It’s September 2010, and I’ve finished a lesson in my first-period Pre-Calculus class. While the students begin their homework assignment, I retreat to my desk in the back corner to wade through some grading I need to catch up on.
This is my second full year at the school but my first with a full slate of classes to teach. I’ve got three preps every quarter, plus fall baseball games around Elk Grove for two separate organizations. This is all to say: I less sit down at my desk than collapse into it. I have infinitely more energy and delusional optimism than I will have a decade later, but I flop into my chair out of sheer exhaustion nonetheless.
Seated next to my desk by the random number generator in Making the Grade’s seating chart feature is Kyle. The son of my Pre-Calculus teaching partner, Kyle is a bright and earnest kid who would eventually be the singular reason I attended my first Challenge Day. At this moment, though, he is just Kyle, the kid who doesn’t do much homework. Which is fine—his approach doesn’t offend me—but it does mean Kyle engages me in conversation while his classmates work.
If I dig into my old journal, I’m sure I could locate snippets of several conversations he and I had. That year marked the beginning of my transcriptive writing phase when I recorded everything every day. Several talks with Kyle appeared in such pieces. Only this one sits prominently at the front of my memory, though.
“My best friend just moved to San Diego,” Kyle says to me. “I miss him. I’m pretty sad to know he won’t be around anymore.”
I, not yet in tune with the privilege it is to have a student trust me with authentic emotion, surely dart my eyes between some scribbled-out Standards Quiz and him. A generic “I’m sorry” serves as my automatic response.
Kyle turns and catches my eye. “Do you see your best friend a lot? As an adult, how often do you see your closest friends?”
My shoulders become rigid as he calls me into action. I weigh his words and gauge my answer. How often do I see my best friend?
Kyle’s question is quantifiable, so I know that my answer should be a ratio involving time, like “once per month”, but I’m aware too that he’s asking something bigger. At the start of his senior year, he’s waving farewell to his one-year-older friend and contemplating his own transition that will begin in earnest one year later. I’m not yet sharp emotionally like I’ll later become, but even as a 24-year-old, I understand his question is greater than the sum of its words. He’s asking me for hope. He wants me to certify that his ache of separation will be temporary. Kyle has invited me into my first spontaneous emotional moment as a teacher.
In 2021, I would answer a similar query eloquently with a metaphor involving magnets.
In 2023, I would answer a similar question with a moving story of a missing wedding photo.
In 2010, as a depleted twenty-something making his way through hour two of another draining day, I answer him bluntly.
“Not very often,” I tell Kyle. “Honestly, he lives just a few blocks away, but we’re both so busy…”
Emotion catches in my throat. I realize that my honesty has deflated not just Kyle but me. My eyelids close, crushing potential tears back into my brain. I gulp hard to tamp down the defeat I suddenly feel before anyone notices it.
“It really sucks,” I say, letting the words tumble from my tongue like a reluctant rock slide. I look at Kyle, and we lock eyes. Maybe I’m just projecting my own, but his heartbreak is palpable. It takes every ounce of strength the muscles in my face possess to maintain my composure as two guys, six years apart, confront a sobering truth about growing up.
“It does, doesn’t it,” Kyle says before looking away.
I stare at the quiz that has been in my hands the entire time.
Nothing looks right.
*****
On February 5, 2021, I generated a Google Sheet from a Form I made earlier that day. The ninth row on the spreadsheet it spawned included the name of a student from my sixth-period Honors Pre-Calculus class and two lowercase words that marked the title of her favorite song. That spreadsheet includes 37 songs, and it was my intention to listen to them all.
I got no further than row nine.
The song recommended there was “drivers license” by an artist, Olivia Rodrigo, whom I had never heard of. No less than a dozen plays of “drivers license” later, I was seeking information about who this singer-songwriter was.
For those who haven’t heard “drivers license” by now, the song traces a heartbreaking moment of youthful disillusionment. After achieving the milestone of earning her driver’s license, Rodrigo drives around her town only to discover hollow disappointment where she had expected a freeing high.
There’s a grand cultural weight to a driver’s license forged around its invitation for independence. With a license, one can explore without supervision! With a license, one can at last taste the first flavors of freedom! In the song, Rodrigo had planned to drive to see her older boyfriend. Her older boyfriend who has already moved on.
