Matt Cawley attached this $9,000 family heirloom ring to a sand dollar as part of a surprise proposal to Stacey Scanlon — but it came loose and fell among the rocks on a jetty. A lifeguard suspects the ring has washed out to sea.

By Michael Inbar

TODAYshow.com contributor

updated 8/12/2010 6:24:46 PM ET

A romantic engagement surprise turned into a moment of horror for a prospective Massachusetts bride Monday when she fumbled a $9,000 diamond engagement ring — and it disappeared down a rocky jetty below her.

Matt Cawley, a 31-year-old restaurateur from Deadham, Mass., was trying to make his proposal to 30-year-old schoolteacher Stacey Scanlon a memorable one. So he tied the family heirloom to an oversize sand dollar and placed it on the jetty at Bass River Beach in Yarmouth.

Cawley then took Scanlon for a stroll along the jetty, where he directed her attention to the sand dollar. “I had no idea whatsoever; we were just going on a morning walk,” Scanlon told TODAYshow.com.

When she saw the sand dollar, Scanlon said, “I went to pick it up and I heard something fall; I thought it was a rock. It was a rock! Just not exactly the rock I was expecting.”

Detached from the sand dollar, the ring tumbled down through the rocks. “It was a scene out of a movie: I can’t even describe it — it was unbelievable,” Cawley told TODAYshow.com. “I said as it was falling: ‘Stacey! The ring!’ And she said: ‘Wait — what ring?’ ”

“It was the worst feeling in the world,” Cawley added. “I won’t put it up there with a death, but I was in shock.”

No stone unturned
Little wonder: Not only was the diamond valuable — it was a gift from a family friend. After it fell, a thorough search began. Lifeguards, passersby, and even a retiree with a metal detector pitched in. One man even cut his head open while helping out and had to be bandaged by lifeguards.

“For four hours we all just worked and worked and worked, moving 200- to 300-pound boulders,” Cawley told TODAYshow.com. “It really shows you how nice people truly are; perfect strangers just helping out.”

But it was all for naught. Empty cans, fishing lines and lures were found wedged between the rocks, but no engagement ring. Lifeguard Matt Peterson told the Cape Cod Times that the ring may have washed out to sea.

“The tide does come up, and we tried to get it before the high tide reached where we were looking,” Peterson said. “As soon as the water came up, we had to stop.”

Silver lining
Meanwhile, family members who had secretly gathered to celebrate Cawley’s proposal were wondering what had happened, not knowing of the hours-long search. “This whole romantic thing was supposed to be on the pier, and I ended up asking her in the back of my cousin's Mazda,” Cawley told TODAYshow.com.

Despite the morning’s traumatic events, Scanlon said yes. “His cousin, back at the house, was so sweet,” she told TODAYshow.com. “She made me a string ring ... It's multicolored, purple and orange. It's one of those braided bracelets.”

But though there was no diamond, there was a silver lining: Unbeknownst to Cawley, just three days before the ill-fated proposal, his mother had had the ring insured. “I swore my mom knew,” Cawley told TODAYshow.com. “She insured the ring knowing something could happen. These things only happen to me.”

Now a jeweler is working on making a replica of the lost ring, with a replacement diamond, and the couple are thinking about a wedding in Cape Cod, hopefully in August. But, Scanlon emphasized, “definitely not near a jetty.”

Steve Veres contributed reporting to this story.