Alaina May
Alaina May is a Brooklyn-based singer-songwriter whose music blends indie-pop, indie-rock, and folk influences, carried by an honest and deeply emotional approach to songwriting.
Her latest single, “Casual”, marks the beginning of a new chapter in her artistic journey — one that explores vulnerability, self-awareness, and the complexity of human connection.
In this interview, Alaina opens up about identity, healing, creativity, and what it means to grow into yourself as both an artist and a person.
Photo credit: Logan Morrow
Hi Alaina, how are you? For readers discovering your music for the first time, could you tell us a little about yourself and your journey so far?
Hi! Thank you so much for having me! I am a singer and songwriter based in Brooklyn, NY, and would classify my music as indie-pop/indie-rock ish, with some folk and alternative influences. I've been playing instruments and writing songs for as long as I can remember, but really started to pour into it a couple years back, in college. I recorded a couple songs over the past few years, but really have started to write and produce music that is saying what I've always tried to say over the past year or two, and especially since moving to New York City. I'm finishing up an EP currently, and playing shows around NYC throughout the summer, and that's what I'm currently up to!
Your new single “Casual” explores the tension between self-awareness and emotional vulnerability. What inspired you to write this song, and what does it personally mean to you?
I wrote 'Casual' not too long after a pretty intense ending of a relationship; I was sort of reeling from the emotional fallout of that while also just experiencing a ton of life changes...moving to NYC, a new job, new friendships, etc. During this time, I was trying to do the whole casual dating thing, and it got messy and complicated and confusing. I was sitting in these temporary thrills and moments of emotional intensity, and I think I confused that with healing from the prior heartbreak, when it was really just a grasp at filling that hole in my chest. I learned that 'keeping it casual' is absolutely not my forte, and much more to come on that in my next single, 'The Dog'...
You describe “Casual” as living in the space between wanting something light and realizing you’re not wired for casual relationships. Why do you think so many people can relate to that experience?
I think right now, more than ever, people are craving that immediate gratification and quick highs. Society glorifies it...the 'no strings' of it all. But, humans aren't wired for casual. We are wired to feel things and love freely and not restrain that. But, there also is the element of guarding your heart and recognizing when situations are not healthy, and I think this line is one that so many people find themselves toeing.
Growing up in a conservative environment and later embracing your identity as a queer woman seems to have been an important part of your journey. How has that experience shaped both your life and your songwriting?
I can't even begin to properly verbalize the impact that this has had on my life and my writing and how I exist everyday, but I guess I will just say that I am one with myself now and I am writing from that place. I am saying the things I've always wanted and tried to say, and having a lot of fun and experience a lot of healing in doing so! The fear of judgement and vulnerability has faded, and it has just been the most freeing journey.
Your music often explores identity, self-discovery, and emotional intensity. Do you see songwriting as a form of self-reflection or even healing?
Oh, without a doubt. Writing is the space where I feel the closest to the ground. My brain is full of chaos and hyperactivity, but when I sit down to write, I am able to find clarity and quiet amongst all of this noise. I can listen to and interpret my own thoughts and feelings better, and express them in a way that hopefully moves other people as well. I think humans are perpetually just trying to find our own respective 'gods' in everything we see and feel and experience, and this is where I find mine.
Mental health and emotional wellbeing are topics that resonate with many listeners today. How do you personally take care of your mental health while navigating life and a music career?
Gosh, well I'm definitely still discovering new ways to care for my mental and emotional wellbeing each day considering everything going on in the world around us right now, but I think there are a couple things that I tend to stick to. Being outside is a big one, letting the sun sit on my skin and touching the ground always keeps me present. Interacting with the people around me as well; living in a place like NYC, I've just met the most amazing people who are doing the coolest things and being so authentically themselves; it's been so inspiring and grounding, and I think this human connection is just the most powerful thing anybody can experience. And then of course writing is the single most powerful act for my wellbeing I think...it is an outlet and a safe space and where I feel closest to the divine and sacred things.
The music industry can sometimes feel overwhelming, especially for emerging artists. What has been the biggest challenge you’ve faced so far, and how did you overcome it?
