Sam and Cassie are still keeping their engagement a secret from Nick and Grace. Unfortunately, the couple also finds out that their children are still giving each other the silent treatment over Grace’s meddling in Nick’s relationship with Courtney.
Martha and her husband Tom pay Cassie an unexpected visit at her shop. She is on a quest to find Middleton’s most romantic spot, aside from Grey House and the botanical garden. Cassie reminds Martha that romantic destinations cannot just be decided upon; the title has to be earned. Martha says that the town of Middleton has a new brochure being printed out next week so romance is on a bit of a deadline. Martha finds a set of earrings that catches her eye and she tries them on. As soon as she puts them on, Martha’s demeanor towards Tom becomes softer, but when she removes them, it is back to business as usual. Tom offers to buy the earrings for his wife, but Cassie just gives them to him for free. Sam joins Cassie as she pays a visit to her favorite jewelry shop, only to find out the owner, Don, is in the middle of selling the store to retire. As Cassie looks around, Don tells Sam he has some engagement rings if he wants to check them out. Sam is surprised by Don’s hunch that Sam and Cassie were secretly engaged, but Don says he can tell these things by just looking at the couple. Sam promises he will come back to talk to Don without Cassie.
Back at Grey House, Grace discovers Cassie’s pile of jewelry she was trying to give to Don’s shop. Cassie offers it up to Grace, who chooses a pin that represents drama, hoping it will inspire her later that day in class. As soon as she pins it on her shirt, Grace begins reciting Shakespeare flawlessly. Meanwhile, Abigail finds a necklace she thinks would be perfect for a friend going through a hard time.
Martha hits the coffee shop, determined to locate the perfect romantic spot in Middleton. She asks Stephanie where she and Ben go to find romance. Stephanie suggests a nice patch of greenery outside where she often sees couples taking wedding photos. Martha thanks her for the suggestion and takes off to check it out. Abigail stops by to present Stephanie with the necklace she took from Cassie’s collection. Stephanie is hesitant to put it on and places it in her pocket.
Abigail runs into Sam and wants to know where he is headed. Sam lets her know of his secret trip to Don’s jewelry shop to pick out Cassie’s engagement ring. Abigail insists on going with Sam to help him select the perfect ring. At the jewelry shop, Abigail finds a locket that strikes her interest. Don explains that a woman dropped it off years ago and even though the two really hit it off, she left without leaving her name. Don always hoped one day she would come back so they can pick up where they left off. The only frustrating challenge about the locket is that it refuses to open, no matter how many times Don has tried. Abigail purchases the necklace because she likes the mystery surrounding it. Meanwhile, Sam finds a two-part ring that is missing a third part that connects the ring together. Don breaks the news that this ring has special meaning to him and refuses to sell it.
Back at the house, Abigail lets Cassie know she went ring shopping with Sam earlier that day. Cassie lets Abigail know there is one ring she really is interested in, passed down from generation to generation in the Merriwick household. The ring is supposedly magical and brings eternal happiness to any marriage. She also explains that the ring had vanished over time and nobody knows where it went. She suspects it was probably sold in an estate sale. As she describes the ring, Abigail remembers seeing one similar at Don’s jewelry shop.
Cassie goes upstairs to talk to Grace about her feud with Nick, while Sam confronts Nick about the same. Grace tells her mother that Nick never takes life seriously or takes others’ feelings into consideration. Meanwhile, Nick tells his dad that Grace is always telling him how to live his life. Grace points out that Nick took forever to break up with Courtney and that put Grace in an awkward position. In the end, both Nick and Grace separately tell their parents they have moved on from their friendship. The next morning, Cassie and Sam talk about the conversations they had with their children the night before. Sam sees Grace’s side of the argument, while Cassie sees Nick’s. The bottom line is that Nick and Grace are not getting along, but Cassie says they should step aside as parents and let their kids figure it out.
Nick and Grace run into each other at the Bistro and barely acknowledge one another. Grace finds Stephanie cleaning up the garden outside to get it ready for Martha to check it out. When the necklace Abigail gave Stephanie falls out of her pocket, Grace insists on putting it on Stephanie. As soon as she puts on the necklace, Stephanie backs off on the idea of making the Bistro garden a romantic spot for Middleton’s brochure and heads back inside the restaurant.
Sam returns to the jewelry shop, determined to buy the ring that caught his eye. Don breaks the news to Sam that he did find a buyer for the incomplete three-part ring and he sold it. Sam is unaware that he sold ring to Abigail, who has the missing piece of the three-part ring!
While shopping at Cassie’s, Martha discovers an old wedding scrapbook about Middleton. In the book are photos from an historic wedding in town. Martha thinks this will be the perfect aid to helping her choose a romantic spot around Middleton. She and Abigail track down the beautiful waterfall where the photo from the scrapbook was taken. Martha is surprised to learn that Abigail bought the property where the waterfall is located. Nervous that Abigail will build around the pristine scenery, Martha vows to write regulations to restrict her from doing so.
Nick discovers that his dad and Cassie are engaged, and he shares the news with Grace. The two decide to tell their parents that they are calling a truce and will go back to being friends. But when they are alone, Sam and Grace agree to only act civil towards one another in the presence of their parents so they can make their wedding as stress-free as possible. At the Bistro, Martha notices that Stephanie is completely distracted and asks what is wrong. Stephanie confesses that she and Ben broke up after they both decided that they weren’t going to get married. Abigail overhears Stephanie talking about Ben and offers her condolences. Both Martha and Abigail encourage Stephanie to not give up on love.
Later that evening, Abigail fills Sam in on her conversation about love with Stephanie at the Bistro. At that moment, she presents Sam with the completed engagement ring she bought from Don. Sam is shocked and wants to know where she found the missing piece. She tells Sam the story of finding her father’s old jacket when Cassie was cleaning out the closet, and in the pocket she found a pawn ticket. She called the shop and surprisingly, they still had the ring piece. It wasn’t until she was at Don’s jewelry shop, when she found the other two parts of the ring and knew she had to have it. She tells Sam that she offered up the locket back to Don after she managed to open it. From there, she also found the mystery woman’s name inside the locket and gave it to Don, along with the woman’s phone number. Sam is forever thankful for Abigail’s generosity, even though neither one of them knows how the ring is pieced together.
Tom grabs a few minutes alone with Martha and breaks the news to her that he has a consulting opportunity in Chicago. Tom expresses that this is the chance of a lifetime and he would be home on the weekends to visit her. She encourages her husband to sign the deal and go to Chicago. The moment is interrupted when Abigail shows up with the historic Middleton wedding book. Upon looking through the book, Abigail finds the location of a romantic spot where a lot of couples got engaged. Abigail is going to track down the mystery romantic spot. Martha is surprised by Abigail’s selfless generosity. Later on, Abigail and Martha follow the clues to where Middleton’s historic spot is and it leads them to Sam’s house. Martha realized that the town itself is romantic. Instead of one designated spot, she is going to name all of Middleton the most romantic.
Sam stops by to get Grace’s permission to ask Cassie to marry him. Grace gives him her blessing and tells Sam how much she loves them both. She welcomes Sam’s news with a big hug.
Later on, Sam stops Cassie in front of his house and gives her the engagement ring. Cassie is shocked to see it is the Merriwick ring. Sam points out that he wanted to propose at the place they met: his driveway. Cassie takes the parts of the ring and puts it together. Sam says it is a sign the ring was meant to be hers and he places it on her finger. Cassie describes the entire moment as perfect and tells Sam she loves him. The two share a romantic kiss.