Gay singer/songwriter Mike Maimone has a soul-crushing story to tell. What better way to do it than in song? Maimone and the late, legendary, gay public relations whiz Howard Bragman, who was renowned for his crisis management skills, met in 2022. The pair began a whirlwind, long-distance relationship, marrying in early 2023, shortly before Bragman died of acute myeloid leukemia. Maimone’s two most recent albums, 2023’s “Mookie’s Big Gay Mixtape,” and his latest, 2025’s “Guess What? I Love You” (8Eat8), address the relationship with a broad range of emotions. Listeners can expect to be taken on a roller-coaster ride of feelings, concluding on an unexpectedly uplifting note with “Waiting In The Light,” which closes the new album. Mike spoke with us about the album before its early 2026 release.
Gregg Shapiro: The dedication on your 2023 album “Mookie’s Big Gay Mixtape” reads “In loving memory of my husband, Howard Benjamin Bragman.” It was released the year Howard passed, and your new album, “Guess What? I Love You,” arriving a couple of years later, is also dedicated to Howard, whom you call “my forever guy.” Were any of the songs on the new album originally intended for its predecessor, or were they all written specifically for the current project?
Mike Maimone: The songs on “Guess What? I Love You” were all written specifically for the album. The only exceptions are “Forever Again,” which I wrote for Howard when we first got engaged, “Big Kiss,” which I started writing after Howard and I returned from a road trip through the Southwest, and “Paranoid in Paradise,” which I wrote after a misguided attempt to get high with him. Those three ended up on Side A of the record, chronicling our love story from first meeting through our wedding.
GS: There’s a certain blush to the songs written for and about Howard, on both albums, that made me wonder if he was your first serious relationship.
MM: I’m glad to hear you say that, because no, this was not my first serious relationship. In fact, “Forever Again” was written because I’d been previously engaged, and Howard had been divorced, and I wanted to ease any trepidation about putting our hearts on the line again. I was in that prior relationship for seven years, before that I was with a man for six years, and had a yearlong relationship before that. Because Howard and I met later in life, we had the experience to recognize what an incredible thing we had from the moment we met. It made us giddy. We were genuinely grateful for each other. I’m glad that shines through the songs.
GS: There is a distinctive shift in tone from the “Mixtape” to “Guess What?” although the new album does open with more upbeat numbers, including “On My Way,” “Big Kiss,” and “Meet Me.” Was it important to you that you ease the listener in for what was to come later?
MM: Similar to “Mixtape,” I added interlude tracks to guide the narrative, including some voicemails. The new record flows chronologically, so it starts with songs about those first exciting trips to see each other, falling in love, and deciding to spend the rest of our lives together. On the vinyl, “Forever Again” closes Side A, about our love story. Side B begins with “Beautiful Mess” about being by Howard’s side through his diagnosis and, ultimately, holding him as he passed away. It took me about two years to write and record, and eventually I realized that the album needed to be about beginning to heal, as well, so there is a trio of hopeful songs to close the album.
GS: You mention “the Windy City” in “Meet Me.” You lived in the Chicago area for 12 years, and Howard was also from the Great Lakes Region. How much would you say that sharing that Midwestern sensibility played a part in your mutual attraction?
MM: It was a large part of what made me comfortable with Howard in the beginning. We met on Scruff and immediately moved off the app to phone calls and FaceTime. We had a lot of differences on paper, not the least of which was that he lived in LA and I was in Nashville. But we talked several times a day, falling in love long-distance as we discovered our commonalities.
GS: The songs on “Guess What? I Love You” are propelled by a combination of retro and regional musical styles. Please say a few words about how those kinds of influences work their way into your music.
