt advises Jonesy to go through with it quickly, but when Jonesy tries to walk up and just tell Nikki she's being broken up with, he finds that he can't do it. Jonesy concludes that there's only one thing he can do: refund Stone his money and move on. Stone refuses the refund, though, and threatens Jonesy with telling everyone that he's dating five girls on the rebound. Jonesy is offended by what he considers a violation of the guy code, but when Stone stands his ground, Jonesy fires himself, leaving Stone to attempt the breakup himself.
When Stone breaks up with Nikki, she doesn't take it well, especially when he admits that he tried to hire Jonesy to break up with her. The Clones, who have been watching eagerly, then wheel over a table of socks for Nikki to throw, which she uses to drive Stone out of the store. Jonesy comes in at the tail end of this conversation, and a sad Nikki asks him if it's true that she's harsh. Jonesy confirms that she is, and then tells her that its one of the things that makes her who she is and he likes that about her.
Later, the group is gathered around the table, except for Caitlin, who is feeling too ugly. Wyatt suddenly receives a call from Caitlin, who wants some money to help her face, and soon Nikki pinpoints the call as coming from behind the Big Squeeze. She drags Caitlin out, but sees that Caitlin has continued to use the makeup that wrecked her face. Jen authoritatively demands that Caitlin hand over the makeup, but Caitlin just laughs, and when Jen claims that the Escalator Girls listened to her, Caitlin responds that she told Jonesy to tell the girls Jen was a champion kickboxer who killed a guy in a match. While Caitlin is distracted, though, Nikki grabs her makeup and throws it to the Escalator Girls, and Caitlin's shoulders slump because she knows she'll never get her makeup back. She swiftly recovers her smile, though, as she realizes she's finally free of its pull.
The next day, the Escalator Girls have started using the makeup, and true to form it has given them darkened and acne-ridden skin. Rita then comes by with invitations to a party for everyone, including Jude. Jonesy walks up at that moment, and requests an invite; in response, Rita slaps him several times, declares it a message from the rebound girls, and then walks away angrily.
Sub-Plot One: Smashface
When Caitlin gets to the store to buy the new makeup, she finds one container left and one customer reaching for it as well. This customer is Tricia, who fights her for it; however, the fight is broken up when a saleslady notices an extra container and puts it out. Tricia runs over and grabs it, while Caitlin takes the original container.
Caitlin immediately starts using it on her face. The first effect it has is to give her an incredibly dark tan; soon after, the makeup has the effect of triggering a reaction that gives her really bad acne. Caitlin doesn't notice this at all, as she hasn't checked a mirror. When she finally does so at Jen's insistence, she immediately closes the Big Squeeze and heads to the spa. There, she gets treated but soon finds out that it had no effect, as the spa couldn't do anything for her zits.
Caitlin chooses to leave behind her friends, due to her being too ugly to be there in person. However, they find her hiding behind the Big Squeeze, and find out that she's continued to use the makeup. Jen, having newfound confidence due to her running off the Escalator Girls earlier, goes up to Caitlin and demands that she hand over the makeup, but Caitlin just laughs, because she's the reason that the Escalator Girls were scared. However, while Caitlin is distracted, Nikki grabs the makeup and throws it to the Escalator Girls. Caitlin is at first disappointed by this turn of events, but quickly comes to realize it's for the best. The next day, this is proven true when the Escalator Girls come in with all the bad side effects of Smashface on them.
Sub-Plot Two: Jen's Keys
Jen is talking to Caitlin at the Big Squeeze when she realizes she has to get back to work at the Penalty Box. Twirling her house keys around her finger, she gets ready to leave, but before she can her keys slip off of her finger and slide over to the Escalator Girls. The Escalator Girls take possession of them, and Jen fears for her life for the next few days, as she doesn't know how to get her keys back. However, when she sees them bullying Stanley, she decides she's had enough and heads over to stand up to them. Oddly enough, her confrontational yet polite approach works, and they do everything she asks them to. Jen basks in the glow of her new, strong personality–until she learns from Caitlin that the only reason it worked is because she paid Jonesy to tell the Escalator Girls that Jen was a champion kickboxer who once killed a guy in a fight.
(The Clones see Nikki and Stone kissing.) Chrissy: What does he see in her? Kirsten: Maybe his mom dropped him on his head when he was a baby.
Jonesy:(over the phone) Yeah, you can pay me later, Wayne-o. (Jonesy hangs up and turns to Jude.) Jude...GET BACK TO WORK! Jude: You took money from Wayne to yell at me, bro? Not cool! (Jude walks away and Wyatt looks at Jonesy disapprovingly.) Jonesy: Hey. Money's money.
Wyatt: I don't know, Jonesy. You were pretty harsh out there. Jonesy: Please. I'm just the messenger. (Wayne comes in.) Wayne: YOU! Gimme back my fries! I'm serious, man! Jonesy: Hey! I don't care if you're fat, dude! Talk to your mom! (Wayne begins chasing Jonesy around the store.) Wyatt: They always shoot the messenger.
Jen: The Escalator Girls are holding my house keys hostage. Wyatt: You can kiss those goodbye. Jude: Seriously. This one time, my skateboard wheeled over there and I just left it. Forever. Wyatt: Oh, yeah. I remember that. Their leader said if you ever tried to come get it, she'd stick it somewhere really painful.
Jonesy: Money and chicks can't buy happiness. Wyatt: Okay. Now I'm really worried.
Stone: If you don't break up with Nikki for me, I'll tell everyone you're dating five rebound chicks. Jonesy: That's completely breaking the guy code. Stone: Watch me. Jonesy: Whatever. Nikki's more important to me then some stupid business or rebound chicks. In fact. You know what, I'll save you the trouble. "Jonesy, you're fired!"
Nikki: Jonesy? Can I ask you a question? You don't think I'm harsh, do you? Jonesy: Totally. You're a pain in the butt. And if Stone's too stupid to love it, then it's his loss. Don't ever change. Got that? (Nikki hugs Jonesy.) Nikki: Got it. Thanks. Jonesy: Anytime.
Jen: The Escalator Girls thought I was pretty tough. Caitlin: Yeah, only because I paid Jonesy five bucks to tell them that you are a champion kickboxer who killed a guy in a fight last year. Jen: Jonesy! Jonesy: What can I say? Five bucks is five bucks.
Goof: Kai appears as a security officer here, even though he was fired at the end of "The New Guy."
Goof: Caitlin says that she's sixteen years old when she's mad at her cosmetician. She can't be sixteen, however, as she only turned sixteen in the Season 3 premiere "Sweet 6teen."
Jonesy's job: Bad news breaker (self-employed). Reason for firing: He fired himself because he didn't have the heart to tell Nikki that Stone wanted to break up with her.
This episode's plot contains many references to the 1998 film Dirty Work. While the episode and a plot is a reference to said film, it is also a reference to the idiom "dirty work," which describes unpleasant, sometimes illegal work.
Apparently Stone's girlfriend's dad had a short-lived job in Montreal. This shows that the show is not set in Montreal.
Stone's former ex is named Jill, but when he appears in "Wrestlemania," the girl he's with is named Mimi. This indicates that he and Jill broke up at some point between the two episodes, and Stone began going out with someone new.
Jen and Nikki in shock.
Jonesy flirts with the Blue Dress Girl.
Stone and Nikki kissing.
Stone pays Jonesy to break up with Nikki for him.
After breaking up with Nikki, Stone runs away from the Khaki Barn in fear as she angrily throws socks at him.