“But today, I drove through the suburbs,” she laments. “Crying 'cause you weren't around.“
The song touches on numerous themes that characterize the teenage years—insecurity, rejection, the future—but it’s that disappointment that captivated me. Where other artists bask in the glow of youth and beckon for glorious tomorrows, Rodrigo meditates on the empty promise of a threatening sunrise. There’s a preternatural wisdom to “drivers license”, captured nowhere better than in its final lines:
'Cause you said forever, now I drive alone past your street.
Yeah, you said forever, now I drive alone past your street.
I swear you can hear her harden between those lines.
Months after I first got hooked on “drivers license”, Rodrigo’s sensational debut album, SOUR, released, and the collection’s emotional palette won me over almost instantly. I wrote a piece around “deja vu” that month, and I still play that song and its manic flamethrower counterpart, “good 4 u”, on every mixed playlist I cobble together. The songs on SOUR span several genres and characters, but each offers incredible specificity as a vehicle for the emotional chaos of being young and in the kind of love that feels eternal while marked with an expiration date.
SOUR, though written by someone who could conceivably be my daughter, never plays like a generational curio; its themes of love, rejection, and growing up land with listeners of any age. The 35-minute album is barely longer than a 90s sitcom episode, but each piece packs a punch that feels broadly universal. I’ve never donned a cheerleading uniform and set an ex’s bedroom ablaze, but I stare unblinking into the mirror with a Blumhouse grin whenever “good 4 u” plays. Rodrigo just gets you onto her wavelength. Still, it’s not just about the themes her songs evoke: the powerful stories SOUR tells pair beautifully with her tender voice to make even obsessively repeated listens rewarding.
After two years of cultural presence—a tour, a concert film, several Grammys—Rodrigo released her second studio album on September 8, 2023. Titled GUTS, the album sees Rodrigo return to the well of her teenage experiences, but this time expanding her scope to even larger markers of that transition into her twenties.
The first album single, “vampire”, touches on the dangers of trusting while a young star on the rise; its second, “bad idea right?”, playfully interrogates the challenges of mature decision-making in the face of naïve self-destructive desire. There are songs about being gaslit, a song about envy, and another that picks apart her own appearance. In 39 minutes and twelve tracks, Rodrigo’s efficiency doesn’t diminish her achievement: it’s an album that effectively interrogates that tricky time at the tail end of adolescence. Ultimately, her intense focus and brevity are gifts: the emotions are there on first listens, but looping through again nourishes deeper reflection. Her best tracks pierce my heart by the first chorus; her least accessible grow on me like kudzu.
Still, I could tell something had changed between SOUR and GUTS. Rodrigo and I are an identical two years older, but I see myself differently today than I did in 2021. I feel further from the emotional experiences she sings about; I didn’t bounce with her beat so much as listen compassionately from the sidelines. The stories GUTS conjures in my head are of me as a teacher, as an adult, not as a lovesick high school senior. Ninety minutes melted away in 2021 as Claire, Gaby, and I talked about every track of SOUR; yesterday, I withheld any mention of GUTS amid my classes. Potentially offering my commentary felt intrusive.
That didn’t mean her songs weren’t playing on the edge of my ears all day. I’ve enjoyed “vampire” throughout the several elapsed weeks since its music video dropped, but it was the final track that I found myself thinking about during every break I had.
Glancing at the track list before beginning my first listen at 2:45 AM, the title immediately caught my eye. “teenage dream” immediately evoked the identically-named Katy Perry track (that I infinitely prefer Darren Criss’s rendition from Glee! to).
Is this a cover? I wondered. Why would she end the album with a cover?
Rodrigo’s “teenage dream” is no cover, though; the song could not be further from its pop predecessor. Whereas Perry belts out a wish-fulfillment fantasy of the future complete with cliche invitations to a lover like “Let's run away and don't ever look back, don't ever look back”1 and “We can dance until we die//You and I, will be young forever”, Rodrigo wrings every bit of unbridled optimism out from her version.
Somber and anxious, “teenage dream” is insecurity from its very first lyrics. It opens with a series of questions:
When am I gonna stop being wise beyond my years and just start being wise?
