In the kitchen, Kevin turns to Connor and Bree for love advice since Sarah stopped talking to him. Connor says it is up to Kevin to open the lines of communication with her. He also offers up the same advice for Bree who is currently avoiding Simon, who is staying at Jess’s bed and breakfast while visiting Chesapeake Shores. Connor also admits he hasn’t told their father about quitting the law firm yet and says he will get around to it. When Mick walks in, the family bolts, leaving Connor alone with their dad.
Back at the bed and breakfast, Jess is staying busy doing what she can to avoid talking to David about their kiss. She turns to her guest, Simon for advice. Before he can give her any sound feedback, Jess takes it upon herself to tell David the kiss never happened. When David still wants to talk about it, she quickly tells him she has already forgotten about it.
Simon surprises Bree at the bookstore and lets it slip out that Jess kissed David. Judging from her reaction, Simon guesses that Bree has feelings for David. She admits she once did, but gifted him to her sister, instead. She also goes into detail of how her mother believes Bree always sabotages herself when it comes to relationships. Simon reveals that he and his family have a similar relationship, especially when it comes to meddling in his love life.
Kevin joins Sarah for coffee and the two begin to talk about their relationship. Sarah admits she wants to keep things uncomplicated between the two. He jokes that the two can always just do dinner.
Trace and Abby are on a romantic getaway, camping in the woods. Right off the bat, Abby begins complaining that she doesn’t have cell service. Trace assures her this trip is just about them and it is time to put the work away. The two spend their afternoon fishing and enjoying the great outdoors. Trace points out that the peace and quiet is a perfect way to get back to their roots. Just then, Abby catches their dinner on her fishing line.
Thomas finds his nephew Connor shooting hoops and wants to have a little conversation. He tells Connor he is proud of him quitting the law firm because that is not the kind of place where someone can embrace individuality. Thomas then surprises Connor by offering him a job working on some litigation in New York. Connor agrees to mull it over, then quickly changes his mind and accepts the gig.
Kevin and Sarah are on an ice cream date and Kevin swoops in for a kiss. Sarah pulls away again, telling Kevin that she has to put a stop to it. She then tells Kevin that she lost her husband three years ago when he died while serving in Mosul. She admits that is why she has such a tough exterior and why she became a firefighter, so she can help others.
Trace and Abby are warming up at the campfire and talking about the past. Trace tells her that they should have no regrets because life brought them to where they are now. He then picks her up and slow dances with her under the moonlight.
The next morning, Sarah runs into Kevin jogging on the beach and she apologizes for revealing too much to him during their date. She also lets him know she is not ready to move on from the past and he admits he is not ready for anything serious, either. The two hug and part ways.
Gran finds Thomas and Mick talking over coffee at the house. Thomas brings up scaling back Mick’s land development. The two agree to have an open and honest conversation about the O’Brien trust.
Breakfast is being served at the inn, where Bree, Jess, Simon and David are all getting to know each other. The four of them start to compete with who can share the saddest love story. In the end, they all agree to raise their glasses and toast to each other.
Mick and Kevin grab some alone time and Mick encourages his son to open up about what happened when he was in war. A tearful Kevin recollects the bombing that killed his best friend. Mick guesses that Sarah must have brought up a lot of painful memories from the war. Mick himself just lost a good friend and tries to give Kevin some comforting words about love and time.
Trace and Abby’s camping trip is winding down and Abby once again wants to know if Trace is ready to make her and her daughters a serious priority, and he tells her to trust him. Later on in the day, the sisters all have a spa day and catch up on each other’s love life. Jess and Bree point out that Abby’s in love and begin to tease her in a joking manner.
Thomas and Connor are going over Thomas’s case. Thomas is impressed with his nephew’s
work and tells him that life is too short to only be concerned with time and money.
Back at the club, Kevin stops by to show Trace that someone uploaded a video of him performing “Free Fall” and it is already going viral!
At the bookstore, Bree gives Simon a sample of her writing for him to read. She also tells Simon she is terrified of criticism but appreciates him taking the time to give it. When Simon goes in for a kiss, Bree kisses him back.
Jess and David are working outside on the sprinklers and he assures her that whatever she is feeling for him, it is mutual on his end. He then pulls Jess into a romantic kiss just as the sprinklers turn on.
Abby joins Trace at the club and he shows her his video. Trace points out that the video now has 400,000 views and maybe his Nashville dreams aren’t over yet.