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Paulie 's been in and out of jail ever since he dropped out of Barringer High School at age 17 and hooked up with Johnny Boy Soprano 's crew . One of the State 's witnesses testified that defendant had told him that he had been fooling around with pre-teenage boys since he was 18 years of age . Back when this story began she was n't even a Catholic , and was n't likely to become one : a student in the 1930s at Kinman Business University , her classmates told her never to go out with Gonzaga boys : " They're always broke and always hungry . I suggest you sit down with your boys , make a list of priorities , and enlist their support . He went through adolescence never quite feeling that he fit in with other boys , yearning to get his confused emotions sorted out .