He Handles Crises for a Living. She Solved One He Couldn’t: Changing the Channel.

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The public relations maven George Regan was pretty sure but not convinced that Elizabeth Akeley would say yes when he asked her to marry him on Aug. 19, 2021. Days before he dropped to one knee in the sand next to the Great Point Lighthouse on Nantucket, his crisis management expertise kicked in.

Mr. Regan commissioned two signs that would be placed prominently at the entrance to Willowbend Country Club in Mashpee, Mass., where he planned a surprise engagement party for 175 vaccinated or tested guests later that evening. One read, “She said yes!” The other, “She said no.”

If he had to post the latter sign, he figured he would just regroup. “I thought, if worse comes to worst, we’ll still have a heck of a party,” said Mr. Regan, 70. Ms. Akeley, 43, eliminated that worst-case scenario by strolling through the club’s door with a three-and-a-half carat oval diamond engagement ring on her finger. Mr. Regan wore a relieved grin.

Ms. Akeley and Mr. Regan met on March 19, 2020, at Logan Airport in Boston. Both were there for work: Ms. Akeley as a JetBlue flight attendant and Mr. Regan to stamp out a fire generated by the Jupiter, Fla., office of his firm, Regan Communications Group, of which he is chairman and chief executive.

“The company had made a major mess,” Mr. Regan said. “I wasn’t happy about having to go down there and apologize to a client.” Seeing Ms. Akeley at his Palm Beach departure gate lifted his spirits. “She was incredibly beautiful and incredibly goofy.”

Ms. Akeley, who then lived in Bath, Maine, had welcomed him aboard with a lightheartedness that was at odds with the mood at the airport that day: few people were flying in those earliest days of the pandemic. “Logan Airport was a ghost town,” Mr. Regan said. “But Elizabeth was, ‘Hi! Hi! Hi!’”

Her friendliness coaxed him out of what he said was a rare bad mood, one that improved further when, struggling with the onboard TVs, he punched all the overhead flight attendant call buttons in his empty row and Ms. Akeley hurried to the front of the plane. “She said, ‘Mr. Regan, are you having a heart attack?’” he said. He told her he was fine but couldn’t figure out how to change the channel.

Twenty minutes later, he was channel surfing confidently while continuing to make conversation with Ms. Akeley. When she eventually excused herself to attend to other passengers, he asked her for a date. “I said, ‘Listen, do you want to have dinner with me tomorrow night in Palm Beach?’” Mr. Regan said. Ms. Akeley, in her third year as a JetBlue flight attendant, had already accumulated a stack of business cards from passengers who had made similar requests.

“I gave him the response I always give,” she said. “I said, ‘I don’t date passengers.’” Mr. Regan’s reply was more off the cuff. “I said, ‘Don’t flatter yourself,’” he said. “I have no intention of dating you. I think you look hungry.”

“He made me laugh,” Ms. Akeley said, “and he hasn’t stopped making me laugh since.” So she made an exception to her rule. Instead of flying to Los Angeles the next day, she changed her flight schedule to meet him.

Both consider that date, on March 20, 2020, as kind of a joke. Mr. Regan, unable to get a restaurant reservation on the first night of Florida’s Covid shutdown, picked up hot dogs from his favorite Florida hot-dog stand, Dune Dog Cafe, and paired them with a bottle of chardonnay. Then he arced out a spot on the beach near Ms. Akeley’s Jupiter hotel, where they talked for hours.

Their 27-year age difference was an issue for neither. “George is young at heart, and he looks young,” Ms. Akeley said. Mr. Regan joked that he is in denial about the May-December pairing. Undeniable, though, was his eagerness to see her again when both returned to New England.

It happened in less than a week. Though Ms. Akeley had several back-to-back flights scheduled, four days after their hot-dogs-in-the-sand dinner, she called him. “I said, ‘Hey George, it’s Elizabeth,’” she said, adding, as a joke, that she was hungry.

Ms. Akeley grew up in Bath with a brother, three sisters and a large extended family. Her first marriage, which lasted five years, ended in divorce in 2015. Mr. Regan was born in Boston and raised alongside two sisters in nearby Quincy. He has never been married, but not for lack of trying. Two previous engagements were called off. Until he met Ms. Akeley, “I had real reservations” about marriage, he said.

But he rarely lacked for company, or a place in the spotlight in his home state. Mr. Regan’s best friend is Bill Bratton, the former police commissioner of New York City and Boston. Charlie Baker, the governor of Massachusetts, is another longtime friend.

