Due to Abby’s work schedule, Trace gets her daughters up from school and teaches them a few lessons about performing on the stage. Abby picks them up at the club and expresses her gratitude for Trace stepping in. Abby asks Trace for an update on his recording, he says his viral video for “Freefall” has hit 800,000 views online but he is still staying level-headed about it. Their moment is interrupted when the rest of the band shows up to rehearse.
It is Carrie’s 10th birthday and the family gathers around the kitchen to celebrate. Abby wants to make sure Jess has the inn ready for the weekend celebration. She assures Abby she has everything under control.
John and Leigh approach Trace with trying for another contract in Nashville, especially since their song has become a hit online. Trace tells them emphatically no and walks away before discussing any further.
Kevin is getting ready to visit his late friend Tom’s mother in Philadelphia and asks Bree if she will accompany him on the trip. Bree is happy to join her brother. Kevin wants to let Tom’s mother know her son died a hero.
Jess and David have agreed to watch over Wordplay while Bree is with Kevin. While at the bookstore, Jess gets her hands on some self-help books about relationships. One relationship book advises that the new couple have eight stages to go through in order to make it last and Jess is certain that they can complete all stages in just two days.
Back at the office, Abby has to tell her dad that one of his big development investors, Matt Fox, is pulling out of the deal. A confused Mick wants to know why and she tells him Matt felt uneasy about the way Mick caved in on his brother’s demands. Mick is determined to
confront Matt about this decision, but first he pays his brother Thomas a visit to discuss the deal.
Meg is busy promoting the city’s Art Walk which headlines the Trace Riley Band as entertainment. Back at the club, the band is rehearsing for the big event. They are interrupted by Mark Hall, all the way from Nashville, to tell the band that he wants a second chance to record with them. John and Leigh want Trace to consider a deal, but Trace tells Mark he is not interested. Mark says he heard that the band was looking for a big label after Trace originally said they were going to independently produce their album. Mark leaves and Trace immediately realizes that it was John who was shopping the band around to big labels without discussing with Trace first. John doesn’t regret shopping the band around, citing that he is ready to make money.
Back at the bookstore, a gigantic shipment of books arrives and Jess realizes that she didn’t follow her sister’s instructions when filling out the week’s order. Instead of placing her order for 100 books, Jess accidentally ordered 1,000! Jess immediately blames David for being a distraction while she was placing her order, but the two make-up soon after. Jess points out that this crosses off two more relationship stages from her self-help book.
Kevin and Bree arrive in Philadelphia to meet with Tom’s mother. While waiting for her to arrive at her house, the two begin talking about the book that Bree is writing. She confesses that it is about the O’Brien family, leaving Kevin feeling a bit uneasy about all their dirty laundry being published in a book.
Connor and Danielle grab a drink at the club, and he talks about just how much joy he is having working for his Uncle Thomas. Danielle jokes that maybe Connor is realizing that money isn’t everything. Trace shows up and Connor points out the club is certainly more crowded than usual. Their conversation is interrupted by a man representing a record label wanting to schedule a meeting with Trace. Trace takes the guy’s card and tells Connor that record labels and managers have been approaching him all night because of his video. Trace excuses himself to hit the stage with his band. Mark grabs a seat in the audience to watch them perform.
The next morning in Philadelphia, Kevin and Bree are unsuccessful at tracking down Tom’s mother. This gives the brother and sister some time to catch up. Kevin opens up about his second thoughts about being a doctor. He wants to know what his character does in his sister’s book and all she hints that he “figures it out.” Just then, the two are interrupted by a phone call from Tom’s mom saying she is back home and would be happy to see Kevin.
Abby and Trace talk about the new popularity of the band. Trace maintains a level head and
tells Abby that despite what John and Leigh think, he is not ready to make any big career decisions. Abby offers up her support and thanks Trace for being by the girls’ side, especially for Carrie’s upcoming birthday party. Trace points out that he not trying to replace Wes in their lives but enjoys the time he spends with them.
Back at the bookstore, Jess has arranged a sidewalk book sale to try to get rid of the extra books she accidentally ordered. She and David are also trying to continue to get through all the stages of their relationship book. One of Jess’s former high school teachers stops by and Jess tries to persuade her to purchase the piles of books, but she politely declines.
Kevin meets Tom’s mom at her house and the two share in memories of Tom. Kevin breaks down and says Tom should be alive today. She assures Kevin that Tom was all about living and she is not in the mood to hear about how he died. She also tells Kevin that Tom would want his friend to keep living his life and stop clinging to the past.
Trace tracks down Mick to seek out some business advice about the band and how to avoid taking too big a risk. Mick points out that there is always risk involved and contracts are always a two-way street, but having a faith of heart is a good start.
Jess worries about what Bree will say when she discovers the over-ordering of books. Instead, she is pleasantly surprised to see Bree in a good mood, because the local high school just ordered a huge amount of books, thanks to Jess’s former teacher. Bree points out that David and Jess make a good team and Jess is delighted because she gets to cross off another stage in her relationship book: Happiness.
Kevin surprises Gran, Meg and Mick with news of a big decision. He doesn’t want to be a doctor; he wants to be a paramedic. The family is not surprised, and in fact they are delighted with Kevin’s career choice.
Trace, Leigh and John are talking about the six record labels they were approached by, when Mark walks in and interrupts the conversation. He tells the band he is not there to pressure the band for a contract and before leaving, he gives them back their master recordings.
It is officially time for Carrie’s princess party and all the plans seem to go off without a hitch. Jess runs into her teacher and thanks her for the large book purchase. She in lets Jess know that the high school didn’t purchase the large order of books; it was David who bought them for the school, all $10,000 worth. Jess is shocked to hear of David’s extreme generosity, crossing off another stage in the book.
Bree runs to Jess and tells her that a publishing company just contacted her and want to turn her manuscript into a book. Simon who shopped it around in the first place. It dawns on Bree that she needs to call Simon and thank him.
Douglas approaches Abby and thanks her for inviting his daughter, Courtney, to the party. He also tells her he heard from the grapevine that Matt Fox dropped out of the land deal and his firm might be interested. She says she will relay the message to her dad. Wes shows up in time for the celebration and the girls run to his arms smiling. The party really kicks off when Mick unveils the beautiful castle photo op for the entire family.