When the Griffins go swimming in the Quahog Swimming Pool, Peter assumes Stewie knows how to swim and forces him to swim. Lois suggests he takes swimming lessons, and during the time, Stewie jealously tries to kill the star pupil, Brad, by rigging a lifeguard chair with dynamite and luring him beneath it with a piece of marzipan.[3] However, Stewie's detonator malfunctions, blowing himself up and crushing him beneath the lifeguard chair. Stewie ends up in hell, which surprisingly looks like a hotel room, but when he is rescued by Lois (from what he thought was being raped by Steve Allen, who actually only wanted Stewie to fix his shirt collar), he believes it is a sign for him to be a good boy.

Meanwhile, Peter gets a job at Quahog's channel 5, hosting a segment called What Really Grinds My Gears, in which he rants about things that bother him. Peter becomes extremely popular, overshadowing Tom Tucker and making him feel jealous. Tom tries to ruin Peter's reputation by trying to distract him and by placing a sign next to him saying "I am a rapist", but is fired.

Stewie attempts to be a good boy by smothering Brian with affection, which he finds "more disturbing than that cartoon he saw the other day". Brian finally goads Stewie into reverting to his old, violent ways by crushing a spider web. Deciding to follow Brian's example of controlling anger through drunkenness, Stewie becomes an alcoholic; Brian, seeking to cure Stewie, takes him out for a night of drinking at the Drunken Clam to make him to never drink again, which culminates in Stewie ramming Brian's car through the wall of the bar. Knowing Stewie is Peter's son, Tom takes advantage of the situation and presents footage of the accident at the news station. Peter is fired and Tom regains his job.

The next morning, Stewie becomes extremely hungover and laments his lonely existence in the world, and wishes that there were someone else to whom he could relate.

Elsewhere, in San Francisco, a man looking exactly like Stewie is seen checking in a hotel.[4]. When Peter buys a Tivo box for his TV, Stewie spots this man in San Francisco on the news that has the same face and hairstyle as him. Stewie then believes that he may be his true father.

Learning that Quagmire is going on a cross "cuntry" tour with the intent of having sex with a woman in every state, Brian and Stewie hitch a ride in his "Wanna-bang-o". At a motel in New Jersey, Quagmire is handcuffed to a bed and mugged by a cleaning woman; Stewie finds Quagmire, and rather than free him, steals the "Wanna-bang-o", driving off with Brian. Quagmire eventually manages to rescue himself by reaching the phone and dialing 911 with his erect penis.

Stewie crashes the vehicle in the desert after going insane from eating an entire bottle of caffeine pills (being supposed to eat only one pill). After wandering through the desert, Stewie and Brian manage to get a rental car; they arrive in San Francisco and track down the man from TV. Stewie confronts the man on a trolley, and is shocked to discover that the man is actually Stewie from 30 years in the future.

Meanwhile, Peter and Lois teach Meg and Chris how to get dates so they can have some peace and quiet together, only to question if their kids were really ready for such responsibilities.[5][6]

Elsewhere, "Stu", as Stewie's future self is called, is taking a time-travel vacation. When Stu travels back to the year 2035, Stewie stows away with him. Stu passes off Stewie as a Nicaraguan boy named Pablo.

Stewie discovers that in the future, Chris will become a traffic cop and marry a hateful, foul-mouthed woman named Vanessa, who belittles him and insists on putting Peter and Lois in a retirement home; Meg will undergo a sex-change operation and become a man named Ron; and Brian will die of theobromine poisoning by eating chocolate he found in the garbage. He will then spend his afterlife drinking with Ernest Hemingway, Vincent van Gogh, and Kurt Cobain (whom all committed suicide due to the fact that they didn't want their work to be just like every other persons. Stewie also learns that at age 35, he will be a virgin working for the Quahog Circuit Shack and living by himself in an apartment. Furthermore, he will be a mama's boy, having long ago abandoned his matricidal tendencies.

Disgusted with the way his life will turn out, Stewie remodels Stu's apartment and gets him to lose his virginity to his co-worker Fran, but the sex does not go well (involving only 8 seconds of sex and 40 minutes of Stu crying). The next day, Fran tells everyone about it, costing Stu his job for having relations with a co-worker. Returning home, he finds that his apartment is in flames, ironically caused by "stress-release" candles Stewie placed while redecorating.

His life now ruined, Stu laments the day of his near-death experience at the Community Pool, revealing that memories of the experience will re-surface when young Stewie is 20, causing him to regress and preventing him from taking any risks. Armed with this knowledge, Stu and Stewie proceed to the retirement home where Lois now resides to ask for money to purchase a new time-travel watch; Lois, who reveals she knew all along that "Pablo" was Stewie, obliges. They buy the watch, and Stewie travels back in time first to kill Vanessa and then to the day of the accident. He prevents himself from getting crushed by the chair, only to be vaporized by the altered timeline's Stewie. The family heads home, with Meg bidding farewell to a boy whose name she likes: Ron.[7]