Out with Dr. Bill: Boots, Boats & Bourbon: A Bill-Sized Spring Start

I'm writing this latest column from the second floor of our house on Fire Island, watching the waves roll in over Memorial Day Weekend and sipping Starbucks drip coffee made with love by my bestie, Rick. While I'll be diving into all the island festivities in my next piece, I couldn't resist offering a quick teaser – High Tea is officially back at the Pavilion in the harbor at Fire Island Pines!

Last night, DJ Aquaria – winner of "RuPaul's Drag Race" Season 10 and a true icon of fashion and nightlife – was in the booth, spinning tracks that had the entire crowd moving. Out on the front deck, handsome, barely clothed bartenders served drinks with a view of the harbor, while energetic MISTR ambassadors roamed the party, capturing every social media-worthy moment. The vibe? Electric. It felt like the very best of the old Pines – only now with better lighting and phones that do more than beep. (Back then, I'm pretty sure I was rocking a pager.)

I first met the MISTR crew at Aspen Gay Ski Week back in January, where they set up at the Limelight Hotel – the event's main hub – and handed out everything from educational resources to branded swag. They were the perfect mix of sexy and smart. MISTR offers free and discreet access to PrEP and long-term HIV treatment for gay men, making it possible to skip the waiting room and get care delivered right to your door. While I don't use the service myself, several of my younger friends do, and have nothing but good things to say.

A huge thanks to Tryst Hospitality Founder & CEO Tristan Schukraft for bringing a bold new vision to The Pines. After years of holding space for solace, community, and celebration, this place we love is getting the thoughtful refresh it deserves.

Tristan isn't just renovating buildings – he's reimagining a legacy. For those of us who have found chosen family here, it's exciting to see this haven evolve to welcome and inspire the next generation of queer youth and the allies who stand with us.

As for our past events, I'll have to keep this column tight and high-level, as we did so much over the past weeks that I couldn't possibly share it all – as 10,000 words would be a New Yorker-worthy column.

Cactus, Cocktails & Captain Chic

We kicked off our trip in the desert Southwest after hearing that our Fire Island housemates, Luigi and Alex, would be in Phoenix for a wedding. We convinced them to arrive a few days early and head down to Tucson so we could give them the full Baker/Kapfer tour. Since the guys were flying in Friday night, Eric and I went down Thursday to get everything ready – turning on the pool, stocking the fridge, and making the essential stop at RumRunner on Speedway for Whispering Angel Rosé.

A surprise reunion with our dear friend Anthony Nunziata made for the perfect kickoff to the weekend – he wrapped his Arizona residency with a sold-out show, stayed the night with us instead of a roadside hotel, and joined us the next morning for breakfast at Bisbee Breakfast Club before flying to his next gig in Seattle. Unforgettable from start to finish.

Alex and Luigi arrived late Friday night, and Eric – very happily – picked them up just in time for cocktails by the pool at midnight.

The next few days were packed with classic "first time in Tucson" adventures. We explored Sabino Canyon via the electric shuttle and got off at the turnaround point to hike 3.5 miles back – shirts off, sun-soaked, and slathered in sunscreen. We also took a sunset walk through Saguaro National Park's Tucson Mountain District (West), one of my favorite places. The Desert Discovery Nature Trail never disappoints, and the towering Saguaros stretching endlessly in every direction always steal the show. We didn't wander too far into the brush – rattlesnake season is not when you take chances!

As luck would have it, two of Tucson's biggest events happened that same weekend: The Pima County Fair and The Great Centurions Regatta. Talk about timing. We had an absolute blast at the fair, a Tucson staple since 1911. Thanks to my brother-in-law, Jon Baker, the CEO, we got the full VIP experience. He scooped us up in a golf cart, handed us cold Bud Lights, and zipped us right into the heart of it all. One of the highlights? Running into my sister, Sheila, and her family – completely unplanned, and totally heartwarming.

We skipped the funnel cakes and deep-fried Oreos, and went straight for the main event: The award-winning Sonoran Fire Dog. This Tucson icon – a bacon-wrapped beef frank on a bolillo roll from Alejandro's Tortilla Factory, topped with pinto beans, grilled onions, tomatoes, jalapeño crema, and fire-roasted salsa – never disappoints.

After soaking in the rides and 4-H exhibits, Alex Mach and I braved the 120-foot-tall "Mach 1" thrill ride (we couldn't resist the name). It spun us upside down so many times I lost count. Thankfully, the Fire Dog had time to settle, or we might've been raining jalapeño and pinto bean bits on the crowd below.