Honestly, I'd say just learning the ins and outs of the industry has been quite a whirlwind; there is so much I didn't know and was definitely overwhelmed with the amount of moving parts that go into the music we listen to every day. From the creative side to the marketing to the artist development to the commercial aspects of it, I was taken for a bit of a spin. But, I've met some of the most incredible people EVER who are helping me digest all of these moving pieces, and I could not be more grateful. I'm also just super stoked to be in a place like Brooklyn, because so many people here are doing the music thing and have so much wisdom to offer to people who are earlier in their careers and just figuring everything out (like me <3)!
Having recently moved to New York and started working closely with TOLEDO, how has this new chapter influenced your creative process and artistic vision?
Oh my goodness, first I just have to say that living here has been an absolute game changer for how I approach my writing and production. There are so many local artists who are doing insane stuff with their music, blending genres and styles, putting on incredible live shows, writing stuff you've never heard anything like before. It's just been a ton of inspiration in my own creative process, and also a push to making more 'risky' creative choices that I probably (definitely) would not have made in the music I was making a couple years back. Working with Dan and Jordan (TOLEDO) has obviously been a huge part of that as well...I mean they are so incredibly talented and also just the best humans ever. Our sessions are always a blast and I walk away with a track that I'm just so excited about every single time. I've always adored their music and I love hearing some elements of their sound find their way into my tracks, it's just such a fun creative process and very full-circle.
As an independent artist, what is your perspective on the music industry today? Do you think it has become easier or more difficult for new artists to build sustainable careers?
Oh man, I mean given I'm such a new artist, I'm just sort of getting all of this exposure to the industry over the past couple months. It's been like drinking from a fire hose, because it is such a black box of an industry, but I have some awesome people guiding me thru it all. I will say it's definitely daunting because of how social media and virality play a role, but then you also see people on insane rises with less social media presence and just insanely incredible music. I'm excited to see how the coming months play out and to just keep making music I'm excited about and see what happens!
Social media has become an essential part of being a musician. How do you balance the pressure of being visible online with staying authentic to yourself as an artist?
I'm not historically a huge social media girl, and I am DEFINITELY not an influencer type at all; I've never been on TikTok really, which is obviously where a ton of artist discovery is happening in the current industry environment. I always feel this sort of anxious worm in my brain telling me I have to post more, or record more content, etc, etc., and then I'm like...I don't know where the hell to even begin! So, I've sort of just started recording silly clips of me and my friends, and sometimes my dog, set to the 'Casual' audio, or videos of acoustic, stripped-back versions of my songs or other folks' songs that I'm loving at the moment. I just try to keep it real and authentic, unscripted, just being silly and posting without putting pressure on myself to perfect the content or post exactly what will go viral, but rather just keeping it light and fun.
Looking back at your journey so far, what advice would you give to young artists who are still trying to find their voice and place in the industry?
Take all of this with a grain of salt because I am still very much in the infancy of my development and career as an artist, but I think it is just so important to cling to the wonder that all artists experience when writing or hearing something that moves them. So many people have been telling me that it all boils down to good music; if you are writing and creating music that you are proud of and that resonates, the rest will start to take shape. I'm trying to keep this mantra at the center of everything I'm doing, because after all, I just want to play songs for people and experience the joy of a room filled with music. Now obviously, to do this as a career is a long journey of ups and downs and logistics and industry hoops to jump through, but it all goes back to that love for the creating and clinging to that.
Finally, “Casual” marks the beginning of a new chapter. What can listeners expect from Alaina May in the coming months?
For the better part of the last year, I've been working on an EP that I am so stoked about. It explores everything I chatted about in this conversation; finding indentity, navigating emotional complexity, experiencing love and loss, etc.. It is sort of a peek into the chaos of my brain throughout the absolute beautiful mess that is my early twenties, and I think a lot of people will be able to relate to and find themselves within these songs. We are sort of figuring out all the logistics and details with release plans at the moment, but this music is on the way and I couldn't be more excited for it to be out in the world. I will also be playing a couple shows around NYC in July / August; the details will be on my socials for these shows!
Connect with Alaina: