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Jan 27, 2024

Taylor Swift Songs We Need to Hear in Season Two of ‘The Summer I Turned Pretty'

This article contains spoilers for the Jenny Han book trilogy, The Summer I

This article contains spoilers for the Jenny Han book trilogy, The Summer I Turned Pretty.

Grab your beach bags, tissues, and your infinity necklaces because we’re headed back to Cousins Beach for season two of The Summer I Turned Pretty, and after the debut of the first teaser trailer and the beautifully redone song by Taylor Swift, we’ve been dreaming of all things Conklin, Fisher, and summer this afternoon.

For those who read Jenny Han's book trilogy years ago, the story has always seemed deeply intertwined with Swift; even before the series and the moments in which her beautiful songs helped drive a story forward, there seemed an unspoken connection between them. Han's characters seem fit for a Swift-narrated world, and they were so perfectly suited for it, in fact, that when the series premiered, it felt like Christmas morning every time one of her songs played in an episode. Belly loving Conrad felt like a Swift song, as did the moments when she couldn't understand why he was breaking her heart.

While the first season ended on a beautiful note for our true OTP, season two is going to take our dream couple through more ups and downs than they could have prepared for when they shared their long-awaited kiss on the beach, and as the teaser trailer for season 2 proves, Swift will be right alongside them for the musical stylings of their love and heartbreak.

Here are the Swift songs we hope to hear play during the highs and lows of Belly and Conrad in season two, and here's hoping there are more smiles than there are tears.

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Our journey back to Cousins Beach is just on the horizon, and the teaser trailer that invented us back to the next chapter of our favorite summer love story kicked off with the most incredible Taylor Swift song — and it brought tears to our eyes. "August" is a song about longing, something Belly has experienced for most of her life when it comes to Conrad, but it's not exactly the song of great promise and adoration you might have been crossing your fingers for.

Anyone who has read Han's trilogy knows that the road to love isn't easy for Belly, Jeremiah, or Conrad, but that didn't mean that there wasn't a small and naive part of us that hoped we’d avoid some heartache where Belly and Conrad were concerned. As the teaser unfolds, however, we learn that we won't be spared tears this summer.

"Your back beneath the sunWishin’ I could write my name on itWill you call when you’re back at school?I remember thinkin’ I had youBut I can see us lost in the memoryAugust slipped away into a moment in time‘Cause it was never mineAnd I can see us twisted in bedsheetsAugust sipped away like a bottle of wine‘Cause you were never mine"

The silver lining here is that if we’ve got to spend a summer with tears in our eyes, there's no place like Cousins to do so, and no soundtrack like Swift's voice to help us through it.

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"Back to December" just has to be on the season two soundtrack for several reasons, one of which has to deal with a specific trip to Susannah's beach house between just Conrad and Belly; fans know that the hot cocoa scene at the beach is as important to Han and co as it is to all of us, and we were already shown a script page with that very scene.

It's a critical moment for Belly and Conrad, and while they understand the weight of it as they’re experiencing it, it's impossible that they’d have been able to grasp what it would grow to mean to them. While the season will undeniably throw curves in the love story of Conrad and Belly, there will be scenes of longing once more. How perfect (and tear-inducing) would a scene be with Belly looking back at this moment?

While that in itself would be quite the scene, it would be even more powerful if it were Conrad looking back at it and hearing this song; be still our beating hearts.

"So this is me swallowin’ my prideStandin’ in front of you sayin’ I’m sorry for that nightAnd I go back to December all the timeIt turns out freedom ain't nothin’ but missin’ youWishin’ I’d realized what I had when you were mineI’d go back to December, turn around and change my own mindI go back to December all the timeI miss your tan skin, your sweet smileSo good to me, so rightAnd how you held me in your arms that September nightThe first time you ever saw me cryMaybe this is wishful thinkin’Probably mindless dreamin’But if we loved again, I swear I’d love you right"

Here's to going back to December for Belly and Conrad, and Swift's song helping us through it.

