Late at night at the B&B, Jess frantically tosses and turns in her sleep. The dream is one she’s had many times before and that has haunted her for years. In the dream Jess plunges into the ocean only to surface in the middle of a raging storm. Jess screams frantically for Rebecca but gets no answer. Finally, off in the distance, Rebecca calls out for help but Jess can’t find her in the pounding waves and driving rain. As Jess begs for Rebecca to grab her hand, Rebecca cries out to her that she can’t swim anymore. Suddenly Rebecca’s screams become muffled and gurgled. Jess calls again for her friend but before she finds her, Jess’s eyes snap open and the dream is over.
Early the next morning Abby stops by Trace’s cabin for an early visit before he heads off to work. The romance between them now in full swing, Abby thinks nothing of flinging her arms around him and giving him a tender kiss. But as she does, Trace’s mother Dee steps out of the front door, startling and embarrassing Abby. Dee’s surprise visit is ostensibly to bring Axel a new dog bed, but Trace is pretty sure that his parents are having problems…again. Dee casually asks Abby what brings her by so early and Abby, searching for a good excuse, tells her that she needs paintbrushes so she can paint her daughters’ rooms. Completely aware of Abby’s lie, Trace jokingly tells her that she passed the hardware store miles back. Dee scolds him for the bad joke and he heads off to grab some spare paint brushes. While he’s away, Dee and Abby talk about Abby’s move home and her custody battle with Wes. Dee is compassionate towards Abby’s situation and does her best to assure her that it will all work out for her and the girls…and for Trace too. Just then Trace arrives back with the paint brushes and Abby takes her leave. After she departs, Dee tells Trace how wonderful Abby is. Trace says he knows where this is headed but Dee insists that she only wants him to be happy. He tells her that he is happy and she responds, “Happy with Abby.” Trace smiles then tells his mom that he needs to head off to work.
Meanwhile at Sally’s, Jess nervously goes over the menu for a party she’s throwing at the B&B. Behind the counter, David does his best to keep her calm and follow her, but her frenetic changes have him at a loss. As she runs through the menu again, she announces that she needs to have potato salad, coleslaw, and she also needs to break up. David is shocked into silence as Jess explains that after their date at the mini golf course, she realized that he and Bree have far more in common than she and he ever could. While David tries to compose his thoughts, Jess then asks him if he would consider being her chef at the B&B. She’s wanted to offer him the job since the night he made dinner for her and Bree but unfortunately, she can’t afford to pay him yet. Even with the caveat, David jumps at the chance to have his own kitchen and he happily agrees, making this the best breakup either of them have ever had.
In Boston, Mick pays a visit to his business partner Darryl. When he first arrived earlier in the day, Mick first went to check in on the site of his latest project. When he met with the foreman, he learned that the project had become stymied by problems with the unions, material delays and financing. He ordered the foreman to get the project moving again with the promise that he and his partner would settle the financing problems. But standing in Darryl’s living room, Mick realizes that Darryl is more preoccupied with meeting his wife at a fundraiser than with their failing venture. Mick is having none of Darryl’s waffling and demands that he sit here and work out their “numbers” problem. Darryl tells Mick that his wife Candace won’t be happy if he’s not at the fundraiser. Mick then takes a look around and calmly tells Darryl that he should tell Candace that he’s busy doing everything he can to keep their nice house.
In Chesapeake Shores, Bree is frustrated as she restocks the lending library to replace the books that have been stolen. As she does, Jess tries to explain to her why she broke up with David. They both feel awful about the situation and Jess’s hiring David as her chef just adds another layer to an already awkward situation. Just then David walks out, saying how angry Sally is now that he’s quit his job. Jess is flabbergasted and reminds David that she clearly told him that she couldn’t pay him until the B&B was up and running. David tells her he was miserable waiting tables and that he honestly can’t wait to get started on the menu for the party. Satisfied with his reasoning, Jess hands him a handful of crumpled up bills and he heads off to get the last ingredients for the party.
Back at the house, Abby’s busy painting the girls room when she gets a text from Wes saying that he’s in town and needs to talk. Abby meets him at the waterfront and they take in the breathtaking scenery, talking about happier times in their relationship. Wes then confides in Abby that he’s had a change of heart and has seen the life Abby and his daughters have in Chesapeake Shores. With that in mind Wes has decided to drop his petition for sole custody and instead, wants to go back to their previous arrangement. What’s more, with his career in finance over, Wes no longer has any reason to live in New York. Instead he’s decided to move closer Chesapeake Shores and his daughters. Abby is overjoyed at Wes’ change of heart is excited for a chance at a fresh start with him and the girls.
Having finally finished repainting the row boat, Connor runs inside the house to grab a drink. Sitting at the kitchen table, Kevin is taking a rare break from his physical therapy. Connor jokingly asks if he’s training for a marathon or planning to reenlist. Kevin is certain that his future doesn’t include a return to the military, and instead he’s decided to return to medical school in Baltimore. He then confides in his brother that he’s also decided that he’s not ready to get married. He admits to Connor that he’s scared of marriage, and that seeing Georgia leave filled him with a sense of relief. Those feelings convinced Kevin that while he loves Georgia, he’s not ready to be a husband.
