Ralph Wiggum’s ‘I Choo-Choo-Choose You’ Card Was a Real Valentine

It’s almost Valentine’s Day, which for many people, means buying chocolate and flowers for their significant other just one day before the exact same items are sold for 75 percent less. But for fans of The Simpsons, Valentine’s Day is mostly remembered as the day that Lisa Simpson sent Ralph Wiggum a valentine, and he took it way too seriously. 

In fairness to poor Ralph, Lisa did technically declare that she wanted to “choo-choo-choose” him.

Like many of the best episodes of The Simpsons, Season Four’s “I Love Lisa” was partly inspired by a real-life event. As longtime Simpsons producer Al Jean revealed on the episode’s DVD commentary, the storyline began with a childhood memory. “When I was in third grade, I got a valentine from a little girl that said, ‘I Choo-Choo-Choose You,’” Jean explained. “And underneath it, she wrote ‘I really do.’ Years later, I thought, did she really like me? I don’t know.”

After relaying that anecdote to his Simpsons co-workers, they decided to use it as a story idea, in which Lisa gifts a valentine to a boy who would then “take it too far.” Eventually they settled on making the boy Ralph. 

They also decided that Ralph, who had already been in a few episodes, should be a Wiggum. “We thought, ‘Oh, It would be funny if Ralph was Chief Wiggum’s son,’” Jean revealed. “Up until that point in the series, he wasn’t the son of Chief Wiggum, but we thought it made perfect sense, especially because they’re both pretty dumb.”

They also decided to use the same exact valentine from Jean’s past. It’s hard to say which one it was exactly, apparently there were a number of vintage valentines featuring the exact same phrase, along with a picture of a train. You can get one on eBay right now for six bucks.

In most older versions of the card, the phrase is coming from a kid or adorable animal engineer, not a deranged anthropomorphic train. But the Simpsons version of the card has taken on a life of its own. Countless online resellers have copies of the valentine to buy, for those willing to risk giving casual acquaintances the wrong impression. And in 2023, there was an entire line of “I Choo-Choo-Choose You”-themed merchandise, including socks, keychains and pajamas. 

“The fact that it is now the most famous Valentine in history flabbergasts me,” Jean said during a 2017 interview. “I’m amazed and honored at its status.”

The episode also has a special significance for Jean, but not because he’s still hung up on a third-grade crush. “On my wedding band, my wife wrote, ‘I Choo-Choo-Choose You,’” he revealed during the commentary track. “It says that on the band, in honor of this episode, and the fact that Ralph is her favorite Simpsons character, and she did choo-choo-choose me.”

He did not divulge whether or not their first dance was to “Monster Mash.”