A Classic Connecticut Rehearsal Dinner Under the Stars

A charming outdoor celebration with a rustic touch.

Charlotte and Charlie rehearsal dinner in Connecticut

Photo by Rachel Pearlman Photography

Charlotte De Santis and Charlie Gumz first met thanks to some helpful friends. "We owe it all to Jenna and Peter Macartney. It was July 2020 and as we know, things in the city were very bleak," remembers the couple. "Jenna and Charlotte were texting one morning about how the Macartneys were considering a move to Denver. Charlotte said how it wouldn't be very smart for her to move out of the city as she was newly single. Jenna took this as an opportunity to circulate Charlotte's photo and phone number to all the eligible bachelors she knew. One of the recipients was Peter's 'very successful and fun' friend from Columbia Business School, Charlie." That night, the two began texting and went on a date the following week. They share, "After three dates, Charlotte had a plane ticket booked to meet Charlie on Nantucket for two weeks. After a couple of days on Nantucket, we said I love you."

On September 24, 2021, the couple were planning to host a housewarming party after moving into a new apartment on the Upper East Side together. Charlotte held a suspicion that Charlie might pop the question because a few of her closest friends agreed to fly out to New York City for the celebration. "When I got home from work that Friday, Charlie asked if I would come up to the roof with him to check out the area we had rented for the party. At the time, I was training for a marathon and so I quickly changed out of my work clothes into my running clothes—AirPods included," says Charlotte. "When we got to the roof, we stood looking at the area for a bit before he asked me to come over to a spot on the roof that overlooks the entire city. As we walked over, I looked to my right and immediately saw my best friend, Hayley, hiding in the bushes. Complete chaos ensued. I immediately started screaming as poor Charlie is getting down on one knee. He didn’t even get the chance to get his pre-planned speech out before my two best friends and future MOH’s ran out with champagne and tears streaming down their eyes. Turns out our 'housewarming' party was our engagement party! The final touch was that Charlie was able to recite his engagement speech that night when it was just the two of us."

Before they would say "I do" in a coastal celebration, the couple hosted family and friends for a charming rehearsal dinner at the Roger Sherman Inn in New Canaan, Connecticut. "Growing up in Darien, my family and I would frequent the Roger Sherman Inn for lunch on the patio in the summer or for a drink in the bar for the holidays," shares Charlotte. "When I started planning the rehearsal dinner with my mother-in-law, I knew I wanted to keep to the 'Classic Connecticut' wedding theme. What’s more classic than a picturesque Inn built in the mid to late 18th century? There are so many things to love about the RSI. From the green and white striped awning that covers the big wrap around porch to the beautifully landscaped grounds with blooming hydrangeas, choosing the RSI as our venue was a no brainer."

Charlie's mother and Charlotte teamed up to execute the design and planning for the event, with help from the Roger Sherman Inn. "I am very lucky to have a mother-in-law that is very detail-oriented and organized. The two of us worked very well together as we have different strengths," says the bride. "I would say I am the creative one and she is the organized one. When it came to planning, I would come up with the vision, and my MIL would execute it while constantly making sure that we were sticking to my vision. Obviously, there were a few bumps in the road along the way but overall, the process was smooth sailing and very enjoyable!"

Ahead, see all the lovely details from Charlotte and Charlie's outdoor affair, photographed by Rachel Pearlman Photography and planned by the bride and her mother-in-law.

blue, white, and green invitation suite with monogram

Photo by Rachel Pearlman Photography

Charlotte and Charlie had a monogram crest designed for their invitations and other paper goods inspired by their venue throughout their wedding. "I wanted elements of both the rehearsal dinner and wedding to be represented," notes the bride. "I used the hydrangeas from the Roger Sherman Inn as the featured flower, and nautical rope as the border to represent the yacht club where our wedding was held. Sadly, come September, all the hydrangeas were dead due to the unusually hot weather and lack of rain. At least the hydrangeas looked beautiful on our custom crest!"

Charlie and Charlotte in blue attire at rehearsal dinner

Photo by Rachel Pearlman Photography

Blue and white were the colors of choice for the couple's rehearsal dinner attire. However, the bride almost wore black. "I always knew I didn’t want to wear white to the rehearsal dinner. I had picked out a black Zimmerman dress months in advance that I had planned to wear with Dior slingback kitten heels," Charlotte explains. "I remember my mother’s reaction when I told her I wasn’t wearing white and instead was wearing black. Let’s just say it wasn’t good." Instead, she found a stunning floral style by her favorite designer, Markarian, in a Bergdorf ad. "I immediately fell in love with my dress but, of course, they only had one size left. I ordered it praying it would fit and thankfully it did. I had a lot of different outfits throughout the weekend, but I think this dress may have been my favorite."

Charlie sought out the "suit guy" of Charlotte's best guy friend Brian to create custom looks for his wedding events. "Mike Guerrieri is so talented and took care of me. Every suit he makes is custom made and so it fit me perfectly," he shares.

