A light snow falls as Cassie and Sam walk out of the bistro. When Sam called to tell her the news that Linda had gone back to New York, Cassie left John's faculty formal to make sure Sam was okay. Sam explained that before leaving, Linda made amends for the way she had treated Nick and he seems to be handling her leaving well. Sam then asks Cassie about her date with John, adding that it's nice of Cassie to fill in for John's girlfriend. Cassie hesitates before telling Sam that John and his girlfriend broke up. She then reveals that John was a bit of a player in college, with lots of girlfriends but none of them serious. It's also why he and Cassie have always been just friends. Sam chuckles and then suggests they need to celebrate. Sam then conjures an inspired idea and suggests that the location of their date be a surprise for Cassie.
The next day, at Abigail's flower shop, Stephanie is still trying to recover from her sudden breakup with Ben. Despite repeatedly telling him how much he meant to her, Stephanie is more than a little stunned that Ben wouldn't accept her apology. Cassie suggests that instead of telling him, Stephanie should show Ben how she feels. But now, after all this, Stephanie is no longer sure that she and Ben have any future together.
Nearby, Sam drops Nick off at school. With Linda gone, the two need to rework their routine, starting with Nick's afterschool schedule. While Linda was still in Middleton, Nick confessed that he really didn't like basketball and was quitting the team. While Sam respected his son's decision, he still wants Nick to find a productive use of his time. Nick halfheartedly tells his dad that he'll find something, but Sam is much more insistent. While he doesn't give Nick any limitations, he does want, by the end of the day, for Nick to have found a club or activity to put his energy into.
Across town at the Mayor’s office, Martha's son Michael stops by to share the good news. After putting zero effort into finding himself a job, Michael has now decided to start his own business. Martha tries to redirect him but Michael has decided that things will be better if he is his own boss. He tells his mother he's going to start a car service with "limos, town cars, you know... like that." Hoping to dissuade him, Martha asks if he's got any of the things he'll need, like a commercial driver's license or a business plan, but he's got nothing more than the idea. Still more jarring is Michael's decision that Blairsville is more cosmopolitan and would make a better location for him to start his business. Martha nearly explodes when she hears his plan but the worst is yet to come. In order to get things started Michael needs investors to put up $50,000 to start the business as well as more money for him while he gets the business up and running.
At Sam's office, Grace arrives for her first day as his intern. Eve arrives to start Grace's training and from the start, it's clear that Eve has a unique way of doing things. Fortunately, Grace is a quick learner and has a special ability to digest Eve's instructions.
Back at the bistro, Stephanie is personally making sure that Adam, the handsome lawyer visiting Middleton, is enjoying his meal. Stephanie bumped into Adam at Bell, Book and Candle when he was looking for an herbal cold remedy. On paper, Andrew is everything Stephanie is looking for and he is a welcomed distraction from the situation with Ben.
As Stephanie and Andrew chat and get to know each other, Cassie arrives to pick up her own order. As Cassie stands waiting at the bar, John walks in, thrilled that he's run into her. A new zip line course is opening nearby and John hopes Cassie will join him to try it out. Not only are Cassie's zip lining days done, but she couldn't go without anyone to look after the shop. But, just as Cassie prepares to leave, Abigail arrives. Cassie introduces John to Abigail and, before leaving, wishes him luck finding a zip lining partner. Cue Abigail, who asks John what he could possibly need luck for. Sensing an opportunity, John offers to buy Abigail a cup of coffee and tell her his plan.
Back at town hall, Martha tries to convince her husband they should invest in their son's business. Despite her best rhetorical efforts, Tom is unmoved and instead suggests Martha help their son by not bailing him out. Later, certain that his mom has secured the seed money, Michael arrives to celebrate. Instead, he learns that both of his parents have decided not to give him the money.
At Sam's office, Grace is coming into her own and even beginning to surpass Eve. Not only is she smart and talented, she also has a harder work ethic and is closer to Sam. He even takes her out for an early lunch, hoping to get her help with planning his date with Cassie. Despite all her efforts to break through with Dr. Radford, Eve can only sit back and watch Grace assume the role she wants.
Early the next morning, as Cassie opens the shop, John arrives with Abigail in tow. John convinced her to run the shop so Cassie will go zip lining with him. Cassie begrudgingly accepts the invitation and heads off with John. Later, Cassie and John arrive back at the shop, and Cassie is exhilarated. Hoping to capitalize on her feelings, John asks her to go to dinner with him. Unfortunately for John, Cassie already has a date with Sam. John nods and promises that next time he’ll get his invitation in early.
Later in the day, fresh off passing her driving test, Grace drives with Sam into the driveway at Sam’s house. Grace runs next door to tell her mom and Nick approaches his dad with his own exciting news. Nick’s finally found an extracurricular activity that he’s passionate about. Nick’s decided that for the coming semester, he’s going to study abroad in London. Sam is taken back and stutters for words. As Nick excitedly talks about the trip, Sam looks on stunned and unsure what to do next.
In town at the bistro, Andrew stops in for a celebratory meal. He’s just won the final motion for his client and his business trip is about to be done. As he and Stephanie talk, Ben walks in to get a cup of coffee. He looks on as Stephanie sits down and at the table to talk more with Andrew. Looking at Stephanie's smiling and laughing, Ben simply shrugs and walks away.
The next day, Sam and Cassie arrive at a nearby farm for their surprise date. With a little help from Grace, Sam’s gathered everything he and Cassie will need for an afternoon horse ride. Cassie had no idea Sam rode horses and Sam explains that he learned to ride during the summers he spent on his uncle's cattle ranch. The scenery is beautiful but she’s also nervous and she tells Sam she hasn’t ridden for years. Sam smiles at her and tells her not to worry—he’ll be there for her.