On Glass Slippers, Jake Ryan, and the Myth of the Job Prince
You May Have Worked Hard for Your Success, But Did You Choose It?
Having a tween and teen in my household, we are embarking on a pop-cultural rite of passage and making our way through the John Hughes cinematic oeuvre … starting with Sixteen Candles.
I was exactly 12 years old when I first saw the film. I remember this because I went with friends on my birthday, and to avoid being charged the adult rate I lied at the box office and said I was 11.
Forty years ago I recalled cheering for Samantha, or Sam, the tortured Sophomore heroine of the film, who endured numerous slights and indignities, from having her birthday forgotten by her family to being publicly humiliated by a Freshman nerd hitting on her at a school dance. These were tragic experiences to me at the time. And I felt a sense of vindication for Sam in the penultimate scene when, leaving her narcissistic sister’s disastrous wedding, she looks up and sees her major crush, Senior Jake Ryan, someone she had never spoken to before, leaning back on his cherry red Porsche 944, waiting to take her away from her dreary suburban family to what one could only assume was a stratospheric height of popularity and enduring romance.
The last scene of the film seared into my brain at age 12 and triggered all the feels: Sam and Jake share a first kiss leaning over her birthday cake, in dreamy birthday candlelight, with the Thompson Twins song, “If You Were Here” intensifying in the background.
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Seeing the film again, 40 years later, I believe some of it still held up. Jake Ryan is still a Babe. The Nerd’s antics are still cringeworthy. I still love the soundtrack, which inspired multiple mixtapes.
But there were some very questionable aspects of the film that star Molly Ringwald has already very powerfully articulated as problematic in a New Yorker article, looking back at her experience as a John Hughes “muse”. I found it impossible explaining to my girls, for example, when they asked about the now-infamous “morning after” scene between The Nerd and the Prom Queen, how teen sexual assault could be so neatly tucked into a happy plot ending. “It was a different time then,” seemed like a wholly inadequate explanation.
And of course, representation was sparse or insulting. One of my kids remarked, watching one school scene, where the panoply of student body diversity ranged from North Shore Princess to Consignment Shop Emo: Why is everybody white?
The most glaring ethnic insensitivity can be summed up in three words: Long Duk Dong.
Despite her objections to the film’s insensitive ethnic depictions, my 12-year-old daughter signaled her approval of the film by requesting the movie’s soundtrack at the end. And my 14-year-old, who cringed at the end said it was more out of concern for Sam’s safety, given the presumed flammability of her poofy taffeta bridesmaid dress and proximity to open flame. She ultimately bestowed on the film her highest rating: Decent.
But something unexpected stuck in my craw.
As I watched the credits I found myself thinking very differently about Sixteen Candles, despite my unwavering nostalgia for it. My hyper pragmatic, neofeminist brain went to the day after Sam’s dream come true. Was she really girlfriend material, given she couldn’t even look at Jake two days before? Would she feel pressured to act according to expectations bestowed on a girl who snagged the hot senior guy, or would she follow her gut and be authentic? As a result of the latter, would Jake get bored and dump her by Spring Break?
Would the Nerd and Jake’s ex-girlfriend make a go of it? Would the $70 he made selling views of Sam’s underwear sustain the hedonistic demands of his new fling? Would the newfound status he inevitably gained from his sexual acquisition build his confidence and propel him into a career as a billionaire tech CEO? Or a sociopath? Or maybe both?
How pissed would Jake’s parents be when they got home and found their Rolls Royce and North Shore manse had been trashed by a bunch of teenagers?
And, most critically: Would Sam, weeks into dating Jake, look up at him while in his arms and wonder, “so this is what I signed up for? He’s cute and all, but he doesn’t talk much, and he doesn’t even know me!”
In my 12-year-old mind, Samantha was rewarded with her prince for what she “didn’t* do: Stay out late; party excessively; fool around; look like a freak. But in my 52-year-old mind I struggled to understand what she DID do to earn Jake’s attention.
And what did he do to earn hers?
The answer to my question had seemed obvious to me when I was 12, but it was much less so now.
Jake’s pursuit of Samantha started when he intercepted a note meant for Sam’s friend in which Sam confided that she was attracted to Jake and would have sex with him. He had no other knowledge of her than this and asked his friend for his opinion of her, which the friend could not provide.
“What do you think of her?” Jake asked his friend.
“I don’t,” his friend replied.
“She’s not ugly,” Jake responded, perhaps to justify his curiosity.
