Playlist: I Asked My Friends What the Most Romantic Song of All Time Is, And Now They’re All Mad At Me

This week as I was brainstorming lil things to write about Valentine’s Day, I had a brilliant/evil idea! I would make a playlist for the holiday by texting a slew of my friends: What do you think the most romantic song of all time is?

Everyone I asked is queer, but I told them they didn’t have to limit themselves to songs that are explicitly queer. The initial replies I got were all along the lines of:

Why are you doing this to me?

This is too hard!!!!!!!!!!!

ONLY ONE?

I’m feeling attacked

And, my personal favorite:

Can they be romantic but also sad?

In other words, I deeply upset everyone with this request. In the end, I did let people pick more than one song if they insisted upon it, for I did not wish for my friends to be in agony. I will not expose anyone by revealing what they individually chose, but you can find the results of this experiment in the playlist below.

The playlist presents an all-over-the-place collage of vibes and quite the spectrum of definitions of “romantic.” Here are some behind-the-scenes playlist details I would like to highlight:

  • The first two people to respond with actual songs both picked songs by The New Pornographers — unbeknownst to each other. So, briefly, this playlist was just two New Pornographers songs.
  • A pair of wives both said “Slow Show” by The National — also unbeknownst to each other.
  • Shortly after The Wives said “Slow Show,” another gay said “Slow Show.” “Slow Show” has my friend group in a chokehold.
  • Nine of the people I polled are friends I met on tumblr when I was a teenager, and multiple of them mentioned their selected song had imprinted on them due to a fanvid and/or character playlist.
  • “In The Air Tonight” was definitely said as a joke having to do with the famously romantic (jk) television program The Americans, but I left it in to add to the chaos.
  • One of the polled people was my sister’s gf Meredith Shock, who is a queer singer-songwriter herself. Most of her singles are about heartbreak lol, but that doesn’t inherently make them NOT romantic! Also, she promised more romantic songs are coming 👀
  • One of the polled people has a cat named Romance, so she is indeed an expert at romance.
  • I also asked my gf, who notably DID NOT pick Our Song (our song is a punk cover of “Mambo Italiano,” and it is our song because one time it played three times in a row when we were making out in the back of an East Village bar).

Romantic Chaos Tracklist

  1. Strange Currencies – R.E.M.
  2. Challengers – The New Pornographers
  3. Day Dreaming – Aretha Franklin
  4. Violently – Natalie Prass
  5. Distance – Emily King
  6. Lover – Jeff Buckley
  7. Can’t Help Falling In Love – Live At Daytrotter – Ingrid Michaelson
  8. Slow Show – The National
  9. Ice Cream – Sarah McLachlan
  10. Possession – Sarah McLachlan
  11. Ain’t No Mountain High Enough
  12. We Found Love – Rihanna
  13. Gotta Have You – The Weepies
  14. 6 O’clock Blues – Solange
  15. The Only Exception – Paramore
  16. Can’t Help Falling in Love – Elvis Presley
  17. The Bleeding Heart Show – The New Pornographers
  18. With You – Jessica Simpson
  19. In The Air Tonight – Phil Collins
  20. Make You Feel My Love – Adele
  21. Body Party – Ciara
  22. Kiss from a Rose – Seal
  23. Séduction – Joanna
  24. L’Amour Looks Something Like You – Kate Bush
  25. Kiss – Scout Niblett
  26. That’s Us/Wild Combination – Arthur Russell
  27. Body – Syd
  28. Without You – Lana Del Rey
  29. A.M. 180 – Grandaddy
  30. Lover – Taylor Swift
  31. You Make Me Feel So Young – Frank Sinatra 


What would you add to the playlist?


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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Miami. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 394 articles for us.

38 Comments

  1. Hey Kayla, so I *kinda* followed your advice from last year and I went on tumblr and I met a sweet wonderful cinephile who got all my Agnes Varda references and was kind and lovely and we had a great connection and things got kind of romantic and we did…some things…but we’ve broken up I guess (even though it was never official in the first place.) but yeah I think we’re still gonna be friends. But anyway that happened last night. I’m sad. I’ll be okay. Thank you for the stellar playlist. I’m going to listen to it on repeat and cry for the rest of the weekend. I’m wishing you well❤️

    • Second this! (My partner and I didn’t have a marriage ceremony but if we had gone that more traditional route this would definitely have been our song to dance to. Now we get to enjoy our small children dancing around the living room to it instead)

  2. Can’t decide between Adrianne Lenker’s sweet and very gay “Anything” from her Songs album, and my old go-to, Liz Phair’s “Shatter.” But if you’re ever up in the middle of the night feeling IN LOVE, either one will definitely work.

  3. “The Look of Love” Dusty Springfield.

    Having read the story of her recording with the Pet Shop Boys, I can just imagine Dusty doing a million takes to get the phrasing of “the look” just right. And the way she sings “Be mine… tonight” Such a top !

  4. Fair by The Amazing Devil

    also, funny story, I recently discovered spotify’s for you tab, and it said “would you like a playlist of romantic music?” and I said sure why not? well, at one point it gave me phantom of the opera followed by lenny kravitz, so there was a bit of tonal whiplash. they were both technically romantic songs, but the vibes were completely different

  5. i have to vote for sex (with my ex) by fletcher. i don’t know if i would have picked this out myself, but soon after the song came out, i had a friend go on an emotional ramble about how SOFT the song is. i had never really recognized its gentleness unless she pointed it out to me. she also emphasized the point that it is such a clearly QUEER song. you tell the title to straight people and they laugh. you tell the title to queer people and they get it.

  6. Omg, I remember going on this huge Sarah McLachlan kick in high school and the one songs that I still listen to is Possession. That music video made me feel things I didn’t have the words to describe at the time. Fifteen years (and hundreds of femslash fanfics) later, I’m living my best top life:) I still have it on my sexy-getting-ready-songs playlist, lol.

  7. “finding you” by kesha. i’d listened to the whole album multiple times already and then one time this song just jumped out and grabbed me as one of the most romantic songs i’d ever heard. idk if it’s *actually* the most romantic song i know but after that time i can’t think of anything else!

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