Across town at Trace’s new music space, Abby stops by to tell him the news about Wes dropping his custody suit. Trace is thrilled for her and gives her a big hug, but as they celebrate, a familiar voice calls out to Trace from up in the rafters. To Abby’s surprise, she turns to see Leigh Corley staring down at her and Trace. Leigh says hello before continuing her thought about the possibilities for the space. Before Abby can say a word, Trace starts to explain how Leigh’s presence, but Leigh interrupts and begins to mock Trace’s anger at her. She tells them how excited she is that Trace finally has a venue and that she’s even more excited to start working on their final album. But despite her excitement, Leigh can also sense that she’s become a third wheel and abruptly leaves to go and get herself settled in town. As she leaves, Trace tells Abby that he had no idea Leigh was coming back. Abby takes a deep breath and calmly tells Trace that it’s okay.
Later in the day, David is busy at the B&B prepping food for the big party. As he does, a man stops in looking for Bree. David offers to show him the way to the cottage but the stranger tells him that he wants to surprise her. A few minutes later Jess arrives and finds Abby at the kitchen table peeling vegetables. She asks Jess who the guy is at Bree’s and Jess grabs her handy binoculars to take a look. She instantly recognizes the guest as Martin Demming, Bree’s ex who cheated on her. David also mentions that Martin left his bags at the front door, but Jess points out that they could be Leigh Corley’s. Abby is less than thrilled to hear that Leigh is staying at her sister’s B&B, but since the battle with Wes is over she feels confident that she can handle the situation. That is until Jess points out that Wes has just pulled into the driveway. Abby walks outside and Wes tells her that his car died on the highway and he needed a place to stay. Abby tells Wes that she’s is fine with him staying the night at the B&B and invites him to the party. Just as Wes walks inside, Trace pulls into the driveway. Abby then mutters under her breath, “Now it’s weird. And awkward.”
As the party gets underway, Kevin, Connor and Megan all arrive and take note of the unusual gathering of friends and family. Inside Kevin rummages through the refrigerator when Jess walks in. Jess produces a bag of s’mores but before they go back to the party Jess needs to get something off her chest. Despite Kevin’s assurances that he’s on his way to being back to his old self, Jess can see the truth. She knows Kevin won’t ever be the same, but she knows that in time, he will learn to live with his near death experience. Confronted with the truth, Kevin admits that despite all his attempts to shake off his fears, he knows she’s right. She tells him that there are stages to getting better but that no matter what, she’ll be there for him when he needs to talk.
Just as Kevin and Jess finish their conversation, Megan walks in, putting on her coat, ready to leave. Before she walks out she stops to tell Jess how proud she is of all she’s accomplished. At first Jess just offers a halfhearted smile but then she feels compelled to speak. On the first night Megan stayed in the B&B, she asked Jess the same question she asked her every night when she was a little girl: “What did you dream about last night?” Jess is now ready to answer and she calmly tells her mother that she dreamt about the Citation. In the dream, Jess is on deck, watching the storm. When the ship goes down, she finds herself in the water, surrounded by her classmates’ screams for help. But just as it happened on the real Citation, Jess is unable to help any of them. She then tells her mother that in the four years since the incident, she has the same dream every night.
Sitting outside around the fire, the topic of conversation turns to Bree’s plans for the future. Since she and Martin broke up, Bree has been noncommittal about her plans to either stay in Chesapeake Shores or return to Chicago. But when Kevin directly asks her if she’s going back to Chicago, Martin takes the cue and stands to deliver an announcement. He leans in close to Bree and gives every indication that he’s finally going to propose. Bree begs him not to do this and David looks on, nervous and dejected. Then Martin tells Bree that The Stage Left Theater Company would like her to be this season’s playwright in residence. Bree is stunned into to silence as her family, realizing that it’s good news, begins to cheer for her success. Sitting adjacent to Bree, David lets a smile of relief wash over his face.
As the sun sets on the evening festivities, Trace is noticeably absent from the O’Brien family celebration. Early on during the party, he received a phone call that his father had been rushed to the hospital. Without saying a word to Abby, Trace took off in his truck to get to his father’s bedside. As he frantically speeds to the hospital, a state trooper pulls him over. The officer orders Trace to produce his driver’s license and orders him to stay in the car. A few moments later the officer returns and forcefully orders Trace out of the truck. Trace tries to explain that his father is in the hospital but the officer is not listening. He slams Trace against the side of the truck, pulls his hands behind him and places handcuffs around his wrists. Hey then reads Trace his Miranda rights before taking him into police custody.
As daylight turns to evening, Mick finally arrives back from his trip to Boston. All the other guests have left and only the O’Brien siblings are left around the fire. With all of his children sitting around him, Mick takes the time to tell them all how grateful he is for each of them. He starts by acknowledging how close they came to losing both Kevin and Jess. Mick tells them that it’s obvious to him that there is no stopping either of them. He then turns to Bree and again congratulates her on her new job and promises that wherever she goes, her family will always be there with her. To Connor, Mick acknowledges that the complexity of their relationship is due in part to the fact that the two are more alike than either of them realizes. Lastly Mick turns to Abby, his first born, and says that despite those who think she is following in her father’s footsteps, he sees her walking her own path. He then tells them all how proud he is of them and toasts them with a saying from his own father, “May we live as long as we want and never want as long as we live.”