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 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.

“August” – Folklore

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 sun
Wishin’ I could write my name on it
Will you call when you’re back at school?
I remember thinkin’ I had you
But I can see us lost in the memory
August slipped away into a moment in time
‘Cause it was never mine
And I can see us twisted in bedsheets
August 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.

“Back to December” — Speak Now (Taylor’s Version)

“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 pride
Standin’ in front of you sayin’ I’m sorry for that night
And I go back to December all the time
It turns out freedom ain’t nothin’ but missin’ you
Wishin’ I’d realized what I had when you were mine
I’d go back to December, turn around and change my own mind
I go back to December all the time
I miss your tan skin, your sweet smile
So good to me, so right
And how you held me in your arms that September night
The first time you ever saw me cry
Maybe 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.

“Enchanted” — Speak Now (Taylor’s Version)

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 go
I’m wonderstruck, blushing all the way home
I’ll spend forever wondering if you knew
I was enchanted to meet you
The lingering question kept me up
2 AM, who do you love?
I wonder ’til I’m wide awake
And now I’m pacing back and forth
Wishing you were at my door
I’d open up and you would say, “Hey”
It was enchanting to meet you
All I know is, I was enchanted to meet you”

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

“All Too Well” — 1989

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 night
We’re dancing ’round the kitchen in the refrigerator light
Down the stairs, I was there
I remember it all too well, yeah
And maybe we got lost in translation
Maybe I asked for too much
But maybe this thing was a masterpiece ’til you tore it all up
Running scared, I was there
I remember it all too well
And you call me up again just to break me like a promise
So casually cruel in the name of being honest
I’m a crumpled-up piece of paper lying here
‘Cause I remember it all, all, all
Too well”

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

“I Almost Do” — Red (Taylor’s Version)

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 bet
This time of night, you’re still up
I bet
You’re tired from a long hard week
I bet
You’re sittin’ in your chair by the window
Looking out at the city
And I bet
Sometimes you wonder ’bout me
And I just wanna tell you
It takes everything in me not to call you
And I wish I could run to you
And I hope you know that every time I don’t
I almost do
I almost do
I bet
You think I either moved on or hate you
‘Cause each time you reach out there’s no reply
I bet
It never ever occurred to you
That I can’t say “Hello” to you
And 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.

“Long Live” — Speak Now (Taylor’s Version)

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 feeling
I passed the pictures around
Of all the years that we stood there on the sidelines
Wishing for right now
We are the kings and the queens
You traded your baseball cap for a crown
When they gave us our trophies
And we held them up for our town
And the cynics were outraged
Screaming, “This is absurd”
‘Cause for a moment, a band of thieves
In ripped-up jeans got to rule the world
Long live the walls we crashed through
How the kingdom lights shined just for me and you
I was screaming, “Long live all the magic we made”
And bring on all the pretenders; I’m not afraid
Long live all the mountains we moved
I had the time of my life fighting dragons with you
I was screaming, “Long live the look on your face”
And bring on all the pretenders
One day we will be remembered”

Belly had the time of her life with Conrad.

“Invisible String” — Folklore

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 grass
Where I used to read at Centennial Park
I used to think I would meet somebody there
Teal was the color of your shirt
When you were sixteen at the yogurt shop
You used to work at to make a little money
Time, curious time
Gave me no compasses, gave me no signs
Were there clues I didn’t see?
And isn’t it just so pretty to think
All along there was some
Invisible string
Tying you to me?”

Conrad has always been tied to Belly.

“Snow on the Beach” — Midnights

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 ago
I saw flecks of what could’ve been lights
But it might just have been you
Passing by unbeknownst to me
Life is emotionally abusive
And time can’t stop me quite like you did
And my flight was awful, thanks for asking
I’m unglued, thanks to you
And it’s like snow at the beach
Weird but fuckin’ beautiful
Flying in a dream, stars by the pocketful
You wanting me tonight feels impossible
But it’s comin’ down, no sound, it’s all around
Like snow on the beach
Like snow on the beach
Like snow on the beach
Like 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.