Morning in Chesapeake Shores finds Abby O’Brien out jogging along the waterfront. As she jogs back to the house she’s greeted by a handsome man bearing a bunch of red roses. Unfortunately for Abby, the flowers are an effort to soften the blow of the subpoena that is actually being delivered. Abby leaves the flowers and heads indoors with her subpoena. Inside Abby runs into her father who, absorbed in his own paperwork, asks her to wake Connor. Abby is all too eager and bursts into Connor’s room, angrily waving her subpoena and telling him that his legal advice backfired. Still groggy, Connor reminds Abby that his advice was free and since she had nothing to do with the insider trading, Connor doesn’t see any problem with Abby answering the subpoena and turning over documents to the DOJ. He does have an issue with his sister interrupting his beauty sleep and asks her to kindly close the door on her way out.
Downstairs, Mick casually watches as Carrie and Caitlyn make pancakes. Abby comes down and tries to talk to Mick about her legal woes but he’s distracted by his own stack of papers. Just then the doorbell rings and Mick runs off to answer it. On his way to the door Carrie and Caitlyn remind him that he promised to take them to play miniature golf today but Mick’s so focused on the door that he doesn’t hear a word the girls say. Looking on Abby tells her daughters that Grandpa has a lot of work to do. The girls aren’t fazed and remind their mom that they’ve seen her like that too.
Meanwhile in town, Bree steps outside of Sally’s with a fresh cup of coffee. As she does she sees David, Jess’s new boyfriend, standing at the lending library. Not wanting to reveal her excitement at running into him, she pauses before nervously walking up and asking if he’s “taking or leaving.” Happy to see Bree, David turns and shows her the book he’s leaving, “My Life in the Pits.” Despite the title, David assures her that it’s a pretty inspiring book and that in the end, the author falls in love. As luck would have it, Bree is returning the book he left during their first meeting. They talk briefly about writing and literature before David asks her about their awkward dinner with Jess. Bree says she’s not sure why she overreacted but she apologizes for the confusion it may have caused. The two smile at each other before David realizes that he needs to go inside and start work. He grabs his bag and heads into Sally’s and Jess cheerfully follows along, telling David she was just going in to grab a coffee. David looks at the cup of coffee cup in her hand and asks “Isn’t that?” Jess suddenly remembers the hot coffee in her hand and, embarrassed again, tells David to have a good day before slinking away.
Along the waterfront at his cabin, Trace plays with Axel when an unexpected guest arrives. Lawrence Riley has only ever been to his son’s cabin twice and never by himself. Lawrence sits on the walkway with Axel, telling Trace that Mick was at the bank going over loan documents. While there, Mick told Lawrence about his plans to go into business with Trace. Trace tells his dad that Mick floated the idea past him but that he hasn’t said anything since. Slightly jealous that his son would consider working with Mick, Lawrence reminds Trace that 95% of small businesses fail in the first year. He then asks Trace to reconsider working at the bank with him. Trace flatly rejects the offer. Hurt, Lawrence then asks if it’s because Trace doesn’t like him. Trace is confused by his father’s response and, while he concedes that they are two different people, is unsure where his father’s feelings are coming from. He goes on to tell Lawrence that they’ve never connected as father and son but that’s no reason they should stop trying. Trace then asks his dad if he will reconsider his loan. After a pause Lawrence gives Trace a dejected look and tells him that there is nothing to reconsider.
Back at the O’Brien house the siblings are all gathered around the table enjoying breakfast. As they talk Kevin suddenly gets a painful cramp in his leg. Georgia looks at him and immediately suspects that he’s pushing himself too hard during his physical therapy. She asks the others if they can make sure he doesn’t overdo his PT and Connor volunteers. After the treehouse incident Connor seems an unlikely choice to handle Kevin’s well-being, and his siblings waste no time in laughing and joking at the mere notion. The joking is too much for Georgia and she angrily walks out of the room. Realizing that Georgia’s feelings are hurt, Jess volunteers to go talk to her. Outside with Jess, Georgia reveals that she’s afraid Kevin may be starting to show signs of PTSD. Jess offers to keep an eye on him and tells Georgia she knows what signs to look for. Georgia turns to Jess, dubious that she has any idea about PTSD or its signs. Jess looks at her and asks if Kevin told her about the Citation. Kevin told Georgia that the Citation was a ship Jess sailed during her senior year of High School but Kevin wouldn’t share any more of the story. So, with just the two of them, Jess begins her story.
A few hours after talking with Jess, Georgia takes the last of her bags to her truck and prepares to head home to Daytona. With Kevin’s recovery in full swing, Georgia had hoped to begin the life they had planned, but it’s clear to her that Kevin is not ready to leave his family. After hearing Jess’s story about the Citation, Georgia realizes that Kevin may need to stay in Chesapeake Shores to fully recuperate. Georgia tells Kevin that she’ll be waiting for him when he’s ready to come home to Daytona.
