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Jesse James Rose’s Book Notes music playlist for her memoir sorry i keep crying during sex

“Off the page, when I was living this story, music got me through the hardest moments and helped me celebrate the happiest.”

In the Book Notes series, authors create and discuss a music playlist that relates in some way to their recently published book.

Previous contributors include Jesmyn Ward, Lauren Groff, Bret Easton Ellis, Celeste Ng, T.C. Boyle, Dana Spiotta, Amy Bloom, Aimee Bender, Roxane Gay, and many others.

Jesse James Rose’ssorry i keep crying during sex is heartrending memoir that wields its vulnerability and dark humor to profound effect.

Publishers Weekly wrote of the book:

“Rose debuts with a heartbreaking and genre-bending exploration of grief, trauma, and gender identity. The emotional intensity and sexual candor won’t be for everyone, but open-minded readers will be wowed—especially if they’re grappling with their own self-definition.”

In her own words, here is Jesse James Rose’s Book Notes music playlist for her memoir sorry i keep crying during sex:

Music is at the heart of SIKCDS. There’s a rhythmic cadence to the Tumblr-style comedy, pop songs are mentioned to ground us in time and space, and sounds like laughter, crying, and moaning appear in nearly every scene. Off the page, when I was living this story, music got me through the hardest moments and helped me celebrate the happiest. I’ve compiled some of them for you to listen along with, if you so choose. They’re marked with page numbers so you can match the moment to the song as you read, if you so choose. Some are mentioned in the book, others are what I was listening to at that time, a few are songs so current that I picked them out while writing this piece. Let the music move you, buoy the story, soothe you, cry with you, whatever you need. These songs held me and now I’m giving them to you to hold.

All my love,

Jesse James Rose

I.

“Well You Don’t Wanna Hear about 9/11” – Mariah Carey

I know this isn’t technically a song, but she said it about her album!! In case you forgot, Mariah Carey released the soundtrack to her film Glitter on September 21, 2001, ten days after 9/11. The soundtrack was a commercial flop – her only album without a number one hit – but it is credited for saving one person’s life on 9/11. In a Global Citizens Festival concert many years later, Carey gave us this iconic clip which I used as my epigraph. Perhaps your reaction will be similar to Carey’s concert audience. By the end of the book perhaps you’ll understand.

(p.17) – BLOOM – Troye Sivan

This was actually the song playing at the time, I remember it distinctly. Even then I saw the irony between the lyrics and the moment:

“I bloom just for you // I bloom just for you.”

I was emotionally willing to bloom for Finnegan, but physically closed off as a result of my recent trauma. He was physically blooming for me, but emotionally closed off. This song has a cheery backbeat to it, which represents where I wanted this moment to be, what I wanted it to feel like…but not at all what it was.

I first alluded to this song on p.7 (did you catch that?) which begins one of the only ways I mark time in the book; pop culture songs. You can measure the distance between the release date of this song, and the last one mentioned in the book to get a general idea.

(p. 19) – YOUR SIDE OF THE BED – LOOTE

This is my go-to Slutwalk Song! If you’re not familiar, a Slutwalk Song is what you play when you’re walking over to a man’s place who’s going to do all the things to you (consensually!!!!) that men do to/with/on/around/inside me in these Hookup vignettes.

The lyrics represent exactly what I was thinking with #5:

            “I got me someone else instead
he’s taking your side of the bed.”

For years to come I would listen to this song on my Slutwalks – I felt sexy, it pumped me up, it drowned out how nervous I was each time.

(p. 36) – Sleep Tight – Holly Humberstone

At this point you know there’s been at least ten men before, so you know this is a pattern I’m repeating. I’m chasing a feeling – a high, a connection, an orgasm. A need to be seen for who I am. The lyrics here perfectly capture the moment.

“…In the back of your car
We’re gonna take it too far
God knows I’ve missed this
I missed this feeling

You take off your jeans and
My heart started screaming
God knows I’ve missed
God knows I missed this feeling.”

I did miss it. I missed being loved, held, fucked, wanted.

(p.56) – KISSING ON YOUR DAD – Myylo

This cheeky song cracks me up every time I hear it. It was introduced to me by one of my great singer-songwriter friends (shoutout Kate Yeager!) and it absolutely encapsulates the feeling of wanting to fuck someone’s dad….in the shower at the gym. Oops.

(p.70) – Ready to Love You – HEDEGAARD

This is another one of those played-it-at-the-time songs. I remember looping this track over and over on the way to dates with Finn, because I was “ready to love [him].”

There’s something about the production of this remix that feels like a summer dreamcloud to me, which is how I want all the snapshots with Finn to feel like. Primrose sunsets. Cherry Coke. Stained popsicle sticks. Sunglasses. Sandals. Kisses on scruffy necks. A Teenage Dream, but one that only lasts a few minutes.

“Why’d you gotta go and do that?
Steal my heart up in a whiplash
Didn’t know I could be kissed like that, no.”

