Ruby and Roarke rush to the pier but instead of a plane, their new guest arrives by boat.

The guest is Shay Fury, a country superstar. She’s so well-known, Ruby recognizes her right away and the bellboy drops her bags so he can ask for a selfie.

As she finishes talking to the bellboy about her hit “Gotta Walk a Country Mile”, her assistant, Beau, insists they move along.

Shay tells Roarke and Ruby that she hasn’t been able to write a new song in years. Roarke assures her the Island is a very creative place and she’ll know when her fantasy begins.

After Shay leaves, Beau asks Roarke if Shay’s personal espresso machine has been arranged for. Roarke asks Beau what his fantasy would be. He tells her he doesn’t want to have to worry about Shay’s coffee.

Helene catches sight of Beau walking and freaks out. She asks if he’s really Beau Braddock and begs him for an autograph.

Shay arrives at her room and it’s not to her specifications. Also, her luggage has been reduced from five matching pieces to one roller bag.

Helene gushes about Beau’s song “Gotta Walk a Country Mile” while Shay realizes her concert tee has changed from her own face to Beau’s.

Shay finds Beau in a soaker tub in the suite she was supposed to be staying in. They work out that the Island believes she needs to be the assistant instead of the star in order to unblock her songwriting. He sends her for his favorite tropical drink.

Javier checks in with Helene and is surprised she knows who Beau Braddock is. Country music isn’t what he thought she'd be into. She informs him that before her mother got sick, she was into art classes, clubs, and even skiing.

Shay makes an entrance but no one seems impressed and she quickly switches gears and orders the six most popular tropical drinks for Beau. She flirts with Javier who comments her boss seems a little high-maintenance. She replies that fame makes you that way sometimes.

She brings the drinks to Beau. His favorite is in among the six so that works out. A fan approaches and asks for a selfie. Beau obliges but when the fan asks him to video call her sister, he cues Shay to step in and tell the fan they have other things to do and he doesn’t have time to do the call.

Roarke checks in on them. Beau sneaks in a dig that the fantasy would be perfect if he had a well-trained assistant. Roarke suggests Beau perform a concert while he’s staying on the Island. Beau is taken aback but Shay insists he’d love to do it.

As Beau prepares for his concert, Shay finds his demands over-the-top which leads to them clearing the air and Beau letting her know how much he resents the things she asks him to do for her.

They both quit their jobs and fire each other.

On a cabana on the beach, Ruby cuddles Isla. She jumps up when she sees Roarke walking towards the cabana, leaving Isla behind, who insists she doesn’t need to tell Roarke anything, that this can be their secret forever.

Roarke asks Ruby to introduce Beau at the concert that night which Ruby happily agrees to. She then asks Roarke if she’d like to meet the friend she’s become close to. Roarke is honored but when they walk over to the cabana, Isla is gone.

In her room, Shay’s writing a new song, but it’s not flowing yet. Roarke comes in and reminds Shay that the Island’s gift to her is the anonymity she hasn’t had for years. Shay decides to change into comfortable clothes and go flirt with Javier.

Javier finds videos of Helene when she was into skiing. She was highly competitive and successful, winning lots of races. She could’ve gone to the Olympics.

Javier offers to pay so she can continue her training and get back to her schooling. She’s resistant to the idea, but he asks her to think about it.

Ruby checks in on Beau before she goes out to introduce him. When he hits the stage, his nerves get the best of him, and after singing only a few lines, he runs from the stage.

Roarke finds him drinking alone in his room. He tells her that he gave Shay a demo tape once and she said it wasn’t bad and that was discouraging enough to keep him from ever trying again. Roarke points out the dream must still be in him if the Island gave him that opportunity.

He feels like he’s truly failed. Roarke offers to give him some space. He thanks her for the experience.

Shay finds Javier playing his guitar by his fire pit. She discusses the time she lived in a silver trailer like Javier’s. She was eighteen and had left home with her dog after fighting with her mother. She realizes she only had the confidence to strike out on her own because her mother had always made her feel safe in herself.

Javier shares that he wishes he could give Helene the same sense of safety so she can risk a little.

She flirtatiously tries to wrangle an invite to Javier’s trailer and he explains he’s still getting over someone. She understands. He still offers to show her the trailer, just a tour. She steps in and the door slams shut. Javier can’t open it and Shay’s been transported to the trailer of her youth.

She finds a loaf of bread and a letter left by her mom. Picking up her guitar, with her dog at her feet, she is inspired by the letter to write a new song.

Helene invites Ruby to have breakfast at her bar so they can talk about Javier’s offer. Ruby says to go for it.

Shay’s humming her new song as she returns to her room. She hears a drunken Beau singing a song about how much he sucks.

Roarke comes to Shay’s room and Shay asks her to listen to something. She plays Beau’s demo for her. He sounds really good and Shay admits she told him he wasn’t. She thinks lying to him is why she can’t write anymore. She feels guilty that she crushed his dreams so she wouldn’t lose a good assistant.

Her mother’s letter commented that she’d write great songs living in that trailer because she knew who she was there. Now, after all her success and fame, she realizes she’s forgotten who she is and how important other people are.

She asks Roarke for a favor.

Shay heads to Beau’s room and tells him to get dressed up because he has another concert to play. She tells him he’s going to sing her new song. He reminds her he can’t sing. She sits him down and apologizes for lying to him when he played his demo for her. After moving a heavy pointy trophy out of his reach.

Ruby finds Isla on the beach. Isla promises to explains everything sometime soon. She just needs Ruby to wait a little longer.

Backstage, Shay gives Beau a pep talk. Javier lets them know it’s showtime.

Beau does a great job with the new song. It speaks to everyone in the audience.

Javier’s sitting with Shay and tells her how great the song is. She thanks him for helping her find her way and kisses him. Roarke sees the kisses and looks stunned.

Helene’s waiting when Javier gets up the next day, startling him. She tells him she called her trainer and they’re willing to take her for free. She’d need to leave today, just needs help with the plane ticket and some expenses. Javier’s sad to see her go so suddenly but is all in with helping pay for her school and training.

People are cheering Shay as she and Beau head for the pier. Roarke and Ruby see them off. Shay plans to focus on songwriting, leaving the performing to Beau.

Javier comes to say goodbye, explaining he won’t be captaining the boat as he’s needed to fly some special cargo. He thanks Shay for her song because it helped Helene recognize she has roots on the Island with him.

Helene comes to say goodbye to Ruby and Roarke. Ruby chokes up and walks away for a moment. Helene hugs Roarke and tells her she’ll always admire her. She thanks her for giving her and Javier the room to get to know each other and she asks Roarke to take care of him now that he’s all alone.