High winds prevent Javier from bringing the guests in by float plane. He and Elena have a day together. The guests are arriving by helicopter on the other side of the island and will arrive by chauffeured vehicles.

Javier reminds Elena that Helene’s birthday is coming up. He’d like them to celebrate it together, just the three of them. Elena is delighted.

Javier drops Elena off with Ruby. Elena shares the news about the birthday dinner.

The first guest, an exhausted therapist named Nancy, arrives by Jeep. She would like to rest so her fantasy can start the next day. Elena agrees, making an appointment to talk in the morning.

Next, they greet Emilio Hernandez and Oliver Gold. This is the first vacation out of three planned ones they haven’t had to cancel due to Emilio’s work conflicts.

They sit down to discuss their fantasy. Emilio takes the lead and explains they want to spend their time together with no distractions so they can connect again.

As they stand up from the meeting, Elena asks Oliver about his dietary restrictions. Oliver tells Emilio he’ll meet him in their room. Oliver and Elena reveal to Ruby that Oliver’s fantasy is to propose to Emilio in the perfect way. He provides Ruby with the instructions for his plan.

Oliver wakes up with a smile on his face the next morning. A loud squawky bird outside their room annoys them a little. They’re getting frisky when Ruby arrives with a breakfast cart. Emilio checks his phone. The cart is full of all of Emilio’s favorites. Ruby spills a little of the tea and offers to get a new tablecloth but Emilio insists it’s fine.

Elena meets with Nancy. She feels frustrated with the process of therapy. She feels like she knows how to solve everyone’s problems but wants her clients to get there themselves, but faster.

Elena is slightly distracted by Javier and Helene having breakfast nearby.

Nancy’s fantasy is to be able to just tell people what their problem is, naming it without wasting time talking about it, no holds barred. She figures if she can just tell them their problem, they can get started fixing it right away.

Elena proposes the Island present Nancy with some new clients she can be forthright with. Nancy starts with Elena, diagnosing her emotional distancing and counseling her to show people her soft, mushy center.

At the tiki bar, Oliver prepares to pop the question. Emilio arrives and Oliver breaks into a choreographed dance performance with the bar staff. Ruby records it all. At the finale, Oliver proposes and Emilio says no.

At dinner with Javier and Helene, things are awkward when Elena learns Helene didn’t include her willingly.

Ruby checks in with Oliver. Emilio’s moved out to his own room. Oliver cries himself to sleep.

He wakes up to the same first morning and the same squawky bird. Emilio is asleep next to him.

Ruby brings the breakfast cart in and spills the tea just as she did the first time. Emilio checks his phone. Oliver runs out to find Elena. She confirms that he’s in a time loop and so is she. They’re both stuck.

Oliver is determined to fix the loop by learning how to change it. Elena’s less confident.

Javier finds Nancy meting out her new form of therapy, sending clients away in tears. She’s still sure it’s the right way to help people. Javier declines her offer of a session.

Oliver and Emilio are walking on the beach. Emilio comments it feels like Oliver is always trying so hard with him. Oliver proposes and Emilio says no again.

The day starts again. Oliver keeps Ruby from spilling the tea this time.

Ruby goes to Elena to ask what’s going on. Elena explains about the time loop and asks Ruby to find out what Helene’s favorite cake is. She wants to go big for Helene’s birthday since the simple dinner didn’t work out. The fancy dinner goes even worse and Helene walks out.

The day starts again. Oliver sneaks out and finds Ruby before she arrives at their room. He explains about the time loop which makes sense for her. She promises to see if she can help him suss out why Emilio keeps rejecting his proposals.

Oliver takes a blindfolded Emilio on a hike. They arrive at a glamped up camp site. Emilio confesses this is his dream setting for a proposal. Oliver proposes. Emilio says yes. Oliver screams in happiness.

The day starts again. Oliver is frustrated, yells at the bird, and sends Emilio to get the door when Ruby knocks. Because Emilio’s at the cart, Oliver sees his phone light up and grabs it. There’s a message from “JC” asking if he’s broken up with Oliver yet.

Javier finds Oliver sitting alone on the beach. He offers to help if he can. Oliver asks if he knows why Emilio’s sister sent him that text. He’s desperate to know why Emilio would want to break up with him. Javier suggests he meet with Dr. Nancy.

