Everyone seems to have a teen romantic comedy that holds a special place in their heart. For most, these films evoke a strong level of nostalgia, like the fond memories of watching “Mean Girls” for the first time at a middle school sleepover. Upon rewatching, however, these films tend to be a mixed bag. While some — like “Ten Things I Hate About You” — are able to remain on their pedestal, others fall flat when examined with a scrutinizing, grown-up eye — as seen with “The Kissing Booth.” For me, Amy Heckerling’s “Clueless” is perhaps the most nostalgic teen rom-com of all time. I first watched the film at 14 years old, and it’s been imprinted on my mind ever since. But, as time passes and our once juvenile tastes grow more sophisticated, does this film still hold up? For the most part, yes. With privileged, yet unconventionally wise female characters, eternally quotable dialogue and an escapist setting that borders on fantasy, “Clueless” is the quintessential teen rom-com to be enjoyed by viewers of any age. 

Films geared toward teenage girls often have a habit of villainizing or demeaning their target audience. Many of the young female characters in these films, especially the “girly” characters, are either portrayed as stuck-up, vindictive popular girls or vapid, air-headed blondes. If a female character does have depth, it is generally because she is “not like the other girls” and does not have traditionally feminine interests. As the main character of “Clueless,” Cher Horowitz subverts these expectations in a way that is unusual for a teen rom-com of the 1990s. She appears to fit the classic popular girl stereotype: a wealthy shopaholic obsessed with makeup, weight loss and fashion. However, while Cher is often naive and self-centered due to her economic privilege, she is never presented as unintelligent. 

In fact, Cher is quite the opposite. She is confident and savvy, with enough charisma and social acumen to successfully negotiate higher grades for her report card and propel Tai Frasier, the outcast-bound new girl, into the popular crowd. Cher is a master of persuasion — with a few choice words and actions, she is able to make her teachers fall in love and turn Tai’s attention from Travis Birkenstock, a stoner who would ruin her reputation, to Elton Tiscia, one of the few acceptable high school boys to date. Cher also has a surprising amount of academic knowledge, which she shows off when she corrects her ex-stepbrother’s female friend when she misquotes Shakespeare’s “Hamlet.” She is generally not unkind, at least not intentionally. Though Cher gives Tai a makeover partly for her own entertainment, she also genuinely believes that she is helping Tai navigate her new school. She cares deeply about her friends and family, supporting Tai when Elton breaks her heart and constantly making sure her father eats healthy. Cher is a smart, refreshing take on the classic teen rom-com popular girl, ensuring that “Clueless” never talks down to its primary audience.

Many criticize teen movies for not being realistic enough to the average high school experience. Directors cast gorgeous 27-year-old actors to play high school sophomores who should, by all accounts, be suffering from crippling acne and palpable awkwardness. While I agree that there is a considerable gap in the market of genuinely relatable teen films, I believe that “Clueless” does the unrealistic high school setting right. The world of rich, carefree teenagers living in Beverly Hills is already an unrelatable environment to many viewers. As such, the film leans into its fantastical elements, displaying a universe in which everyone has exceptional fashion sense, endless time for shopping and parties and a computerized closet that chooses outfits for its user. This universe has a language all its own, creating dialogue that continues to be quoted decades after the film’s release. Cher is not disappointed when she realizes her crush, Christian Stovitz, is gay; instead, she is “totally buggin’.” Cher’s frenemy Amber Mariens is not poorly dressed; she is either a “fashion victim” or “ensemble-y challenged.” No one can forget Cher’s iconic expression of disgust — “Ugh, as if!” — though I prefer to quote Tai’s brutal jab at Cher: “You’re a virgin who can’t drive.” Way harsh, indeed. Since it is so far removed from reality, “Clueless’” setting is one in which viewers can escape and indulge themselves without deeply examining its incongruence to the real world.

One criticism I have of the film is that the romantic side of its plot is “a full-on Monet: from far away, it’s okay, but up close, it’s a big old mess.” The choice of having Cher’s love interest be her ex-stepbrother is questionable at best and unsettling at worst. According to Cher, Josh Lucas’ mother was “barely married” to her father, and the two of them have not been step-siblings for several years. While it is technically fine for them to be together, it does not make this aspect of their relationship less odd. Additionally, though Josh and Cher are only two years apart in age, a college student romantically pursuing a high schooler is a plot point that becomes more distracting as the years pass. Their witty, argumentative banter throughout the film is charming to watch. But the dynamic between Cher and Josh for the bulk of the film reads as that of a brother and sister to me, further exacerbating the strangeness of their inevitable union. However, if one can look past these admittedly glaring issues, the positive effect that Josh has on Cher is rather sweet. Josh’s social consciousness is what drives Cher to give herself a makeover of the soul, participating in charitable work and finding a deeper appreciation for her friends and peers of different social statuses. Cher does this not necessarily to win Josh’s affection, but because Josh inspires her to better herself for herself and those around her. Overall, though the “rom” half of this teen rom-com has its issues, “Clueless” is still a film that surpasses most of its contemporaries, whether the viewer feels nostalgia for it or not.