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"Sentimental Education" is the 58th episode of the HBO original series The Sopranos and the sixth of the show's fifth season. Written by Matthew Weiner and directed by Peter Bogdanovich, it originally aired on April 11, 2004.

Tony is finding it increasingly difficult to take care of A. J., who is sent back to Carmela. She lets him move back in on the condition that he improve his grades and behavior. Carmela goes to see Robert Wegler at the school and agrees to have dinner with him the following evening. After dinner, they go to his home and have sex. Carmela meets Father Phil Intintola for lunch and tells him of her new relationship; he reminds her that she made a commitment to her husband before God. However, she continues the affair, even after making formal confession to Father Phil
Carmela abruptly leaves during another date with Wegler, saying she is upset about A. J.’s academic performance and troubled by the laws of the Church. The next day, Wegler pressures A. J. 's English teacher to raise his grade for a poorly written term paper. After several rounds of sex after which Carmela talks each time about strategies to elevate A. J. 's academic standing, Wegler concludes that she is just using him to get her son better grades and confronts her, telling her that she uses people. Carmela, deeply hurt, vehemently rejects his assessment, but Wegler calmly stands his ground and Carmela storms out. The next day, when her father suggests that she look for other men, Carmela replies that, as Tony's wife, her motives will always be distrusted. Tony B tries to adjust to civilian life. His Korean American employer, who was pressured by Tony into giving Tony B a job, is hostile due to Tony B's mob connections. The employer changes his mind when he realizes how hardworking Tony B is, both on the job and in his efforts to pass the state massage board exam. He offers to partner up with Tony B, offering an empty storefront in West Caldwell. Tony B passes the exam and begins work on the storefront, preparing it for business. However, he comes across a bag containing $12,000, apparently thrown away by fleeing drug dealers, and goes on a self destructive tear, wasting most of the money on gambling, alcohol, and expensive clothes. Tony B's employer visits the store and encourages him to keep on working; Tony B snaps and beats him up. With Tony at Nuovo Vesuvio, Tony B hints that he screwed up and asks if Tony still needs someone to cover the airbag scheme.

Sentimental Education is a novel by Gustave Flaubert, who also wrote Madame Bovary, which Mr. Wegler recommends to Carmela.

The episode was directed by Peter Bogdanovich, who also has a recurring guest role as Elliot Kupferberg (Melfi's psychotherapist) on the show, although he does not appear in this episode. Although the sixth episode of the season, it was produced seventh, due to the scheduling availability of director Peter Bogdanovich, as the following episode was directed by cast member Steve Buscemi, who wanted to direct an episode in which his character was minimally featured.

Carmela finds the book The Letters of Abelard and Heloise in Wegler's bathroom and asks him about it. She later tells Father Phil, who erroneously corrects her pronunciation of 'Heloise'. During her confession, Carmela tells Father Phil Intintola that her affair makes her feel like "walking around on a cloud" as the character Maria from the West Side Story. Tony Blundetto refers to "piping in a little Keith Jarrett" when discussing his plan for a massage studio. Tony Blundetto buys his twin sons a pair of Nintendo Game Boy Advance handheld game consoles. A. J. tries to write an English school paper on Animal Farm but ends up plagiarizing it. He later tries to write a paper on Lord of the Flies, which he also plagiarizes. When Wegler tells A. J. 's English teacher, Mr. Fiske, to raise the grade of his term paper that was "90 percent CliffsNotes," Fiske refers to A. J. as "Fredo Corleone," a character from The Godfather novel and films, alluding to the fact that he is part of a powerful family despite being an unintelligent member. After Tony Blundetto tells Paulie and the others at Satriale's Pork Store about his business opportunity with Kim, Paulie comments "Word to the wise, remember Pearl Harbor! ", ignorant to the fact that Kim is actually Korean. Kim compares Tony B to Henry Ford.