When Jake attempted to connect with Sam later that night at the school dance, she lost her composure and walked away from him. And yet, he continued to pursue her, calling her home, going to her house, and finally showing up at Samantha’s sister’s wedding, practically a stranger. He even bought her a birthday cake.
See! If you just want something (or someone) badly enough, and you are ‘not ugly’, you, too, will get your Jake Ryan!
I audibly shared my insight while watching the end credits (something I do frequently lately – literally speak my mind), causing my daughter to snap, “Oh my Gaw, Mom! It’s not that deep! It’s just a teen movie!”
My other daughter felt it incumbent upon herself to defend the teen fictional movie character and her new best friend:
“She was a good, deserving person! She gave the Nerd her underwear … And she wasn’t a dork!”
If re-watching 16 Candles has taught me anything, it’s that teenagers are assholes, and I have recovered from Good Girl Waiting Syndrome. A condition so many of my peers seem to be recovering from.
Some of you may be wondering what that is. After all, you did the work, got the grades, went to an elite college, graduated from Stanford GSB, worked at Google. You hardly waited for your career redemption, whether it be a top role at a Fortune 500 company or a Unicorn startup exit.
You were, by all measures, a get-it-doner. You took the hard jobs. You stayed the latest at the office. You went right back to work after having your kids. You looked difficult people in the eye and made your point. You hardly waited for opportunities; you earned them.
So then, why do you not feel redeemed?
Why didn’t Jake Ryan pick you to be CEO? After all, you’re not ugly!
Why do you now question the path you decided to take?
Good Girl Waiting Syndrome is a chronic tendency to hedge one’s career bets by positioning oneself favorably against an ideal of success, even before knowing if it’s a desired path, and then wondering why, after following that path, one feels unfulfilled.
Or stuck. Entrepreneur and Hello Alice Founder
calls this feeling of stuckness the “New Midlife Crisis”., Optionality member, contributor, serial achiever, and host of the Solopreneur Billionaire podcast, said something to me recently that resonated. After many years as a senior executive in big tech, she left her last role unceremoniously as so many of us have, unsure of what was next. She wrote about it:“Midlife used to be about fast cars and questionable haircuts. Now, it’s about existential dread and too many tabs open on your browser. According to a recent study, 50% of people aged 40-55 feel “stuck” in their current career paths, but less than half take steps to change it. Why? Analysis paralysis.”
“Your brain ticks through, how do I explain how I went
- From big title to no title
- From 100s of texts, WhatsApps and Slacks to 0
- From triple booked meetings to an empty calendar.
For months, I didn’t have an answer.
I latched onto things just to regain structure in my day.
- I partnered with a friend to help her grow her recruiting business.
- I watched a lot of procedural BBC murder mysteries.
- I bought a TON of plants,” she wrote.
I asked her what moved her into her next definitive chapter, running a practice helping others to leverage AI to enable their next chapters. She said:
“I stopped waiting for the glass slipper to fit.”
“Your next chapter doesn’t need a perfect plan or a new title.
It doesn’t even need to make sense to everyone else.
Here is what a business is made of:
- Something you care about so you will do it
- An audience, people who you know already
- A package, how you offer your brilliance
Share one idea that keeps circling your brain.
You don't need to be a unicorn.
You don’t need to be perfect.
Take one step.
Clarity comes.
Trust me.”
As an entrepreneur I stopped harboring any illusions that someday my Job Prince would come. But fully committing to other opportunities terrified me, because if I wasn’t successful at a career entirely of my own choosing it would be entirely MY fault. Not God’s. Not Jake Ryan’s. Not the Patriarchy’s, as much as I’d like it to be. Now I had to actively choose a path.
And actively choosing a path would mean exorcising any last trace of Good Girl Waiting Syndrome from my soul.
We may all know intuitively that our Career Prince will never come, so let’s stop waiting for him.
In my head I’ve written an alternative ending to Sixteen Candles. Jake still shows up with the Porsche and gets Sam a birthday cake. But when he asks Sam to make a wish, instead of replying, “It already came true,” she says nothing; she just smiles.
In our heads we can fill in the blank what she wished for.
Great piece Jory, and I can picture every scene of 16 Candles. You're right about 'good girl waiting' syndrome; totally had that before connecting with HiPower women who are not waiting for that (horribly uncomfortable anyway) glass slipper.
I enjoyed this, Jory. I also like your ending better. Grateful for the gift of space to reflect, revisit, get curious, explore, embrace, let go, move forward! I’m all in!