Drew and Jess first meet in the hallway at school, after a football thrown by K.C. Guthrie hits her on the back. Both boys rush over to apologize to her, and talk about how cute she is after. They make a bet as to who would recieve a wishing star from her, and after Jess finds out that K.C. is the father of Jenna Middleton's baby, she sends Drew a star, and he asks her out. The two go to Degrassi's movie night, and Drew runs away, thinking he saw Vincent Bell, leaving Jess alone.
In Halo (1), Jess makes her official debut, when she is accidentally hit by a football thrown by K.C. and Drew, so they ran up to her to make her she's okay, and she expresses that her spine hurts. Drew asks her what her name is, and she tells him that it's Jess. K.C. wants to know how they can make it up to her, and she jokes around saying, "I'll have to check with my personal injury lawyer" and walks away. It is acknowledged that both Drew and K.C. are interested in her. Jess is later seen sitting at lunch with Drew, K.C. and a few other people. When Jenna wants to sit at their table, Jess makes confused facial expressions. When Jenna tells K.C. she has her first prenatal class today, Jess again eyes them with a look of confusion.