The boys are playing football when Bebe walks up behind Stan (who is the quarterback) and tells him that his girlfriend, Wendy Testaburger, has broken up with him. As he begs for an explanation, she just says that, "She just doesn't want to be with you anymore. She says she still wants to be friends". Stan seems to be in some kind of trance as the other boys tell Bebe to "Get the hell out of our football game you stupid skank". Stan simply walks away. Stan is then seen looking over a bridge into the water, crying in the rain and looking at pictures of Wendy.
As Stan attempts to win back Wendy, he asks Kyle if he will talk to her for him. All Wendy says is that Stan is really nice but she just doesn't want to be together anymore. Stan begs Kyle to ask her to be more direct with him but Kyle just tells him to talk to her himself, and to be poetic. So Stan gets Jimmy to talk to her. Because of his disability he is unable to talk normally, he makes the mistake of saying, "Stan says you're a cunt..." when the original phrase was "Stan says you're a continuing source of inspiration to him." Wendy simply tells Stan to "Fuck off". Stan realizes that more attempts would be in vain.
Stan begins to withdraw from life, staying in bed for days. After seeing Stan in that condition, Kyle and the other boys take him to "Raisins", where all of the waitresses are cute pre-teens with heavy make up. Afterwords, Stan says that he feels worse, while Butters has fallen in love with their waitress, Lexus.
Stan tries to take control by asking Bebe to talk to Wendy for him. She tells him to do the most romantic thing he can think of, and orders him to hold a boom box over his head and play Peter Gabriel. He chooses the very unromantic and unintentionally racist song, "Shock the Monkey". Wendy gives Stan a guilty look from her window, and Token walks up to her. She looks down and walks away while Token shuts the blinds.
Stan is moping around in gym class and Kyle tells him, "You might as well go hang out with those Goth Kids who dress in black and talk about pain all the time!" Stan takes this advice so literally that he joins the goth kids who are obsessed with trying to not be conformist, yet they convince Stan to conform to their ways.
Kyle catches Stan at "Benny's" (a parody of "Denny's) drinking coffee and wearing all black, with the other goths. While Kyle tries to convince Stan to come back, Stan asks about whether Wendy and Token are still together. After Kyle confirms this, he says (in a strange deep voice) "...People shouldn't care about me, because I don't care about them. What's the point of caring if all it brings is pain?"
Butters is obsessed over his relationship with Lexus, who obviously doesn't have any interest in him. While Butters is oblivious to this, he continues to give Lexus large tips and gifts. Eventually he brings his parents to Raisins and they are appalled with the way the Raisin girls are using boys for tips and possibly with Butters' stupidity. They explain that girls can make men do anything by flirting and that they turn that into a profession. Then Butters just tells his parents to go to "heck" and storms out with Lexus, only for her to tell him that they are not boyfriend and girlfriend.
Butters does the same thing as Stan did after his heartbreak; crying in the rain. When the other goth kids stumble across him, they tell Stan (who they call "Raven") to check out "the tortured soul". When Stan asks what's wrong with him, he tells him how Lexus broke up with him, thus the goth kids offer to let him into their clique. However, Butters explains about "beautiful sadness," meaning that he and Stan can't go through life thinking everyone they meet would let them down. Stan is touched by his speech, though the Goth Kids are unable to understand, and begins to recover. After Butters walks away Stan says "He's right. I don't even know who I am anymore. I liked liking life a lot more than hating it. Screw you guys. I'm going home".
The next day at school, as the other boys are struggling in football, Stan shows up in his old outfit and claims how he realized that there are a lot of painful times in life an that he need to deal with the right way. When Wendy and Token walk by, he says to them proudly, "Hey Wendy, you're a bitch! Token, (flips him the bird) right here buddy!" They both angrily walk away, and the boys get back to football. When Wendy returns we have yet to know.