10 Songs From The Most Awkward Playlist Ever


Something weird is going to happen. My recently single, reliably wonderful friend named “Mansion” is going on a road trip with a (very) old boyfriend. Okay, so her name’s not really “Mansion.” But so what if it was? You would just have to sit there and take it.

Anyway, I’m developing the most awkward playlist I can possibly think of for their car ride. Trust me, this trip deserves it. What’s the opposite of star-crossed? Is it  “hole-circled”? Yeah, this relationship pretty much circled around a hole for as long as humanly possible way back when.

Surely, it did this in a very amusing, at times confounding, but ultimately non-harmful way. It is precisely because of these attributes that I am attempting to honor this unconventional pairing, and it’s resurrection, with a few unusual and exceptional song choices. Where there is love, there are songs about love. Where there’s weird love, there are these two individuals and this playlist. Weird love needs love too.

I’m sure you’re starting to wonder about this former couple. Why are they embarking on a nationwide road trip? How blond is their hair?  Is hearing about their interactions like watching a movie starring Oprah and Sling Blade, but in a very special endearing way, where you end up rooting for them to get together?

Well, I can’t tell you. What I can do is something even better. I can share my awkward playlist with you. Sometimes it’s just better to let the music do the talking. Please feel free to suggest below any song that celebrates weirdness, discomfort, or awkward interactions and the people we love who have them.

1. I Would Die For You – Garbage

Pretty self-explanatory why anyone, and by “anyone” I mean no one, would want this song on a road trip playlist.

2. I Wanna Sex You Up – Color Me Badd

This song is a terrible choice because it’s old, trite, and this kind of sentiment is way too early into a very long ride.

3. Bring Your Whole Crew – DMX

The first lyrical couplet in this song is, “I got blood on my hands and there’s no remorse./I got blood on my dick ‘cause I fucked a corpse.”

4. Send Me On My Way – Rusted Root

This song really captures the feeling of delightful and incredulous confusion many experience at the hands of weird relationships.

5. Red Light Special – TLC

I dare you not to feel uncomfortable listening to this song.  This is the kind of song someone alone in a desolate wilderness cabin would sheepishly turn down.

6. Mother, Mother – Tracey Bonham

This song is the opposite of romantic.   I’m actually a little worried about frightening the driver with this one. But weird love is about taking risks!

7. Too Close – Next

No one writes a disgusting song about boners like Next. No one.

8. Touch Me in the Morning – Diana Ross

Diana Ross is incredible. This is literally the most up tempo song ever created about the moment “when love dies” and I’m really excited about what that tonal dissonance is going to produce in this situation.

9.  Blood Roses – Tori Amos

I’ve said it before and I’ll say it again, Tori Amos is my favorite singer whose songs all sound like she’s casting a spell for a coven.

10.  I Can’t Make You Love Me – Bonnie Raitt

I’m not a cruel person. I want to reiterate that there is absolutely no lingering sadness between these individuals, just a lingering weirdness—that’s why this is the perfect awkward anthem to cap off the list.

image – TLCVEVO/ YouTube