Jenny Medina is a client of Bobby Hill in Talking Shop. She is the voice of Lindsay Lohan.
When Bobby was in his first meeting for his peer counselling class he saw that Jenny Medina was one of his clients. He was excited about this because he wanted to ask her out. However April made it clear that he was not allowed to date any of his clients.
Jenny Medina is later revealed to be his very first client. The beginning of their session is just awkward silence until Jenny breaks the silence asking Bobby isn't he suppose to say something. He then tells her the same thing to her, which gets her talking. She tells him about how she got invited to Debby Reeds slumber party, take a nap and woke up with her hand in a bowl of hot water. She proceeds to ask Bobby if she should tell other people that Debby's father is an alcoholic. He tells her that he cannot give her any advice. She decides that she will tell people about Debby's dad. Jenny feels much better and asks if she can make another appointment with him.
Jenny is later seen with Bobby hanging around his locker. He tells her that problems don't take the weekend off so neither should he. He indirectly asks her for Saturday night date at the movies. She asks him to clarify if he means a date. Bobby then explains that sometimes putting labels on things are helpful so If she wants to use terms like dating, boyfriend, and making out with him then it's fine. Jenny proceeds to kiss Bobby on the cheek as she walks away.
Jenny confronts Bobby telling him that she heard that he drove Stacey Gibson crazy. She tells him she's not looking for that right now; thus breaking up with him.