Bart and Lisa Simpson’s Crushes, Ranked

10 Darcy, “Little Big Girl” (Season 18, Episode 12)

The Interest: After 10-year-old Bart is awarded a driver’s license by Mayor Quimby, he meets 15-year-old Darcy (Natalie Portman). Since he’s seen driving, he manages to convince her he’s 16, and they start dating and soon plan to marry(!). At the ceremony, he reveals to her he’s 10, and she reveals to him that she’s pregnant (albeit not with his baby).

The Love: Bart and Darcy don’t end up getting married, but this would be the first of two consecutive seasons that Bart got engaged (in addition to his engagement to Mary Spuckler (see entry number two below), a future Bart will marry — and divorce — his high school girlfriend Jenda (Amy Poehler) in Season 19). Redundant narrative choices aside, this relationship is the definition of “that escalated quickly.” 

9 Greta Wolfcastle, “The Bart Wants What It Wants” (Season 13, Episode 11)

The Interest: Bart saves Greta (Reese Witherspoon), the privileged daughter of movie star Rainier “McBain” Wolfcastle, from a pack of bullies, sparking her interest in him.

The Love: In perhaps Bart’s biggest roller-coaster ride of a relationship, he breaks up with Greta for being too needy. For revenge, she dates Milhouse, causing Bart to get jealous and try to win her back. Both Milhouse’s and Bart’s subsequent actions to win her over causes her to break it off with both of them and put her off dating “for at least four years.” 

8 Gina Vendetti, “The Wandering Juvie” (Season 15, Episode 16)

The Interest: After Bart is sent to juvenile detention for scamming the town, he meets the unhinged Gina Vendetti. They initially hate each other, but after being forced into a number of unexpected adventures together, they become a modern-day Bonnie and Clyde.

The Love: Gina (Sarah Michelle Gellar) and Bart often get physically violent with each other in the throes of love. As such, their relationship is perhaps the most passionate — and unstable — of all of Bart’s romantic entanglements.

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7 Jessica Lovejoy, “Bart’s Girlfriend” (Season 6, Episode 7)

The Interest: Bart falls for Jessica, the beautiful, seemingly innocent daughter of Reverend Lovejoy, after seeing her at church. He tries to “play good” but fails to impress her until he starts being his bad self and soon realizes she has a bad streak, too, transforming them into an inseparable pair of pranksters.

The Love: Bart meets his match with Jessica, as she causes him to question the level of his own immorality when she steals from the church collection plate. The writers (and guest star Meryl Streep) did a great job at making Jessica really unlikable, pushing the audience into hoping that Bart wises up.

6 Ralph Wiggum, “I Love Lisa” (Season 4, Episode 15)

The Interest: When dim-witted Ralph Wiggum is the only kid in Lisa’s class who doesn’t get a Valentine’s Day card, she gives him a pity one. Ralph naturally falls for her, getting them tickets to the Krusty the Clown anniversary show. But after he declares his love for her on live TV, she breaks his heart by telling him she “never liked him.”

The Love: Love is a two-way street, and Lisa was obviously never going to be into the simpleminded Ralph. The writers did, however, find a way to make him a bit more “normal” before the episode concludes, as he somehow nails the part of George Washington (opposite Lisa’s Martha Washington) in the President’s Day pageant. In the end, they agree to be friends, although Lisa still fears in a later episode that she’ll grow up to be ignorant and married to Ralph.

5 Hugh Parkfield, “Lisa’s Wedding” (Season 6, Episode 19)

The Love: Everything seems perfect with Hugh (voiced inconspicuously by Mandy Patinkin) until their wedding day, when Lisa realizes he’s asking her to essentially abandon her family for him, which she refuses and breaks off the wedding instead. The fortune teller teases that Lisa will still have a true love after Hugh (which we may never get to see since Lisa, like the rest of the Simpsons, doesn’t really age). 

4 Laura Powers, “New Kid on the Block” (Season 4, Episode 8)

The Interest: The Simpsons get new neighbors, and Bart falls for their teenage daughter, Laura Powers, voiced by Sara Gilbert, who channels a similar character to her Darlene Conner from Rosanne. Bart tries to impress Laura when she babysits the Simpson kids, but she breaks his heart when she tells him she has a boyfriend. 

The Love: Although they never date and this technically would be categorized as “infatuation,” this is the first time Bart takes any interest in the opposite sex (in Season Three, he tells Milhouse women “all look alike” to him). Age seems to be the biggest barrier here, as Laura mentions that if Bart was old enough “to grow a bad teenage mustache,” she’d want to date him, too. 

3 Colin, The Simpsons Movie

The Interest: Lisa meets Colin, an Irish boy who just moved with his family to Springfield, while going door-to-door to warn the town about pollution in Lake Springfield. When she realizes Colin is doing the same thing, they finish each other’s sentences and fall in love.

The Love: Colin is another boy who has everything Lisa’s looking for in a partner. He even writes and performs a song for her as she and her family are escaping Springfield, leaving him behind. They were still together at the end of The Simpsons Movie, but were no longer dating by the time the next television season rolled around. So we’re left to ponder what might have caused the breakup of their seemingly perfect relationship. 

2 Mary Spuckler, “Apocalypse Cow” (Season 19, Episode 17)

The Interest: Among the many children of slack-jawed yokel Cletus Spuckler, Bart unintentionally proposes marriage to Mary Spuckler (Zooey Deschanel) when he saves a cow from being slaughtered by gifting it to her family. 

The Love: After the wedding is called off, Mary returns (and has oddly aged a couple of years) in two separate episodes of Season 24. She and Bart date and break up again in both episodes, but the attempts at reconciliation provide Bart with his most fully realized relationship as he explores his capacity for true love. 

1 Nelson Muntz, “Lisa’s Date with Destiny” (Season 8, Episode 7)

The Interest: Springfield Elementary’s resident bully Nelson Muntz has almost nothing going for him. He’s unattractive, he’s unintelligent and he wants to nuke the whales (“Gotta nuke somethin’”). But Lisa somehow brings out some sensitivity in him, which is ultimately what makes her fall for him.

The Love: Lisa had plenty of crushes — including pop star Corey and unseen classmate Langdon Alger — before Nelson appeared on her radar. He was, however, responsible for her first kiss. While working out their feelings for each other, Lisa tries to make him into something he’s not. That’s eventually why they decide to part ways with a mutual “smell ya later,” but their surprising connection is a reminder of just how mysterious love can be.