Imagine a montage of moments with Finn – running down the street, eating ice cream, laughing after sex – against the instrumental chorus. Imagine the beat is the sound of my heart pounding.

(p. 82) – The Wizard & I – Ana Gasteyer

LET’S GET INTO SOME WICKED LORE. Wicked is making a comeback, I know, but you have to understand I AM AN ORIGINAL FAN. I grew up on bootlegs of Idina, Stephanie, Ana, Shoshanna, and Eden. They raised me. It would take me way too many years to figure out I was a Glinda because all I wanted to do was belt Elphaba’s songs.

ANYWAY, everyone knows Idina was the first Broadway Elphaba, but everyone forgets that Ana Gasteyer was chosen to lead the second professional company of Wicked in Chicago. This is almost absurd to think now – considering all our current Elpahabas are vetted, tried-and-true beltresses and Gasteyer is largely known as a comedian. But TRUST ME – watch this performance. Her notes may not be pitch perfect, but they’re honest. I believe every word she’s saying. I believe she’s an outcast. I understand why she’s screlting these high notes, because she needs what she’s singing about so badly. You can find Broadway recordings where she’s pitch perfect and it’s wonderful, but to me there’s something magical about the rawness of this clip – Wicked in its earliest stages, Ana as the saddest, most sincere, heartbreaking Elphaba.

It really has no connection to the book other than that I mention it in this chapter, but I thought you should know the thesis of my defense.

(p. 88) – Juno – Sabrina Carpenter

This gumdrop pop melody sounds like what being fucked by Felipe. The guitars sound like stars in someone’s eyes, and the lyrics get at something deeper I was feeling in this chapter: letting someone do something to me (doggy for me, pregnancy for Sabrina) because I like them so much.

“…God bless your dad’s genetics…”

is such a funny line. I played this song for my best friend Zach and he said “Jesus. Of course you’d be thinking about someone’s dad while they fuck you.” We laughed so hard we had to replay the song.

(p. 97) – Between the Lines – Sara Bareilles

This is the first scene written as a play in the book, and intentionally so. I don’t imagine there would be music in the play version of this book, but if I were getting into character for this scene this is the song I would play. These lyrics always hit me:

“Until now
He told me her name
It sounded familiar in a way
I could’ve sworn I’d heard him say it ten thousand times
Oh, if only I had been listening.”

They capture the moment I see how fractured my relationship is, and how long I’d either been in denial, or not noticed. “Leave unsaid unspoken,” from the refrain, captures the last moment when I refuse to answer Finn over and over again.

(p. 109) – Duck Duck Goose – cupcakKe

At first listen it might sound like this song embodies the absurdity of the orgy. And at face value that’s true; the hypersexualized lyrics mirror the graphic sex of this chapter, and in the context of this playlist bring a clearly distinct vibe to this collection. To me the meaning is deeper – cupcakKe has publicly spoken about being a survivor of childhood sexual violence, and one could theorize her work blends humor with criticism of society’s views of sexuality. If this song were played over the orgy montage in the HBO 6 episode miniseries of my memoir you might laugh, but by the end of the scene you might not.

(p. 126) – NISSAN ALTIMA – Doechii

I almost picked “ANXIETY” instead – because the growls in the background remind me of the growls in this chapter, but the lyrics in “NISSAN ALTIMA” touch on some main developments at this point:

“Wake up, A-cup, get your tits sucked
In my makeup, face-fuck, get your bake up”

alludes to how I’m exploring femininity, how I like that it’s something I can sexualize, and it’s small boob representation! I love that this refrain (and the rap that follows) comes flying at you almost dangerously fast, because it reminds me of how I was flying though this time in my life (and flying through all of these men) at lightening speed.

Fun Fact: Doechii and I went to the same high school! I didn’t know her, but we were there at the same time!

(p. 135) – Cornelia Street / On The Street Where You Live – Me!

Back in 2023 I did a solo show in New York called “Men I’ve Had,” and my director Ali Funkhouser conceptualized this medley, and my music director Bree Lowdermilk made it happen. It perfectly blends two of my favorite things – musical theatre and pop – and the moment I’m describing in the show is exactly this moment in the book.

(p. 161) – The Subway – Chappell Roan

I distinctly remember the moment Finn disappeared from view – out of the park, down the street, and onto the subway. I love the structure of this song – it’s so rare to get a post-chorus in a pop song, and even rarer to get a second chorus like this. (Some claim it’s an outro, but I argue it functions more as a second chorus because it takes up the same amount of track time as the choruses combined and it follows a similar rhythmic progression). The way Chappell belts these lyrics guts me and takes me right back to this moment:

“She’s got, she’s got a way
She’s got a way, she’s got a way
And she got, she got away
She got away, she got away…”

In the HBO 6 episode miniseries this is the song that plays while we slow zoom-in on my reaction and cut to Finn disappearing into the crowd.

II.

