Originally Published on July 21st, 2026

“Without a doubt, loving deeply is so beautiful and is one life’s wonders, but I’ve learned that healthy love will always consider the self alongside the other person.” ~ Alaina May

If I try to psychoanalyze love, I can’t think of anything more historically traumatic. I am in my mid 40’s and I’ve been with the love of my life for more than twelve years now. Thinking about it, I wonder if people cling to the people that make us feel safe and content. Do we eventually just tire from the emotional volatility?

Recently, there was a thriller/horror movie that came out called Obsession. I watched it and, I gotta say, it’s pretty terrifying. It also got me thinking about my youth and past crushes and young relationships I experienced. It was all such a tragical experience. The feeling of liking somebody that doesn’t know me, wishing they did, and wishing we could be together. Then finding a relationship and claiming to “do anything” for them, and obsessing over them.

I wonder if we ever really grow out of these bad practices or if they just evolve. Law enforcement has a description they use for scenarios like this: a “crime of passion.” These are often the result of dissolved relationships, obsessions, fixations, or other resulting factors that could be derived from trauma.

Originally from Wisconsin, Brooklyn-based singer/songriter, Alaina May is looking at the tipping point of where love is (and isn’t) healthy.

“In the past, when I’ve loved someone, I’ve turned a bid of a blind eye to my own wellbeing in order to preserve peace or keep things pretty.” Alaina May

May was raised in a small, conservative suburb of Milwaukee. She identified with that culture: small town, church-going, because it was familiar. It wasn’t until moving to Boston for college that she began to come into her own identity, embracing her authentic self as a queer woman.

In 2025, she moved to New York where she has begun to take these dynamics of her life to shape her songwriting. Working with the duo, TOLEDO, May is finding and refining her voice.

In May of 2026, she debuted her first single, Casual, and in two months it has earned nearly 240,000 streams on Spotify.

The Dog

The Dog released on July 13th and is May’s second single. It runs at around three and a half minutes. It features May singing with an accompaniment consisting of warm acoustic guitars, bass, and light percussion and piano.

The Dog was inspired by May’s relationship with a puppy named Aspen. It was here where she began to ponder that line between healthy and toxic, balanced and obsessive, or as she describes, “loving like a dog.”

Stylistically, the music falls into the indie/alt folk category, maybe even whisper folk, similar to Iron & Wine or William Fitzsimmons. There is a little more of a pop edge to her sound that gives her music a little bit of diversity.

I love organic music. May’s voice is silky to perfection. She is so thoughtful in her songwriting. Yesterday, I hadn’t heard the name Alaina May. Now that I have, I can’t wait to hear more. This is easy and relaxed listening for those of us who like to ponder in the still moments of life.

Go press play.