Love Island’s Will admits he ‘should have’ proposed to Jessie

Will Young on podcast
-Credit: (Image: Instagram/Agree to Disagree)


Love Island’s Will Young has admitted that he should have proposed to girlfriend of two-years, Jessie Wynter. On their podcast, Agree to Disagree, the pair were discussing marriage, when Will recalled a moment when Jessie thought he was going to propose.

The clip teasing their podcast opened with Jessie stating: “Marriage is big, we've been together two years and I ain’t even got a ring.” Will then added: “Oh disclaimer, Jessie actually did think I was going to propose one time. This is actually f*****g horrendous when I heard Jessie thought I was going to propose. Do you remember? She told me, I took her on a beautiful trip to the Maldives for her birthday and she thought I was going to propose. I should have really.”

Jessie Wynter
Jessie previously thought Will would propose while on holiday -Credit:Instagram/Agree to Disagree
Will Young and Jessie Wynter
Will and Jessie first met on Love Island -Credit:ITV

Some fans took to the comments section to tell the couple what they thought of the situation. One wrote: “Hopefully he doesn't miss the next opportunity”. Another added: “You know what to do will”. And a third predicted: “it'll happen soon”.

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It hasn’t been the first time that the pair have teased engagement with fans believing Will had put a ring on it last month. In November, the Love Island couple posted a snap of themselves suited and booted. Jessie even appeared to be flashing a sparkly ring on her fourth finger, suggesting that her farmer lover had finally popped the question.

The pair even captioned the photos with the date appearing to suggest it was of significance. Fans then realised things weren’t as they seemed. The pair uploaded the snap of the 16th November, the date included in the caption was actually in the future - Jessie wrote: "19.11.24." And, the supposed engagement ring appeared to be on the wrong hand as Jessie wore the sparkler on the right hand as opposed to the left.

Will Young and Jessie Wynter posing
Will Young and Jessie Wynter sparked an engagement frenzy in November -Credit:Instagram/Jessie Wynter

It was later revealed that the pair were starting a podcast together, Agree to Disagree. The pair wrote on Instagram that they were ‘so proud’ of the project. Some fans weren’t impressed by the deceit with one writing: “Advertising their new joint insta by pretending they are getting married” another said: “They are not engaged it’s a new insta . I wish however they were they are my absolute favourite couple a fairytale romance.”

Will and Jessie met on the ninth series of Love Island that aired in January 2023. The pair coupled up as soon as Jessie entered the villa and have since moved in together.