again, again — Drew Regan introduces his most honest era yet on debut EP

One of our favorite releases of the year so far.

There’s something quietly powerful about an artist choosing honesty over polish — choosing to sit in the mess instead of rushing toward resolution. On again, again, Drew Regan does exactly that.

Serving as his debut EP, the project feels less like a formal introduction and more like a snapshot of a specific headspace — one shaped by repetition, reflection, and the kind of self-awareness that only comes after sitting with your own patterns for a little too long.

In conversation with Everyday Jams ahead of the release, Drew opened up about the emotional weight behind the project — and the cycles that ultimately shaped it.

For Drew, again, again isn’t just a title — it’s a lived experience.

“I was treating myself awfully, yet I kept reverting to these behaviors and people that made me feel even worse,” he shares. “Again and again I would make the wrong decision, left wondering why I did it.”

That sense of repetition becomes the emotional backbone of the project — not just lyrically, but structurally. Each track feels like another pass through the same internal loop, slowly unraveling what’s been holding him there.

The EP opens with “lesson/friend,” a stripped-back introduction that immediately sets the tone. Built around the same intimacy Drew brings to his live sets, the track feels less like a performance and more like an invitation.

“I love starting a set real intimate with just me and a guitar. I feel like it helps build vulnerability between me and the audience,” he says. “We need to be more vulnerable as people — this is where connection lies.”

That idea — vulnerability as connection — runs through the entire project.

Tracks like “my curse” and “let it die” dig deeper into that internal tension, tracing the process of identifying the habits and relationships that quietly erode you. Where my curse names the problem, let it die becomes something closer to acceptance — or at least the beginning of it.

“‘let it die’ was the last song written,” Drew explains. “It kind of acts as a mantra to myself. I finally had come to terms with letting these things go.”

It’s also the track that feels the most exposed.

“I feel like I laid my heart out on the floor when I wrote this… I said a lot of things I can’t believe I said out loud,” he admits. “But it was the most honest I had been with myself in a long time.”

That honesty shows up in quieter, more subtle ways too. On “one time healer,” Drew reflects on the temporary fixes we reach for — the habits, distractions, and dependencies that feel like solutions until they aren’t.

“These things will only ‘heal’ me for a short moment,” he says. “It was never enough.”

Meanwhile, “If I Could Get Away” captures a different kind of tension — the emotional limbo of waiting for something (or someone) to change, even when it’s already draining you.

At the time, “getting away” meant escape — but looking back, it’s clearer now.

“It was really about wanting clarity and freedom from that emotional limbo.”

By the time the EP reaches its closing track, “lookin@thetime,” there’s a noticeable shift. Not resolution, exactly — but reflection. A step back. A moment of awareness.

Drew describes it like revisiting old journal entries — something that didn’t make sense at the time, but reveals itself later.

“It’s like reading old journal entries… I find it healing in a weird way.”

That’s what makes again, again such a striking debut. It doesn’t try to present a polished version of who he is — it captures him in the middle of figuring it out.

And maybe that’s the point.

“I want this to be a reminder for all of us to be more honest and vulnerable,” Drew says. “Tell people you love them, stand up for yourself… just be honest about how you feel.”

On again, again, that honesty becomes the foundation — messy, unfiltered, and ultimately what makes the project resonate long after it ends.

It’s rare to hear a debut that feels this fully realized — not because it has all the answers, but because it’s willing to sit in the questions.

And if this is where Drew Regan is starting, again, again feels like the kind of project that won’t just define this moment — it has the potential to stand as one of our favorite releases of 2026 by the time the year comes to a close.

Out now, again, again marks a striking debut from Drew Regan.