The Teenage Babysitter is a character that makes her first appearance in "Penny-Wiseguys" where she is seen waiting in a line to get her ears pieced by Dan Gillick" who now works as a ear piercer after being kicked out of the Mafia. Her second appearance was in "The Winter of His Content who was hired by "Homer Simpson and "Marge Simpson" while the couple spent a couple of hours to themselves, the Teenage babysitter was looking after Bart, Lisa and Maggie Simpson while the husband and wife went out for an evening alone without their three children, once they entered the house after coming back going out, the Teenager babysitter is seeing leaving the house, but before she leaves the Simpsons House when Homer pays her money for looking after their three children while they spent the evening