There haven’t been many Valentine’s themed Simpsons episodes over the show’s history. In fact you could probably count them all on one hand. However, the first ever attempt at one carries a special place in the cannon that is classic episodes. It’s equal parts funny, sweet and heartbreaking; all the hallmarks of a good love story.

The centrepiece is Ralph Wiggum, normally used as the town outcast, an oddball who is both erratic and strange but in “I Love Lisa” he stands in for every oblivious guy who ever deluded himself into thinking that with persistence, determination, and a pure heart he can win the girl of his dreams. So while Ralph generally seems to inhabit a different, more childlike and happy universe than everyone else here his yearning and heartbreak are eminently relateable. Ralph sometimes appears to be a magically demented sprite in the form of a boy, but he’s never been more poignantly, nakedly, movingly human than he is here.

The episode opens with radio jocks Bill and Marty on Valentine’s Day. Easily one of the most underrated running jokes, the duo maintain a passive-aggressive, quietly contentious relationship. Their exchanges begin joyfully innocent but quickly turn to heated debate. Here Marty plays ‘Monster Mash’ and Bill calls him out on it. Marty hilariously tries to justify his mistake by arguing that ‘Monster Mash’ is “kind of a love song; monsters enjoying each other’s company, dancing, holding their evil in check.” Unconvinced, Bill presses on, accusing Marty of playing the wrong record, to which Marty can only reply with a defensive, wounded, “Why are you doing this to me?”

PHOTO SOURCE: The Simpsons, Fox

The episode then goes on to show the way Valentines affects the different parts of Springfield and what it means to them. Grandpa hates the commercialization of the holiday but grasps at getting just an envelope, Moe is disgusted at his limited options (Barney), Flanders serenades Maude in full heart costume, Homer forgets the day but guesses correctly and is forced to buy $100 chocolate and Bart seizes to prank as many people as he can.

For Lisa, it means taking pity on Ralph and being the only person in her entire class to give him a Valentine after noticing him looking sad and alone at his desk. This one noble act, however, turns out to have major consequences.

Ralph misinterprets the gesture as a genuine display of romantic interest rather than a gesture of pity. After school, he continues to test the boundaries of Lisa’s tolerance for him by asking to walk her home, then desperately trying to fill the dead air with open questions like, “Do you like stuff?” The question itself only adds to the awkwardness of the situation and you can feel the unease in both of them. The sequence is wonderfully written and acted and represents a masterclass on the comedy of discomfort.

PHOTO SOURCE: The Simpsons, Fox

Ralph and Lisa then both go to the worst possible place for advice: their fathers. Chief Wiggum advises his son to win Lisa over through sheer persistence (he demonstrates this by shooting a walnut open with his gun). Meanwhile, an equally unhelpful Homer shares lines women over the years have used to tell him that they just want to be friends, including “I’m married to the sea,” “I don’t want to kill you but I will,” and, finally, “Six simple words: I’m not gay but I’ll learn.”

In the background of all this is Krusty’s 29th Big Anniversary Special. Everyone wants to go but as Lisa points out to Bart “to get those tickets our parents would have to be part of Springfield’s cultural elite.” Homer then proceeds to walk in wondering why Flanders threw out a ‘perfectly good’ toothbrush.

This is where Ralph makes his move and offers Lisa the chance to go to the live taping but only if she goes with him. Lisa’s moral compass is put to the test but ultimately decides to accept the deal. Her worst fears come to fruition however when Krusty talks to the audience. What follows is one of the most memorable scenes in the show’s history which I’ve laid out in full below:

Is there a moment in The Simpsons as heartbreaking as this scene where Ralph boldly proclaims his love for Lisa on live TV and Lisa screams at him that she doesn’t reciprocate his feelings and only gave him a Valentine out of pity? Arguably not.

There is still hope for Ralph though as he’s cast as George Washington opposite Lisa’s Martha Washington in the upcoming school play. In an interesting turn of events Ralph morphs into an incredible actor and delivers a stirring climatic performance. The play gives him a moment of dignity and allows him to reconcile with Lisa at the end by agreeing to be friends. In the background Chief Wiggum rejects the call to stop a riot and turns on the radio; Monster Mash plays in a nice callback to end the episode.

PHOTO SOURCE: The Simpsons, Fox

‘I Love Lisa’ stands out because its the first time we see the development of Ralph, a character relegated to easy laughs because of his otherworldly detachment. He was understandably devastated when he got rejected the way he did and it’s hard not to feel his pain. The episode highlights his difficulties at social interaction, a quality that even the best of us find terribly difficult. For Ralph, this is compounded by his general aloofness and inability to receive proper direction. His sudden turn at the end into a great actor shows one of his hidden talents and a realization that underneath the surface lies a depth that remains to be explored.

Aside from the main, the episode also has some funny one off moments like Principal Skinner’s flashback to Valentine’s Day in Vietnam, the scene where Chief Wiggum chases a duck to get his badge back, and the one where Bart and Milhouse play John Wilkes Booth and Abraham Lincoln at the school play.

There are many Valentines themed movies and shows already out but if you have time give this Simpsons classic a watch, you will not be disappointed.