I should have foreseen that things between James and me would end in violent chaos on the night of my 29th birthday when he, my best friend Phoebe, and I were each contemplating who our No. 1 most bangable celebrity is. Phoebe and I had declared our respective loves for Harry Styles and John Malkovich. Then James said, “You know, I’ve always had a soft spot for Gwyneth Paltrow.”
“Gywneth Paltrow?” I repeated back to him in horror.
“Yeah, there’s something about her, I don’t know what it is!” And in that moment, every thought or daydream I ever had about our potential future together filled with broad-smiled children, adopted cats, and phenomenal sex evaporated. Because there is no future with a Gwyneth man when you’re a Winona woman, particularly a Winona in a world made for Gwyneths.
My “Winona in a world made for Gwyneths” complex is a theory that positions these one-time best friends as two distinct categories of white women who are conventionally attractive but whose public images exemplify dramatically different lifestyles and worldviews. One lives a messy but somehow more authentic life that is at once exciting and a little bit sad. The other appears to have a life so sufficiently figured out as to be both enviable and mundane. Gwyneth Paltrow is, of course, the latter. She has always represented a collection of tasteful but safe consumer reflexes more than she’s reflected much of a real personality. I imagine that she writes the GOOP newsletter, her laughably out-of-touch dispatch about vegetables and fashion, wearing overpriced clothes in colors like “camel” and scowling at her staff. That is, when she’s not referring to Billy Joel as “William” and seeking nannies that know ancient Greek and play at least two instruments.
Winona Ryder I imagine very differently.
For girls of my generation who were awkward or a little bit strange, Winona Ryder was both relatable and aspirational. The few recorded interviews she’s done reveal that she is a bottomless well of uncool and discomfort. She stumbles over metaphors and laughs sincerely at bad jokes. She is also a movie star who is unreasonably beautiful, but there was always a sense that she still belonged to the Island of Misfit Toys.
She epitomized the Mall Goth ethic and aesthetic in Beetlejuice long before Hot Topic was mass-producing the look, and in Heathers, she enacted high school revenge fantasies long before Mean Girls was either a movie or PG shorthand for “fucking bitches.” In the '90s, she did her grungiest best as the Generation X poster child in Reality Bites but never met a corset she didn’t like and came at us with The Age of Innocence and Dracula. I can’t even talk about Little Women because I’ll just start crying about the fact that I’m not currently sitting under a pile of kittens and sisters.
Then there’s her romantic life, which reads like a who’s who of my sexual awakening. Val Kilmer, Rob Lowe, Christian Slater, Beck, David Duchovny, and a bunch of indie rock stars who are probably still in love with her. Gwyneth had a shorter and more predictable list of conventional handsome dudes like Brad Pitt and Ben Affleck before she married Chris Martin. But Winona’s love stories seem like a series of elaborate fan fictions come to life for the charming and constantly bewildered pixie of a person. And I’m sure I don’t need to remind anyone that Johnny Depp wore her name on his bicep when he was still starring in daring, quirky films instead of predictable Tim Burton cash cows.
But as interesting as I always found her love life, it was still her personality and talent that drew me in. Rumor has it that Winona had the script for Shakespeare in Love and that Gwyneth saw it at her house and surreptitiously sought out the producers to get the role that landed her the Oscar. It is one of many Hollywood whispers that Gwyneth is not so sweet as she presents. And the long list of “best friends” she seems to have had over the years (Winona, Madonna, Tracy Anderson, Beyoncé) looks more than a little opportunistic.
It would have all been fine for Winona, because she was starring in the adaptation of Girl, Interrupted. Except that turned out to be the movie that would actually work to catapult Angelina Jolie to stardom and earn her an Oscar. And then came her 2001 arrest for shoplifting. The incident revealed a more complicated, less whimsical Winona; she was actually unwell, an inconvenient reality better dealt with through punchlines than public sympathy. And while male performers have gone on violent and destructive benders and bounced back in the time since that incident, Winona’s reputation has never fully recovered.
