After a trip to a local lake where they honored the memory of their son, Olivia returns to her house with her ex-husband, Stan. There, she and Stan reminisce about their old times together. Jack had come by when they were out to keep a date with Olivia and was concerned to find her gone, so he is relieved when he returns and sees her car in the driveway. He is about to knock on her door, when he sees Stan and Olivia together through the window. Confused and threatened, Jack decides to leave.
Olivia’s brother Will is still in town and runs into Grace. He tells her he will be in nearby Seattle on business for a few weeks. Grace is happy that he will be around for a while and since he owes her a date from the town’s charity bachelor auction, they make plans to go to dinner that very night at the Captain’s Galley.
Olivia goes to see Jack to explain why she was out when he came by. Jack is angry and reveals that he saw her with Stan. Olivia tries to assure Jack that she and Stan were connecting as parents and nothing more. Jack worries that they have history together and that is something he can’t compete with. Olivia tells him that her relationship with Stan is in the past. She wants to build a new history with him, and Jack gladly accepts her explanation.
Seth tries to teach Justine how to fish and the drive his boat. She is not very good at it, but she is determined and Seth is charmed. Seth asks Justine to move in with him on the boat. Justine is unsure for many reasons, so he asks her to think about it.
At the pier, Grace runs into Cliff and explains what happened at the bachelor auction. She didn’t know about Olivia’s plan to get them together, stressing that she only bid on Will because he is married and unavailable. Although Cliff is uncomfortable at first, he believes her, and is pleased when Grace notices a flyer he has just posted about his new horseback riding business. Despite her recent hesitations in dating, Grace has the courage to ask Cliff for a horseback ride on the beach. Cliff couldn’t be happier, and replies, “You’re in luck. I know the owner.”
Jack has lunch with Bob Beldon with the news that he has decided to build a boat. Bob thinks that a novice woodworker like Jack is biting off way more than he can chew, but Jack is determined to do it. Jack sees John Bowman passing by and asks him if he can do an interview with him. John has no interest in being interviewed and refuses.
As Grace readies for her “friends” date with Will, Maryellen prepares for her own auction date with John, who cooks dinner for her at his new apartment. They have a nice time, but John is evasive about his past and Maryellen happens to see a box in his apartment filled with unopened mail addressed to another man. It immediately raises her suspicions—what is he hiding?
Grace meets Will for their dinner, and he sympathizes over her recently failed marriage. Will confides that he had a crush on Grace in high school and Grace confesses that she had a crush on him as well. There’s chemistry between them, and noticing that Grace is uncomfortable, Will turns the conversation to other subjects.
Justine tells her mother about Seth asking her to move in and can tell that Olivia is not crazy about the idea. Olivia tells her that it is a big step and that she needs to make sure that the decision is made on the right terms for both her and Seth. Justine doesn’t really want to live on a boat, so she so she asks Seth to move in with her instead. She’s surprised but happy when he quickly agrees. In a bid to reconnect, Justine and her dad Stan go out to the lake and talk about her brother. Stan asks Justine about Jack and she worries that he only wanted to see her to find out about her mom’s new boyfriend. Stan assures her that he is there for her. Justine tells her father that she and Olivia are both in a good place now, but warns him that it took a long time to get there and it wasn’t easy.
Grace and Maryellen catch up on their previous evenings, and Maryellen shares her uncertainty about John’s past. Later, John stops by to invite her out on a photography shoot with him in the rainforest. She’s speechless, but Grace is conveniently nearby to answer a resounding “yes” on her behalf.
With only a few possessions to his name, it takes Seth little to no time to pack up and move in with Justine. Despite his pleasure at having so much space to spread out in, it’s difficult for Seth to live on land; he has trouble sleeping without the motion of the boat. Justine sees him struggle to adjust, but he tells her he just needs time and everything will be okay.
As Grace gets ready for her riding date with Cliff, she gets a visit from Will, who needs someone to talk to. Over a cup of tea, he confesses that his marriage is over--he has moved out of his house. Just then, Cliff calls to finalize their arrangements. Knowing that Will needs a friend who understands what he is going through, Grace asks Cliff if they can reschedule.
John brings Maryellen to his favorite place in the forest to shoot. She is impressed by the beauty and peacefulness of it all. John finally confides in her that he has always be a bit of a loner and that it is tough for him to let people into his life, but with her, it's different. It has been a long time since he felt this way about anyone, and they share their first kiss.
Cliff goes to see Jack to put an ad in the paper for his horseback riding business. When Jack asks him how things are going with Grace, Cliff says that nothing is going to happen because Grace is interested in someone from her past. He tells Jack that when people have a history it is hard to compete. Jack’s thoughts drift to Olivia and Stan, and the shared past that binds them together.
Stan has decided to head back home to his wife and drops by to see Olivia to thank her for all the support she has given him. She tells him she hopes he will be back more often to see Justine, as it will mean a lot to her to have her father back in her life. She also tells him that she will always care about him and be there for him. Stan leaves, feeling wistful for what he has lost with Olivia. John brings Maryellen home after a great date and the two agree to see each other again.
Jack happens to be passing and asks John again for an interview. John says again that his answer is no and Jack is a little taken aback by the sharpness of his reply. Maryellen witnesses the exchange, and her worries resurface. She decides to call his former employer and finds out he was let go because he lied on his application, but learns nothing more.
Grace meets Will for another dinner but doesn’t notice that he keeps checking out the attractive woman at the next table. When dinner is over they and they’re saying goodnight, Will suddenly pulls Grace into a kiss. Grace pulls away as Will awkwardly tries to apologize. She gets in her car, panicked and uncertain about what just happened.
Olivia surprises Jack with tickets to see his favorite team play baseball in Seattle. Not only that, but the tickets are box seats--best in the house. They have a wonderful time and Jack tells Olivia how lucky he feels to have found her. He is not used to things working out in his life, but he hasn’t been this happy in a long time. Olivia tells him that they’re both lucky to have found each other and that she is happy too. Jack confesses to Olivia that he thinks he is falling in love.