While not strictly a romantic relationship, Bart's bond with Milhouse is one of the most significant and enduring friendships in the series. The two have shared countless adventures, supported each other through thick and thin, and even had their fair share of falling outs. Their relationship has been a cornerstone of the show, providing comedic relief and heartwarming moments.

Mary Spuckler (voiced by Zooey Deschanel) is arguably Bart’s most significant long-term love interest. Appearing in multiple seasons, their relationship is grounded in genuine affection. Whether it was the "accidental" marriage proposal or the musical tribute Bart wrote for her, Mary represents the "girl next door" (or rather, the girl from the farm) who truly understood Bart's chaotic nature. 4. Darcy: The Mature Reality Check ( Little Big Girl )

: Introduced as a classmate of Bart's, Jessica was one of his early romantic interests. Their relationship was depicted in a few episodes, showcasing Bart's attempts at navigating early crushes and relationships.

Throughout The Simpsons Bart Simpson 's love life is a repeating cycle of "bad boy" charm meeting its match, usually ending in heartbreak or a hard-learned lesson

In later seasons, Bart revisited his crush on Mililani, but their relationship ultimately fizzled out. He also had short-lived romances with other girls, including Gina and Bernice Hibbert. While these relationships were not as significant as some of his other connections, they contributed to Bart's growth and maturity as a character.