I loved Winona as a kid but grew even more affectionate for her in my late teens and early adulthood, long after the “Free Winona” T-shirts had cycled out of ironic fashion. She was wide-eyed and wistful but managed to find love from time to time anyway. I felt I could reasonably aspire to that. Before James, I dated a series of insecure addicts or men who treated me as an afterthought before unceremoniously disappearing into the ether without so much as an “I’m just not that into you” text. In a dating scene so normally steeped in nonchalance, messages from James that said, “I miss you. I want to see you” felt like love letters. He had endless words of affection for my peculiarity. For my inscrutability. He told me that I was hard to get a read on, a source of fascination and frustration for someone as socially intuitive as he was. And while James is hardly the first man to use praise for a woman’s particular brand of insecurity to his advantage, he did do an especially thorough job.
He’d ask, “What’s going on in that pretty head of yours?” Over time, I revealed a lifelong struggle with mental illness and self-doubt. He was the first person I told about my part-time work at a strip club, an industry I was in and out of for years when untreated mental health issues left me suddenly jobless and increasingly less employable during daylight. The work fueled his fascination with me and he’d request that he always get the first dance when I bought new outfits for work. But the revelation also sharpened his protective edge, and he'd remark often, “I gotta take better care of you,” when I’d report poor treatment by customers. Having spent a lifetime feeling like a blight in an otherwise beautiful world, I suddenly desired visibility without a subsequent desire to retreat to the shadows in a panic. My bottomless well of discomfort and uncool was finally charming someone.
His long hours and reliance on prescription drugs made it easy to excuse occasional neglect, particularly in light of how brightly the sun shined when I had his attention. Trust seemed to materialize from thin air around him. His imposing but non-threatening height made him an immediate presence as he easily made conversation with deli cashiers and conjured laughter from even the most timid children.
After a year, it became increasingly clear that my broad-smiled children and adopted cats were never going to be shared with James. He was noncommittal but remained protective and fascinated. I had met his siblings but not his parents. These were tell-tale signs that I was playing an interesting chapter in his memoir but would never play his happily ever after. I tried to break up with James the first week of May and I tried again the first week of July. He begged me to come back, making appeals about grilled cheeses in bed and missing my cat. And since I’m a sucker for a breakable promise to do better, I never followed through on ending things. We both had slept with other people but seemed to be still mostly committed to each other.
Then in the last week of July, James told me he had a new girlfriend and would be moving to California to be with her (his job brought him to Los Angeles often). Even though we were not exclusive, one of my very few requests of him was that if he were to commit to someone, that he not make me complicit in his infidelity. He made grand claims about his commitment to sexual fidelity with his new girlfriend a mere hour after sending me pictures of sexual positions he’d like to try with me. He told me how he was going to be different for this girl in the same breaths that he told me “I love you” for the first time. Lying on my bed, he pulled me closer to him as he made the case for sex while simultaneously texting with someone named “Amber.” This must be the woman that had changed everything for him, his present tugging at my belt loop notwithstanding. I kicked him out, refusing him closure or forgiveness.
One thing that stripping has given me is a ferocious commitment to other women, and so while many believe that what came next was an act of revenge against him, I am sincere in saying that I was outraged on Amber’s behalf. I went on Facebook and there was only one Amber among his friends and she lived in California. And there she was. A total. Fucking. Gwyneth. In addition to long blonde hair, she had earnest gratitude posts featuring all the super-boring emoticons. She posted photos of sunsets and filtered her selfies to hell and back with Instagram. On Facebook, she posted photos of a white SUV and nights out at the club. A quick Google search brought up a photo of her cheerfully giving what appears to be a presentation about industrial label makers. In sharp contrast to my online life, a collection of mostly dryly despairing essays for online magazines and unfiltered Twitter jokes, her entire digital footprint accumulated into a collection of safe consumer reflexes more than a personality.
And though I am easily given to fits of envy, I looked at her life and couldn’t find a single thing to covet. I was a haphazardly medicated bipolar 29-year-old stripper and I didn't want anything she had. I felt the way I imagined Winona felt surveying the foreign landscape of GOOP, laughing incredulously at the appeal of such dull aspirations but also completely and utterly alone.
I sent her a polite message detailing how James had been unfaithful and dishonest for the short duration of their relationship with several attached screenshots of explicit sexts from recent days as proof. Her response was one of profuse thanks for “saving her years of heartbreak” and a swift decision not to speak to James anymore. Within hours of sending the message, James began to call me repeatedly and when I didn’t answer he began sending texts asking where I was, then where the fuck I was. “I hope you choke on your own vomit and die you whore,” he wrote, a dig at my history of disordered eating. It was the first of many messages gruesomely detailing several ways he wanted to see me die in an inundation of text messages and calls where he threatened my life and his own. “If I ever see you again, run,” he wrote. It is a threat I’m still sometimes afraid he’ll make good on.
