Fashion / Weddings

Houston Couple’s Romantic Stroll Gone Wrong Quickly Turns Into a Dreamy Island Engagement

Sweating It Out for the Ring

BY // 02.21.20

Ah, February, the month of romance. Love is in the air. Cupid is warming up his bow. And our thoughts are turning to romantic engagements. This is a new PaperCity series of engagement stories that will continue throughout the year.

A beautiful hotel suite in Anguilla readied with bouquets of roses, flickering candles and a bottle of champagne — the stage was set for a very romantic, surprise engagement evening. It was perfect, almost.

Ann Harris, a director at PTO Legal Search Ltd., was not expecting anything more than a romantic holiday at the Viceroy Resort (now a Four Seasons property) with her beau Jonathan Ayre, a partner at Orrick, Herrington & Stucliffe LLP, a global law firm with its headquarters in Houston. But he had exciting plans — a romantic stroll along the sand to a beachfront restaurant and a return to the hotel for the roses, the champagne, the candles and the ring.

“The night Jonathan proposed,” Ann recalls “the typical romantic walk along the beach did not play out the way you see in the movies.”

The Viceroy concierge had suggested that they take a stroll along the beach rather than take a taxi.

“We started our walk before sunset and could see the restaurant’s lights in the distance, the walk was much longer than we anticipated . . . By the time we made it to the restaurant, it was dark, and the island humidity had gotten the best of us.

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“Even though we were late to dinner, and a little wrinkled, we ended up having a lovely time and laughed about our pre-dinner excursion.”

Jonathan & Ann Ayre, the Four Seasons Hotel in Anguilla where they took a suite for a summer vacation.
The Four Seasons Hotel in Anguilla where they took a suite for a summer vacation.

Jonathan, says Ann, always has a calm demeanor but he later admitted that he was “sweating it out” all night. They were running so late that he worried that the candles would have burned out, that the ice in the champagne bucket would have melted and the rose petals shriveled back in their hotel room.

“He was so concerned not to give away what he had planned by rushing things,” she says, “and fortunately it all worked out in the end.

They took a taxi back to the hotel where the romantic setting awaited.

“The next thing I knew, Jonathan was on his knee asking me to marry him with a beautiful diamond ring inside a little box in his hand,” Ann says. “I immediately said yes!”

Almost a year later, in June 2013, they were married at Meadowood Resort in Napa Valley. Later this year, they are planning on celebrating their seven-year anniversary where the couple spent their honeymoon — the Four Seasons Lanai and Hualalai properties in Hawaii.

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