When am I gonna stop being a pretty young thing to guys?
When am I gonna stop being great for my age and just start being good?
When will it stop being cool to be quietly misunderstood?
Acting and performing for most of her youth, Rodrigo notes the praise she’s heard but lingers on its implicit condescension. A compliment like “great for your age” might send a fifteen-year-old to the moon, but now Rodrigo hears it less as joyous than cautionary. Everything that set her apart thus far, she posits, has been judged relative to her 2003 date of birth. In this verse, she betrays fatal self-awareness; this is her realizing that precociousness won’t carry her any longer. It’s difficult to argue her point, I might add: while discussing “drivers license”, even I waxed poetically about Rodrigo’s beyond-her-years maturity.
There’s no stronger song thematically to invoke alongside “teenage dream” than “drivers license”. Once again, we see Rodrigo wearily regarding a threshold—it’s birthday candles here—and once again, disillusionment becomes the heartstring of the piece. Her lamentation after extinguishing the flames atop her cake—“I fear that they already got all the best parts of me”—is a numbing dagger of self-awareness: she might have already peaked.
Amid so many questions, it’s the final one she submits to close the song that says it all:
Oh, they all say that it gets better
It gets better the more you grow
Yeah, they all say that it gets better
It gets better, but what if I don't?
Listening to “teenage dream”, I feel less heartbroken than I feel heartbroken for her. Rodrigo’s uncertainty, her distrust of that canned narrative of perpetual progression—both are loud and palpable at school during those terms when I’m surrounded by 75 Calculus BC seniors. Even the most brash among them still hesitate; all of them feel some dread for the approaching unknown. They see through the inductive leap that the previous generation hurls downstream for them to nibble on.
How can that promise of a brighter tomorrow convince me? they wonder, regarding the chaotic world dumped at their feet. What if this, right here and right now, really is as good as it gets? These kids are barely kids, and most are savvy enough to feel growling vacancy in the “It gets better” platitude. Even when they want to believe it, there’s a struggle to assure themselves that it even might get better. It might? All this for might??!
Unlike Perry’s song, which conveys its perspective immediately, Rodrigo’s “teenage dream” took me a few plays to puzzle out. Both feature several runs of second-person point of view, but Rodrigo isn’t addressing a romantic partner like Perry nor some cold ex-boyfriend as she did in “drivers license”. It’s all there in the song’s most devastating line.
For Rodrigo, it doesn’t feel any better on the other side of those nineteen candles. The future she once hoped for isn’t anywhere to be found in the melancholic limbo she’s aged into. She could be singing to anybody who once told her to look forward, but in this crushing moment, she is alone with those platitudes she’s discovered are as bare as she’d feared.
And I'm sorry that I couldn't always be your teenage dream
Drenched in regret and clear-eyed woe, Rodrigo sings these words to her younger self.
*****
People always laugh when I talk about my feelings toward the Santa Claus myth, and too many miss the truth hiding in plain sight: I am authentically bothered that I was lied to about the man’s existence. Come at me all you want with your talk of good intentions and inspiring wonderment; I can totally see every single one’s validity. I still resent that so many people lied to me. The magnitude of my discomfort with this deception carries far more nuance than the meme objection people often hear.
Setting aside that nuance for now—feel free to read this piece if you want more—I bring this up because it speaks to a fundamental truth about how I use the pedestals I speak from. Unlike those who leverage their authority to sing sanitized songs that repeat the closing refrain in “teenage dream”, I resist painting syrupy sweet scenery while eyeing smoggy horizons. My position working alongside older high school students suits my inclination: these are the young people with sufficient life experience under their belts to grasp some subtlety.
When I speak at Diamond Day, I paint a hopeful picture of what lies ahead, but I refuse to promise everlasting sunshine. I already know that it might not get better for everybody; I’m wholly aware that our respective teenage dreams may fail to have been prescient. It’s right there on the giant Post-it paper where I draw with a purple scented marker: the future I describe from my distant-to-them place in the middle of it is not some ascending linear arrow tending directly to infinity but a massive sine curve summed with a line. Gradual growth that mitigates the ups and downs is what I map back for those who listen to my monologue. I don’t even proclaim it their future; I call it a valid goal for their forward progress as people.
