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The Sopranos S06E16
Plot: At the Borgata Casino, Tony decides to let it ride after winning at roulette. Tony loses everything he'd won, and then some, on 23. Meanwhile, Vito Jr. is going through a rebellious phase. Tony asks Phil to talk to Vito Jr. Phil grudgingly agrees. AJ proposes to Blanca over a nice dinner, promising her that he will rise from pizzeria night manager to restaurant chain owner in no time, and coaxes a "yes" out of her. At the Puerto Rican day parade, Blanca meets up with AJ and returns his engagement ring, telling him she just doesn't feel it.
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