My Boyfriend and I Competed to See Who Could Make the Most Horribly Awkward Sex Playlist

Awkward Sex Playlist
Jason Hoffman/Thrillist
Jason Hoffman/Thrillist

Role play. Bondage. Toys.

These are the typical suggestions when looking for advice on how to spice things up in the bedroom. The only problem? They’re about as predictable as a finger in the butt. So one day, I thought up the most ridiculous idea: What if I tried to get intimate while some of the most embarrassing, least-sexy songs ever created played in the background?

I told my boyfriend, Steven, about my plan. We came up with an even funnier idea: We’d both create playlists and surprise each other with them. It was a competition for who could make the worst one, with me convinced I'd be able to access the darkest recesses of humanity (and the internet) to bring my boyfriend down. Judgment day arrived; and Steven and I stripped down -- and giddily shared our playlists with each other.

Playlist one: Dana's Ditties

“Dance with My Father”

Luther Vandross
Awkward factor: 6/10
Let’s just say I came in guns a-blazing. The fact that I opened with a song almost every woman chooses to dance with her dad to at her wedding proves my boyfriend’s theory that I am a monster who cannot be stopped. Also, I know this song is only four and a half minutes, but for some reason it felt like it went on forever. Fun fact: There are 40 bridges in this song and 27 choruses.


Awkward factor: 8/10
Steven’s immediate reaction: “Is this… 'Funkytown?'” Twelve seconds later: “Is this 'Funkytown' being performed by children?” Yes. And... yes.


“You’re A Grand Old Flag”

United States Air Force Concert Band
Awkward factor: 4/10
I’ve never felt more American. I also felt like I was a teenager hooking up under the bleachers of a football game. This was a pretty awful song to hook up to. Steven asked me why I hate freedom.

“I Believe I Can Fly”

William Hung
Awkward factor: 10/10
Did you almost forget about William Hung from American Idol? Me too. And I am so glad I remembered both his existence and the fact that he put out an album of covers in 2004.

“You’ve Got a Friend in Me”

Randy Newman
Awkward factor: 9/10
Randy Newman’s voice should be considered a homeopathic form of birth control. No one can successfully get freaky while Randy Newman is singing in the background.

You may indeed have a friend in you. Still -- don’t play this song.

Playlist two: Steven's Serenades

“That’s How I Beat Shaq”

Aaron Carter
Awkward factor: 10/10
Upon hearing this first song of his playlist, my first thoughts were dammit, this dude didn’t come here to mess around.

I concede this was a brilliant opening song.

“Achy Breaky Heart”

Billy Ray Cyrus
Awkward factor: 9/10
It shouldn’t come as a shock to hear that I never want a Cyrus in my bedroom ever again.

“Circle of Life”

The Lion King soundtrack
Awkward factor: 6/10
The opening shouting of this song made me lose it. Well played, sir. Well played. Rather than initiate the circle of life, this song makes you sexually paralyzed.

Jurassic Park theme song

Awkward factor: 7/10
“This one won’t be awkward unless you recognize this!” Steven warned me. Please note that he likes to joke that I have only seen three movies and two of them were part of the Air Bud franchise.

He took a chance with this one. And, he was in luck -- I have indeed seen this movie and I did indeed immediately recognize this.

“The Super Bowl Shuffle”

Awkward factor: 5/10
The only thing more awkward than listening to football players rapping is farting in a crowded elevator.

What's your awkward-sex playlist?

The next time you want to do something new and fun in the bedroom, try creating an awkward sex playlist. No need to click on the usual Ginuwine playlist you have saved in your phone (I’m pretty sure we’ve all gotten busy to “Pony,” even if it was meant ironically... or not), turn on the theme song from Space Jam and see what happens. I can guarantee it will be a night you’ll always remember.

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Dana Hamilton is a writer in New York City who has a passion for all things body-related. She writes about sex, dating, relationships, body image, and eating disorder recovery. Her work has appeared in Cosmopolitan, MarieClaire, and XOJane, among other publications.