Rufus eventually agrees to Jenny being home-schooled after seeing how committed and good at her job she is. At work, Jenny befriends Agnes Andrews (Willa Holland), a model who convinces her to start her own fashion line. Realizing that working for Eleanor won't help her develop as a designer and that Eleanor has begun to take advantage of her talents, Jenny leaves. Jenny also begins a short relationship with Nate when they share a passionate kiss after he rescues her from being taken advantage of by an older photographer. Jenny and Rufus argue over her quitting Eleanor's and Jenny moves out of the Humphreys' apartment and moves in with Agnes, who suggests that they plan a guerrilla fashion show at the charity gala honoring Lily and Bart. The show is a big success but Vanessa witnesses her kissing Nate, thereby straining their friendship. Rufus tries to get her arrested but is stopped by Lily. Agnes's fiery temper and their growing disagreements over the clothing line make it hard for them to close a business deal. Jenny steals Agnes's contact list, attempting to make a deal by herself. Upon learning of Jenny's betrayal, Agnes burns all her dresses and kicks her out of her apartment, leaving her with nothing.