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As we’ve said before, we can't be sure what pieces of the books will translate to the Prime Video series, but Han hasn't strayed too far away from the source material so far. So while we are crossing our fingers for at least a beautiful dance or two between Conrad and Belly after that teaser trailer, we’re not banking on it.

If we could dream up the right prom song and dance moment for them, however, it would be this: Conrad asking Belly to dance, ushering her out onto the floor in her beautiful purple dress, and this song playing as their background music. Belly has always been enchanted by Conrad, and he's always been taken by her too.

If we don't get this in a prom moment, maybe it could be playing in the background as Belly anticipates the big dance. She knows things between them haven't been perfect, but she's still that "same old Belly" who believes in the magic of what they have — he still enchants her in every moment.

"This night is sparkling, don't you let it goI’m wonderstruck, blushing all the way homeI’ll spend forever wondering if you knewI was enchanted to meet youThe lingering question kept me up2 AM, who do you love?I wonder 'til I’m wide awakeAnd now I’m pacing back and forthWishing you were at my doorI’d open up and you would say, "Hey"It was enchanting to meet youAll I know is, I was enchanted to meet you"

We, too, are enchanted by the magic of Belly and Conrad.

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While Belly's heartbreak isn't something she experiences in isolation, it stays a part of her after she and Conrad separate. Yes, book lovers know that Belly and Jeremiah end up giving things a go once more, but Belly herself admits that she still dreams of Conrad; as we all know how impossible it is to give up on your first love, especially when the person you love is hurting so much.

Everyone in the Fisher and Conklin families will undeniably be in a place of heartache and turmoil when we see them again for season 2 of The Summer I Turned Pretty, and depending on how much is told in flashbacks vs. real life, we may only get a few brief moments of joy between them. So we think "All Too Well" would be the perfect song for one of those moments when Belly dreams of Conrad, when she spends time thinking of him and their time together — wondering if he remembers, too.

"‘Cause there we are again in the middle of the nightWe’re dancing ’round the kitchen in the refrigerator lightDown the stairs, I was thereI remember it all too well, yeahAnd maybe we got lost in translationMaybe I asked for too muchBut maybe this thing was a masterpiece 'til you tore it all upRunning scared, I was thereI remember it all too wellAnd you call me up again just to break me like a promiseSo casually cruel in the name of being honestI’m a crumpled-up piece of paper lying here‘Cause I remember it all, all, allToo well"

Conrad always remembers; that's the silver lining in that.

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When it comes to reflection, no one takes it harder than Conrad. When we first greet him in The Summer I Turned Pretty; we hear a lot about how he's changed. No longer the boy with dreams in his eyes, life seems to have hardened him. As the story unfolds, we learn why — he found out his mother's health secret, and he's trying to be strong for everyone else.

When season two comes around, fans are gearing up for the heartache that lies just around the corner; for the loss that will inevitably shake everyone to their core. While Conrad will have to shoulder more weight than he's responsible for, trying to take care of everyone around him, he’ll let Belly slip from between his fingers — and it’ll wreck him. As he looks back at their time together, we have a feeling this Swift song would be playing in his head.

"I betThis time of night, you’re still upI betYou’re tired from a long hard weekI betYou’re sittin’ in your chair by the windowLooking out at the cityAnd I betSometimes you wonder ’bout meAnd I just wanna tell youIt takes everything in me not to call youAnd I wish I could run to youAnd I hope you know that every time I don'tI almost doI almost doI betYou think I either moved on or hate you‘Cause each time you reach out there's no replyI betIt never ever occurred to youThat I can't say "Hello" to youAnd risk another goodbye"

Of course, the same sentiment exists for Belly; she can't say hi to Conrad again without the knowledge that there would be something else to rip them apart — and we’re not crying, you are.

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I’ll be honest with you, this song choice and 11:11 wish is a little bit self-indulgent, but hear me out: Swift fans can all relate this song to a great first love. The kid you grew up playing on the playground with, the one you fought dragons with, the one you had all of your not-so-serious but life-altering firsts with. There's something about growing up together, about pieces of time that belong to you and that person; it cements first love as the best love — the one you allowed your hopes and dreams to exist within.

