Out With Dr. Bill: From DreamScape to Daily Grace: A September of Love, Legacy & Community

September arrived almost unnoticed, carried on the whirlwind of travel, work, and celebrations that filled the final weeks of summer. In between conferences, birthday dinners, and evenings with dear friends, I found myself gathering moments—big and small—that spoke to love, resilience, and the joy of community. Whether in Chelsea, Dallas, the West Village, or Las Vegas, the same thread ran through it all: the reminder that life’s richest experiences are those we share with others.

And yet, there’s no place where that truth shines brighter than the Fire Island Pines, where the season’s most iconic gathering unfolded under this year’s theme, DreamScape. Looking out from our Fire Island home as the Atlantic stretched endlessly beyond the horizon, enjoying my cup of Starbucks, I felt compelled to pause and reflect. Fire Island is more than a sanctuary; it’s a stage for one of the longest-running and most iconic queer celebrations in the world—the Pines Party.

This year’s theme, DreamScape, carried with it all the wonder, spectacle, and magic one might expect—and then some. But what I discovered as the month unfolded is that the magic didn’t end when the last beat faded on the beach. Whether gathered around a Chelsea dinner table with dear friends, celebrating a 95th birthday at a beloved Italian spot, standing on stage with a trailblazing keynote in Dallas, or indulging in cinnamon buns in the West Village, the same threads of joy, resilience, and community continued to weave themselves through my days.

From Fire Island to Las Vegas, from intimate dinners to grand plenaries, this September has been a reminder that the true DreamScape isn’t just a party—it’s the life we’re all building together, marked by love, creativity, generosity, and the bonds we choose and cherish.

From Dalí to Dawn: Finding Love and Legacy at Pines Party

The Friday of Pines Party weekend began with Eric meeting me at the ferry. After stocking up at the Pantry with lunch and dinner fixings, we headed over to the DreamScape Lounge at The Tryst Pool Club to pick up our wristbands. The newly remodeled space felt like stepping into a boutique resort—crisp loungers, sleek finishes, and a lively open bar already setting the tone. The anticipation was palpable. Later that night, Whyte Hall pulsed with HYPNOTIC VIP, a kickoff that set the weekend ablaze.

This year, our housemates joined forces to fully embrace the DreamScape theme. Eric and I channeled our inner Salvador Dalí—surreal, whimsical, and delightfully offbeat—while others shimmered like golden cuirassiers, their sculpted armor and masks gleaming under the moonlight as we made our way toward the main event. With each step, their presence cast an eerie, enchanted glow across the sand, forming a luminous pathway that guided us to the party entrance. It felt as though we were walking on a carpet of light—thanks to James and Chris for illuminating the night. 

Another layer of joy came from our friends—new and old—who welcomed us into their VIP cabana, Hypnautica. It was a world within a world, adorned with colorful paper lanterns and hypnotic imagery, including oversized eyes—an homage to Dalí’s recurring symbols of perception, dreams, and the subconscious. From its perch along the dance floor, the cabana struck the perfect balance—immersed in the action, yet grounded in the warmth of community. For their generosity and spirit, we’ll forever be grateful.

A full list of our cabana hosts’ names can be found in the Pines Party Community Journal on page A33. The official journal is a 260+ page, perfect-bound, flip magazine—a collector’s item that will adorn our coffee table for years to come.

The main event, DreamScape on the Beach, drew the largest crowd in years—dancing barefoot on a beautifully restored stretch of sand to the beats of Eli & Fur, Chris Cruse, and Someone from Berlin, until sunrise painted the horizon.  

While the music, costumes, and spectacle were unforgettable, what resonated most was the deeper purpose. Pines Party, presented by The Pines Foundation and Free Radical Design Group, is more than just a celebration—it’s a fundraiser. Over the past 25 years, it has raised more than $4.5 million for LGBTQ+ nonprofits and local preservation efforts. That enduring spirit of generosity is what makes the weekend truly legendary.

Sunday flowed into LUCID at the Pavilion with The Carry Nation, and then into BREAKFAST, where David Harness and Tedd Patterson gave us one final chance to dance beneath the morning sun. Yet beyond the parties, the music, and the laughter, the most magical moment always comes at the very end—leaving hand in hand with Eric, watching the sun rise over the Atlantic. As the music fades and the ocean glows ahead, I’m reminded that life’s greatest magic lies in love, joy, community—and in having someone beside you to share the journey. 

Pines Party 2025 was not only a dream, but a legacy of resilience, creativity, generosity, and love—one I’ll carry with me through the rest of the year and beyond.

The Magic of a Shared Table

As the post–Pines Party month unfolded, Eric and I found ourselves grateful for the chance to break bread with friends who bring such joy and richness into our lives. One of the first dinners that week was at our beloved Elmo in Chelsea—a place that always feels like home and never fails to provide the perfect backdrop for connection. 

Around the table was a truly special group: our dear friend Nathan Lee Graham—actor, singer, and originator of more than 17 roles on stage and screen, known for films like Zoolander, Sweet Home Alabama, and Hitch. He’s currently dazzling audiences as Hermes in the North American tour of Hadestown and just wrapped filming the Hulu comedy Mid-Century Modern with Nathan Lane, Matt Bomer, and the legendary Linda Lavin. 