Sometime later, the entire O’Brien family arrives for a day of fun at Paradise Mini-Golf. Even Wes is on hand to make sure his daughters have the chance to spend time with both of their parents. While playing through, Connor takes the opportunity to grill Wes about the insider trading investigation. Wes is hesitant to talk about the investigation with the young and unlicensed lawyer, but Connor is persistent. Despite his lack of experience, Connor is certain that he can keep Wes and Abby out of jail if Wes is willing to roll on the mastermind of the entire operation, his ex-girlfriend Gabrielle. Wes is hesitant at first but both Connor and Abby agree that testifying against Gabrielle is the only way Wes can save himself. Hoping to save time, Connor invited the investigator from the DOJ to join them at the mini-golf course so they can discuss a plea deal. Neither Wes nor Abby knew about Connor’s plan and they are both furious, but Connor promises them both that he can handle everything.
On the other side of the mini-golf park Jess and Bree talk about their love lives. Bree is still devastated over her breakup with Martin and reveals that at one point, she expected that he was going to ask her to marry him. As they talk David arrives, late from the lunch rush at Sally’s. He runs off to grab a drink at the concession stand and while he does, Bree offers to leave and give the two some privacy. Jess asks her sister to stay and confides in her that while she likes David, she’s not sure they really have much in common.
Back in town at the Chesapeake Shores bank, Trace arrives at his father’s office. Trace sits down and Lawrence finishes his work, closes the door then looks at Trace and tells him that he’s got his loan. Lawrence then tells Trace that he and his mother are putting up the money. Trace angrily tells his father not to do him any favors and that he doesn’t need a handout. Lawrence is confused as to why Trace would refuse to take the money he’s so generously offered but for Trace, this is an issue of respect. As Trace sees it, no matter what he does, his father will never respect him. Trace tells him that he doesn’t want the money because doesn’t want his father to control him like he does his mother. The next thing Trace knows Lawrence has grabbed him by the t-shirt and is slamming him into the wall. As Trace struggles to break free his father’s breathing suddenly becomes labored. Trace asks if he’s okay and tells him to sit down. Lawrence angrily shouts that he’s fine and tells Trace to just leave.
Back at the mini-golf park, Jess, David and Bree are having a playful time on the park’s bumper boats. As they splash around David makes a reference to the literary classic “Moby Dick.” Bree immediately recognizes the quote and the two begin to laugh and talk about literature. Jess looks on silently, realizing that the two have far more in common than she does. Bree suddenly reads the expression on Jess’s face and quickly changes topics to the B&B. Jess plays along but having had her fill of bumper boats, she suggests they all go for some ice cream.
On the other side of the park, Connor sits with Investigator Whitcomb from the DOJ. Connor’s handed over a signed deposition from Wes stating that he’ll testify against Gabrielle. Investigator Whitcomb is suspicious of Connor and of Wes’ motives, but Connor points out to him that the investigation will ensure that Wes will never work in the financial industry again. And even with immunity, Wes will certainly have to do some kind of community service. Despite the argument Investigator Whitcomb points out that practicing law without a license is a serious, criminal offense. Fortunately, Connor prepared for that eventuality and reminds the investigator that he, Connor, never said he was an actual lawyer. Connor also points out that he’s helped hand over to the DOJ the mastermind of the entire scheme, Gabrielle. With no real need to push the issue any further, Investigator Whitcomb grabs his jacket and the deposition and leaves, meanwhile Connor heaves a big sigh of relief.
Back in town, Trace and Axel explore a large abandoned warehouse. While it’s not the space Trace was hoping to buy, he can immediately tell this venue has potential. As Trace looks around, Mick appears from out of the shadows. He tells Trace that the deal he’d put together for the other warehouse fell through and he’s decided to drop his bid. He is however interested in buying this place and he hopes Trace will consider going into business with him. Trace is surprised and unsure how a deal between them would work. But, as he stands in the warehouse he can see that the potential and realizes that that he’d be a fool to pass up this deal. Mick tells him that the place will need a lot of work, but after the work they put into the church, Mick’s sure they can make it happen. They agree to talk again once Mick returns from Boston and before he heads off, Mick turns and tosses Trace the keys to his new music venue.
After the scene on the bumper boats, Jess and Bree decide that it’s time for the two of them clear the air about David. Before leaving the mini-golf park, Jess confronted Bree over her flirtatious attitude towards David, but with their mother and Abby looking on, they decided that was not the time to talk it out. Now, standing in the yard of the B&B, Jess reveals she knows that David was the guy Bree was gushing over from the lending library. Bree is hesitant to say she has feelings for him and even if she does, Jess is her sister and that trumps any feelings she could have for David. Having seen them together Jess doesn’t believe that Bree could just let David go, but she also doesn’t know if she really has feelings for him either. Bree tells Jess that the spark between her and David comes from their common interests, something Jess admits that she and David don’t have. But Jess has a surprise up her sleeve and she announces to Bree that she’s considering hiring David as a chef for the B&B. Neither sister knows how to respond to this news.
It’s nighttime when Trace and Abby arrive at the warehouse. Trace promised to take Abby dancing but when they arrive, she’s less than impressed. That is until Trace tells her that it’s the new music venue that he’s opening with her father. He then flips a switch and the room is illuminated with thousands of twinkling lights. Abby is stunned as Trace takes her by the hand and leads her onto the dance floor. They join hands and dance, looking deeply into each other’s eyes. Finally, as they draw closer together, Trace kisses Abby.