Kevin goes to Abby for hypothetical advice on how to propose to someone – though he denies it has anything to do with Sarah. Jess and Bree interrupt and the three girls pass along their “hypothetical” advice. Trace returns home to an empty house and leaves a message for Abby. Kevin and Sarah take Jess back to her new bed and breakfast back Tanglewood and decide to do a romantic weekend away. Mick checks in with Abby to see how she is doing now that Trace is back in town.
Abby tries to keep busy and takes on a new fund manager as a client at work. Bree gears up to meet with potential producers for her play, but is not feeling a connection with any of them. Trace shows up at Abby’s house with flowers but instead finds Mick. Mick encourages Trace to give Abby some time. When she is ready to talk, she’ll come find him. Trace says he’s here to stay and he’s not giving up on her. Meanwhile, Kevin tries to find the perfect moment to propose to Sarah, but mishaps keep occurring. Trace takes notice of a new talent, Emma, at The Bridge and talks to her about songwriting.
Mick discovers one of his contractors has engaged in suspicious business practices and is shocked when he tries to put the blame on both of them. Jess confides in Kevin that the “ghosts” of David’s parents are at their bed and breakfast and she really wants to come back home and try to start over there. Kevin shares with Jess that it is harder to propose than he thought. Connor runs into Trace at The Bridge and suggests he may try running on the beach around 7am if he’s interested in connecting with Abby.
Bree meets Hannah, a playwriter that Bree admires and is thrilled to learn she wants to produce and direct her new play. Jess opens up to David about being miserable at the bed and breakfast and asks if he’d be open to going back to Chesapeake Shores to rebuild their inn. He happily agrees, and the two kiss. Connor questions his career path, but finds confidence in a case that gives him some clarity. Over a flat tire, Kevin proposes to Sarah and she says yes!
On the advice of Conner, Trace bumps into Abby on her early morning runs. Abby stops Trace as he proclaiming his love for her and says she can’t put herself through this again. He promises this time will be different. She says she can’t go back and runs away.