After passing out flyers to the residents of Cedar Cove, Charlotte places an ad in Jack's paper for the town's upcoming charity bachelor auction. She cheerfully urges Jack to participate, but he gives her a definitive no. Meanwhile, at the library, Cliff Harting visits and once again indicates that he would like to get to know Grace better, but a flustered Grace isn't quite able to agree to a date.
At her chambers, Olivia gets a visit from her ex-husband Stan. He reminds her that he's been going to therapy to deal with past issues, and asks Olivia if she will join him in his next session. Olivia needs time to decide, and she goes to see Grace to talk it over. Grace is glad that Stan is getting help, but doesn't see why Olivia has to be there. Grace then confides in Olivia about Cliff's visit and how she wants to be strong and confident, but even the word "dating" makes her nervous. She has no idea how to move forward as a single woman.
Maryellen and Justine are having lunch when they spot photographer John Bowman. Maryellen is interested in John, but he has been so distant that she doesn't want to tip her hand. John reveals that he will be moving to Cedar Cove since his job at the Captain's Galley seems to be working out. A cool Maryellen gives him the brush off, but Justine offers him a hand in searching for a new apartment.
Olivia visits Cliff and tells him that he and Grace would be great together, but that Grace needs a nudge in the right direction. She persuades him to join the bachelor auction and promises that if Grace doesn't bid on him, she will, and she'll gift the date to Grace.
Justine is waiting for Seth when she runs into her ex fiance Warren, who insists on showing her his plans for a development on the waterfront. Unimpressed, Justine is relieved when Seth interrupts them. Seth is not happy about any development along the water and it is clear there hard feelings between the two men.
Jack interviews Charlotte about the auction and is surprised to find that even Moon has agreed to be in it. Moon tells him that he was won by the feisty Edna Stanton the year before, and Charlotte confesses that Edna is the reason they had to institute a rule saying that the ladies can only win one bachelor. Charlotte is again unable to persuade Jack to join the action, but when Olivia arrives, she teases him into agreeing.
An uneasy Olivia joins Stan for his therapy session, and the former couple is finally able to talk about the death of their son. At the time, Stan was overwhelmed, and he confesses that he didn't know how to fix things after the tragedy. Olivia has always resented the fact that he cleaned out their son's room without asking her. Among the things he got rid of was a toy boat he and his son used to take to the lake. Stan explains that he was trying to help her by getting rid of reminders, but Olivia says that it just made things worse. She later tells him how abandoned she felt when he walked out on their marriage. After Stan explains how hard it was to talk with her, the therapist tries to help Olivia understand that Stan was doing the best he could at the time. Her words begin to change Olivia's perspective on how they both dealt with their loss.
Justine and Maryellen conspire about the bachelor auction. Justine tells Maryellen that she will persuade John to join, but Maryellen is reluctant to bid on John, thinking that it will make her look desperate. Justine decides that she will bid on John and Maryellen will bid on Seth and then they will switch. Seth thinks the plan is crazy, but he goes along with it.
Meanwhile, Justine goes directly to John about her plan to get him a date with Maryellen. She makes it sound as if Maryellen doesn't know anything about it. John is uncomfortable with being in front of so many people, but he considers the idea.
Olivia meets with Grace and Charlotte to tell them about the therapy session, explaining how much it's helped her see the end of her marriage in a new light. Grace tries to persuade Olivia to let her throw a small birthday party in her honor, but Olivia is adamant that she doesn't want a celebration. However, she was happy to receive a card from her brother Will. Grace confesses that she had a huge crush on Will in high school but didn't act on it. Sensing an opening, Olivia puts her plan in motion and tries to persuade Grace to go to the bachelor auction. Grace agrees but reserves the right not to bid on anyone.
Jack visits Olivia in her chambers to give her a birthday present he has been working on. He has mounted one of Justine's paintings in a frame he made himself. Olivia loves it, but their evening is briefly interrupted when she gets a call from Stan, who needs to talk. Olivia agrees to meet him the following day, upsetting Jack. He's uncomfortable with the fact that Olivia is reconnecting with her ex.
The next day, Olivia meets with Stan, who tells her that he has had a fight with his current wife. She is unhappy that Stan is dredging up all his past issues in therapy, and has refused to attend a session with him. Olivia is supportive and encourages him to keep working on his marriage.
With the bachelor auction about to get underway, Justine and Maryellen go over their plan, only to run into Warren, who isn't participating. He prefers to write a check directly to the charity instead. At the auction, Jack reminds Olivia to bid on him and she tells him that she may have to bid on Cliff if Grace doesn't. Jack is confused, but Olivia assures him that she has arranged for Charlotte to bid on him if she can't. Unbeknownst to Olivia however, Charlotte has locked her keys in her car and is running late to the auction.
The best laid plans quickly go awry as a surprise bachelor appears: Olivia's brother, Will. Though he is not really a bachelor, Will is available for a friendly dinner, and Grace quickly bids on him and wins. From backstage, Cliff is disheartened to watch Grace bid on another man. Knowing that she will now have to bid on Cliff, Olivia looks for Charlotte to bid on Jack, but her mother has not arrived.
Seth goes up for auction and Maryellen bids, but the bidding soon becomes fierce as a pretty rival joins in. Seth is flattered until he realizes that Warren is directing the rival and has engineered this to make trouble. Maryellen runs out of money and stops bidding, but Justine, unwilling to see Seth go to another woman, makes the winning bid just in time. Now Justine is unable to bid on John, but Maryellen, inspired by Justine's bid for Seth, decides to bid on John herself. She wins, and John seems shyly pleased.
As Jack comes up for auction, Olivia is still searching for her mother. She notices a disappointed Cliff leaving before his turn. He saw Grace bid on Will and has decided that there is no hope. A moment later, Charlotte arrives, but it's too late: Jack has been won by another bidder.
The auction is a big success, and John and Maryellen happily discuss their upcoming date. Seth decides to confront Warren about his interference. Things quickly get out of hand and John has to step in to keep Seth from hitting Warren.
Olivia tries to explain the long, complicated story of her unsuccessful bidding plans to Jack, who cracks up and lets her off the hook. He promises to visit her after his auction date... with the elderly Edna Stanton. However, when Olivia arrives home, she catches Stan placing a wrapped birthday present on her porch. She decides to open it then and there, and is stunned to see that it's her son's toy boat-Stan has kept it all this time. The two decide to take the boat to the lake, where they launch it into the water and remember their son together. Meanwhile, Jack arrives at Olivia's for their evening in, but she is nowhere to be found.