Charlotte visits Jack at his office to invite him to the bachelor auction that is being held to raise funds for the animal hospital. He says he will pay for the ad himself if he doesn't have to participate.
Grace shows up at the library at the same time as Cliff. She recommends a book to him and he offers to meet after to talk about it. She mentions the book club but he was hoping for something more like a date.
At the courthouse, Stan invites Olivia to one of his therapy sessions. Later on, Olivia discusses this with Grace. She thinks that the therapy is great but she doesn't really have to go too. Grace complains that she is terrible at dating. Cliff asked her on a date and she panicked. Olivia says one date isn't too much pressure.
John heads to work early to read apartment listings. He greets Maryellen and Justine but Maryellen, still playing hard to get, quickly excuses herself. Justine agrees to help him look for apartments.
Bob asks Jack how his woodworking project is going. Bob gives some advice and says that Olivia will appreciate the gift even if it isn't perfect.
Olivia drives out to Cliff's ranch to convince him to enter the bachelor auction. She thinks Grace needs a shove to get started dating again. This will be the first time Cliff is the one being bid on in an auction.
As Warren walks by the lake front with his business associates he spots Justine painting. He stops for a second to look at her and then continues on. Later on, Warren shows Justine his plans for the waterfront. Seth interrupts their conversation and says that the stores will ruin the coastline. Warren warns that people who stand in the way of progress get left behind.
Olivia and Charlotte convince Jack to enter the auction. Jack warns Moon that the contest to be the highest bid upon bachelor is on.
Olivia attends the therapy session with Stan. It brings up a lot of old pain but also helps her to realize that she didn't do much to help Stan with his emotions. Through the course of the session they reconcile some of their old problems and pain.After their session, Olivia tells Grace about it. Grace says that she shouldn't blame herself. Olivia wants to invite her brother, Will, for Christmas since he was the first one to wish her a happy birthday. She convinces Grace to attend the auction with her.
Justine and Maryellen come to an agreement regarding the auction. Maryellen, who still wants to play hard to get, will bid on Seth and Justine will bid on John. Then after the auction they can trade their dates. Later, Justine convinces John to enter the auction with the guarantee that he will end up with Maryellen.
Jack visits olivia at her office to give her the birthday present he helped create. It's a painting of Justine's that Jack made a frame for. He hangs the painting while Olivia answers a phone call from Stan. Jack thinks it's weird that she gets call from her ex-husband but she assures him that they are only friends.
The next day Stan tells Olivia that he got in a fight with his wife. She didn't want to go to therapy with him and she got mad when she found out that Olivia went with him the other day. He has checked into the bed and breakfast but Olivia tells him he can't run from his marriage again. She says it wasn't just his fault that the marriage ended and he thanks her for telling him that.
Grace feels lonely and asks Maryellen how to date again. She doesn't even know how to text.
Everyone is showing up at the auction except for Charlotte who has locked her keys in her car. Olivia tells Jack not to be surprised if she bids on Cliff. The mayor is sick so Bob will be announcing the auction. There is a surprise late entry, Will Jeffers, Olivia's brother. Grace bids on him as Cliff watches from behind the curtain. Olivia leaves to find Charlotte and runs into Cliff. He's leaving the auction because he saw Grace bidding for Will. olivia tries to explain that they are just old friends. Olivia finds Charlotte but when they get back to the auction it's too late, Jack has already been bought.
When the bidding for Seth starts another woman bids against Maryellen. Seth can see Warren over on the side instructing the woman to bid. Justine gets frantic and ends up bidding for Seth herself. She apologizes to Maryellen. It's okay though because Maryellen is feeling inspired and will bid on John for herself. She wins the bid herself.
Bob announces that they have beat last year's record for money raised. John was surprised at Maryellen's bid but he was happy about it. Seth confronts Warren in the parking lot about the girl he made raise the bids. He pushes Warren but John holds him back and says he isn't worth it.
Warren tries to explain what he did to Justine but she doesn't want to hear it. She thought he might be a decent person deep inside but now she thinks she was wrong.
Olivia returns home and finds Stan dropping off a birthday present at her house. It's their dead son's favourite toy that he could never throw away. They decide to go together to the lake and drive Jordan's boat.
Jack shows up at Olivia's but doesn't find her home. He leaves her a voice mail asking where she is and promises to meet up later.