My AI Maid Of Honor Planning A Wedding With ChatGPT

The Four Month Wedding Challenge

“How are you going to plan a destination wedding for 150 people in four months?”

“You’re not hiring a wedding planner?”

“No wedding designer? How are you going to ensure that everything looks cohesive?”

These were the questions I heard from friends and colleagues when I announced my ambitious wedding plans. My answer? A mix of ingenuity, decisiveness, a healthy amount of delusion, and a lot of grit. Oh, and my secret weapon: ChatGPT.

After getting engaged, I faced the classic late-30s bride's dilemma: forgo the big wedding to start a family, or live out my Pinterest-fueled dreams? With our Italian-sized circle of friends and family, a small wedding was never an option. As someone who works in the wedding industry at Minted, a low-key event was also a non-starter for my maximalist tastes.

My professional experience has meant I’ve been thinking about my wedding for years. But with a self-imposed four-month deadline, I needed support. While I know many brilliant planners, my Aries-eldest-daughter personality has always wanted the challenge of doing it myself. I needed a partner who could keep up.

My AI Maid of Honor

Enter my mAId of honor, creative brainstorming partner, fashion historian, meteorologist, travel agent, and personal assistant: ChatGPT.

While some brides use AI to manage budgets or negotiate contracts, I found it was the perfect tool to hone my creative vision and drill into the details. It had the precision and speed necessary to pull off a celebration of this scale in just a few months.

Finding Our Dream Destination with AI

First, we needed a location for our November wedding. My fiancé and I are both of Italian descent and dreamed of a 17th-century Tuscan venue, but we quickly realized a European trip would be too difficult for some key family members. Our New York backup, St. Patrick’s Cathedral, was booked solid.

I started querying ChatGPT like I would a friend, asking for destinations easily accessible to senior citizens from the East Coast that would still feel like a transported paradise. The resounding answer was Bermuda. We had never been, but we were definitely intrigued.

ChatGPT got to know my preferences for a Slim Aarons and Truman Capote’s Swans-inspired vibe. The first venue it recommended, Cambridge Beaches, was a perfect match. A historic hotel built in 1923 on a private peninsula, it was discreet, full of history, and only a two-hour flight for most guests. Once I confirmed our date was available, the search was over.

An AI Partner for Every Little Detail

With the venue set, it was back to chatting with my AI assistant. The questions came fast and furious.

What is the exact percentage risk for a hurricane in November? About 0.5%.

What’s the ideal timing for Botox and a CO2 laser treatment? One and two months out.

What perfume did Grace Kelly wear for her wedding? Creed Fleurissimo.

What moon phase will it be on our wedding day? Waning gibbous, symbolizing reflection and gratitude—a detail I decided to add to our after-party menus.

Getting my colors done with ChatGPT and getting inspired to find a warm-toned wedding gown. Photo: Courtesy of Sarah DeThomasis

I uploaded a selfie to find my color "season" (a “warm spring”), shared my guest attire mood board to name our dress code (“Island formal”), and researched Italian and Southern American wedding traditions. My AI partner even helped me debunk an old wives' tale from my facialist about not wearing pearl jewelry as a bride.

A Sartorial Story Brought to Life

With the details falling into place, it was time to build my sartorial story. I envisioned a start-to-finish vintage wardrobe with a British-inspired narrative. Through my queries, I discovered new designers like Caroline Castigliano—the designer of my vintage gown—and rediscovered old favorites like Matthew Williamson. My AI BFF helped me connect the dots, creating a story that extended from a 1950s-era Pucci getting-ready robe to a hand-beaded Temperley London gown for the after-party.

My letterpress invitation border was an oceanic take on the floral embroidery of my wedding gown’s bodice, complete with seven iridescent pearls in clamshells to represent the seven years we have been together and illustrations of three distinct fish species, as suggested by ChatGPT, to best represent me, my fiance, and our dog. Photo: Courtesy of Sarah DeThomasis

From mocking up the invitation border to communicate my vision to our designer, to determining the exact tablecloth dimensions for our custom linens from India, the tool was as helpful as my prompts were detailed.

A decor prompt via ChatGPT. Photo: Courtesy of Sarah DeThomasis

A Word of Caution When Using AI

As our big day approached, I did uncover a few pitfalls. ChatGPT delivers all answers—both correct and incorrect—with the same absolute confidence. Blindly trusting its results can lead you to believe the sun will set at 4:23 p.m. when you know it's actually 5:23 p.m. As with any partner, human or machine, my advice is simple: use your brain. AI has a tendency to err, too.

You Can Have Your AI-Designed Cake and Eat It Too

Despite its potential for error, ChatGPT was a helpful and free tool that brought my creative bridal visions to life with no concessions on detail or personalization. If you learn to prompt it creatively, you can have your cake and eat it, too. And in my case, that will be a cannoli-flavored wedding cake decorated with edible seashells, an idea envisioned by ChatGPT and brought to life by our resort’s baker.