 Shapiro's first experience in the entertainment business came as a reality contestant on "Blind Date" (hosted by Roger Lodge) in 1999 when the American show had come up to Toronto to film 5 episodes, choosing their "daters" via CityTV's "Speaker's Corner" booths.Over 10,000 people auditioned for spots, but 27-year-old Shapiro, a student at Seneca College's radio/TV program, stood out enough for the show's producers to call him back shortly after he recorded his video.When the "Blind Date" footage, that had been shot in July 1999, was to air on CityTV in November 1999, Shapiro was invited to discuss his "Blind Date" experience on "Humble & Fred", a morning show on 102.1 The Edge radio station that had a commercial tie-in with CityTV via having the Toronto "Blind Date" couples as guests on the morning of their respective episodes' scheduled air dates.