Finally, he claimed he had taken 30 Klonopin and that his imminent death would be my fault because I took his love away. When he stopped responding to my texts, I begged Amber to talk to him again so he’d go to a hospital, which she did. In hindsight, faking an overdose was a brilliant Trojan Horse to ride back into her life in.
And once he alerted Amber to my job and my mental health status, her gratitude turned to concern about the veracity of my claims. The change in tone made it clear in real time how easy it is to dress down a real woman to the vulgar trope of a delusional whore. Amber noted casually how he put her health at risk by sleeping with me. It is not uncommon to be treated like a vector of disease when your work so easily reduces you to salacious but interesting book chapters in people’s lives, but it still hurts a fully formed human being to be reduced to a public health hazard. She demanded more proof of his infidelity, asking that I put even more of my sex life on trial. I sent her James’ death threats instead.
She ultimately chose to “work through it” and said to me, “I don't want to always be looking over my shoulder or fearing that you will do anything to sabotage his or my happiness.” That’s a bold thing to say to a woman who has just had her life threatened in very descriptive ways by a man who purported to love her. But the vague threat of a woman with sexual mores you object to is more dangerous than the explicit threat of a man with a violent sense of entitlement. And at the end of the day, I also know very well that a place in his crosshairs feels like a place in sun.
As humiliated as I was to be left for a Gwyneth and as hurt as I was by her words, most of my thoughts about Amber are hopes that she’s safe and happy. Because that thing about Gwyneth Paltrow that James couldn’t articulate is that there’s not really anything about her. Or at least there’s not anything about her public image that is especially unique or controversial. She’s a safe canvas onto which others can project their own desires. I know very well that Amber is not an empty collection of label makers and earnest Facebook posts just as I know that Gwyneth Paltrow is not her terrible newsletter.
Her breakup with Chris Martin was widely mocked in the press for being identified as a “conscious uncoupling,” as though she could not bear to have anything so human and messy as what it was: a divorce. For months after the split, rumors flew that Gwyneth was terrified that details of their marriage would emerge, that the perfect filter she had chosen for the world to see her through would be ripped off for all of the blemished and broken parts to be revealed. Such forms of protected and limited self-projection are calculated and intentional. And that seems like its own kind of solitude.
So while I originally thought that the whole ordeal was my moment where Gwyneth snatched up Shakespeare in Love, I realize now that Amber getting James was less like getting an award-winning movie script and more like getting that scary VHS tape from The Ring that eventually ruins your life. I’ve instead come to see the whole experience as my moment on a surveillance camera in Saks Fifth Avenue. It was the episode in which the Manic Pixie Dream Girl was revealed to be the Depressive Witch Nightmare Woman that she was all along. It brought to life my sadness and desperation outside the vacuum where being mentally ill was a fascinating quirk that had no potential to create real consequences. I was breakable and broken and would not be confined to the narrative James had in mind for me.
I’ll turn 30 in June, the age that Winona was when the shoplifting scandal went down. There is some fear that I’ll be forced to turn the corner from wide-eyed and wistful to just sad and sick. And when you rely heavily on celebrities like Winona Ryder to make sense of your life, it is easy to stare down your early thirties as the period of darkness and uncertainty following a fallout. And that might end up being true. But the truth about the women who are forced to play these interesting chapters is that they are doing so in the memoirs of men who never deserved them. That the really good story, the story worth telling, was hers all along. She just has to survive to tell it.
And that’s what Winona did. In the fall of 2014, she became the face of the Rag & Bone fashion line and was featured in a series of promotional videos for the launch. She doesn’t appear to have aged a day since 1990 and she smiles through red lipstick as she plays arcade games at Coney Island. The arcade is dimly lit and deserted except for her. But she seems perfectly content to make goofy faces and have her own fun, telling herself a bad joke that no one else can hear, and laughing and laughing.
Aileen Wuornos come back as a cupie doll.
Contact Alana Massey at email@example.com.
Got a confidential tip? Submit it here.