"I'm with Cupid" was written by Dan Greaney and directed by Bob Anderson. Because the episode was to air on Valentine's Day, Fox wanted the episode to relate to the holiday, although the idea for the episode was pitched by Greaney. The title of the episode is based on the popular T-shirt slogan "I'm with stupid". Elton John guest-starred as himself, and recorded a new version of his song "Your Song" for the episode. The episode also features references to "Breakfast at Tiffany's", Tiffany & Co. and "Lisa the Vegetarian", an earlier episode in the series.