|Relatives|| Aunt: Belle|
Ex-Boyfriend: Bart Simpson
|First Appearance||"The Good, the Sad and the Drugly"|
|Voiced By||Anne Hathaway|
Bart first met her after seeing her volunteer at the Springfield Retirement Castle. She was a Christian and prayed to God at school. At first she thought Bart was a nice guy, but then she dumped him when he admitted his bad side to her when Milhouse began to jeopardize their relationship without her knowledge. Jenny is about 11 years old, as she is in the fifth grade. She reappeared in a cameo in Moonshine River, where Bart visits her at her house to ask for another chance, but she is obviously still angry at him for lying to her, saying "Eat my shorts!" upon seeing him and slamming the door on him.
Jenny seems to have numerous similarities to Bart's previous crushes, a subject that has been touched upon by the episode's reviewers. She is older than Bart, like Laura Powers and Darcy, but she isn't a teenager. Bart also had to hide his bad side from her, just like what he did temporarily with Jessica Lovejoy. Additionally, she put a strain on Bart and Milhouse's friendship, just like Greta Wolfcastle did; however, Jenny wasn't aware of it as she continued to date Bart, while Greta went out with Milhouse only to get back at Bart when he dumped her. In addition, she is also similar in appearance to Samantha, a girl who Milhouse briefly dated, and whom also unknowingly jeopardized Bart and Milhouse's friendship. Similarly, one of them also did something very cruel to break them up (Bart reported their date to Samantha's father, and Milhouse forced Bart to admit his bad side to Jenny).