Jeff Winslow was the first of three boyfriends Theresa had during her lifetime.
He is described as a "geeky kid with red hair and glasses," but a "nice" and "cheerful kid" nonetheless, and one who took Theresa to "all the school events including the Senior prom." Apparently, Jeff was "the only high school boy" with the nerve to ask Theresa out, because she was a baseball star and "so beautiful boys were afraid of being put down." The two of them dated for about three years. According to a forum post made by Norman, Theresa started dating him before she really knew anything about him.
Theresa says that Jeff helped her through her teen years, made her feel like she was worth something, and showed that a boy could be a friend. She says of Jeff, "I owed him a lot." She also attributed the "steady dating" between her and Jeff as part of what helped "build [her] psyche to where [she] could step up as Empress Theresa."