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Sara Toomey is Jeremy's on-again/off-again girlfriend. Although Jeremy thinks the world of her, she apparently likes Jeremy a lot, but has thought of him as a "salvageable male". Her parents are divorced and her behavior wavers between kindness and aggravation. She and Jeremy have broken up many times, but they always seem to make up sooner or later. Sara's genuine kindness and generosity is evident in one story arc where she cuts her hair short and donates her ponytail to a charity for children undergoing chemotherapy. In the January 15, 2008, strip, Jeremy revealed he did not want to date Sara exclusively anymore, but was upset when she readily accepted this change. Sara has a locker next to Jeremy in their second year. There seems to be a suggestion on Feb. 7, 2014, that Sara is Jewish, as her mother is taking her to a "Success Through Abstinence" seminar at what Sara describes as "the temple," though in an earlier comic, she and Jeremy exchange Christmas presents.

Weather is an ongoing issue to her. When she gets ready to go outside, the conditions will end up being the exact opposite of what she's dressed for.