The one thing that went wrong during Adelaide man’s risky proposal

When Jesse Trout decided to propose by hiding an engagement ring underwater in The Maldives, he couldn’t have foreseen how it would unfold.

The Adelaide local, 34, told nine.com.au he considered a couple of scenarios to pop the question to his girlfriend Alicia Sheppard before deciding on his underwater adventure.

Ultimately, he decided to hide the engagement ring in the shallow of the ocean, grabbing an underwater camera ahead of retrieving it to capture the moment.

“I actually put it in the ocean three hours before proposing. She went to the bathroom and I was like, ‘I’ve got to do it quickly’,” Trout told Today.

“I was stressed the entire time. She kept asking what was wrong because I looked anxious.”

He remained committed to the surprise scenario, doing his hair and putting on cologne before jumping into the water and emerging with a ring box.

Sheppard, 24, said she was “so shocked” when Trout took the plunge after they’d spent “an hour getting ready” to have drinks while watching the sun set.

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“It just made no sense for him to be diving into the water after putting in all that effort,” she told Today.

Before Sheppard could figure out what Trout was doing, he was down on bended knee.

While she always knew she’d say “yes” to a proposal, Sheppard surprised herself with an impromptu dance, which can be seen in their now-viral social media video.

“Honestly, I’d thought about it and I was like, ‘I’ve got this. I’d handle it well’,” she said.

“When it happened, I was really speechless ... I was just so happy, and I was shaking and I couldn’t stop giggling. In the video we took I did a little dance as well. I didn’t think I’d do that!”

The best part is she didn’t suspect a thing, telling nine.com.au, “I don’t know how he pulled it off.”

Trout explained he had the ring box hidden in another room and ran to retrieve it while she was in the bathroom.

He cleverly used the cover of being on a family holiday for Sheppard’s birthday to distract from the fact he was planning to propose.

While the video fo the moment looks perfect and magical, there was one part of the plan Trout couldn’t pull off.

Trout had placed the ring box inside a little treasure box he thought was waterproof.

“I think it was just a little bit waterproof. It was technically meant to have a little light in there that was going to make the ring glow,” he said.

“Unfortunately, that didn’t survive three hours in salt water.”

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Trout and Sheppard met just over a year ago while jetskiing at Silver Sands Beach in South Australia. They soon began dating and quickly realised they had found their forever person.

“The ring took 12 weeks to make, because I wanted to make something custom and special,” Trout said.

The proposal was several weeks in the making. A couple of alternate plans he had for a proposal included a helicopter wine tour in South Australia, however the cold weather nixed that one.

The birthday trip to much warmer Maldives seemed like too perfect an opportunity to pass up.

“The Maldives is honestly the only place I’ve ever been to in the world that looks like the photos and feels like the photos. You can’t explain it. It’s so beautiful,” Trout said.

The couple are already discussing equally adventurous ideas for their wedding, although they’d like it to be small and intimate.

“Jesse’s talked about a glacier in New Zealand,” Sheppard said. The idea was sparked by a video Trout saw of people visiting one in a helicopter.

“I was like, ‘What if we have small wedding and we have our families in two helicopters and we quickly get married on a glacier or something?’” he adds.

“I’ve also loved that little white church from the kids movie Monsters vs Aliens, the little white church on top of a hill. That’s the second option we were talking about.”

Trout’s advice for those planning an elaborate proposal is to accept “things aren’t going to be perfect”.

“You have an idea and a concept, but just kind of let it happen. I think that’s the main thing. Creating a story about the love you have for someone else is more important than where and how you’re going to do it.”

A ‘beautiful’ shift in proposal trends

A recent shift in proposal trends has seen move away from elaborate proposals, perfectly captured using the latest technlogy, to more personal and intimate moments such as Trout’s.

Blake Asaad, Founder and Creative Director of Goodstone, said couples in 2026 are prioritising deeply personal, meaning-driven moments over Instagram-perfect spectacles.

“We’re seeing couples who want their proposal to reflect their actual relationship, not someone else’s idea of what romance should look like,” the jewellery expert said.

This includes designing the rings themselves, as Trout as done.

“The shift is quite beautiful. People are asking for rings that capture specific memories, inside jokes, or meaningful symbols only the two of them understand,” Asaad said.

“It’s about creating something that resonates personally rather than impressing an audience.”

This shift also applies to the way clients discuss their proposal plans.

“They’re describing wanting to propose over morning coffee in their favourite corner of the flat or during a quiet evening cooking together. These moments feel real because they’re rooted in the daily rhythms that actually define their relationship,” Asaad added.