Charlotte holding a martini while wearing sunglasses

Photo by Rachel Pearlman Photography

"Anyone who knows me knows that my personal 'signature drink' is a dirty Tito’s martini with olives—blue cheese if they have them," says Charlotte. "We didn’t have an official signature drink at our rehearsal dinner, but I do know that I requested to have martini glasses. It also provided a great prop for photos!"

woven shell bag and martini

Photo by Rachel Pearlman Photography

Another fun accent to show off in snaps? A chic woven shell-shaped purse by Minnow. Charlotte carried it to tie in the nautical theme of the wedding the next day.

Roger Sherman Inn backyard rehearsal dinner

Photo by Rachel Pearlman Photography

rehearsal dinner wood table with cane chairs

Photo by Rachel Pearlman Photography

"When thinking about design, I knew I wanted the dinner to be outside on big farmhouse tables under a ceiling of twinkle lights that made it look like we were dining under the stars," says Charlotte.

tablescape with greenery centerpiece and bud vases

Photo by Rachel Pearlman Photography

"Once we confirmed the layout, my mother-in-law and I started thinking about the table decor. Because of the rustic setting, I wanted to keep the florals simple and went with a mix of various eucalyptus down the center of the tables. We then brought in a mix of florals for a slight pop of color in bud vases," Charlotte explains. In fact, the bride and her wedding party arranged them all themselves. "Friday morning, my mother-in-law went and grabbed all the flowers and brought them back to my mother’s house. I enlisted the help of my MOH and a bridesmaid to help arrange them in the small bud vases," she says. "Luckily, the weather was beautiful that day, so we sat by the pool and create an assembly line. I am so lucky to have had so many people lending a hand."

tablescape with wood plates and printed napkins

Photo by Rachel Pearlman Photography

Each wood plate was topped with a charming printed napkin. "My mother and I found squirrel napkins that mixed perfectly with our rustic theme on Amazon of all places," says Charlotte. "I tied twine around each one and put a square tag with our custom crest to finish it off. They were adorable."

bartender with monogram on apron and napkin

Photo by Rachel Pearlman Photography

"The second way we incorporated our crest was through our custom cocktail napkins. Every time someone picked up a drink, there our crest was," says the bride. Charlotte shares she was able to include the crest on so many items thanks to the site Zazzle. "If brides are unfamiliar with Zazzle, prepare to become addicted," she says. "It was so fun seeing our custom crest on matchbooks, aprons for the bartenders, cocktail napkins, candles, and many other little things throughout the wedding weekend. It is such a great tool for personalization!"

rehearsal dinner tables under twinkle lights

Photo by Rachel Pearlman Photography

"Our final design element had to do with the light. The side lawn at the Roger Sherman Inn has a ceiling of very fine twinkle lights that create the most beautiful glow," explains the bride. "To finish off the light, I added pillar candles down the center of the tables which helped make our dinner feel intimate and romantic."

Charlotte cries at rehearsal dinner

Photo by Rachel Pearlman Photography

There were many, many laughs coupled with a handful of tears.

Charlotte hugs mother at rehearsal dinner

Photo by Rachel Pearlman Photography

Speeches at the rehearsal dinner were a true highlight for the couple. "Charlie and I are so lucky to be surrounded by so much love. Collectively we had about a dozen friends and family members give thoughtful speeches," shares Charlotte. "There were many, many laughs coupled with a handful of tears. Additionally, Charlie’s groomsman, Lucas, provided some very good entertainment as he MCed the event."

Slideshow at rehearsal dinner

Photo by Rachel Pearlman Photography

"My mother-in-law is the queen of slideshows," gushes the bride. "Months leading up to the rehearsal dinner, my MIL reached out to our friends and family for anything from baby photos to embarrassing college photos you hoped would never resurface. As the rehearsal dinner started to wrap up and guests started to arrive for the welcome party, a big projector screen displayed the photos as songs by James Taylor, Taylor Swift, and Dave Matthews Band played along. It was such a thoughtful touch to wrap up an incredibly magical and touching night. I really do not think there was a dry eye at the dinner."

Rehearsal dinner under twinkle lights

Photo by Rachel Pearlman Photography

Speaking of dinner, the couple and their guests feasted on a delicious selection of fresh herb chicken, oven-roasted sea bass, and asparagus risotto. "There are many wedding venues that are very picturesque, but the food is lacking. This does not apply to the Roger Sherman Inn," reflects the bride. "The food is really good."

Charlie and Charlotte at rehearsal dinner table

Photo by Rachel Pearlman Photography

The best part of the rehearsal dinner for the bride? "Sitting at the table and looking around at all the people that mean the world to me and Charlie. Next to exchanging vows with Charlie, this is one of my favorite memories from the weekend," she says. "Everything in that moment was perfect."

Wedding Team

Venue Roger Sherman Inn 

Bride Outfit Designer Markarian

Shoes Lulus

Hair and Makeup Kechmara Beauté

Groom’s Outfit Designer: Mike Guerrieri at My.Suit  

Shoes Brunello Cucinelli Penny Loafers 

Wedding Bands The Clear Cut 

Floral Design Darien Flowers 

Invitations LaurenQDesignStudio 

Music Vinnie Ferrone 

Catering Roger Sherman Inn 

Transportation Red Oak Transportation

Photography Rachel Pearlman Photography

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