"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. Starring James Gandolfini as Tony Soprano Lorraine Bracco as Jennifer Melfi * Edie Falco as Carmela Soprano Michael Imperioli as Christopher Moltisanti Dominic Chianese as Corrado Soprano, Jr. * Steven Van Zandt as Silvio Dante Tony Sirico as Paulie Gualtieri Robert Iler as Anthony Soprano, Jr. Jamie-Lynn DiScala as Meadow Soprano Drea de Matteo as Adriana La Cerva Aida Turturro as Janice Soprano Baccalieri Steven R. Schirripa as Bobby Baccalieri Steve Buscemi as Tony Blundetto * = credit only Guest starring Synopsis 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 Mr. 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; he reminds her that she made a commitment to her husband before God. However, she continues the affair, even after making formal confession. One evening with Wegler she abruptly leaves, saying she is upset about A.J.’s academic performance, and also 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 A.J., Wegler concludes that she is just using him to get her son better grades, and tells her he wants to end the relationship. Carmela is deeply hurt and, after an argument, storms out. 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. Kim, his Korean-American employer, who was pressured by Tony Soprano into giving him a job, is hostile. But he changes his mind when he realizes how hard Tony B is working, both on the job and in his efforts to pass the state massage board exam. Kim offers to partner up with him, since he has an empty storefront in West Caldwell. Tony B passes the exam and begins work on the storefront,