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As a trans woman, I’ve long been obsessed with the cinematic trope of the makeover montage. We’ve seen them all a million times: the scenes in The Devil Wears Pradawhere the previously fashion-agnostic Anne Hathaway learns how to turn a look, or the end of The Breakfast Club when Ally Sheedy transforms from a gothic outsider to the girly girl next door. Romantic comedies in particular often hinge on these scenes where a character is completely rebooted, their inner beauty now visible to the outside world — a process I longed for in my own life but never received.
I had to take my gender into my own hands instead of having someone else tell me who I was; there was no fairy dust to transform my body or help actualize my identity, no long-lost monarch grandmother to tell me I was actually a princess all along. The idea of the makeover might be a fantasy, but like so many fantasies, it can distort your perception or expectations of your own life. In reality, it takes years of practice to learn makeup and feminine poise; it takes messiness to become your truest self.
Growing up in the 1990s and 2000s as a closeted trans women, romantic comedies seemed to be the cultural zenith of femininity, and so I secretly consumed them in spades, never letting my guy friends know I was a Nancy Meyers stan behind closed doors. In public, I scoffed at “chick flicks.” Privately, I found myself drawn to actresses like Meg Ryan and Julia Roberts, who were the kind of women I wanted to be: smart and writerly, sexy and emotional, so much more than mere lovers of men.
And so while romcoms didn’t necessarily make me trans, they were a crucial fantasy realm and secret source of refuge for me as I felt more and more uncomfortable with the identity I’d been assigned at birth.
I soon realized that 13 Going on 30 was just the tip of the iceberg when it came to rom-coms featuring their own kind of miraculous gender transformations. At first, these magical changes bring fear and insecurity for the characters, but eventually allow for something close to euphoria and self-actualization. Sometimes it’s a literal supernatural and physical change, like the overnight adolescence Jennifer Garner experiences in 13 Going on 3o, or just a complete makeover à la The Princess Diaries.
Other rom coms explore the feeling of regret that you don’t get to do your earlier life over, or that your real self is in the past, waiting to be recovered. These themes, too, are almost painfully poignant for viewers like me. In Never Been Kissed, Drew Barrymore gets an absurd chance to do her traumatizing high-school experience over again, this time as a self-confident and beautiful popular girl.
By deliberately riffing on Shakespeare’s plays, so often fascinated by the emotional and metaphorical implications of disguises and masks, there’s a heavy trans subtext behind Never Been Kissed’s ruminations on authenticity and honesty. At one point, once Josie is accepted by the popular girls, they even tell her that she’s “totally transitioned,” from one of a thousand losers to one of the hottest and most sought-after girls in school. “You crossed over into our group. Some people go all through high school trying to transition and never make it,” one tells her point-blank.
But the most trans rom-com I latched onto as a child is The Princess Diaries, which in many ways is quite literally about the experience of having your “egg cracked,” the slang term we often use for the moment when one realizes who they really are — and can never go back.
When Mia (Anne Hathaway) learns she is a princess, her impression of her life and herself completely shatters, and she eventually becomes a much fuller version of herself, but not without having to condense a years-long syllabus of feminine presentation and elocution into a crash course.
The Princess Diaries isn’t even subtle about Mia being in some kind of a “closet” as she tries to shield her royal identity from the rest of the world — multiple characters joke about how she’s been “outed” after her secrets have been exposed publicly. Once other people have the knowledge of who she truly is, it’s impossible for her to deny it any longer, and she finally embraces all the possibilities that come with living as your authentic self.
Of course, the golden age of 1990s and 2000s rom-com are as much about the performance of race and class as they are gender. For as much as I might have projected upon her story, her primary fear is something that almost no trans person can fathomably relate to: giving up her authenticity in exchange for endless riches and state power.
While the sense of self these films arrive at is somewhat limited, the journey they depict can still be relatable. All of us must find ourselves in one way or another, balancing your own self-perception with who the world wants you to be, and this is exactly at the heart of films like 13 Going on 30, The Princess Diaries, and Never Been Kissed.
As queer and trans viewers, we have to do these subtextual readings of films that are still cisheternormative because there has been so little room for our real lives onscreen. I hope that someday in Hollywood there’s a true transgender rom-com — not just hollow token representation to fill a diversity quota, but films that use the very queer tropes of the genre, from fairy tale transformation to body swapping to Shakespearen identity switcheroos, to tell intimate and honest stories about how trans people experience romantic relationships, that give us as much room for fantasy as reality.
How These Iconic Rom-Coms Cracked My Egg
As a trans woman, I’ve long been obsessed with the cinematic trope of the makeover montage. We’ve seen them all a million times: the scenes in The Devil Wears Pradawhere the previously fashion-agnostic Anne Hathaway learns how to turn a look, or the end of The Breakfast Club when Ally Sheedy transforms from a gothic outsider to the girly girl next door. Romantic comedies in particular often hinge on these scenes where a character is completely rebooted, their inner beauty now visible to the outside world — a process I longed for in my own life but never received.
