The Simpsons: Every Girlfriend Bart Had On The Show

The sole son of The Simpsons clan has had a string of high profile guest actor love interests over the years, but just who are the many, many girlfriends of Bart Simpson? Like a lot of ten-year-old boys, Bart Simpson has claimed to hate girls on occasion. Unlike most ten-year-old boys, however, he’s spent three decades stuck at this age as the show has no regard for the Simpsons’ real ages. Thus despite this professed hatred for girls, his continuing adventures with Springfield’s first family mean that Bart has racked up a considerable number of love interests over the many seasons of The Simpsons.

Springfield’s favorite son has left a string of broken hearts in his wake over the years, with Homer and Marge’s eldest offspring dating characters played by the likes of Reese Witherspoon, Natalie Portman, Sarah Michelle Gellar, Sarah Silverman, and Meryl Streep. With such an impressive cast list in his little black book it’s only fair to ask, who were these girls and when did the loveable punk go out with them? Well, to answer that inquiry it’s necessary to establish ground rules before beginning this ambitious rundown.

In the thirty years The Simpsons has been on the air the show has amassed over six hundred episodes, meaning an exhaustive list of Bart’s unrequited crushes, one-off dates, and would-be love interests would take forever. For the purposes of this count, the only girlfriends included will be the lucky few who the series explicitly stated Bart dated in canon installments of the show. So, sadly, iconic figures like teenage babysitter and Jimbo-dating heartbreaker Laura Powers and Bart’s future ex-wife Jenda, played by Amy Poehler don’t count. Per the rules, the former never returned Bart’s feelings and the latter only appears in non-canon (and notoriously hard-to-explain) future Simpsons timelines.

Jessica Lovejoy

The first and arguably greatest of Bart’s love interests, Jessica was the character’s seemingly innocent first love. The daughter of Reverend Lovejoy, she was a (not-so-)secret rebel who set Bart’s world alight in the classic season six installment ‘Bart’s Girlfriend’. But despite a stellar turn from guest star Meryl Streep (yes, really), their love wasn’t meant to be, with Jessica double-crossing Bart and using his bad reputation to divert suspicion from her misdeeds. Bart’s (not-so)good name was cleared by the episode’s close but this one was still a formative heartbreak for the character, and maybe for some romantically-minded kids of the nineties.

Greta Wolfcastle

The Legally Blonde star may have been too busy to return to the role of Rachel’s sister on Friends, but Reese Witherspoon nonetheless found time to play Bart’s sophomore love interest on The Simpsons. Greta Wolfcastle was the somewhat spoiled offspring of deadpan action star Rainier. Given how quickly this plot got messy it’s probably just as well that, like Witherspoon herself, Greta ended up focusing on producing movies over romance. She and Bart dated briefly before perceived neediness led him to end the affair, only to promptly try and win her back when Greta chose to Milhouse as a rebound.

Gina Vendetti

An angsty juvie inmate, Gina is a volatile customer who Bart briefly dates after the pair break out of juvenile detention centers while handcuffed to each other Midnight Run-style. One of Sarah Michelle Gellar’s post-Buffy outings, Gina and Bart’s pairing made for a poignant little love story, with the tough love interest taking the rap for their escape for Bart’s sake when they’re eventually caught. Here’s hoping that will undo some of the trust issues Jessica left behind.

Mary Spuckler

Played by the New Girl herself Zooey Deschanel, Mary Spuckler is a rare departure from form for the “adorkable” actor. The character is the daughter of Cletus, the slack-jawed yokel, and for a short while looks set to marry Bart after he accidentally exchanges a calf for her hand in matrimony. Luckily the shotgun wedding is called off before things get too serious, leaving Bart a free agent once more and able to date…

Darcy

North Haverbrook’s Darcy! Before she was Thor’s vanishing love interest Jane, Natalie Portman played this sixteen-year-old who briefly dates Bart, believing him to be the same age, and then promptly tells him he got her pregnant. This character may only appear season eighteen’s ‘Little Big Girl’ (and momentarily in a later cameo), but this is a truly bonkers Simpsons installment that disproves the myth that the show’s later seasons have nothing to offer. Fans of the series should check it out, even if only for a jaw-dropping storyline worthy of the show’s weirdest outings.

Jenny Jenkins

Played by Anne Hathaway, the unoriginally monikered Jenny Jenkins was a good Christian girl Bart had a brief fling with in season 20’s ‘The Good, The Sad, and The Drugly’. Unfortunately, the character’s unimaginative origins extended beyond her name, with her plot being a loose assemblage of parts cribbed from other “Bart has girlfriend” stories. This one embodies why viewers opted to stop watching The Simpsons after season 12 as, like Greta, she gets between Bart and Milhouse, like Jessica, Bart tries to hide his bad side to woo her, and like Darcy, she’s a little his senior.

Nikki McKenna

Played by comedian Sarah Silverman, Nikki is a precocious fourth-grade rebel who blew hot and cold on Bart throughout their tumultuous one-episode romance. The character is most notable for hating Bart when he liked her and liking him when he hated her, as well as reading a pretty blatant and slightly dated Twilight parody. She also showed up for a brief cameo later! Which just repeated her one-joke character trait. Still, at least the show has consistency.

Melody Juniper

Season 22’s ‘Flaming Moe’ saw Skinner strong-arm Bart into dating third-grader Melody Juniper so the Principal could win over her mother. Said mother is played by Wonder-Woman 1984‘s Cheetah, Kirsten Wiig, but beyond being adorable, obsessed with Bart, and voiced by American Pie‘s Alyson Hannigan (another Buffy alumnus), there’s less than nothing notable about her daughter Melody. Chalk this one up to the board of extremely short-lived love interests, more canon than ‘Barthood”s Sherri and/or Terri fling but still not particularly impactful on the series.

Shauna Chalmers

Daughter of the infamous Super Nintendo Chalmers, as Ralph memorably misnamed him, Shauna is the most recent of Bart’s many love interests with the pair dating after she ended things with Jimbo Jones in season 23’s ‘Beware My Cheating Bart’. A tough customer and a bit of a bully, Shauna recurs throughout numerous later season Simpsons installments although the duo’s relationship only lasts a mere one episode.

And so that’s it. Until whenever The Simpsons finally reaches its inevitable ending, that’s every single girlfriend Bart Simpson has had over the many years the show has been on the air. Heartfelt commiserations go out to Kamala the alien (Treehouse of Horror episodes aren’t canon), “Sarah, plain and tall” (as there’s no knowing whether they ever dated), Clara Stetson and Annika Van Houten and Caroline Berrera (all unrequited crushes), and the nameless summer romance of season 17’s ‘The Monkey Suit’ (because they never dated, as she was just a summer romance… this one is pretty self-explanatory).

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Cathal Gunning
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Cathal Gunning has been writing about movies and TV online since 2020. His obsessions include The Simpsons, Stephen King, the Scream series, and the horror genre in general. He has spent more time thinking about Stranger Things than the writers of Stranger Things, and he has never seen a Star War.

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