Season 2 of 90 Day: Hunt for Love is already serving chaos in Puerto Rico, with a new episode landing Monday night. But before the salsa-night fallout continues, it is worth asking an uncomfortable question about the season that started it all: did Season 1 actually work?
The first trip to Tulum premiered in May 2025, bringing back franchise favorites like Chantel Everett, Tim Malcolm, Colt Johnson and Rob Warne alongside newcomers hoping for a fresh start. The Tell All filmed in June 2025, and a year later the scoreboard is brutally mixed: two engagements, at least three splits, and one love story nobody saw coming. So was Season 1 a success, or proof that the format is better at making drama than making couples?
The Scoreboard: 2 Engagements, 3 Splits
Strip away the beach games and the confessionals, and this is what Season 1 left behind. On the win column: two cast members got engaged after filming, though only one engagement is still standing. On the loss column: three relationships alive at the Tell All are now over, according to reports and social media clues. The rest mostly left Tulum exactly how they arrived: single and unbothered.
The One Undeniable Win: Chantel and Ashley
Every argument for Season 1 starts and ends with Chantel Everett. Instead of chasing someone at the resort, she shocked the cast by asking out her longtime friend Ashley Bowen. The relationship survived even a massive on-stage argument between Ashley and Chantel’s mother at the Tell All. The couple now run the joint Instagram account @ChantAshleyDiaries, and Ashley proposed on December 17, 2025. Chantel said yes.
The Messiest Exits: Jeniffer, Tiffany, and Cortney
Then there is the other side of the ledger. Jeniffer Tarazona and Cole Anderson were still together at the Tell All, but tension over her past hookup with Rob Warne never went away. The two no longer follow each other on Instagram, which fans read as the quiet end of the relationship, though neither has announced a confirmed breakup. Tiffany Franco left Tulum with Rocky Russo, only to confirm at the Tell All that they had already split — and her next relationship, with family friend Ronnie, appears to have fizzled too after their shared photos vanished. And Cortney Reardanz announced her engagement to boyfriend Phil in May 2026, only for the couple to break up soon after, according to reports.
The Ones Who Walked Away Better Off
Not every Season 1 story ended in heartbreak. Tim Malcolm left single after his planned date with newcomer Elise Benson never happened, but he has stayed busy across Instagram, TikTok and YouTube, and even popped up on the Last Resort Season 3 Tell All. Colt Johnson recovered from a serious leg injury and a later car accident, moved on from Cortney, and moved in with Diana, his girlfriend from Brazil. Rocky Russo leaned into his wellness world as a fitness coach and podcast host. And Usman Umar, who left Tulum vowing to marry by the end of the year, is still single as of October 2026 — but still releasing music as Sojaboy.
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Here is the case for the prosecution: one lasting engagement out of an entire cast is a rough hit rate for a dating show. Here is the case for the defense: that one engagement is real, the cast stayed relevant, and Season 1’s messiest player — Rob Warne — is still shaping Season 2, with his boy band 90 Day Bad Boys and the Emma Perry hookup claims feeding directly into the Jamal-Emma triangle airing Mondays.
So now it is your turn to settle it. Team “Season 1 worked — Chantel and Ashley are proof” or Team “One engagement does not save a flop”? Drop your verdict in the comments, and tell us which Season 1 star deserved a better ending.