That night, we switched gears and got nautical. We suited up in matching captain outfits and headed to The Great Centurions Regatta: A Naughty Yachty Affair, a benefit hosted by The Centurions, a local nonprofit supporting healthcare, education, and underserved families in Southern Arizona. Big thanks to Eric for the VIP tickets, which got us into a special section within the 7,000-person event – perfect for people-watching and enjoying live performances by Barenaked Ladies and Yachtley Crew. We didn't make it to the costume contest or charity casino, but it didn't matter; people stopped us all night to complement our outfits. Credit goes to Luigi for the perfect execution. In fact, Yachtley Crew wore nearly identical outfits, and, after their set, people kept coming up to us for photos, convinced we were part of the band. And who were we to break the illusion?

We closed the weekend with a cozy dinner at our dear friends Steve and Ronnie's stunning foothills home and capped things off with a "last supper" at Tito & Pep, a beloved midtown bistro recently featured on The New York Times' list of "50 places in America we're most excited about right now." It was one of those weekends that fills your heart and reminds you how special it is to share your favorite places with the people you love.

A Decade of Love, A Week of Connection

Back in New York, the pace didn't slow down. We had two great dinners at Elmo – one with our friend Jeff Brackett, a talented actor whose award-winning performances and social media savvy make him a true standout, and another with Byron LaMotte, a brilliant real estate leader known for his strategic vision and influence on the New York skyline. Both evenings were filled with thoughtful conversation, great food, and the kind of connection that makes this city feel like home.

The true highlight of the week was celebrating the 10-year wedding anniversary of our beloved friends, Evan and David. There's something deeply meaningful about being part of milestone moments like this – birthdays, anniversaries, and all the beautiful markers of life's journey. Eric and I always feel honored to be included in these celebrations, and a decade of marriage is something truly special. The room was filled with love and laughter, packed with friends and family who clearly adored them. Among the many familiar faces were City Councilman Erik Bottcher and New York State Assembly, Tony Simone – two incredible men who always show up for their friends, no matter how busy their lives may be. They say you make time for the people who matter, and that night it was clear just how much David and Evan mean to so many.

The following weekend, we were back in the Pines for the always-enchanting Kentucky Derby party at Mark and Craig's stunning Fire Island home. As expected, the mint juleps were flowing, served in traditional frosty Julep Cups that added an extra touch of Southern charm. This year, they outdid themselves with handmade sugared bacon strips, a delicious and decadent addition that perfectly reflected their warm hospitality and signature flair. Guests showed up in fabulous Derby hats, many adorned with fresh live flowers that brought a burst of color and joy to the afternoon. It's become a truly cherished tradition – a celebration of friendship, community, and springtime that Eric and I look forward to every May.

One minute we were sipping mint juleps in seersucker, and the next we were swapping them for margaritas and mariachi, because in our world, Kentucky Derby flows seamlessly into Cinco de Mayo! This year, we had the joy of celebrating the traditional Mexican holiday with our longtime friend Shen. He's only in the U.S. for a short work assignment from the UK, so we wanted to make sure he got to experience a tradition that, for those of us raised in Southern Arizona, is a must. A big shout-out to Rosa Mexicano on 18th Street for saving the night; our original reservation at another spot somehow disappeared, leaving us at 7:30 PM on May 5th without a table or a margarita in sight. Thankfully, tech-savvy Shen quickly jumped online and scored a last-minute reservation. Rosa Mexicano welcomed us with open arms and delivered the warmth, food, and hospitality we were hoping for.

A Celebration of Family—Louder, Braver, Together

The last event I want to highlight – though there were so many special moments I couldn't possibly fit them all into this column – was Family Equality: Night at the Pier. Eric and I were honored to be guests of two incredible gay dads, Joe and David, whom we first met years ago at Aspen Gay Ski Week. We knew right away they were a dynamic duo, so when they invited us to join them at their table for this heartwarming celebration of LGBTQ+ families, allies, and advocates, we didn't hesitate; we cleared our calendars on the spot.

Held at Pier Sixty at Chelsea Piers, the evening was nothing short of magical. The room was filled with familiar faces and inspiring allies. Early on, we ran into our dear friend Lisa Linsky, which immediately set the tone for a night full of warmth and connection. Lisa was attending with the iconic Jim Obergefell, the lead plaintiff in the 2015 Supreme Court case that brought marriage equality to the nation. Hearing Jim speak alongside powerful voices like Bill T. Jones, Demi Moore, Marlo Thomas, and Debbie Harry was moving in every sense. The stage came alive with performances from Tony Award nominees Darren Criss ("Maybe Happy Ending"), Megan Hilty ("Death Becomes Her"), and Nicole Scherzinger ("Sunset Blvd."), while heartfelt speeches by honorees Jason Weinberg and Merritt Johnson brought the room to tears.

It was one of those rare nights that reminded me how far we've come, and just how powerful we are when we show up for one another. A true celebration of family, in every form it takes.
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As I sit here listening to the waves roll in, I'm filled with gratitude – for the memories made, the friends who feel like family, and the moments that remind me just how beautiful this life can be. Thank you for letting me share a piece of it with you. Together, we can make the world a warmer place to live.