Peter e Chris terminam em último em um jogo "Generation Gap" em um carnaval, forçando-os a tentar se reconectar. Brian começa a namorar uma ranhosa, com quem não consegue terminar mesmo depois de testemunhar alguns de seus hábitos grosseiros.
Stewie e Doug candidatam-se para ser o capitão dos "snacks". Stewie encontra um vídeo-clipe na sala secreta do Chris, que mostra como o Stewie foi feito.
Os amigos contam suas primeiras histórias de amor verdadeiras, levando a paródias de “Castaway”, “Dirty Dancing” e várias comédias românticas de Meg Ryan.
Meg joins the Adam West High basketball team, and her play is fueled by Peter's lambasting from the crowd. Meanwhile, Stewie goes down a rabbit hole of conspiracies, which ultimately ends with him developing multiple personalities.
To take advantage of a work policy granting leave in the event of a pet's death, Peter adopts the oldest bird he can find... and realizes it used to belong to Hitler. Meanwhile, after giving Stewie a signed copy of his book, Brian finds it in a free library, causing Brian to give up writing.
Lois is blocked from a vacation rental app and accused of stealing after the family's trip to Nantucket. Meanwhile, Stewie and Brian buy saltwater taffy in bulk, and try their hands at door-to-door sales in the community.
When Peter gets a job as the new night watchman, he and the guys turn Pawtucket Brewery into an after-hours bar. Meanwhile, Stewie and Brian's plan to collect "lost dog" return money backfires when Brian is used for a dangerous TikTok stunt.
After Brian's Instagram is hacked, Meg takes Stewie and Brian to Russia, only to realize she'd rather stay there. Meanwhile, Lois reverts to her tormented teenage self when Quagmire starts dating her high school bully.
Meg gets married in Russia but returns home after discovering she was used for a green card marriage. Meanwhile, Chris, in need of an extracurricular activity, joins Principal Shepherd in shooting pornos at the high school.
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