They are actually engaged. Finally.
Honestly, if you had asked a Love Island skeptic back in 2023 whether a London sheep farmer and a Tasmanian personal trainer would still be together three years later, they would have laughed in your face. Most "villa couples" have the shelf life of an open carton of milk. Yet, Jessie and Will Love Island fans were just treated to the news everyone was waiting for: a secret proposal on the cliffs of Tasmania.
Will Young (better known as Farmer Will) popped the question to Jessie Wynter on December 9, 2025. They kept it under wraps for nearly a month, soaking in the silence before the Instagram storm hit in early January 2026. It’s a rare move for influencers. Usually, the ring is on the feed before the knee even hits the dirt. But these two have always been a bit different.
The Tasmanian Proposal: Why It Mattered
Will didn't just pick a pretty spot for the sake of a photo op. He took Jessie back to her home island, specifically the east coast of Tasmania. He spent over a year planning this. For a guy who rose to fame dancing with sheep on TikTok, the proposal was surprisingly high-brow—white flowers, candles, and a massive diamond that probably cost a fair few shearings.
He admitted it wasn't easy keeping the secret while they were traveling. They’ve spent the last few years bouncing between the UK and Australia. That kind of long-haul lifestyle kills most relationships. Basically, they decided early on that the only way to survive was to be a team.
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From the South African Villa to the Muddy Farm
When Jessie first walked into the South African villa as a bombshell, people were suspicious. She had already been on Love Island Australia. Critics called her a "game player." They thought she was faking her tears. They thought she was just looking for a way into the UK market.
Then she moved to Buckinghamshire.
Living on a farm isn't "aesthetic" in the way Pinterest makes it look. It’s poo. It’s mud. It’s waking up at 5:00 AM because a sheep is stuck in a fence. Jessie didn't just visit for a weekend; she moved into Will’s family home. She traded the Tasmanian beaches for Aylesbury rainy seasons.
- The Emus: To help with her homesickness, Will famously bought three baby emus.
- The Podcast: They launched Agree to Disagree, where they talk about everything from relationship dilemmas to the "tornado" of post-show fame.
- The House: They’ve been renovating their own place, a process Jessie described as "never-ending" and "stressful."
Proving the Haters Wrong
It’s easy to forget how much heat they took during Season 9. Fellow islanders like Casey and Tom (the "three musketeers") were often at odds with Jessie. There was that whole "snakes" comment. There was the drama surrounding Jessie’s intentions.
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While other couples were hitting every red carpet and signing fast-fashion deals, Jessie and Will went back to the farm. They did lambing season. They filmed TikToks in overalls. That authentic "wholesomeness" is exactly why they’ve outlasted almost every other couple from their season. They didn't try to be the "it" couple; they just tried to be a couple.
What Most People Get Wrong About Them
People think it’s all been sunshine and baby animals. It hasn't. Jessie has been incredibly open about her struggles with an eating disorder relapse and body dysmorphia after the show. The "tornado" of public opinion is brutal. She credited Will and professional therapy for helping her pull through.
They also had to navigate the "business" side of love. It’s a job. Their lives are content. Will once mentioned that a 30-minute farm task takes two hours when you’re trying to get the right TikTok angle. His dad wasn't exactly thrilled about the "messing around" at first, but the results speak for themselves. They’ve built a brand on being the weird, lovable outliers of the reality TV world.
What’s Next for Jessie and Will?
Now that the "fiancé" title is official, the focus is shifting. They’ve already talked about kids. Jessie, who is now 29, has been vocal about wanting to start a family once their house is fully sorted.
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The wedding will likely be a massive affair, potentially split between the UK and Australia to accommodate both families. Will has joked about whether the emus will be in attendance. Honestly? They probably will be.
Actionable Insights for Fans and Creators:
- Value Privacy: Even if your life is public, keeping big milestones (like an engagement) private for a few weeks builds genuine connection and mental health stability.
- Commit to the Pivot: Jessie moved across the world for this. Long-distance rarely works without a concrete plan for someone to move.
- Authenticity Over Aesthetics: People connected with them because they were "pooey and smelly" on a farm, not because they were perfectly polished.
If you’re looking to follow their journey more closely, check out their weekly podcast Agree to Disagree or keep an eye on Farmer Will’s TikTok for the inevitable "wedding planning on a farm" chaos that is sure to follow.