Despite being a 10-year-old, Bart has had quite the list of love interests. Obviously, nothing goes much further than a kiss seeing as Bart is perpetually a child, but considering the sheer amount of romances he’s had in his short life, some were bound to be better than others.
Whether they’re brief but recurring or heart-felt and fleeting, we’ve ranked ten of Bart’s best love interests in The Simpsons. Get out your tissues, folks, because when Groening gets sentimental there's always a danger of waterworks. And laughs. And relatability. And, since it's Bart, possibly cow-having.
Sherri & Terri
The creepy purple-haired twins both seem to truly despise Bart and take any opportunity to put him down. They tell him just how ugly, smelly, creepy and weird he is, but despite this, Bart still seems infatuated with one of them. It’s pretty hard to tell which one though.
In season 12’s ‘Hungry, Hungry Homer’, Bart is desperate to get a date for the school dance and ends up going with one of the twins thanks to Homer's interference. They've also both kissed him on the cheek in order to get him to sing on the school bus and on top of this, a non-canonical future Bart is in a relationship with Terri and makes out with Sherri. So who knows how this one will play out.
Darcy
Voiced by Natalie Portman, Darcy is a girl from North Haverbrook who ends up in a very questionable relationship with Bart. Convincing her that he was 16 and eventually having her propose marriage to him was strange enough. It also turns out that she was pregnant (from someone else!) yet somehow happy marrying Bart even when she eventually found out he was 10. One of Bart’s stranger moves, and one that didn’t particularly go anywhere anyway. Fast forward to season 24 and Bart doesn’t seem to have had much luck. She rejects him without much thought even though their relationship ended on good .
Greta Wolfcastle
At first, we feel sympathy for Greta Wolfcastle. Bart steps in to save her from bullies and they go on to have about as much of a whirlwind romance as two ten years olds can have. She was a bit much for Bart, though, and he ended things with her pretty quickly.
However, jealousy reared its head soon after and Bart made it his goal to break her and her new boyfriend Milhouse up. Neither boy won in the end, but the fact that she went on to produce her father Rainier's films suggests her lifestyle might not have fit Bart’s well anyway.
Jessica Lovejoy
Voiced by Meryl Steep, Jessica seemed like the perfect girl for Bart. At first. Able to pretend to be sweet and kind on the outside, therefore gaining the trust of the adults around her, but also a creator of even more chaos than even Bart can keep up with.
Their love affair was cut short when we found out her manipulation could go far enough to harm Bart. She blamed him for the theft of church collection plate money, leading to a scandal that traveled around the whole of Springfield. Bart apparently still wasn’t put off entirely, though, as he does her punishment for her while she rides off for a date with someone else. We aren’t big fans of Jessica Lovejoy.
Becky
Becky isn’t a particularly prominent character, but pretty much all of her scenes revolve around Bart. Maybe he should have picked up on it because she was at a sleepover and was dared to kiss Bart. She also showed her affection for him by clasping her yearbook to her chest an exclaiming ‘he writes the way people talk!.' Bart really seems to have missed a trick with Becky. Then again, we know pretty much nothing about her. She could be ten times worse than Jessica Lovejoy, who knows.
Clara Stetson
Her one-off appearance was marred by Lisa’s interference and false accusations, causing Clara to get lost on her way to visit her brother Luke. Luckily, when she met Bart, she became very interested, very quickly.
The depth of her attraction to him seems particularly deep, especially considering she’d literally just finished telling Lisa that there was more to life than boys. Bart doesn’t seem very interested, though, and promptly turns his attention elsewhere, calling her 'cootie breath' in the process.
Sarah
In an episode appropriately titled ‘Bart’s Girlfriend’, we see Bart with Jessica (who, , we do not like) talking about an ex of his. Sarah, who we have absolutely no interaction with, is seen watching from behind a fence when he describes Jessica as ‘so much better than Sarah, plain and tall.' ittedly, a bit like Becky, we know nothing about Sarah. She could be terrible. However, in response to Bart’s meanness, she runs off crying never to be heard from again and we can’t help but wonder what could have been.
Mary Spuckler
One of Bart’s more consistent love interests, Cletus Spuckler's daughter is initially introduced to him as a sort of arranged marriage. Eventually, this turns into an unexpectedly genuine attraction that spans multiple episodes.
She is seen as Bart’s last hope to find true love in ‘Moonshine River’ and reappears in ‘Love Is A Many-Splintered Thing’ playing a song she wrote for him. He threw it all away, as usual, and we never got to see what might have happened between Bart and one of the more educated Spuckler kids.
Gina Vendetti
Bart seems to have a natural attraction to girls whose behavior resembles his. Gina Vendetti played it cool and distant while she and Bart were locked up in juvie, but before long, she revealed a tough upbringing that left her with no family. Even though it takes her about five seconds after this story to attack Bart, she demonstrates a slightly softer side when she its to the police that their fight was her fault. They’re seen having dinner back in juvie after the fight, but we never get to find out if she and Bart overcome their complex circumstances and meet up again.
Laura Powers
Bart’s most memorable and iconic love interest was Laura Powers. The daughter of Marge’s exotic new friend Ruth took a shine to Bart, and the two became fast friends.
We all shared Bart’s heartbreak when it was revealed she was in a relationship with Jimbo, and then it broke our hearts, even more, when she explained how she’d go out with Bart if he was a little older. Poor, misguided Bart never sees her again (which is weird, considering they’re neighbors- we still don't know where they ended up). Maybe one day, when they’re both older, this perfect match will reconnect.