Belly and Conrad's love story is a lot like that; it's that first true love feeling, the embodiment of taking on the world together, and no song sums that up better than Swift's "Long Live."

The teaser released today shows that we’ll get either a current timeline or flashbacks of a happy Belly and Conrad, and we’re crossing our fingers that somewhere in the midst of it, we’ll hear notes of this song. It's magical; it's full of hope and love; it's Belly and Conrad — and your own first love story, too.

"I said remember this feelingI passed the pictures aroundOf all the years that we stood there on the sidelinesWishing for right nowWe are the kings and the queensYou traded your baseball cap for a crownWhen they gave us our trophiesAnd we held them up for our townAnd the cynics were outragedScreaming, "This is absurd"‘Cause for a moment, a band of thievesIn ripped-up jeans got to rule the worldLong live the walls we crashed throughHow the kingdom lights shined just for me and youI was screaming, "Long live all the magic we made"And bring on all the pretenders; I’m not afraidLong live all the mountains we movedI had the time of my life fighting dragons with youI was screaming, "Long live the look on your face"And bring on all the pretendersOne day we will be remembered"

Belly had the time of her life with Conrad.

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This one needs no explanation, and the first time we thought of it, the scene in the picture above came to our mind. It was a stolen moment between Belly and Conrad. She’d just seen him kissing another girl at the beach after a tough conversation at home, and she was still trying to find out where her Conrad had gone.

In the car, he twists her hair between his fingers and tells her something sweet, something her Conrad would say; and it all comes flooding back. We have a feeling season two will be full of more of those moments, and their romance is the epitome of Swift's "Invisible String," there's something that's always been pulling them back to one another.

"Green was the color of the grassWhere I used to read at Centennial ParkI used to think I would meet somebody thereTeal was the color of your shirtWhen you were sixteen at the yogurt shopYou used to work at to make a little moneyTime, curious timeGave me no compasses, gave me no signsWere there clues I didn't see?And isn't it just so pretty to thinkAll along there was someInvisible stringTying you to me?"

Conrad has always been tied to Belly.

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This one goes hand in hand with "Back to December," and that integral scene when Conrad and Belly go to the Cousins Beach house in the middle of winter. They sneak away, spending a night together in a home that's usually full of the rest of their people, life, love, and noise.

This time, it's just for them — they spend a night together with Belly's hot cocoa, and they go to experience something special, snow on the beach. In our minds, this song shows up in the series like this: Belly is driving on her own or to see Jeremiah, and we hear the notes of it — it's on the radio, and soon, she's living in that moment again.

Conrad is taking a night drive, going somewhere to clear his head and try to make sense of his heartache, and this song comes on. Suddenly, he's caught between a smile and a tear — thinking of his time with Belly like snow on the beach, magical but fleeting — something he's undeserving of witnessing more than once.

"One night, a few moons agoI saw flecks of what could’ve been lightsBut it might just have been youPassing by unbeknownst to meLife is emotionally abusiveAnd time can't stop me quite like you didAnd my flight was awful, thanks for askingI’m unglued, thanks to youAnd it's like snow at the beachWeird but fuckin’ beautifulFlying in a dream, stars by the pocketfulYou wanting me tonight feels impossibleBut it's comin’ down, no sound, it's all aroundLike snow on the beachLike snow on the beachLike snow on the beachLike snow, oh, oh oh"

If only Conrad realized that Belly would travel infinity with him forever.

Of course, there are many other Swift songs we’d love to hear in the second season of The Summer I Turned Pretty, but for now — after watching the teaser more times than we can count, these are the tunes we’re hoping hit our ears this summer as we see Belly and Conrad in all of their ups and downs together.

Ashley Marie is a staff writer, beat leader, Disney fanatic, and Yellowstone expert. When she's not filling her friends in on all the entertainment news they can handle, she's drinking her go-to Starbucks order — a caramel macchiato, thank you — and wishing she was at Disney World or spending time at the Yellowstone Dutton Ranch. With a focus on positivity and kindness in journalism, Ashley has been writing for a decade and hopes to keep bringing you articles for decades to come.