Winick applied to be on MTV network’s reality TV show, The Real World: San Francisco, hoping for fame and a career boost. During the casting process, the producers of the show conducted an in-person, videotaped interview with Winick. When asked how he would feel about living with someone who was HIV-positive, Winick gave what he thought was an enthusiastic, politically correct answer, despite reservations. Winick was accepted as a cast member on the show in January 1994. The producers informed the housemates that they would be living with someone who was HIV-positive, but they did not reveal who it was. Winick and his six castmates (Mohammed Bilal, Rachel Campos, Pam Ling, Cory Murphy, David "Puck" Rainey, and Pedro Zamora) moved into the house at 953 Lombard Street on Russian Hill on February 12. Winick became roommates with AIDS educator Pedro Zamora, who informed Winick that he was an AIDS educator, and showing his scrapbook to Winick and the other housemates.
Winick's Nuts and Bolts strip began running in the San Francisco Examiner in March of that year.
Winick, who is Jewish, was offended at David "Puck" Rainey's wearing of a T-shirt depicting four guns arranged in the shape of a swastika, and by Rainey's refusal to accede to Winick's request not to wear it.
After filming of the season ended, Winick and Ling moved to Los Angeles to continue their relationship.
By August 1994, Zamora's health began to decline. After being hospitalized, he asked Winick to substitute for him at a national AIDS education lecture. When Zamora died on November 11, 1994, Winick and Ling were at his bedside. Winick would continue Zamora's educational work for some time after that.
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