Where Are They Now? The Shocking 2025 Update On Love Island USA 2021 (Season 3) Couples

The third season of Love Island USA, which aired in 2021, remains one of the most talked-about installments of the American franchise, delivering high drama, unexpected winners, and a major mid-season exit that shook the Fiji villa. Now, over three years later, fans are constantly searching for the latest updates on the islanders who captured their hearts. As of the current date in December 2025, the landscape of relationships formed in the villa has completely shifted, with the shocking reality being that *zero* couples from the 2021 season are still romantically together, including the fan-favorite runners-up who tried to make it work for years.

This deep dive into Love Island USA Season 3 reveals the current status of the most memorable contestants, from the $100,000 winners Korey Gandy and Olivia Kaiser to the dramatic love triangle involving Cashay Proudfoot, Cinco Holland, and Trina Njoroge. Prepare for a comprehensive look at their lives, careers, and the final fate of the season's most promising connections.

The Love Island USA Season 3 Winners: Korey Gandy & Olivia Kaiser Biography

The finale of Love Island USA Season 3 concluded with a surprise victory for Korey Gandy and Olivia Kaiser, who secured the $100,000 prize. Their journey was unique, evolving from a friendship coupling to a genuine romance in the final weeks of the show.

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Korey Gandy

• Age (During Show): 28
• Hometown: Virginia Beach, Virginia
• Occupation (Pre-Villa): Rental Car Agent
• Current Career: Korey has leveraged his reality TV fame and has been reported to hold a Branch Manager position at an Enterprise Rent-A-Car, while also focusing on his social media presence and personal endeavors following his appearance on the CBS show.
• Relationship Status: Single.

Olivia Kaiser

• Age (During Show): 28
• Hometown: Anchorage, Alaska
• Occupation (Pre-Villa): Business Owner/Cosmetologist
• Current Career: Olivia is a licensed cosmetologist and owns and operates her own salon business, Liv Beautifully, based in Scottsdale, Arizona. She continues to work as a business owner and influencer.
• Relationship Status: Single.

The Final Verdict: Which Love Island USA 2021 Couples Are Still Together?

Despite the promise of finding lasting love in the Fiji villa, Love Island USA Season 3 has unfortunately followed the trend of most reality dating shows. As of late 2025, all romantic relationships formed on the show have officially ended. This includes the winners, the runners-up, and the most dramatic connections.

Korey Gandy and Olivia Kaiser (Winners)

Korey and Olivia's relationship, which began as a strong friendship, unfortunately, did not last long in the outside world. The pair confirmed their breakup in November 2021, just a few months after the finale. They cited the difficulty of maintaining a relationship while living on opposite coasts—Korey in Virginia Beach and Olivia in Scottsdale, Arizona—as the main reason for their split, though they remain on friendly terms.

Kyra Lizama and Will Moncada (Runners-Up)

Kyra and Will were arguably the most stable and fan-adored couple of the season, taking second place in the final vote. Their relationship was a rollercoaster, with a brief split in November 2021, followed by a reconciliation. They were one of the few couples from the franchise to try and make things work over a long period. However, after much speculation, Kyra confirmed in mid-2024 that she and Will had broken up again. This final split officially marked the end of any remaining romantic connection from the Season 3 cast.

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Josh Goldstein and Shannon St. Clair

Josh and Shannon were a powerful, fiery couple and strong contenders to win the season. Their time in the villa was cut tragically short when Josh received the devastating news that his sister had passed away. The couple chose to leave the show together to mourn and support each other, a moment that remains one of the most emotional in Love Island USA history.

They continued their relationship outside the villa for a significant period, moving in together and sharing their life on social media. Despite the strength of their bond, they announced their separation in August 2022. Josh has since focused on his personal life and career, while Shannon has become a prominent social media influencer, with updates on her life continuing into 2024.

The Biggest Drama and Controversies of Season 3

Season 3 of Love Island USA was not without its explosive moments and serious controversies, contributing to its high viewership and lasting impact on the reality TV landscape.

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The Cashay, Cinco, and Trina Love Triangle

The most enduring storyline of the season was the complicated love triangle involving fan-favorite Cashay Proudfoot, Melvin "Cinco" Holland Jr., and Trina Njoroge. Cinco initially coupled up with Cashay, but his head was turned by Trina, leading to weeks of emotional turmoil and a divided villa.

Though Cinco was eventually dumped from the island, he and Cashay reunited shortly after the show and attempted to make a relationship work, becoming the beloved "Cashco" to fans. Unfortunately, they officially announced their breakup in early 2022. Trina Njoroge, a psychiatric nurse before the show, has since focused on her career and advocacy work, maintaining a close friendship with Cashay that was forged in the villa.

The Shocking Removals of Yulissa Escobar and Cierra Ortega

The season was marred by a serious controversy involving the removal of two contestants, Yulissa Escobar and Cierra Ortega. The women were removed from the villa after it came to light that they had previously used racial slurs on social media. This incident highlighted the ongoing need for rigorous background checks and accountability for reality TV contestants.

Jeremy Hershberg and Bailey Marshall

Jeremy Hershberg, an original islander, had a difficult time finding a connection until the very end, eventually coupling up with late arrival Bailey Marshall. Despite only being together for a short period, they managed to place third in the finale.

Their relationship quickly dissolved after leaving the villa, with Bailey confirming their breakup shortly after the season ended. Jeremy, an entrepreneur, and Bailey, a marketing executive from Portland, Oregon, have both moved on, focusing on their respective careers and social media influencing.

Looking Back at the Legacy of Love Island USA Season 3

While Love Island USA Season 3 may not have resulted in any long-term romantic relationships, its legacy is defined by its dramatic moments and its memorable cast. The season, hosted by Arielle Vandenberg, was a pivotal moment for the American version, solidifying its place in the reality TV landscape with its move to the Peacock streaming service in later seasons.

The islanders, including Cashay, Trina, Korey, and Olivia, have all continued to build careers as social media personalities and entrepreneurs. The season proved that while the search for love may fail, the connections and friendships—like the unbreakable bond between Cashay and Trina—can often last far longer than the romantic pairings. The 2021 season remains a benchmark for the drama, twists, and unforgettable personalities that define the Love Island experience.