Politics propelled Mr. Regan’s career: In the early 1970s, he was then-Boston Mayor Kevin White’s press secretary and director of communications. Mr. White, he said, taught him how to negotiate and solve problems on the fly. “I wasn’t doing P.R. for a muffin company,” he said.

Occasionally, he followed the political spotlight past New England. In 1976, he was a national advance person for Jimmy Carter’s presidential campaign.

Mr. Regan, whose current client roster includes New Balance and Bank of America, still acts as an unofficial adviser to his politician friends. But his connection to Boston’s power players wasn’t of much interest to Ms. Akeley in the early months of their courtship, conducted mostly over takeout dinners at his condo in Boston’s Seaport district.

“I was trying to figure out what was going on with my job,” she said. The pandemic’s grip was tightening and flights were getting scarcer. By the end of April, she had taken a six-month leave of absence.

That freed her to spend more time with a delighted Mr. Regan. Before Covid, “I was out morning, afternoon and night,” he said. “People would say to me, ‘George, you’ve got to be going crazy with the pandemic.’ But I was having the time of my life.”

He and Ms. Akeley were falling in love. When they threw a small outdoor party in July 2020 for friends and family at Mr. Regan’s summer house in Mashpee, those feelings didn’t go unnoticed. Despite the downshift in his social life, “I was so happy,” Mr. Regan said. “People said, ‘He’s up to something.’”

Those people included Mr. Bratton. “When George met Elizabeth, it was like when Al Pacino meets Apollonia in ‘The Godfather,’” he said. “That was it.” But the proposal took even Mr. Bratton by surprise. “You could have knocked me over with a feather when he told me he was going to get married,” he said. “I thought he was going to be a lifetime bachelor.”

In the summer of 2021, Ms. Akeley, who had gone back to work and is still a JetBlue flight attendant, moved in with Mr. Regan. Around the same time, Mr. Regan called Mark Akeley, Ms. Akeley’s father, to say he planned to propose. Mr. Akeley warned him against the surprise.

“He said, ‘Elizabeth doesn’t like surprises; maybe you should tell her,’” Mr. Regan said. Instead, Mr. Regan dreamed up the engagement party and the “yes” and “no” signs and enlisted Mr. Bratton to be his beard.

On Aug. 19, 2021, “we were supposedly going to Nantucket for a photo shoot for a new book Bill Bratton had coming out,” Ms. Akeley said. But when their helicopter landed and they made their way to the lighthouse with former Boston police commissioner Willie Gross, Mr. Bratton and his wife, Rikki Klieman, the cameras followed Ms. Akeley instead of Mr. Bratton. When she spotted her dog, Levi Jean, in the distance, ferried to the island that afternoon by Mr. Regan’s chief of staff, she didn’t know what to think.

The Shih Tzu, one of the couple’s six dogs, bounded toward her wearing a white harness; zip tied to the pup was a ring box. When she turned around, Mr. Regan was on his knee in the sand. Though her father was right — she confirmed she really doesn’t like surprises — “I was elated,” she said. “I had tears of joy.”

On July 30, the couple were married at Nauticus Marina in Osterville, Mass., before 400 guests, all of whom were vaccinated or had provided a negative Covid test, and eight members of the 12th Baptist Choir, from Boston, who serenaded them with “At Last.” Gov. Baker officiated at the ceremony.

Before the couple said their “I do’s,” the governor reminded the crowd that Mr. Regan “knows everybody” but had to ascend 30,000 feet to find love. Mr. Regan and Ms. Akeley, both in tears as they read handwritten vows, promised to cling to that love for the rest of their lives.

When they were pronounced husband and wife minutes later, the choir kicked in again, this time to the gospel standard “Oh Happy Day.” For Mr. Regan, who tacked on a “yahoo!” before his “I do,” there was no happier day.

On This Day

When July 30, 2022

Where Nauticus Marina in Osterville, Mass.

More Beantown Bold Names New England Patriots owner Robert Kraft, who gave a reading from the Jewish Book of Sirach during the ceremony, was among the famous wedding guests; Massachusetts Lt. Gov. Karyn Polito, who also attended, welcomed the crowd to a post-wedding cocktail hour and reception steps away from the altar.

A Breeze Getting acquainted with Mr. Regan’s famous friends has been effortless for Ms. Akeley. “George makes everything feel normal,” she said. “He always makes sure I feel comfortable in every setting.”

More Dogs Cocktail hour began with live saxophone; snacks included hot dogs from the Deepwater Hot Dogs truck, among the groom’s local favorites for his favorite food.

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