- “You're bad, and I like it.”
- ―Jessica Lovejoy[src]
While appearing sweet and calm on the outside, Jessica actually has a penchant for mischief and chaos, and can cross the line farther than Bart Simpson himself. Amongst boys smitten by her, she falls right into the role of femme fatale, and isn't afraid to use it. She has had numerous boyfriends and is rarely ever single; one drove up on a motorcycle to pick her up as she hoodwinked Bart into cleaning the church steps in her stead. She uses her beauty to manipulate boys and uses timidity to manipulate adults and girls.
Jessica went to a boarding school, but was expelled for destroying school property, stealing collection money on Sundays and starting up fights with whomever she could. She was also Bart's girlfriend for a while. According to Bart's experiences with her, Jessica wasn't afraid to manipulate him into skating down an extremely steep hill littered with truck accidents, or even to go far as activating the fire alarm during the school day as a prank. It is stated (by Bart) that she has an IQ of 108, and that "she's like a Milk Dud; sweet on the outside, poison on the inside." She inevitably went too far, however, stealing collection money from her parents' church and blaming it on Bart. Lisa Simpson, however, brought her to justice. After showing the evidence that Jessica is bad, her father doesn't want to admit his daughter is a criminal, and he continues to blame the theft on Bart until Jessica finally admits to it. Later, Bart lets her take advantage of him, but as part of a plan to frame her for vandalizing the church steps that she had been cleaning.
Despite the fact that she's a wicked, misbehaving, antisocial girl, she does try to get attention from her father, who is shown to ignore and deny her behavioral problems. She also explains that her behavior, in part, is because of her desire for attention from her father.
Jessica has since made cameos throughout the series. She and her father were participants in Robot Rumble. Their creation, a centipede-like machine by the name of Kill-a-Puss, was defeated by "Chief Knock-A-Homer", Homer and Bart's entry. She was also taken to Weasel Island by her father on Mother's Day. When Springface was introduced to Springfield, she became one of Lewis' online friends. She then appeared in a photo that Bart kept alongside the photos of his other past girlfriends. It can be assumed that Bart actually didn't visit Jessica, unlike the rest of his ex-girlfriends, because of what happened between them during their relationship. She also appears in The Simpsons Movie sitting the front row at church when Reverend Lovejoy says, "Lord hear our prayer."
Jessica also appears in the new opening sequence, playing the flute in the school's music class.
Jessica is mature for her age. She is good looking and has long straight black hair with bangs and a thick non-receding hairline. She usually wears pink and purple outfits. She also has high cheek bones, large dimples and eyelashes of unusually long length. Like all good-looking characters on The Simpsons, Lovejoy has deep-set eyes. Her usual outfit consists of a pink headband with a bow in her hair, a pink dress, a light purple T-shirt, and white socks with purple high heels, which belie her true personality.
Jessica has an antisocial personality disorder and is a trouble-maker. As a reckless prankster, she gets along well with Bart to an extent. Putting on a front, she gets away with her crimes. Her disregard for social norms, rules, and obligations get other people in problematic situations. She doesn't listen to anybody, and is prone to putting people on edge. She's also an adrenaline junkie, attracted to risks and dangers. She has a passion for skateboards, motorcycles and snowboards. She mocks her father behind his back.She has such a fiery determination to ignore rules that even Bart Simpson thought she was going too far.
Note: Most of her appearances are brief, background roles. The episode in which she has a star role is in bold.