Enjoying a romantic dinner together, Jack and Olivia laugh and chat about Eric and Shelly. Since the birth of his daughter, Eric has been staying with Jack and working at Moon's. As diner winds down and Jack serves dessert he also makes another attempt to give Olivia a key to his house. While Jack does his best to convince Olivia to accept the key she is still very reluctant. The awkward conversation is interrupted when Shelly and Eric arrive with the baby.
Fatherhood has had a positive change on Eric. He's paying rent to Jack, working every day, and doing everything he can to be a good father and partner. But the financial realities of being a parent are also starting to sink in too. So much so that on the eve of he and Shelly's first anniversary, Eric has to ask Jack for an extension on the rent so he can afford to take Shelly out for a nice meal. Still beaming with pride at his son's newfound maturity Jack agrees. However his mood is dimmed when he realizes that Olivia left without taking the key.
At Moon's, Olivia and Grace enjoy a light lunch. Olivia discusses her reluctance at accepting Jack's key. Grace whose credit card was declined while trying to pay for lunch, reveals that she is struggling with her own issues. With Maryellen gone, Grace has to confront the stress and expense associated with owning an old home. Olivia suggests that she sell the house but letting go of the sentimental attachment seems more than Grace is capable of doing.
At their apartment, Justine helps Seth pack for his new fishing job in Alaska. While Justine is happy for Seth, she also realizes that she needs to move on with her own life. While helping Seth pack she announces that she is leaving their apartment and moving back in with her mom. The lack of direction in her life hits home when, later in the day, Justine runs into a former classmate. Having just finished school, Cecilia is busy taking on every opportunity she can. But when she asks Justine what she is up to, Justine can only respond by saying "that's a really good question."
Meanwhile, in his office, Bob stops in to say hi to Jack. Noticing that his friend is preoccupied, Bob asks Jack what's on his mind. Jack tried to dodge the question, but Bob presses him. Jack then reveals his concern over Olivia's reluctance to accept the key to his house. Hoping to help, Bob offers Jack a simple solution; ask Olivia if she wants the key.
After talking to Bob Jack heads home to work on an upcoming article. Eric, in a panic, comes to him for advice. Having just seen his first pay check, Eric now realizes that he not only can he not afford a nice date with Shelly, he can barely afford the weekly expenses of a newborn. It's then that Eric reveals that he and Shelly have never had a proper first date.
Back at her home, Grace is finally coming to accept the reality of her situation. Her plumber, who had just discovered lead in the pipes, has now determined that the home needs a brand new foundation. Facing thousands of dollars worth of repairs Grace leans on Cliff for advice and comfort. Cliff acknowledges the house is all Grace got from the divorce and that the memories are important, but he also impresses upon Grace the severity of her situation.
The realization of the situation finally convinces Grace to that she has no option but to sell and move on with her life. She meets Olivia at her office to share the news and ask for her help. A few months before, a realtor approached Grace with an offer on the house. At the time Grace passed on the offer, but before heading to Olivia's office, she called the realtor and found out that the perspective buyer is still interested. With the weight lifted, Grace is now free to move on from her past life and start a new chapter.
Meanwhile, Eric and Shelly set out on their first date. The two make awkward conversation as the slowly come to the realization that they know almost nothing about each other. At the end of the night Shelly tells Eric that she and the baby are moving to Seattle. Even though Eric is trying his best, the two are far from making their situation work. They hold hands and star silently into each other's eyes.
Back at home Jack rushes after receiving a message from Olivia, asking him to meet her. He's in such a rush that he doesn't immediately realize that Olivia let herself into his house. Jack sits down and Olivia hands him a key. Her starts to argue about the key again before Olivia interrupts him and points out that the key she is handing him is the key to her house. Relieved, they laugh and bask in the important step they've taken in their relationship. But as they talk, Olivia gets a text message from the realtor handling the sale of Grace's house and the news is not good.