As Olivia readies for her Seattle getaway with Jack, she is unsettled to receive a surprise visit from an ex-con, Lenny Dixon. Olivia sentenced Lenny years before and he is now out and is looking for work. He reminds Olivia that she told him he could turn his life around if he tried, but being honest about his record when trying to find work has done him no favors. All he needs is a chance, and he wants assistance from Olivia. Olivia is moved by his plea and agrees to help him.
Back at home, Grace gives Olivia some advice as she packs for her getaway with Jack: loosen up! But Olivia is distracted by a phone call-she's been asking around to find work for Lenny, but has had no luck yet. Grace insists that Lenny's past won't get him a job in Cedar Cove, even if he has changed. Jack arrives soon after, and they head out for their trip.
Across town, Rosie Weston drops Allison off at her job at the Thyme & Tide. Rosie is not happy with their divorce arrangement, and Allison is relieved to have time away from both her parents. Later, Bob finds Allison repeating some of the work she'd done earlier in the day. She doesn't want to go home, but Bob insists that she's done enough. Peggy notices Allison's unhappiness, but there's not much she can do.
At the art gallery, Stan visits Justine and admires her latest work. Stan asks after Olivia and Justine tells him that she is away with Jack. Stan is slightly uncomfortable knowing that his ex is out of town with another man, but he gets past it. He's really there to tell Justine how much he regrets his absence from her life. He wants to be there for her now, and he won't let her down. Justine wants desperately to believe him.
In Seattle, Jack and Olivia arrive at their hotel. Just as things are heating up between them, however, Jack gets a call that he is needed at the stadium to cover a press conference. As Olivia is getting ready for their date, she gets a call from Jack. He has bad news: the game has gone into extra innings. To make matters worse, he doesn't get back to the hotel until much later. When he gets there, Olivia is fast asleep and it becomes clear that their romantic night isn't going to happen.
Allison hangs out with her boyfriend, Anson, and tells him about her plan to ask Bob and Peggy if she can move in with them. Anson is skeptical that her parents will allow it, but she thinks it will give them one less thing to argue about. Just as she plucks up her courage to ask however, she is surprised to find that Rosie has decided to move into The Thyme and Tide in order to be closer to her kids on her off weeks.
Olivia and a contrite Jack return to town. He is apologetic about the getaway but Olivia assures him there will be other opportunities. As they start to kiss, Olivia happens to see Lenny going into the art gallery. Lenny is just asking Justine for a job, but he is not having any luck. Olivia assures him that now that she is back in town, she will help him find a job. Later she explains to Jack that Lenny had a difficult childhood and that none of his crimes were violent, but she still finds it extremely hard to trust him. Olivia soon learns it is hard to find someone in Cedar Cove--including the usually easy-going Moon--willing to take on an employee with Lenny's background.
At The Thyme and Tide, Rosie is constantly complaining about Zach, which bothers Allison. The one place Allison was always able to go to get away from the chaos at home has now been invaded, and she has nowhere to escape to. After listening to one more complaint about her father, Allison explodes at Rosie and storms out of the Bed & Breakfast. She finds Anson and goes for a walk with him along the waterfront. When it gets late, Anson offers to take her home, but Allison is reluctant to go back to the unhappy house.
Cliff Harting visits Olivia at her chambers-it turns out he wants to hire Lenny help him at his ranch. Olivia is grateful to Cliff, who tells her to say "hello" to Grace for him. Olivia makes a point of passing the message along, but when Grace finds out that Lenny is working at the ranch, she becomes concerned for Cliff and insists that she and Olivia drive out there and make sure everything is OK. Cliff is glad to see them, especially Grace, and assures them that Lenny is working out fine.
Jack and Olivia make dinner together but just as things get romantic they are interrupted once again by the Sheriff calling to tell Jack that the park pergola is on fire. Jack and Olivia race over and, knowing that Lenny has arson in his background, tell the Sheriff that Lenny may be a suspect. The Sheriff drives out to see Lenny who proclaims his innocence and is hurt and disappointed to learn that Olivia is the one who gave the Sheriff his name.
Stan comes to see Olivia and tells her that he is finally going to see a therapist. Olivia is happy for Stan, knowing he has been dealing with his issues for years. She is supportive, but gets the impression that Stan's current wife is less than thrilled that he is working on his problems.
In town, Olivia is confronted by an upset Lenny, who proclaims his innocence and accuses her of lying when she told him he could turn his life around. Jack arrives and steps in to defend Olivia, but Lenny stalks off angrily. Olivia is disappointed to realize she's made a mistake: she believes that Lenny isn't responsible for the fire. When they go back to the park, Anson approaches and takes the blame for the fire. He says that he was trying to stay warm and lit a fire in a trash can. The fire got out of control and he got scared and ran away.
Days later, Anson appears before Olivia to be sentenced in the arson case. Olivia decides to give him one year of probation, provided he pay for the pergola and help Bob Beldon rebuild it. Later, Allison meets with Anson, determined to tell the truth about what happened-that she was really the one responsible for the fire. Anson won't let Allison compound the problems she is already dealing with and insists on taking the blame.
At the bed & breakfast, Rosie tells Bob and Peggy that she wants Allison to stop seeing Anson, but Bob defends the boy. Peggy explains that Rosie isn't paying enough attention to how Allison is reacting to her complaints about Zach, and that it's important that she deal with their issues in private. Rosie takes their advice unhappily, but she hears it.
Olivia goes to Cliff's ranch and apologizes to Lenny for jumping to conclusions about him. She tells him not to let what happened ruin the new life he is building. Before she leaves, Lenny thanks her for what she has done for him.
Bob, Jack and Anson set to repairing the burned pergola. Anson's not very adept with construction, and Jack ends up offering him a job designing a website for the newspaper. It will give Anson the money he needs for the pergola, and help Jack drag the paper into the 21st century. Anson happily agrees and Jack is pleased as well, knowing that everyone deserves a second chance.
That night, Jack brings take-out to Olivia's place, and he promises to turn his cell phone off so they can finally have their romantic night alone.