I don’t promise a trajectory toward some safe harbor, free from failure and heartache, because that isn’t how life works. There are good days, and there are bad days. Internalizing an expectation for bumps and bruises equips them to stay the course, to labor through the valleys while seeking the soaring vistas of subsequent peaks.
It’s so tempting to paint a rosier picture. It would make them so happy! But I still feel the burn from Santa Claus because I feel all the other burns from those who sheltered me from the truth. Life doesn’t just turn easy someday; happiness doesn’t just move in one night and carve out a corner of the couch so it can hang around until we expire. Every person who told me one of those lies meant well—I don’t fault their intentions—but they were lies, lies that only deepened my darkness every time I couldn’t gain traction in Shangri-La. I know that sharing sobering candor inflicts a wound on the truth-teller—pointing out sad realities means you’ve noticed them too—but I still wish they would have grabbed a bandaid and let me journey into tomorrow with open eyes.
In this way, I suppose I should be proud of myself for that honesty to Kyle thirteen years ago. Given the opportunity to lie and pretend that his heartache was destined to wash away, I offered instead pragmatic honesty. I told Kyle what, I suspect, is the truth.
And yet, retroactively, I feel terrible about what I said.
Listening to “teenage dream” on repeat for ten minutes that became ninety, I couldn’t escape a nagging sense of responsibility. Shouldn’t I feel proud to have shared the harsh truth with Kyle that Olivia’s elders never did with her? The answer should be yes, but it doesn’t register that way.
Instead of grave vindication while Olivia’s voice haunts her “But what if I don’t?” question into my inner ear ether, I find myself staring at the Remind app. What would I say if I got a message one Thursday from “o-rod” that spelled out this anxious distrust of the promised pleasures just around the bend? Would I actually tell her there might not be any? What if a new seventeen-year-old Kyle sent 37-year-old me the same question I fielded at 24? How would I respond to his earnest, wounded query about adult friendship?
For calculus-enrolled Olivia, I’d talk about the renegotiation of our enduring teenage dreams. We can enjoy listening to Perry (or Criss!) sing through their fantasies, but such is not—and need not be—the norm. Part of growing older is understanding that unwavering fidelity to our old expectations is unhealthy. As we (and the world) change, so too will the future we want. With greater exposure and wider communities, we become different people than the ones we extrapolated to as teens. There are dissonant notes that play as the melody we once hummed transforms, but modulation between keys always sounds a little bit crunchy. The part of me that can’t discern the final snippets of people talking after the last notes of “teenage dream” curses age’s impact on my ears, but that very same time culpable for my physical erosion is the one that equips me with this perspective. Deviation from old expectations need not be fatal.
For Kyle, though, I went many years where I couldn’t have manufactured a better answer. Even when I talked about magnets and ripped beautiful truth out of a hopeless place two years ago, I still understood that, at heart, my promise carried ripples of pungent sourness. Yes, those good friends vacate the active roster of your life—but it’s great when y’all come together! Just like old times! As they bite into the truth tart I baked them, I hope they chew right through the suspicious wisp of “if” where I technically said “when”.
I stand by my magnets metaphor, but fortunately for the Kyles of tomorrow, my response evolved just this week. It’s been two months since I last saw my best friend, a data point that might disappoint the 2010 edition of Kyle. Others among my closest friends I haven’t seen in weeks or even months. Worse yet, some days, I don’t even notice their absences, too swallowed up by the breakneck pace of adulting.
But Thursday, four hours before GUTS landed in my iTunes library, I connected with one of those cherished friends. It was only through words—literal black text on a white screen—and yet the person felt so impossibly close. I lost track of where I was and what I had intended to do; there was no world around me except that one occupied by the two of us. I was alone where I stood, but yet I was anything but.
Sometimes, we must settle for magnets. That’s the truth. Life’s complexities often command circumstances that shear the characters populating our teenage dreams out of our stories. Yes, Kyle, that does suck. It’s special when the special people are around for every event. But the thing I didn’t understand at 24 that I do at 37 is that one needs only the thinnest slivers to elicit those deepest relationships’ powers. Every interaction you do get, whether a dedicated day trip to the Bay Area or merely a movie and meal followed by talking in a car, is so much richer. It’s richer because of everything that came before it.
