Although Cher and Josh's romance has always been controversial, Clueless' true story actually forms the inspiration for the relationship. The hit 1995 movie, which is a reimagining of Jane Austen’s novel Emma, has continued to raise eyebrows around its central love story in the years since its release. However, a look into director Amy Heckerling's past reveals that Clueless' inspiration is perhaps not as farfetched as it seems.
The rom-com follows wealthy and popular L.A. teenager Cher Horowitz (Alicia Silverstone) as she befriends new girl Tai Frasier (Brittany Murphy) and decides to use her talents by giving her a makeover. Meanwhile, Cher is dealing with the return of her brief ex-stepbrother Josh (Paul Rudd), a college student who begins doing work for her father’s law firm. Clueless features several romances for the main characters before the protagonist Cher realizes who she’s really in love with. After spending much of the movie arguing with Josh over literature, fashion, politics, and being annoyed that he’s spending so much time at the house without even being related to her, Cher finally comes to the realization that she has feelings for him. Alicia Silverstone's Clueless character then begins to outwardly show how selfless and knowledgeable she really is when around Josh, and the two end up as the movie’s core couple.
Considering Josh and Cher met because their parents were briefly married and the two exhibited a minor brother-sister dynamic, many have found their romance to be slightly unsettling. While Clueless’ main romance may seem a bit weird due to their former familial connection, Cher and Josh’s relationship is actually inspired by director Amy Heckerling’s real life. Per Yahoo!, Amy Heckerling based Cher and Josh on her own grandparents, who met as teenagers after becoming step-brother and step-sister. Because her grandparents’ relationship was so natural to her, Heckerling didn’t find it unusual that Cher and Josh would have the same background. This means that Clueless is, to some extent, a true story.
The step-sibling connection isn’t the only way Heckerling’s grandparents inspired Clueless’ true story romance, as she also used their constant bickering and arguing even into their 80s as a basis for Cher and Josh’s playfully quarrelsome dynamic. Cher and Josh are still considered one of the most iconic rom-com love stories, which may seem counterintuitive when considering their familial origins. While Cher and Josh don’t even remotely consider each other family, Cher’s father still thinks of Josh as his child. When Cher complains about Josh coming around the house because their parents were “hardly even married,” her father responds by saying, “you divorce wives, not children.” It’s not really clear what Cher’s dad thinks of her dating the young Paul Rudd character, but since he considers him a son, he probably wasn’t too keen on the idea at first.
At the same time, Clueless makes Cher and Josh’s love story work by distancing each other from feeling any real familial connection. Any time they try to bring up being step-siblings, each of them denies that there was ever any resemblance of them acting like a family or feeling connected in that sense. Cher routinely mentions that their parents were barely even married, so there’s no reason for Josh to keep coming around. In this sense, Josh was really just a young guy who spent a lot of time at her house that equally encouraged her maturity and teenage cluelessness, so it’s not unreasonable that Clueless would culminate in her falling for him. Regardless, Clueless' true story inspiration explains the narrative twist.