"Guess" Again: An Interview with gay singer/songwriter Mike Maimone

By Gregg Shapiro

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 was gracious enough to make time for an interview regarding the album

before its early 2026 release.

Gregg Shapiro: Mike, 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.

Created with formatmagic.ai - One click automated formatting

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.” Being that 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.