Nancy accuses Oliver of not being honest with Emilio. He protests that he’d never lie to Emilio. Nancy asks him when they last argued. Oliver says they never have because he doesn’t like to fight. Nancy points out that being unhappy and pretending he’s not is lying.

She asks him why he doesn’t tell Emilio when he’s unhappy and he doesn’t have an answer to that. She tells him that answer is more important than Emilio’s answer to his marriage proposal.

At dinner with Helene and Javier, Elena takes a risk and asks Helene what’s bothering her. Helene expresses her feeling that her being on the Island isn’t working out. She doesn’t fit into Javier’s life. She feels like she doesn’t fit in anywhere. She leaves the table, commenting she should get off the Island.

Elena finds Oliver at the bar in the morning, drinking mimosas. She joins him.

Ruby’s sitting with Nancy, expressing a sense of weirdness about the day. Nancy is intrigued. Ruby gives Nancy her backstory and explains about her connection to the Island through her tattoo which has been tingling. Nancy is delighted.

Oliver shares how his boyfriend before Emilio dumped him over him not wanting to watch The Lord of the Rings with him. Elena is hungry and orders a huge pile of comfort food, reminding Oliver that everything will reset in the morning.

Nancy is stumped on how to solve Ruby’s feeling, which is a new feeling for her. Ruby asks why she doesn’t feel inspired by her work anymore. She admits her work is exhausting. She’s tired of listening to other people all the time. She wants someone to listen to her. Ruby offers to be her listener.

Oliver and Elena are very tipsy and stuffed full of chocolate cake. Emilio finds them like this. Elena decides to seize the moment and leaves for dinner.

She arrives at dinner with Javier and Helene still drunk and begins to talk honestly about the situation. She points out that Javier loves Helene and because she loves Javier, she and Helene need to make things work. Javier is taken aback to hear her profess her love.

Helene tries to excuse herself from the table but Elena stops her, pointing out how hurt Javier will be if Helene leaves the Island. Elena demands to know what Helene wants and Helene blurts out that she wants her birthday back. To her, her birthday meant that she and her mom would sit and eat her favorite birthday cake and talk. She misses her mother. Elena understands and leaves the table.

The day starts again.

Oliver opens the door before Ruby can knock and informs her that he won’t be proposing. He asks her to tell Elena that he’s decided to stay stuck so Emilio never breaks up with him.

Oliver and Emilio are walking on the beach. When Oliver suggests lunch, Emilio protests that they just had breakfast. Oliver agrees he can wait but then stops and wonders if he’s gotten so good at lying, he does it automatically. Elena appears and he asks Emilio for a minute.

Elena tells him he’s running away from trying to break out of the time loop because he’s scared. She tells him he’s fabulous and that she believes in him.

When they get back to their room, Oliver speaks honestly to Emilio about their relationship. He admits that he secretly feels unworthy of love and believed that if they ever broke up, it would prove it to be true.

Oliver confesses that he’s got a lot to sort out and understands why they need to end the relationship while he does that. He wants Emilio to be happy with someone who is sorted out. He leaves the room to Emilio, having gotten another for himself.

Elena checks in with Nancy to thank her for her advice, which Nancy doesn’t remember giving her. Elena’s realized that Javier’s faced with an impossible choice and she may have to make it to spare him the decision.

The time loop’s broken. Oliver wakes up in his own room, without Emilio at his side. There’s a knock at the door and Emilio’s there, asking if they can talk.

They go for a walk on the beach. Emilio explains that Oliver’s leaving the day before was the closest he’d felt to him in months. He wants Oliver to know he’s wonderful and deserves love. Oliver says he’s trying to accept that. Emilio promises to spend the rest of his life reminding him and proposes. Oliver accepts.

Ruby and Elena join up at the office instead of the dock. Nancy stops by to say goodbye. She thanks them for reminding her about the importance of listening and thanks Ruby in particular for helping her.

Oliver and Emilio come to say goodbye next.

Elena gives Ruby the rest of the day off and tells her she’ll be doing the same. Ruby looks perplexed.

Elena’s waiting at Javier’s trailer when he arrives. She missed Helene’s birthday dinner this time. She explains that she’d been there a lot. She breaks up with him, telling him that there’s nothing more important than his relationship with Helene. She walks away, crying.