It also guest starred Benedict Cumberbatch, famous for playing Sherlock Holmes on the BBC's Sherlock, playing both a British Prime Minister and Severus Snape from Harry Potter. Previously the descriptions of the characters Cumberbatch was playing were described as a "sinister accountant" and a "snake-like character". A clip of this scene went viral in January 2016 due to the fact that Alan Rickman and a David Bowie penned tune both were featured in the clip and both having died in the same week.
Political biographer Robert A. Caro and former Conan O'Brien bandleader Max Weinberg guest starred as themselves.
Narrating the episode, Bart looks upon his failure with girls, particularly Mary Spuckler. At the school, Bart learns that Mary has returned to Springfield due to her failed career as an actress (being only used in commercials) and was allowed back to the Spuckler home after the events of her last episode (Moonshine River). The two soon start a relationship, which quickly spirals downward because Bart is more focused on video games than Mary.
Lisa warns Bart to not take Mary for granted, but he still does, prompting Mary to explain to Bart that the two of them should take a break. Bart soon catches on when he finds out that Mary has found a new love for a Brazilian boy.
Later on, whilst Homer and Marge are in an argument, Bart takes Homer's side by saying men cannot understand what women are saying because women never say exactly what's on their minds. Shocked, Marge explains to Homer what she exactly thinks about him, and soon Bart and Homer are soon kicked out of the house.
The two eventually settle in to Brokewood Apartments, an apartment where other husbands live after being kicked out by their wives. Bart and Homer grow accustomed to their new lifestyle, but are soon tired and, along with the other husbands, attempt to win their loves back.
The men are soon watching British romantic comedies (also known as rom-coms). Later, they invite the women over and serenade them with a song to the tune of The Ode of Joy. Almost all the women are wooed, save Mary, who is still dating the Brazilian boy.
The episode ends with Bart on a social media site and finding that Mary's relationship status is "single." He later writes "I miss you" as a message to her.