Playlist: Crying in a Caftan, Smoking a Virginia Slim

Feature image by suteishi via Getty Images

One night when I was indulging in the pleasures of being pleasantly crossfaded in my own home, I came across an extremely emotional edit of Céline Dion singing “My Heart Will Go On.” Now, I wouldn’t say that crying at TikTok is something that is so extremely rare for me, but something about the emotions and the level at which I was stoned really made the song strike me in my gut.

I was compelled so deeply by it that I had to listen to the song on repeat until I fell asleep to it like a late night CD compilation ad. I imagined myself like Rose, on the front of the Titanic. A strong dyke behind me, holding my waist as we sailed the seas together.

When my Titanic dream ended and I woke up with a huge dankover, I was compelled to create a playlist that captured the essence of longing and pure heartbreak.

Disclaimer, no, I don’t own a caftan. Yes, I wish I did. Maybe I’ll seek one out. But normally I do my brooding in Christmas pajama pants and little gay tank tops with a joint in my hand with headphones on full blast. It’s just the feeling that this type of playlist evokes in me. And yes, I do sometimes indulge in a Virginia Slim when I’m overwhelmed. The drama of it all calms me down.

Now, tune into the smooth heartbreak that is this playlist.

  1. Un-Break My Heart – Toni Braxton
  2. You’re Still The One – Shania Twain
  3. By Your Side – Sade
  4. I Have Nothing – Whitney Houston
  5. Left Outside Alone – Anastacia
  6. On The Radio – Donna Summer
  7. Time After Time – Cyndi Lauper
  8. Without You – Mariah Carey
  9. Linger – The Cranberries
  10. Nothing Compares 2 U – Sinéad O’Connor
  11. Torn – Natalie Imbruglia
  12. 2 Become 1 – Spice Girls
  13. White Flag – Dido
  14. In Another Time – Sade
  15. Butterfly – Mariah Carey
  16. Baby Can I Hold You – Tracy Chapman
  17. Take My Breath Away – Berlin
  18. Listen To Your Heart – Roxette
  19. My Heart Will Go On – Céline Dion
  20. Shadowboxer – Fiona Apple

69.9 FM is a series of playlists from Julie’s poorly organized Spotify.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!

Julie Gentile

Julie is a writer by night and marketing bot by day. She enjoys long video game playthroughs and pretending like she didn’t internalize every single episode of Glee. Contact her at julie[at]autostraddle[dot]com.

Julie has written 23 articles for us.


Contribute to the conversation...

Yay! You've decided to leave a comment. That's fantastic. Please keep in mind that comments are moderated by the guidelines laid out in our comment policy. Let's have a personal and meaningful conversation and thanks for stopping by!