MM: Having loved all kinds of music, I’ve never wanted to stick to a specific style in my own songwriting. My first band was called Mutts for that reason. I’m a ‘90s kid, which may be the most eclectic decade for popular music. The Billboard charts had everything from Dr. Dre to Enya to Nine Inch Nails to the Benedictine Monks of Santo Domingo de Silos. I’m not saying those are my influences on this record; I just mean that we’re in this algorithmic era where new artists blow up by sounding exactly like every other song on a playlist. And if you deviate from that sound on your next track, the algorithm doesn’t know what to do with you anymore. You only get one life, so why limit your creativity to placate an algorithm? I guess if you only want to make one style of music, that works out great. For me, that’s been a challenge. I don’t question whether one song fits with another. I just try to make them flow together on the album.
GS: The transition from joy to despair comes across about halfway through “Guess What? I Love You” on songs such as “Beautiful Mess,” “So Hard To Let Go” and “Oh How Lucky.” How do you prepare yourself to sing such deeply personal tunes for an audience?
MM: It’s difficult. It leaves me emotionally drained to keep going back through that pain. But these songs have brought with them the most powerful connection my music has ever had. Grief is a horrible thing that we all eventually have to go through, and an unfortunate bond we all have. I first played “Oh How Lucky” for my Patreon subscribers. Afterwards, several people messaged me saying how much the song meant to them. It reminded them of their own departed loved ones and helped them realize their own gratitude for the love they shared.
GS: In the midst of all the sadness, there is also a healthy dose of humor, especially on what sounds like an anti-drug song: “Paranoid In Paradise.”
MM: I’d like to clarify that it’s not an anti-drug song – I like marijuana, I’m just allergic to it. But yeah, I wanted to make sure the album reflected how much fun Howard and I had. “Paranoid in Paradise” is about a night when I tried to get high with Howard. I knew I couldn’t handle weed, but we were having a relaxing evening, just the two of us, and I figured it was a good environment to try again. I was so wrong. At first, Howard thought it was hilarious that I thought he was trying to kill me. Eventually, he got tired of my BS and went to sleep, leaving me to spiral out on my own.
GS: In recent years, albums by queer artists, including Sufjan Stevens and cabaret artist Frank Dain, have addressed the loss of a life partner. Did you listen to these kinds of albums while working on your own?
MM: I didn’t. But after Howard’s Celebration of Life, I outlined a documentary about him. He had produced a number of docs and had a lot of friends in that world, all of whom loved the treatment but said they were too swamped with other projects. One of them suggested I write a book first, as that wouldn’t require funding, and if successful, it could open the door for a film on Howard’s legacy. He suggested that I read “Spoiler Alert: The Hero Dies.” It was a brutal read just months after losing Howard, but helpful in visualizing how to make art about my grief.
GS: Even though this is a very personal album, was it your intention for “Guess What? I Love You” to be helpful to others grieving the loss of a life partner?
MM: That was one of the intentions. First was to document the love for my own memory. I needed to capture it through music, or I’d start to second-guess if it happened at all. The next was to honor Howard’s legacy and make sure he’d always be remembered. Channeling my grief into the music helped me begin my healing journey, and as I started sharing it with people close to me, the third intention emerged. Although it’s very specific lyrically, it seems to speak to the universal as well.
GS: In addition to this album, you have also written a memoir about your experience. What can you tell the readers about the book?
MM: The book is my story about love, loss, grief, and healing. It started as a way for me to memorialize Howard’s contributions to the world through the lens of our love story. But it ended up describing the ways Howard changed my life upon entering it, and again upon leaving it one year later. Howard was an enormous personality, and there were a lot of funny moments. There are a lot of sexy stories, too. And some interesting insights due to our culture clash, as he was a Hollywood publicist and celebrity in his own right, while I was a scrappy independent musician living in Nashville. It, of course, gets very heavy. In the writing and editing process, I’ve had to pause many times to allow myself to break down. But I didn’t want to leave the reader – or myself – in sadness. In the two years it took to write, a lot of things changed in my life. I grew as a person. And my beliefs evolved. So it closes with some perspective on hope and healing. I got a fantastic literary agent and a publisher, and we’re looking at February 2026 for release. I’ve pushed the album back so we can put out both at the same time.