Joining Nathan was his husband Shane, along with his talent agent, Michael Goodard—a fellow University of Arizona alum, like Eric and me. Rounding out the evening was our wonderful friend Tophe McRae.

The night was full of laughter, conversation, and that rare kind of ease that only comes when you’re surrounded by people who truly matter. Moments like these remind me that joy is not just in the big celebrations, but also in the simple act of gathering at a familiar table with those you love.

Fred at 95: A Milestone of Wisdom, Love, and Chosen Family

Another dinner we enjoyed—and one of the most meaningful of the month for Eric and me—was celebrating our dear friend Fred Rossiter’s 95th birthday. We gathered with a small circle at our favorite neighborhood Italian spot, Le Zie, to honor this extraordinary milestone. 

To have a friend on the cusp of becoming a centenarian is a rare privilege, but even more special is the wisdom Fred shares so generously—from stories of his days as a young gay man in the military to reflections on the love that has shaped his life. His enduring partnership with Bill Black, and the later gift of welcoming James Spiegelhoff into their lives, has created a bond braided together in devotion, light, and joy. Their love is a true testament to the beauty of chosen family, and it has been a gift to all three of them—and to those of us lucky enough to call them friends.

When Inspiration Takes Flight: Sharing the Stage with FlyGirl

I made a quick trip to Dallas to help host a business event, which included a few on-stage duties—most notably introducing our keynote speaker, my longtime friend Vernice “FlyGirl” Armour. Vernice is America’s first Black female combat pilot, a U.S. Marine Corps veteran, a proud lesbian, author, and an internationally recognized inspirational speaker known for her work in leadership, resilience, and building a “breakthrough mindset.” I always love sharing a stage with FlyGirl—her contagious energy electrifies the room and leaves everyone inspired.

The West Village’s Newest Obsession: Benji’s Buns

When I returned from the West Coast, I made a beeline to Benji’s Buns at 122 Christopher Street in the West Village—finally getting to experience the buzz I had missed while away in Texas during the grand opening. My UK friend Ben Michael, the visionary behind this sweet spot, greeted me with his famous cinnamon bun topped with creamy vanilla frosting—and even placed the very first bite into my mouth, a playful gesture that only heightened the anticipation of his scrumptious creations.

Benji’s Buns isn’t just about indulgence; it’s a labor of love born from Ben’s personal journey of overcoming struggles with food and eating disorders. Baking became his way to reconnect with food in a positive, joyful way, and now his small-batch, sticky cinnamon buns carry that story in every swirl of dough and frosting. No wonder the shop has quickly become the rave among confection connoisseurs and baked-goods aficionados alike.

When Fire Island Meets the Boardroom: Tristan Schukraft at NGLCC

From the West Village to the West Coast, I found myself in Las Vegas for the National Gay & Lesbian Chamber of Commerce (NGLCC) conference—an annual gathering I haven’t missed in more than a decade. Year after year, it remains a cornerstone in my calendar, uniting like-minded peers, business owners, and advocates who are dedicated to lifting up small and diverse businesses—the true backbone of America.

This year, beyond reconnecting with inspiring entrepreneurs, including my mentee of more than 13 years, Anthony Shop, co-founder of Social Driver, the highlight for me was how my Fire Island Pines world collided with my professional life.

The common thread? Tristan Schukraft.

As founder of MISTR and Tryst Hospitality, Tristan has become both a business force and a community visionary, with his hand in many of the iconic retail spaces that give the Pines its unique flavor. On the NGLCC stage, he brought that same entrepreneurial fire, delivering actionable insights from building pioneering ventures—from LGBTQ+ telehealth, now serving more than half a million patients, to revitalizing beloved queer spaces and launching luxury hotels. His journey took center stage during the Lunch Plenary Session: Powering Possibilities: Stories of Brand, Bravery, and Breakthroughs.
And, true to form, Tristan brought his MISTR Models to electrify the room.

Known for their energy, charm—and yes, their Speedos—they added a spark of Fire Island flair to the business stage, proving that substance and spectacle can coexist beautifully.

From Hot Tub Games to High Tea: Fire Island Icons Take Center Stage in the Pines

That throughline of Tryst kept bubbling up when I returned to the Pines. Just two weekends later, I dove right into the Tryst Pool Club for the Hot Tub Games Pool Party, where Fire Island’s spirit collided head-on with pop culture. The first ripple came with Countess Luann’s grand entrance, but the true splash erupted when my longtime gal pal, Sonja Morgan of Real Housewives of New York fame, took the stage. Picture it: blindfolds, bondage ball gags, and a parade of hot models turning up the heat. It was standing room—and swimming room—only, as the pool overflowed with fans ready to toast one of Bravo’s most iconic originals.

And let’s not forget Labor Day, when the grand return of Lina Bradford at High Tea reminded us all why she’s an icon. Having Lina back to spin filled me with joy; her music, her presence, her messages of love and light have long inspired me and so many others.

Two weekends, two worlds, all stitched together by Tristan, Tryst, and the intersections of community, business, and culture.

Love, Legacy & What Comes Next

As August slips into memory, I carry with me the joy of Fire Island’s DreamScape, the laughter of shared tables, the wisdom of milestones, and the brilliance of friends who inspire. From the Pines to plenaries, from cinnamon buns to champagne toasts, each moment has been a reminder that community is where magic lives. And, as always, there’s so much more ahead. Stay tuned.