Those connections don’t feel slight because each one carries all the accumulated love from earlier moments. All it takes to experience that intense, glorious connection is a single message. It isn’t electromagnetism where proximity activates an effect that otherwise lies dormant; it’s there all the time. All day, every day. The most powerful connections form the fibers in our souls.
I know this might sound like the chorus of a sad song, but these truths I’m about to share don’t promise misery. Please. Hear me out.
No, Olivia, you might not live the future your younger self yearned for. And no, Kyle, you might not see your best friend all that often. In both cases, that’s okay.
Because when you finally arrive in that far-off tomorrow, you’ll realize you don’t need to follow any specific script. When you reach that moment, you’ll know I told you the truth. You’ll feel it.
You’ll feel in your guts.
It’s already been a very long week, and it is *checks phone* Wednesday. Ugh. But I was happy that the idea for this piece found me.
When I’m running on fumes, I tend to think big. Too big.
That is all.
This has bugged me for years. It should be “not” shouldn’t it? Right? Right??!
Ah yes, the sort-of industry plant Olivia Rodrigo... while I'm personally not the biggest fan out of overexposure, her songs are popular both because and despite that they fall outside the pop dichotomy of heartmake and heartbreak. Themes that ring with the apathy of a younger generation privileged every way but emotionally are especially poignant in a time with too little time for others and too much focus on material gains - the car, the ice cream, the desirable romantic partner. The lyrics' strong spite fascinate with how they take the transactionality typical in love songs and establish the return and exchange policy rather than shopping, buying, and selling romance.
The part you wrote about your old friends made me think about the relationships I have with my own. To say that things could go well is no lie, as is to say things could go bad, but framing possibilities in the extremes creates a risk of reducing reasoning for an artificial dichotomy. Undeniable anxiety enters between that old hallowed ground of memory and the new arena where old acquaintances become strangers and friends test new boundaries. There are always "friends" who talk if they need something, but fall off because of either a lack of interest, an abundance of other connections, or what may be perceived as the impossible idea of asking for others without looking needy.
Sometimes, sending a video, a meme, or a random thought sparks enriching conversations; texting some of my upperclassmen as a senior helped preserve some of the relationships I now cherish, and a regular group chat without forced activity can be a great joy. I wish I had the easygoing confidence of calling whenever like some of my other pals, but that's something I'll have to develop as I grow older - I believe that sometimes ageism is warranted when I see how much I still don't know.
Perhaps getting involves with more people creates harder maintenance periods - sometimes, getting back to different people all at once feels like a job, or an engaging game - but the unique embers of human connection in all its unlikelihood make all that effort worth the balance.
I had someone who brought up the album tell me her least favorite song is “teenage dream” this week. When I expressed mellow surprise, I asked if she’d listened to its namesake. “Never heard of it,” I was told. My point: it’s as interesting to hear where people with vastly different life experiences land on this stuff as it is to think through it myself.
I appreciate what you’ve shared here, especially the false dichotomy idea. Very few of us, I’d bet end up in precisely the life of our dreams or our nightmares. It’s usually grayer than the blacks and whites so many people and media angle us toward. I trusted those older than me who told me that there was a recipe to success and that happiness was a five-digit zip code. Maybe that was my age’s fault—I’d bet I’m among the few Red Ribbon signers who actually has been as drug free as those pledges compelled me to be—but I’d rather not be that person. I’m happy when young people embrace these songs because it’s means they’re getting a richer picture than the ballads I blasted paint for me. It’s harder to get crushed by a future below an old ideal when a person’s been humming ambivalence during their formative years. I swear it’s all adjacent to Sweet Appeal: a great future isn’t one narrow path but accessible via several forks.
As for the “making room” mindset for friends, that is my favorite outcome (and legitimately the motivation for every word of this piece). As kids, we equate friendship to be the times we are together; as I’ve aged, I’ve discovered that it’s also the times in between. It takes real connection to exist without daily proximity. I didn’t understand that at 24; I do much more so at 37.
Again: thanks for a meaningful response. Enjoy your first week!