A Plaza Hotel Engagement Party With AI Sketch Robots
Night two of Rajitha and Ambar’s engagement weekend was a Plaza Hotel engagement party with four AI sketch robots. Rajitha and Ambar’s engagement weekend was a two-night affair. After a live photo mosaic wall kicked things off in Monmouth Junction, the celebration moved into Manhattan the very next evening for a 350-guest party at one of the most iconic addresses in New York. For night two, the family wanted something just as interactive but completely different, and that is where Milestone’s AI sketch robots at The Plaza Hotel came in.
On Saturday, August 22, 2026, four robots spent the evening drawing personalized, hand-sketched portraits of guests in styles built around the couple’s story, from Harry Potter to Positano.
A Setting Worthy of the Occasion
The Plaza needs little introduction. Since opening in 1907, it has been the backdrop for some of New York’s most legendary celebrations, and the evening leaned fully into that old-world glamour.
Cocktail hour began downstairs in the Palm Court, famous for its breathtaking stained-glass ceiling and towering palm trees. From there, guests made their way upstairs to the Grand Ballroom, a landmark space restored to its white-and-gold, neo-Classical design from 1929, with elaborate chandeliers, Ionic columns, and bas-relief ceiling details. Our robots moved into the Grand Foyer just outside, which retains the same historic character, including gold trimming, placing the experience right in the flow of guests heading in and out of the ballroom.
The Plaza’s event staff made our team feel welcome from load-in to breakdown. Working in a venue like this is a privilege, and working alongside a team this gracious made it even better.
How Night Two Came Together
During the initial planning call, Subha, the mother of the bride, mentioned that a second celebration was happening the day after the mosaic event. She asked Marissa, our Client Experience Manager, if she had any ideas for something equally interactive. Marissa suggested AI sketch robots, and the idea clicked immediately.
The same planner was involved in both events, but Subha was very hands-on throughout the process, working directly with Marissa to shape every detail of the experience.
Custom Sketch Styles Inspired by the Couple
Rajitha shared the themes that best represented her and Ambar: Philadelphia, Harry Potter, fishing, France, London, and movies. Marissa worked closely with our programming team to turn those interests into a custom lineup of sketch styles. When Rajitha saw the final designs, her response said it all:
“Thanks so much for sending these over! These are so cute!!! I’m obsessed, no notes!”
The available sketch styles for the evening were:
Branded Down to the Last Detail
Every sketch was drawn onto custom paper featuring the couple’s gold “RA” monogram on a deep burgundy frame with the phrase “In the Heart of Celebration.” The back of each sheet carried the same rich burgundy, with “The Plaza Hotel” at the center and the date, August 22, 2026, just beneath it, turning every portrait into a keepsake of the night. To tie the setup together, we also created custom signage matching the paper and the couple’s color scheme, included at no additional charge.
Sketched by Hand, Brought to Life Digitally
The heart of the AI sketch robot experience is the physical drawing. Every portrait is traced onto paper by the robot in real time, and watching it happen is half the fun. Guests left with a keepsake they watched being created right in front of them.
For this event, we added animated sketches. When guests texted themselves their digital copy, they could save it three ways: the finished image, a GIF of the robot tracing the sketch, and an animated version where the drawing moves and comes to life. A TV display near the robots played the animated sketches on a loop, drawing even more guests over to see what the buzz was about.
By the Numbers
Across the evening, the four robots produced more than 215 hand-drawn sketches. Nearly 170 digital copies were texted to guests, reaching roughly 120 unique phone numbers. The busiest stretch came early, with close to 40 sketches in a single half hour as guests arrived upstairs, and the robots stayed steadily busy right through the end of the night.
223
Printed AI Sketches
170
Sketches Texted to Guests
120
Guests Received a Digital Copy
4
AI Sketch Robots
What Our Team Had to Say
"This was one of my favorite events of the year. Seeing the couple's personalities come through in every sketch style, and watching guests line up to see their own wizard or red carpet portrait, was the best part. The Plaza is an incredible room to work in, and the energy never dropped."
Moments That Stole the Show
Guests were genuinely wowed by the robots, and the line rarely let up. One guest was so impressed she asked if we would travel to India for her wedding.
The highlight of the night belonged to the couple. Rajitha and Ambar posed for a Wizard Adventure sketch together, and the robot finished it off by drawing the words “Wizards of Love” across the top. It was a perfect fit for a couple whose shared interests shaped the entire experience.
Book AI Sketch Robots for Your Next Event
From intimate celebrations to landmark ballrooms, Milestone’s AI sketch robots turn guests into the centerpiece of the night. Visit www.MilestonePhotoBooths.com or call 908.340.0490 to start planning your experience.
Let's Create Something Unforgettable Together
Planning a celebration of your own? Tell us about it and we’ll design a sketch experience around your story.
