The Sopranos: Season 5 Episode 6: "Sentimental Education"

From Wikipedia:

"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.

Streaming on Max.

Note: Please do NOT binge the show. Watch one episode per week (ideally Sunday evening) and attend the following Monday's virtual water cooler meeting to discuss.