90 Day: Hunt for Love Season 2 Cast: Their Stories Before Puerto Rico

90 Day: Hunt for Love is taking its next round of dating to Puerto Rico, bringing together familiar franchise faces whose earlier relationships played out across very different shows. Some viewers will recognize people from The Single Life; others will remember a marriage, a move overseas or a relationship that began online. Before Season 2 arrives, those earlier stories help explain what each person brings to the retreat.

Meet the seven featured 90 Day: Hunt for Love Season 2 singles

TLC’s Season 2 lineup features Brittany Banks, Chloe Fabiano, Jamal Menzies, Kara Bass, Michael Ilesanmi, Steven Frend and Emma Perry. They are returning members of the wider 90 Day franchise, rather than the returning core cast of Hunt for Love’s first season. The network also confirms a group of new singles, so these seven names should not be mistaken for every participant in the resort.

Brittany Banks

Brittany’s original franchise story was with Yazan on 90 Day Fiance: The Other Way Season 2. Their connection began through a video chat with his sister, and Brittany planned to leave Florida for Jordan. TLC’s original introduction emphasized the differences between her expectations and those of Yazan and his family, particularly around religion and marriage.

Viewers may also recognize Brittany from 90 Day: The Single Life, the show attached to her name in TLC’s new cast gallery. For Hunt for Love, the network says she is open to dating men or women and wants to rebuild trust. That gives her a broader dating setup than her first story, which revolved around making one international relationship work.

Chloe Fabiano

Chloe appeared with Johny Fernandes on The Other Way Season 7. She met the pirate boat tour guide while vacationing in Aruba, then prepared to leave Boston to live with him. His work, her family’s reservations and questions about trust became part of the relationship’s official setup.

TLC now presents Chloe as moving on from that Aruba romance. Her background makes the resort’s central question especially relevant: can a connection that starts in a vacation setting become something sustainable once daily life returns? Hunt for Love gives her another opportunity to test that distinction with different potential partners.

Jamal Menzies

Jamal’s franchise connection began through his mother, Kimberly Menzies, before viewers followed his relationship with Veronica Rodriguez on The Single Life. An exclusive episode clip released by Entertainment Tonight in January 2024 showed Veronica and Jamal discussing exclusivity and their visits between Charlotte and San Diego. They also disagreed about how much communication they needed when apart.

The new season’s introduction emphasizes Jamal’s interest in a more traditional romance. That earlier conversation provides useful background: commitment was already part of his story, but so were differing expectations about what it should look like in practice.

Kara Bass

Kara first appeared with Guillermo on 90 Day Fiance Season 9. They met while she was working in the Dominican Republic, where Guillermo, who is Venezuelan, was living. After an engagement and a pandemic separation, their story shifted toward building a life together in Virginia.

More recently, Kara and Guillermo entered The Last Resort Season 3 to work on their marriage. TLC’s introduction described them as living in separate homes and trying to determine whether their family could stay together. FilmiFeed’s account of Kara and Guillermo’s recommitment decision explains how that retreat ended, with further context in the Tell All Part 1 recap. Hunt for Love introduces Kara in a different position: looking for a new partner who accepts her as she is.

Michael Ilesanmi

Michael is familiar to viewers from his relationship with Angela Deem, including their appearances on 90 Day Fiance: Happily Ever After? TLC’s Season 8 introduction still centered on his life in Nigeria and the spousal visa process, with Angela traveling from Georgia to join him for a visa interview.

For Hunt for Love, TLC describes Michael as newly divorced and rebuilding his life in America. The network says he wants companionship as well as romance. That changes the focus of his screen story from the logistics of joining an existing partner to meeting someone new in a group dating environment.

Steven Frend

Steven is the 90 Day Fiance Season 6 cast member who appeared with Olga, rather than the Steven associated with Alina on The Other Way. TLC’s original Season 6 announcement described Steven and Olga meeting at a beach during her summer visit to the United States. An unexpected pregnancy turned that brief romance into plans for a family and a future together across borders.

The new cast introduction presents Steven as a single father dating again after years away from it. Parenthood was part of his story from the beginning, making the practical future of any new relationship a relevant part of his return.

Emma Perry

Emma appeared with Ziad on 90 Day Fiance: Before the 90 Days Season 8. According to TLC’s introduction, the California resident met him through an international dating app and traveled to Morocco hoping their relationship would lead to an engagement. A previous engagement to another Moroccan man was also part of that season’s setup.

Hunt for Love brings Emma into a group dating setting and teases an existing connection to one of the franchise veterans. TLC’s cast introduction leaves that person’s identity unnamed. It is a question for the season to answer, rather than a confirmed new couple.

What changes when the show moves to Puerto Rico?

Season 1’s retreat was in Tulum, Mexico; Season 2 shifts to Puerto Rico. TLC previews activities including a Festival del Amor, salsa lessons, casino nights and street parties in La Parguera. Relationship coaches will also guide workshops, bringing conversations about compatibility alongside the social events.

The different format matters as much as the destination. The Other Way and Before the 90 Days often follow people pursuing an established long-distance connection, and The Last Resort starts with couples trying to repair their relationships. Hunt for Love places franchise veterans and new hopefuls together to explore fresh connections. Their earlier histories offer context, but do not establish who will leave the retreat together.

Also Read: A Doctor to Die For: The Sarah Harris Story Cast Guide

When does Season 2 premiere in the US?

90 Day: Hunt for Love Season 2 premieres Monday, October 5, 2026, at 8 p.m. ET/PT on TLC. HBO Max’s official US October slate lists the season for Tuesday, October 6, giving streaming viewers a different starting date from the television premiere.

The HBO Max announcement does not provide an exact streaming release time. Those dates are US listings, so viewers in Canada, the UK and Australia should check their local service schedules rather than assume the same availability.