Aussie man takes big gamble with epic destination proposal 20260709 p60dw8.html – Breaking News & Latest Updates 2026
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Aussie man ‘takes big gamble’ with epic destination proposal

Tom Livingstone
Tom Livingstone

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Today

We’ve all heard the saying love knows no bounds, but one Aussie man went to extreme lengths to keep his proposal a secret.

Jesse Trout took his partner, Alicia Sheppard, on a holiday to the Maldives last month, but he had a surprise reason for wanting to take her there.

Jesse Trout hid Alicia’s engagement ring in the ocean for three hours before he proposed. Today

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In video shared to the Adelaide businessman’s social media accounts, Jesse and Alicia appear to be enjoying a champagne sunset overlooking the ocean of their luxury bungalow.

However, Jesse all of a sudden grabs a camera and walks into the water to pull what appears to be a small treasure chest from the sea.

He then returns to a confused Alicia and drops to one knee before opening the small box to reveal an engagement ring.

“I took a pretty big gamble, I actually put it in the ocean about three hours before I proposed because she ran into the bathroom and I was like, ‘I’ve got to get in the ocean, I’ve got to do it quickly’ and I was stressed for the entire time,” Jesse told Today.

In fact, Alicia could tell something was up, continuously asking Jesse what was wrong because he appeared to be very anxious.

“I was genuinely so confused, we just spent like half an hour getting ready to have a nice drink while watching the sunset, Jesse had just finished doing his hair and it just made no sense for him to be diving into the water after putting all that effort in,” she told Today. 

“So when he came out of the water drenched with a box, I was very confused but surprised and once I realised what was happening, it was just the best moment ever.”

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After such a special proposal, the newly engaged couple have contemplated how they might top it, even joking about a potential wedding ceremony atop a New Zealand glacier.

But while they now have the excitement of preparing for the actual nuptials, Jesse said the proposal story will hold a special place in their hearts.

“A little while ago, Alicia mentioned the Maldives and showed me some photos, and she had no idea, but her birthday was coming up and I surprised her a week before her birthday because I thought it would be a cooler surprise,” he said.

“And in my head, something just clicked and I was like, I can make this really weird and unique and something that we can’t wait to tell our grandkids about.”

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