What The Weepies, Kid Cudi, Iron & Wine, K’naan and Emerson Hart have in common.

It’s a question that often comes up when you’ve just met someone, and you’re going through that list of superficial questions you have to ask before you can get to the good stuff.

“So, what kind of music do you listen to?”

Some might argue that they can tell a lot about a person based on this question. But I like to think that all of my dreams, desires and delusions aren’t so explicitly revealed by what songs and artists make regular appearances on my iTunes (and now, Spotify) playlists.

When asked, my initial reaction is always to cringe. Usually, I can see it coming, the second a conversation veers toward the topic of that concert that’s coming up or that song that’s barely audible at a noisy restaurant.

I never know how to answer it. Should I list genres or artists or specific songs?

After the first few dozen encounters with this question, I decided to rehearse an answer. It needed to be one that would exhibit my eclectic tastes, that wouldn’t allow any interrogator to categorize me (or my music preferences) with ease. I decided to pull artists from various genres, listing them in an order that created obvious juxtapositions: The Weepies, Kid Cudi, Iron & Wine, K’naan, Emerson Hart. Five should be sufficient.

Theoretically, this sounded like a great idea. In application, it didn’t work so well. I’d either rush through a list that clearly sounded rehearsed, or I’d fumble, forgetting artists and orders. So after a sufficient number of failed attempts with this strategy, I decided to go with what’s widely regarded as the best policy—honesty. So now, I’ll usually tell the inquirer that I hate this question, and this may or may not be accompanied by an inadvertent eye roll.

Why does the question stump me? It’s because I don’t have many longtime favorites. Where I am, what I’m doing, how I’m feeling—these dictate my preferences in music. And all of these change with some frequency. If you asked me what my favorite artist of all time is, I’d say The Weepies, but this answer beckons a questioning and confused look all the time, and this partially explains why I dread the question as much as I do.

Why the look? The reason, I think, is two-fold. First, despite the fact that their music has been featured on various television shows, movie soundtracks, and even a campaign ad for President Obama, The Weepies remain relatively unknown—at least within my circles. And second, I think it’s the name itself, The Weepies, that sounds depressing and forlorn to unfamiliar audiences. I can’t say that I disagree. They explain that the name “came from wanting to make music that reaches people in that feelingful place where tears come from…for joy or sorrow…that intensity of feeling is why we’re drawn to music.” (Feelingful?) So there you have it. Personally, I wouldn’t be completely opposed to a name-change, granted it’s for selfish reasons.

So no, I won’t snap at you if you ask me what is officially my least favorite question. But if I hesitate, this is why.