This week Martha’s city council meeting has a special guest: Cassie, who gets to witness the honoring of Ben for all the work he is doing on the old Middleton Theater. Martha also approves the spending on new trees to be lined up outside the city hall and a new swing set at the park.
Back at the Flower Shop, Abigail greets Sam who is looking for chocolates for his assistant. She tries to sell him on flowers for Cassie, but he is certain Cassie already knows how he feels about her and doesn’t need the flowers to prove it.
Back at the theater, Ben is teaching Sam how to thread an old movie projector. Grace stops by to drop off a projector movie that her mom found in the attic. Ben threads up the film and Grace watches from the audience seats. Later, at Grey House, Grace is eager to talk about the film she watched at the theater. Grace then asks if she can go see Martha the next morning because she has an idea.
At the bistro, Abigail overhears Stephanie placing food orders for Ben’s big opening night at the theater. Abigail puts the idea in Stephanie’s head that the occasion should be big. Stephanie agrees with Abigail’s suggestion.
Meanwhile as Martha is dining, she gets news that the city has frozen her assets, not allowing her to purchase the new swing set for the park or purchase new trees for the sidewalks. She says it is a mix-up but also says she will deal with the financial crisis on her own.
Cassie surprises Sam at his place before he heads to his office. She officially invites him to be her date to Ben’s big night at the theater’s grand opening. Cassie tells Sam how Grace loved the movie being played, describing it as a romantic black and white film. Sam shakes off the idea of those kind of movies, citing it as impossible for a couple to fall in love so quickly in real life. That leads Cassie to ask Sam how long a real couple should wait before saying “I love you.” Sam is saved by the bell when his phone rings; he has to run to the hospital to check on a patient.
Grace stops by Martha’s office to ask her about how to get funding for a city project. Martha explains that the city funds are historically low at the moment, and in fact, they don’t have any money for extra projects like trees and swing sets. After their conversation, Martha sneaks out before any of her staff can track her down for more funding requests.
Later on, Grace lets Cassie know how her visit with Martha went. Stephanie also shows up looking for fancy containers for Ben’s party. Cassie expresses how excited she is for opening night. Stephanie admits she just hopes she is ready for the big launch.
Back at the theater, Nick continues helping Ben get the place ready for the launch. Stephanie shows up with an old popcorn machine she came across in the basement to put on a display for the party.
Martha tries to sneak out of the office for the evening and gets caught. Jared tells her she needs to start addressing the funding issues with the city council. She dashes away when Abigail stops by asking about sidewalk repairs outside her shop.
Later that evening, Sam surprises Cassie at Grey House with a box of tea. She asks about his day and he talks about one patient of his who had a heart attack scare, which made the guy realize just how much he loved his wife. Cassie just smiles and listens.
When Cassie visits the bistro for some coffee, she spots Martha in hiding behind a newspaper. Cassie wants to know why, and Martha explains that her only crime is wanting to say yes to too many good things for Middleton. As a distraction, Cassie suggests Martha help Stephanie out with setting up the theater’s upcoming party, and Martha thinks that is a wonderful idea.
Back at the theater, Martha is impressed with just how great the theater is looking. Stephanie introduces Ben, Martha and Nick to the vintage popcorn machine that is now on display. She said she had help using lightbulbs she found in Cassie’s Grey House attic.
Back at the flower shop, Sam is back to buy more candy. Abigail casually points out the “I Love You” balloon by her side and asks if Sam has ever said those words out loud. Sam says yes, to a handful of a women, but nobody he is currently with.
Martha sneaks back into her office and is surprised by Grace waiting for her. Grace presents Martha with a folder filled with papers. It’s actually good news for Martha: while cleaning out the Grey House attic, Grace discovered an old bank account belonging to the city. After taking a careful look at the account information, Martha realizes that the forgotten bank account was never closed. In fact, as Grace points out, there is more than enough money in it to start paying for trees and swing sets in Middleton! Martha says Grace will get all the recognition at the next council meeting. Grace says she didn’t bring the account to Martha’s attention for recognition, but because she wanted it to be put to good use for the city. Martha notes that Grace is more and more like her mother, and Grace takes that as the ultimate compliment.
The day of the theater’s opening, the entire town of Middleton shows up for the occasion. Stephanie delivers popcorn to the audience, while Martha makes an announcement before lighting the marquee. She is happy to say that the city will be getting their new trees and a new swing set, all because of the generosity of an anonymous stranger. Cassie smiles at Grace.
Sam wants to know what the old black and white movie they are about to see is about. Cassie says the title says it all: “How to Say I Love You.” She hopes Sam is in the mood for a romantic comedy and he responds he is in for any surprises.
The town of Middleton settles into their seats to enjoy the film. During one of the most romantic scenes of the film, Sam reaches for Cassie’s hand and the two share a smile. After the movie, Sam asks to walk Cassie home and she obliges. Once they arrive at Grey House, Sam tells Cassie that she makes him want to be better. Cassie responds that she looks forward to every minute she gets to spend with him. Sam promises her he is not going anywhere and after a brief pause, he professes his love for Cassie. She tells him she loves him back and the two share a romantic kiss.