The Simpsons has been around for decades now, but how many love interests has Lisa Simpson had during that time? After over 30 years on the air, The Simpsons is almost unrecognizable when compared to the relatively grounded, unusually cynical sitcom series it once was. Beginning as a set of irreverent, critically acclaimed shorts on The Tracey Ullman Show, the Matt Groening created family sitcom soon grew into a cultural phenomenon, and during its golden age in the '90s, The Simpsons was one of television’s most impressive achievements.
Silly, satirical, sweet, sharp, anarchic, inventive, and genuinely clever in equal measure, the animated family sitcom was a one-of-a-kind hit in its prime. But The Simpsons' disappointing season 12 viewership dwindled and the show’s once-formidable critical success fell off, with recent seasons being derided as unoriginal and leaden. But despite its advancing years, The Simpsons still finds time for impressive guest stars (not to mention most US presidents), and some of the show’s most notable names have played the love interests of the family’s eldest daughter, Lisa. So, how many boyfriends has Lisa had, and who were they?
Like ScreenRant’s rundown of Bart Simpson’s many love interests, this one has more members than expected. For the sake of clarity, the only characters listed here are ones who Lisa either dated or had an in-canon crush on, even if said crush remained unrequited. That means that poor well-meaning Milhouse doesn’t get included, since the junior Van Houten’s attraction to Lisa is strictly one-sided. However, after 30 seasons rest assured that Lisa doesn’t need Milhouse to garner a rundown of love interests as impressive as Bart's, some of whom were played by equally impressive guest stars (and Ed Sheeran).
Ralph Wiggum
Lisa’s first boyfriend and arguably still her best, Ralph is the lovable dimwit son of Chief Wiggum. He’s put in quite a few memorable guest appearances on The Simpsons over the years, but Ralph’s best role is undoubtedly in the bittersweet “I Love Lisa." It's a Valentine’s episode that sees the well-meaning Lisa take pity on Ralph, only for him to become relentlessly smitten with her, and it’s one of the sweetest early Simpsons installments, and a hilarious episode to boot. No wonder Ralph survived being killed off.
Nelson Muntz
Mostly known as Springfield's resident bully with the distinctive laugh, Nelson Muntz was also an unlikely love interest of Lisa’s in “Lisa’s Date With Density” (a rare pairing so good that even the famously continuity-dismissing Simpsons actually acknowledges it in later seasons). The pair briefly dated and, although they were far from compatible, brought out the best in each other during their bittersweet episode together. Their unexpectedly adorable chemistry is epitomized by a later season callback during “Wild Parts Can’t Be Broken,” wherein a surprisingly chivalrous Nelson pulls aside a fence post for Lisa to walk under.
Jesse Grass
Played by Dawson’s Creek star '90s teen heartthrob Joshua Jackson, Jesse was a literal tree hugger and “level 5 vegan" who refused to eat anything with a shadow. Meeting Lisa while protesting the environmental destruction caused by the Rich Texan’s construction plans, Jesse may only appear once, but this brief role nonetheless furnished him with some great lines as the leader of “Dirt First.”
Thelonius
Voiced by Malcolm in the Middle star Frankie Muniz, Thelonious is a bookish nerd named after the iconic jazzman Thelonious Monk. Lisa briefly encounters him in the ambitiously formatted “Trilogy of Error.” Lisa and he may only share a short afternoon, but here’s hoping he’s right about them reuniting in high school someday.
Luke Stetson
The country boy (voiced by Simba's original voice actor Jonathan Taylor Thomas) who Lisa dates in “Dude Where’s My Ranch,” Luke is notable for a little other than Lisa assuming his sister Clara was his secret girlfriend in a classic Mystic Pizza-stye mixup. And Clara is Bart’s love interest in the episode! There’s not much else to this one, although "Moe, Moe, Moe" is pretty catchy.
Colin
The Irish environmentalist who provides Lisa’s romantic subplot in The Simpsons Movie, Colin is a hilariously accented addition to the movie’s cast who serenades Lisa and steals her heart early on in proceedings. Not much is known about him, save that he hasn’t been seen since the movie and his dad isn’t Bono. Here's hoping the series can bring Colin and the band back before The Simpsons ends to confirm this.
Nick
Superbad’s Michael Cera plays against type as this smooth-talking lady’s man (or boy rather, since the character is about nine) who charms Lisa in a later season Valentine’s special. Initially wooed by his apparent worldliness and well-read manner, Lisa is eventually put off the Scott Pilgrim star's character by his evident insecurity, thus prompting his eventual confession that he is no good and has a God-given gift for lying to ladies.
Related: Every Time The Simpsons Killed Characters (In Canon)
Luca$
Played by The Hangover’s breakout star Zach Galifianakis, Lucas Bortner is an aspiring competitive eater who Lisa dates during “Luca$.” Marge disapproves since she sees shades of Homer in the kid, prompting her to question her romantic decisions. As far as later-season Simpsons outings that address Homer's eating habits go this lesser episode is no "Treehouse of Horror XXVIII," and other than being the catalyst of that middling plot, Lucas is a pretty forgettable character mostly notable for spelling his name with a dollar sign at the end.
Jack DeForest
Briefly seen in the B-story of “The Burns Cage,” Jack is a new kid and all-round cool customer. He lands the role of Rick in the school’s production of Casablanca, in which Lisa is cast as the female lead: Rick's romantic interest. Milhouse, cast as Jack's understudy, hires bullies to beat up Jack as a plot to get the lead role — all in order to share a stage with Lisa. After the play goes surprisingly well (despite Milhouse's poor acting skills), its revealed Jack was playing Rick while disguised as Milhouse. He then celebrates the play by taking Lisa out for a root beer float.
Blake Black
A preppy love interest for Lisa in “The Great Phatsby,” Blake wanted to date the conscientious Simpson because as a rich kid he’d never met someone with morals before. The uninspired and short-lived subplot falls flat in the ambitious but ultimately wrong-headed Great Gatsby hip-hop homage that failed to offer the commitment seen in other The Simpsons film parodies, like the "Cape Feare" episode.
Brendan
As pointless as Blake’s appearance may be, the Hank Azaria character at least fared better than songsmith Ed Sheeran, whose 2018 Simpsons guest appearance was about as well-received as his infamous extended cameo on Game of Thrones. The singer-songwriter plays a musician named Brendan who Lisa falls for in an underwritten La La Land parody, prompting all manner of talent show shenanigans, East/West Springfield division, and another call-back to Lisa’s relationship with Nelson which proves that The Simpsons would be better off not reminding viewers of its glory days.
Lisa Simpson has had other love interests in the long history of The Simpsons: Special mention must go to Daniel Radcliffe’s Twilight-spoofing Edmund the vampire (who didn’t warrant a place here since the "Treehouse of Horror" specials is not canon), the uptight British snob Hugh Parkfield (again, future episodes aren’t Simpsons canon), and Langdon Alger (who didn’t warrant a section since he might well be imaginary, as he’s never seen onscreen). Also, some might suggest that the Canadian Milhouse "Milhoose" of “Boy Meets Curl” fame counts as a Lisa love interest, but they’d be wrong as the attraction is once again one-sided.