Q&A: Alaina May Explores How Hard It Is to Keep It “Casual” in New Single
WRITTEN BY GINGER
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For her birthday this year, indie singer-songwriter Alaina May is dropping her new single “Casual” that she produced with indie-rock duo TOLEDO. What started as a single Instagram DM resulted in a wonderful partnership of Alaina’s soft, impactful vocals alongside the sounds of Brooklyn-based indie-rock duo TOLEDO that lead up to a powerful bridge exploring the internal struggle of “keeping things casual”. It is through this experience that Alaina is re-discovering her voice in her music.
Alaina’s time spent living in Boston invited a different kind of inspiration in the form of watching people live their authentic lives. She learned to see life differently after moving out of Wisconsin, which in turn translated to shaping her music.
“Casual lives in the space where you mistake limerence for real connection,” Alaina says. She expresses this with profound lyrics that speak to the overthinking voices in our minds when it comes to the connections we wish to experience.
Life of Jupiter had a chance to chat with the now Brooklyn-based artist days after her first live performance of “Casual” in Arlene’s Grocery in New York City.
Read our full conversation with Alaina May below.
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LIFE ON JUPITER: Congratulations on your show the other night! How was that experience for you?
ALAINA MAY: It was sick. I hadn’t performed at Arlene’s before, but I have been there just to go out with friends, so it was funny being there and having to lock in. It was just so fun to play. I usually do acoustic only when I’m playing solo, but some friends had lent me a vintage Stratocaster for the next couple of weeks to play at my shows, including another release party I have next weekend on the 30th, which people are welcome to RSVP with the link in my Instagram bio! I got to play on the electric guitar then and I think that might be my move from now on. It was great!
Love Dan and Jordan from TOLEDO and their song “Sunday Funday,” so how did this partnership come to be?
ALAINA MAY: It’s been really serendipitous. I’ve been listening to them for years, and they’ve always been on my playlist. “Sick!” was my gateway drug to TOLEDO’s music. Last November, while I was at work, I saw that they had posted an Instagram story about wanting to produce more stuff after wrapping up their tour, and asked if anyone would be interested. “We’ll be in Brooklyn,” said the story, so I swiped and was like, “Me!”
They responded to my DM asking me to send over my stuff, so I went into a phone booth at work, pulled all my stuff into a Google Drive, and shared it with them. I remember it was a Friday, and by the time I was leaving work, I had begun texting Jordan about when we would be able to get together and start working on the music. They are the best ever, and it’s been incredible working with them.
As for “Casual”, was it an original song from the partnership or did you have it with you for a while now?
ALAINA MAY: I had actually written “Casual” at work, the idea came to me and I had to go to the bathroom to quickly type it in my notes. It originally started as a slower acoustic song, but then I showed it to Dan and Jordan, and it sort of started to take on a different form.
It was a Saturday, and we just sat down - me with my guitar, Jordan on his electric guitar, and Dan hopped on the drums. We would just jam out for 30 minutes to figure out the structure.
The song went from this super mellow acoustic track to a really groovy, upbeat track, which was so fun to make. I hadn’t really tapped into that more upbeat groove in my writing before so it definitely opened a lot of doors sonically.
“Casual” is quite a vulnerable song. Do you think it is easier or harder to be vulnerable while writing as a musician?
ALAINA MAY: A big part of my writing is sensory details - things I can see, taste, hear. Especially when it comes to something I’m experiencing in my life and I think that is such a raw way to describe something you’re going through.
I like to say I’ve always been one to really write vulnerably because I think those big, heavy-hitting words make listeners kind of feel like “Oh, I feel that too” or like “I’ve experienced that”.
I think being vulnerable is what makes a song really resonate and move someone. I don’t necessarily know if that makes songwriting easier or harder but I just feel things intensely that I want to communicate because it’s like “Damn, I can feel that,” you know?
Who do you dedicate “Casual” to?
ALAINA MAY: “Casual” is for everyone who feels deeply and has waged an internal war over that. It’s absolutely the hardest thing to choose between what you desire and what’s best for you. This song is an ode to that struggle and a testament to how hard “keeping it casual” can be in a world that so often pursues and glorifies intense moments and short-term gratification.
What is your favorite lyric from the song?
ALAINA MAY: When I burn, I’m irrational, and my bed is collateral - when you enter a “no strings” situation, you are expected to suppress emotions in all forms. That is IMPOSSIBLE! It’s not how humans are wired. We are wired to feel things and be aware of and sit with those feelings.
What are you chasing creatively right now?
ALAINA MAY: I’d say what I’m chasing creatively are those beautiful moments where the songs grow legs and walk around you, where the lyrical and sonic environments click. There’s nothing better.
A couple of times during recent sessions, I’ve almost had shivers down my spine when we’ve been tracking songs. Now these are songs I’ve been writing, listening to, and repeating in my head for months, some even years - so it naturally gets to a point where I’m questioning how much I resonate and believe in them, especially after having contemplated each word and note so many times.
However, as we flesh these songs out and build a soundscape around them, I’ve been having these lightbulb moments where I’m just like, “Okay, yes, that is exactly how this song is supposed to sound.” It’s just the most exciting and fulfilling thing when that moment of inspiration I had when initially writing the song returns after so long.
What’s coming up for you next?
ALAINA MAY: I am planning to release another single in June and then an EP closer to the end of the summer. I’m excited to get these songs out into the world!
What’s your proudest moment behind “Casual”?
ALAINA MAY: There really isn’t one specific moment I’m really proud of, but essentially the whole process. Going back to the day I wrote the song in my work bathroom - I had a show that night in Williamsburg, and I wanted to play something fresh, so I played it that night. Obviously, it has changed a lot throughout production, but I’m just so proud of this song. Though it doesn’t necessarily match the original acoustic version, I think it does justice to the sentiments of the lyrics.