(p. 177) – Not a Day Goes By – Stephen Sondheim

This is from a Sondheim musical called “Merrily We Roll Along,” in which the story of a close friendship is told in reverse chronological order. In the musical this song is sung by the ex-wife of a main character when they are fighting about their divorce. The first time I heard the song (back in musical theatre school!) I was struck by how well the lyrics illustrated seeing someone of significance to you for the first time in a long time. In many ways this is how I feel about my rapist, and if I were to get in character for this scene, this is the song I would use.

(p. 196) –  Anti-Hero (ft. Bleachers) – Taylor Swift, Bleachers

    Anti-Hero – ILLENIUM Remix – Taylor Swift, ILLENIUM

This one is mentioned in the book, and while it might hint at the amount of time elapsed since BLOOM, I believe she released it a year before I wrote this section of the book. I included it as a nod to a moment in my personal life that I don’t discuss in this memoir – In 2022 I left an acting contract the day before Midnights was released after I was sexually harassed. (I’ve spoken about this publicly on Instagram and Tik Tok, you can find all the details there if you’re willing to scroll back far enough). I drove home across the country and heard “Anti-Hero” for the first time and played it over and over and over again.

            “It’s me, hi
I’m the problem, it’s me.”

These lyrics hit me in the gut because I had just spent days listening to men in power tell me I was a “problem” in the workplace for organizing the women to come forward about the misconduct we were experiencing. While I have my critiques of Taylor (most notably her refusal to condemn the genocide in Palestine), screaming this chorus out the window of my rental car was exactly the therapy I needed at the time. I included this song in the book mostly as a way to honor the many other sexual offences I’ve endured but ended up cutting from the book for clarity’s sake.

(p. 197) – Heart to Break – Kim Petras

This is another song that’s loosely mentioned in the book, or, well…the singer is! Ordinarily I wouldn’t include a song by an artist who has publicly supported an alleged rapist, but this happens to be the song that my rapist was playing when I arrived at his apartment that night in October. He was trying out new songs for his SoulCycle class. It only felt right to include a hint to this in the book.

(p. 205) – TOXIC – promising Young Woman

As an eternal Promising Young Woman stan this rendition rocked me to my core. Imagine it playing the moment I start moving towards the showers. Enjoy what comes next. It was one of my favorite scenes to write.

III.

(p. 236) – In A Stranger’s Arms – LEON

I only vaguely address this in the book (way back in the first hookup, #5) but I was taking such a safety risk with my continued pursuit of sexual activity. Considering each of these hookups comes after my assault I knew All Too Well (10 minute version) how terrifyingly bad things could go. And yet, I kept pursuing it. Part of it I’m sure was my PTSD trying to “re-mark” my rape (albeit ineffectively) with better experiences, part of it was my insatiable desire to feel worthy, part of it was because it felt good.

            “And you’ll risk it all to feel it all like the first time
In a stranger’s arms…”

Despite the fact that #114 ended up becoming a real-life friend, these lyrics speak to the moment. I did “risk it all to feel it all” in strangers’ arms. It worked, in a way. I wouldn’t recommend this – in fact I think this book might serve as a cautionary tale against some of my methodology – but I think it’s beautiful that this song captures how everyone who means something to me was once a stranger. There is always risk.

Imagine walking home from my time with #114 with this song playing. Compare it to the first Slutwalk. The music will tell you what changed.

(p. 246) – Heart to Mind – Alex G / Alex Blue*

In the HBO 6 episode miniseries of my memoir this is the song that plays with the final image on the road as the credits play. It’s perhaps the most special song to me on this list, because it’s the song I played on loop when I was bedridden after my assault. I used the chorus as a mantra; a reminder to be gentle with myself, that one day I would be free of this.

“I’ll take it easy on me
I’ll find an open highway
I’ll drive, drive, drive
Until I’m free from heart to mind
From heart to mind.”

*Note: Alex Blue changed her name from Alex G, but this song is released under her old name, Alex G.

Thank you so much for joining me on this musical-literary-hybrid journey! I’d love to know what songs you imagined during this book, what songs you use to get through the hard moments, and what you want to see in the soundtrack of the HBO 6 episode miniseries that hasn’t happened yet but WILL (I hope!!!) Message me on IG (@jamesissmling), write me an email, post it to your stories, whatever you’d like. I want to hear from you 🙂


For book & music links, themed playlists, a wrap-up of Largehearted Boy feature posts, and more, check out Largehearted Boy’s weekly newsletter.


Jesse James Rose (she/they) is a transgender actor, writer, and content creator based in New York City. Every president who has attacked her in the media has been shot at. Rose holds degrees from NYU in music theatre and child and adolescent mental health studies, as well as a certificate in diversity, equity, and inclusion from Cornell University. As an actress, Rose made queer theater history as the youngest openly nonbinary professional performer to take on the title role in Hedwig and the Angry Inch. The same year they co-starred in the indie film Adelphe, which premiered at the Cannes Film Festival. They are perhaps most known as a transgender activist attacked by Donald Trump, as covered by Rolling Stone and THEM. Their work lives largely on social media, where Rose writes about gender, queerness, survivorship, mental health, their feelings, and their exes on Instagram & TikTok (@jamesissmiling).


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