Real Weddings

A Boston Publicity Titan, a Lovely Airline Stewardess, and 400 of Their Closest Friends

When George Regan finally met his match on a flight out of Logan Airport, laughs ensued, and the pandemic couple found themselves on the trip of a lifetime.

Photo by Paul Blackmore

The Story

The meet cute. Without it, how would romance movies exist? But even Nora Ephron might struggle to write a love story as endearing as George Regan and Elizabeth Akeley’s. The former longtime bachelor is the founder and CEO of Regan Communications Group (whose client list includes heavy hitters such as the Boston Celtics, New Balance, and this magazine); the latter is the thoughtful, vivacious JetBlue flight attendant who captured his heart. Their chance encounter, appropriately enough, took place on a flight leaving Logan Airport during the first week of the pandemic. “My company has an office in Jupiter, Florida, and they made a big mistake. My mission was to fly down and to try to fix the mess,” George explains. “It was the first day the governor declared a state of emergency and basically closed everything down.” After Elizabeth helped him figure out how to work the TV screen on the plane, some banter ensued, and George was smitten. He then proceeded to ask her out for dinner the next night, but she told him she didn’t date passengers. His response? “I said, ‘Don’t flatter yourself. I have no intention of ever dating or marrying you. You just looked hungry.’” That made her laugh, she says, and he’s been doing so ever since.

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From there, the couple embarked on a unique courtship given the constraints of the time, which they say worked in their favor. “The pandemic was in full swing, and JetBlue asked if we would take leaves of absence to help the company, so I did,” Elizabeth continues. “That gave us a lot of time to spend together, and I think that built the foundation of our relationship, which we wouldn’t have had before. People weren’t going out and seeing other people, so it gave us an excuse to spend even more time together.”

In stark contrast to the solitude of their romance’s early days, George and Elizabeth’s wedding day was packed with family and friends—400, to be exact. While coordinating an event of this magnitude did pose some challenges, everything ultimately came together. On a beautiful July day last summer at Nauticus Marina in Osterville, numerous current and former politicians, business magnates, and other Boston luminaries gathered for the grand celebration.

Photo by Paul Blackmore

The Details

The Dress

Designed by Made with Love Bridal, the bride’s dress—called the
“Georgie”—featured Irish lace with shamrocks on it. “I love it because I thought it was a nod to George’s Irish heritage,” Elizabeth says. “In fact, he’s currently working on getting his Irish passport because his dad was a first-generation Irish immigrant.”

The Cake

Boston baker extraordinaire George Montilio created a beautiful four-tier wedding cake for the big event after the bride attended a special tasting with the master himself. “It was fantastic,” she says, “and we used the topper from George’s parents’ wedding cake—which was more than 70 years old—on ours. That was really special, too.” In fact, the groom admits it’s something he never would have thought of. “Elizabeth actually found it in a box in the house. It was just such a beautiful touch, but that’s Elizabeth.”

The Ceremony

Officiated by former Governor Charlie Baker, the ceremony began in a cinematic fashion with the bride arriving via a refurbished tugboat owned by Suffolk Construction CEO John Fish and to a soundtrack of gospel stylings from the Celebration Singers. “For those who know George, we would never have thought this day would come,” Baker said during the ceremony. “But after all, he did have to go as far as 35,000 feet in the air to find the one woman with whom he trusted his heart.”

The Proposal

Even though George was forewarned by Elizabeth’s father that she hates surprises, he opted to propose at a lighthouse on Nantucket. After getting her there via helicopter under the guise that it was a magazine photo shoot for former police commissioners William Gross and Bill Bratton, a 7-mile Jeep ride ensued, during which Elizabeth was relegated to the back seat. Meanwhile, 175 friends and family were waiting at the Willowbend Country Club to celebrate their engagement. While the groom admits he wasn’t totally sure she’d say yes, he had a backup plan. “We had two signs made up: She said yes. She said no.” Thankfully, Elizabeth chose the former.

Patriots owner, Robert Kraft, said a few words before the ceremony, which was officiated by former Governor Charlie Baker. / Photo by Paul Blackmore

The File

Bride’s Dress
Made with Love Bridal

Bride’s Hair & Makeup
Razzmatazz Hair Studio

Bride’s Shoes
Manolo Blahnik

Montilio’s Baking Company

The Casual Gourmet

The Salty Florist

Groom’s Attire

Invitations/Place Cards
Regan Communications Group

The Celebration Singers; Joe Sparkes; The Zoo

DePrisco Jewelers

Wedding Planner
Ashley Boiardi, Regan Communications Group

Photo by Paul Blackmore

First published in the print edition of the August 2023 issue with the headline “Destination: Love at Last.”

Eva Alexandra Photography

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