Cassie welcomes two new guests to Grey House. The strangers, Annabel and Jim, are both in town for job interviews, and to their surprise, they are competing for the same job! After some friendly bickering, Cassie ushers both inside to help get them settled in their rooms.
Later that evening, Cassie gives Jim a tour of Grey House and they run into Annabel. Jim starts to pry on how her job interview went and the two continue their bickering. Sam gives Cassie a call, hoping their coffee date is still on, and she tells him she would prefer to stay at the inn to look after her two guests. Sam understands. When he hangs up, he takes a look at the romantic dinner setting he had made for Cassie and tells Stephanie he will just have to pull off the surprise some other time.
The next morning, Cassie sees Grace off to school and is surprised when a cab pulls up to Grey House. Jim and Abigail both get out. Both of their flights have been canceled and they’ll each need their rooms back. Cassie happily obliges.
Meanwhile, at the flower shop, Abigail is surprised when another shipment of carnations comes in, especially because she received an order the day before, which Martha purchased.
While Sam is grabbing coffee, Stephanie tells him she is ready to help plan another surprise for Cassie at the bistro. Stephanie says this Thursday will be the special day and she will decorate and make Cassie’s favorite foods. Sam is on board, and when he later meets a violinist during a medical exam, he asks to have her and her quartet play for Cassie on Thursday as well.
Jim hangs out in the Grey House backyard playing croquet and is joined by Annabel. Once again, the bickering begins. The next morning, the two tell Cassie they both received calls that they are up for second interviews and will need another night at Grey House, she gladly offers up their keys.
Abigail continues to be frustrated with her less than exciting job at the flower shop and vents to Martha. She is interrupted by the same delivery man from the day before, with a new box of carnations. She is beginning to feel she is re-living the same day, over and over, again.
Nick is growing agitated with Grace and her lack of studying for their upcoming exam. She assures him she already knows all she needs to know. Nick tells Grace he also needs to get extra credit and wonders if there is anybody who can teach him about Middleton’s history. They wind up getting a lesson from Martha at city hall.
Back at the hospital, Cassie surprises Sam at work to see if he wants to go to dinner. He tells her he is really busy, but she is going to love what he has planned for their date the next day.
Jim is working in the dining room of Grey House and asks Grace where he can get more of the tea Cassie has been serving. Abigail overhears the conversation and asks Grace privately if she noticed it was strange that Jim and Annabel are still staying at Grey House despite both being scheduled to leave days before. She then puts it together that once Jim and Annabel get together, Abigail’s days will stop repeating themselves!
The next morning Stephanie stops by Abigail’s to pick up flowers for Sam and Cassie’s date. She tells Abigail that tonight will be perfect romantic setting for Sam and Cassie’s official first date. Abigail comes up with a plan.
Back at Grey House, Jim and Annabel continue to grow closer while playing croquet. Cassie stops by to check on the two and they share they have gotten to know each other a lot better while staying in Middleton.
Later on that night, the Bistro is lit by candlelight, the string quartet is performing and dinner is ready. Cassie is completely in awe of how far Sam has gone to make their first official date memorable. The romance is interrupted when Jim and Annabel show up holding invitations instructing them to meet at the Bistro. The plan was hatched by Abigail, hoping the two would show up and fall in love and end Abigail’s repeating days. Abigail shows up to tell Sam and Cassie it was she who sent the couple to the bistro, thinking they wouldn’t mind. Just then, both Sam and Cassie receive phone calls that Grace and Nick are at City Hall with the police-- another part of Abigail’s plot. When Sam and Cassie dart off, Jim and Abigail take their place at the table.
Sam and Cassie arrive at City Hall to find Grace and Nick were just letting themselves into Martha’s office to do more research on Middleton. Martha explains to the police that it was all a misunderstanding, since she gave the students permission to use her office for research.
Back at Grey House, Jim and Annabel are surprised to see all the carnations in the entryway. Abigail loves that the two are getting along swimmingly. When the two begin to argue, again, Abigail is disappointed her matchmaker night didn’t pan out.
Sam and Cassie are enjoying ice cream and talking about how despite all the obstacles from the evening, they are having the perfect date and share in a romantic kiss.
The next morning, both Jim joins Cassie in the kitchen for tea. They are interrupted when Annabel enters to announce the company both she and Jim are trying to work for is about to make a decision; they will need one more night at the house.
Back at the flower shop, Abigail is still trying to cancel her carnation order and, like clockwork, a new delivery arrives. When she snaps at the deliveryman, he reminds her just how much joy her flowers bring to people. Martha chimes in that Abigail’s chocolates bring joy to people, too. Abigail looks around at children stopping to smell her flowers and smiles, realizing that the humdrum of her daily life is more valuable than she realized. When she tells the deliveryman she will see him tomorrow, he responds that Abigail isn’t on his call sheet. Abigail is relieved that she might really get a brand new day. She also notices her broken clock is finally working!
Grace is doing homework at the bistro and tells Stephanie she is a little disappointed in her “B” that she got on that day’s exam. Nick shows up with pride because of his “A.” Grace realizes her mistake of not studying, and agrees to work harder with Nick for their upcoming math exam.
A beaming Jim shows tells Cassie that he received a job offer. It wasn’t the job he was interviewing for, but a different one in Seattle more suited for him. Just then Annabel walks in—she turned down her own offer in Middleton, since the town wouldn’t offer her anything better than she already has. But after reading a book in the Grey House library, she came to the conclusion it was time to move back to her hometown of Seattle to be closer to her family and friends. Jim is pleasantly surprised by this announcement, and Annabel tells him she would be happy to show him around. Before taking off, both want to know where they can find the tea that Cassie has been serving. She tells them it is from a valley not too far from Seattle, and it’s a great place to spend a long weekend getaway.
That evening, Sam joins Cassie at Grey House. He still can’t believe all the ways their first date went wrong. He just wanted to let her know how much he cares for her. Cassie already knows, and the two share a kiss.