As you may have noticed, Bart Simpson has had a LOT of girlfriends over the 26-year run of The Simpsons. Now, much of that is due to the show’s incredibly long run. Still, Bart clearly has a way with the ladies, so let’s take a look back at every girl who’s had a fling with our favorite spiky-haired 4th-grader…
Laura Powers
In Season 4’s “New Kid On The Block,” Bart develops a huge crush on Laura, the 13-year-old who moves in next door. She shares his passion for pranks and video games, but unfortunately, she already has a boyfriend, Jimbo Jones, the meanest bully at Springfield Elementary. Bart hatches a plan to break the two up: place a prank call to Moe’s as Jimbo, then give Moe the address. Moe shows up looking to stab Jimbo, who is understandably terrified. This shatters Laura’s illusion that Jimbo is an outlaw, and they quickly break up. Really though, I kinda feel for Jimbo here; if an angry Moe Syzlak showed up at my door with a knife, I’d be cowering in fear, too.
Jessica Lovejoy
When Bart sees Reverend Lovejoy’s beautiful daughter Jessica give a sermon, it’s love at first sight. His attempts to prove to her that he’s a good boy fall on deaf ears. But when she sees him pull a prank on Groundskeeper Willie, she realizes he’s exactly the type of bad boy she goes for. Unfortunately, she’s way more evil than Bart could ever hope to be (“You’re turning me into a criminal when all I want to be is a petty thug!”). She steals money from the church collection plate and blames Bart, and things end for the pair shortly after that. She ends up dating that untameable librarian instead.
Greta Wolfcastle
Greta is by far the wealthiest girl Bart has ever dated. The daughter of Rainier Wolfcastle — aka McBain — Bart meets her at a carnival at Springfield Preparatory School. Things start off well, but when Bart blows off a date so he can watch Principal Skinner bomb at open-mic night, Lisa tells him that if he’s not serious about their relationship, he should end it. When he does, she starts dating Milhouse. Naturally, this makes Bart incredibly jealous, so he travels to Toronto, where Greta’s dad is shooting a movie to get her back. In the end, she decides that neither Bart or Milhouse is the right guy for her, which is probably the right decision.
Gina Vendetti
It was only a matter of time before Bart Simpson wound up in juvenile hall. After holding a fake wedding and attempting to make off with all the gifts from the registry, Bart gets six months in juvie. While there, he meets Gina, a girl who is a lot tougher than he is. She bullies him at first, but when they make their escape, they become friends. When they get caught, Gina reveals that when she gets out, she has no family to return home to. Feeling bad, the Simpsons hold a feast in her honor just so for one day, she can feel like she has a real family.
Darcy
Okay, this one just straight up made no sense. When one of Bart’s pranks accidentally saves the town, Mayor Quimby offers him anything he wants. He asks for a driver’s license, and for some reason, Quimby gives him one. Then, Bart has to drive Homer around everywhere, and finally, he just takes off, ending up in North Haverbrook, where he meets Darcy, who is about five years older than him. Then, she reveals that she’s pregnant, and expects Bart to be the kid’s father. In the end, Darcy reunites with her family, and they take the news of her pregnancy surprisingly well. Really, though, there was just too much silliness to take anything in this episode seriously.
Mary Spuckler
Mary is the rare character to have a serialized storyline based around her. She first appeared in Season 19, when Bart joined the 4-H club, and Mary (the most intelligent daughter of Cleatus and Brandine) taught him how to take care of a cow. When Bart finds out his cow is going to be slaughtered, he sets it free, and searches for a home where he can stay. He shows up at Mary’s door with the cow, but her family interprets it as a marriage proposal. An actual wedding is planned, but Mary eventually talks her way out of it. The pair still developed a fondness for each other, and they would reunite five seasons later, when Mary is living in New York as a Saturday Night Live featured player. Later that season, she would return to Springfield, and reunite with Bart yet again. This time, however, he seemed oddly disinterested, caring more about video games than her. She dumps him for a rich music producer’s son, and we never hear from her again.
Jenny
Jenny actually is the good girl type that Bart mistook Jessica Lovejoy for. He tries his best to act like a good kid, but it can only last so long. Eventually, Bart’s evil ways are made evidently clear to Jenny, and she wants nothing to do with him. At the end of the episode, we see Bart with a bouquet of flowers, and it looks as though he’s going to apologize to Jenny. However, the flowers are actually for Milhouse. Earlier in the episode, he let Milhouse take the fall for a prank, and never visited him during his week-long suspension, because he was too busy spending time with Jenny.
Nikki McKenna
When the two fourth grade classrooms are merged together, Bart meets Nikki, a fellow skateboarder with a penchant for Twilight-esque novels. They kiss, but when her litigious parents find out, they freak out, and Principal Skinner is forced to institute a “no touching of any kind” policy among students. Really, though, what Bart can’t handle is Nikki’s ever-changing personality. She loves him one day, then hates him the next. It all gets a bit frustrating, and Bart decides it’s not worth his time.
Shauna Chalmers
Shauna first appeared in the same episode as Jenny, when she was dating Jimbo. In the later episode “Beware My Cheating Bart,” Jimbo and Shauna go to the movies, when they don’t want to see the same film, Jimbo asks Bart to go to the movie with her. At first, he dutifully keeps other boys from flirting with her, but as time goes on, the pair develops mutual affection for one another. When Jimbo finds out, he plans to exact revenge on Bart, so he and Shauna hide out in his treehouse. Eventually, when the ultimate confrontation takes place, Shauna decides she doesn’t want to be with Jimbo or Bart. In a later episode, we would find out that Shauna is the daughter of Superintendent Chalmers.