I had to take my gender into my own hands instead of having someone else tell me who I was; there was no fairy dust to transform my body or help actualize my identity, no long-lost monarch grandmother to tell me I was actually a princess all along. The idea of the makeover might be a fantasy, but like so many fantasies, it can distort your perception or expectations of your own life. In reality, it takes years of practice to learn makeup and feminine poise; it takes messiness to become your truest self.
Growing up in the 1990s and 2000s as a closeted trans women, romantic comedies seemed to be the cultural zenith of femininity, and so I secretly consumed them in spades, never letting my guy friends know I was a Nancy Meyers stan behind closed doors. In public, I scoffed at “chick flicks.” Privately, I found myself drawn to actresses like Meg Ryan and Julia Roberts, who were the kind of women I wanted to be: smart and writerly, sexy and emotional, so much more than mere lovers of men.
And so while romcoms didn’t necessarily make me trans, they were a crucial fantasy realm and secret source of refuge for me as I felt more and more uncomfortable with the identity I’d been assigned at birth.
The first rom-com that I loved in a waythat was related to my gender was 13 Going on 30, a movie generally about the struggles of female puberty. Jenna (Jennifer Garner) is unhappy with her life as a teen and feels excluded by the popular girls, so she makes her famous wish to be “thirty, flirty, and thriving,” manifesting a fantasy future life in which she is one of the popular girls, a high-femme taste-maker whose still-teenage mind is blown by now having fully-grown tits. The idea of an instant bodily transformation, of becoming a fully-grown adult woman with little more than magic dust and willpower, appealed to me as a closeted trans woman who wanted to be completely different, both in how I saw myself but also in how others perceived me.
I soon realized that 13 Going on 30 was just the tip of the iceberg when it came to rom-coms featuring their own kind of miraculous gender transformations. At first, these magical changes bring fear and insecurity for the characters, but eventually allow for something close to euphoria and self-actualization. Sometimes it’s a literal supernatural and physical change, like the overnight adolescence Jennifer Garner experiences in 13 Going on 3o, or just a complete makeover à la The Princess Diaries.
Other rom coms explore the feeling of regret that you don’t get to do your earlier life over, or that your real self is in the past, waiting to be recovered. These themes, too, are almost painfully poignant for viewers like me. In Never Been Kissed, Drew Barrymore gets an absurd chance to do her traumatizing high-school experience over again, this time as a self-confident and beautiful popular girl.
By deliberately riffing on Shakespeare’s plays, so often fascinated by the emotional and metaphorical implications of disguises and masks, there’s a heavy trans subtext behind Never Been Kissed’s ruminations on authenticity and honesty. At one point, once Josie is accepted by the popular girls, they even tell her that she’s “totally transitioned,” from one of a thousand losers to one of the hottest and most sought-after girls in school. “You crossed over into our group. Some people go all through high school trying to transition and never make it,” one tells her point-blank.
But the most trans rom-com I latched onto as a child is The Princess Diaries, which in many ways is quite literally about the experience of having your “egg cracked,” the slang term we often use for the moment when one realizes who they really are — and can never go back.
When Mia (Anne Hathaway) learns she is a princess, her impression of her life and herself completely shatters, and she eventually becomes a much fuller version of herself, but not without having to condense a years-long syllabus of feminine presentation and elocution into a crash course.
As much as self-realization can open up your life and allow new growth and opportunities, it’s also terrifying to have your entire world changed, and Mia denies her true identity at first. At one point, she exclaims, “You spend 15 years of your life thinking you’re one person, and then in five minutes, you find out you’re a princess,” which encapsulates a feeling that I think many of us trans folks feel at first: a kind of bitterness at not getting to live a “normal” life and having to adjust or change our expectations of reality.
The Princess Diaries isn’t even subtle about Mia being in some kind of a “closet” as she tries to shield her royal identity from the rest of the world — multiple characters joke about how she’s been “outed” after her secrets have been exposed publicly. Once other people have the knowledge of who she truly is, it’s impossible for her to deny it any longer, and she finally embraces all the possibilities that come with living as your authentic self.
Of course, the golden age of 1990s and 2000s rom-com are as much about the performance of race and class as they are gender. For as much as I might have projected upon her story, her primary fear is something that almost no trans person can fathomably relate to: giving up her authenticity in exchange for endless riches and state power.
While the sense of self these films arrive at is somewhat limited, the journey they depict can still be relatable. All of us must find ourselves in one way or another, balancing your own self-perception with who the world wants you to be, and this is exactly at the heart of films like 13 Going on 30, The Princess Diaries, and Never Been Kissed.
As queer and trans viewers, we have to do these subtextual readings of films that are still cisheternormative because there has been so little room for our real lives onscreen. I hope that someday in Hollywood there’s a true transgender rom-com — not just hollow token representation to fill a diversity quota, but films that use the very queer tropes of the genre, from fairy tale transformation to body swapping to Shakespearen identity switcheroos, to tell intimate and honest stories about how trans people experience romantic relationships, that give us as much room for fantasy as reality.
Nadine, Nadine, Nadine, Nadiiiiinnnneeeee
