Oliver's fantasy is to surprise his boyfriend Emilio with the perfect proposal, but when Emilio says no, Oliver finds himself reliving that day over and over again. Meanwhile, Roarke, also caught in the time loop, must confront her fears about her relationship with Javier.
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All episodes — Season 2
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S2 E1Tara and Jessica's High School Reunion; Cat Lady
Jan 2, 202343 min
Longtime best friends, Tara and Jessica, want to rule their 30th High School Reunion, but their plans go sideways when everyone is forced to tell the truth. Andi wants to know if her cat BoBo loves her as much as she loves him. Roarke juggl
S2 E2Hurricane Helene; The Bachelor Party
Jan 9, 202343 min
In the wake of her mother’s passing, Helene visits the island in search of her biological father. Roarke and Javier grow closer. Ruby gives herself a spiritual cleanse with a bonfire and a night swim, where she encounters an old friend.
S2 E3Paymer vs. Paymer
Jan 16, 202344 min
Empty nesters Dolly and Dutch seek clarity on how to spend their next chapter. Meanwhile, Helene helps Ruby tap into her newfound youth. Javier opens up to Roarke as he wrestles with his new role.
S2 E4Mystery in Miami
Jan 23, 202341 min
Three best friends set out to track down the missing fourth member of their squad... in 1980s Miami, Roarke confides in Segundo about letting people in, Ruby's cabin fever is an itch that needs to be scratched.
S2 E5The Urn
Feb 6, 202344 min
After an urn comes off the plane, three siblings must work through their past resentments in order to spread their mom's ashes and fulfill her last fantasy. As the kids wrestle with their past, Roarke remembers their mom, her very first gue
S2 E7#Happy
Feb 20, 202344 min
Amber's fantasy is to have her actual life be as perfect as her Instagram life. But when Amber's family transforms into the perfect Insta-versions of themselves, she soon realizes something about all this perfection is very wrong. Meanwhile