On a sunny afternoon, clad in hiking gear, John and Cassie prepare to repel off a cliff. Through all the years Cassie’s lived in Middleton, she’s never been to this hiking spot. John remarks that the trail is just one of the many surprises he’s discovered since moving to town. John feels an unseen force guided him to a rewarding teaching job, which has also given him the time to pursue an expedition to the Maldives. But while things are looking up for John, he’s got an important deadline that threatens to derail his upcoming dig. By the end of the week, John must name a field supervisor or lose the grant. With Cassie’s help, John’s poured over dozens of resumes and settled on two candidates. Since time is not on his side, John has decided to clear his head and spend the next few days camping. He hopes that the peace and quiet will help him come to a final decision about who will accompany him on the road ahead.
Later in the day, Cassie returns home to find Abigail sitting at her kitchen table. Abigail has come to tell Cassie that Martha is wise to the fact that Cassie is planning a party. She explains that while trying to figure out her next move with Greg, Abigail inadvertently let it slip that she was making floral arrangements for a party being thrown by Cassie. Cassie is surprised to hear that Abigail likes Greg enough to be distracted by him. Cassie advises her cousin that the attraction may be a result of Greg not immediately surrendering to her charms, but Abigail is sure that’s not the case. As they talk, Martha barges in to interrogate Cassie about the party. Having regained her footing, Abigail calmly tells Martha that Cassie is planning a romantic dinner for herself and John. She goes a step further and swears Martha to secrecy, saying that Cassie doesn’t want John to find out. Martha promises to keep the secret and, on her way out the door, laments that she wishes her her husband was as romantic as Cassie.
As night falls across Middleton, Cassie finds Sam outside playing basketball. She’s worried about a guest staying at Grey House and she believes Sam is the perfect person to help. Shortly after arriving at Grey House, Cassie’s guest Dan began seeing ghosts. Believing the problem is mental, Sam offers to give Dan a referral but Cassie suspects that he needs a doctor, not a psychiatrist. Sam relents and agrees to see Dan. Just then Sam’s phone rings. It’s his realtor telling him that another person is interested in buying the lake house and may take Sam into a bidding war. While Sam thinks he wants the house, he knows he doesn’t want to enter into a bidding war. Seeing his concern, Cassie suggests Sam write a pros and cons list and then decide what to do next.
Inside, Grace and Nick are in the kitchen working on homework. Grace asks how Nick’s study abroad entrance essay is going. Nick’s finished the essay but he is less than thrilled with the final product. Grace had expected Nick to be more excited about the opportunity, but Nick reveals that the more he finds out about London, the less enthusiastic he gets. Grace can sense that Nick is losing his passion for the experience and she tells him that he doesn’t have to go.
The next morning, Cassie catches Sam on his way to the hospital. Cassie takes the opportunity to ask if Sam may have an ulterior motive in going to the hospital. Sam knows she’s talking about Valerie, the hospital representative who’s trying to convince Sam to take the chief of staff job. Although Valerie is keeping up the pressure, Sam feels the job is just too much for him to take on; especially as her tries to rebuild his relationship with Nick. Cassie suggests that Sam should change the job being offered into the job he wants. Sam appreciates the sentiment but tells her that jobs like this one would end up bending him to the will of the job.
Meanwhile at the bistro, Ben talks with Stephanie about his friend who wants to invest in her catering business. Ben explains that the investor is a friend of his from high school who became a stock trader. Ben desperately wants to help Stephanie fulfill her dreams, but Stephanie is still unsure she can make a new business work. As they talk, Martha walks in and overhears them talking about catering a party. Fortunately, Ben and Stephanie have sense enough to lie and tell Martha they are talking about Stephanie’s new business idea. Martha then casually lets it slip that Cassie is planning a romantic dinner for John. Unbeknownst that Martha’s juicy tidbit was a lie to throw her off the scent of her own surprise party, Stephanie is immediately intrigued and heads off to get all the details from Cassie.
Nearby at the flower shop, Greg arrives having received a text message saying his arrangement was ready for pick up. Greg tells Abigail he didn’t order anything and she feigns surprise but, since he’s there, she decides to take the opportunity to ask him what his problem is. His problem, as she sees it, is that he and Abigail don’t have a second date. Fortunately for Greg, the universe has granted him the opportunity to right his wrong. Greg tells Abigail that he “doesn’t do the girlfriend thing” but he’s open to discussing the situation. Abigail convinces him to take her to dinner the next night after he helps her deliver flowers to Martha’s surprise party.
At Middleton high school, Grace and Sam are passing between classes when Nick asks Grace to proofread his study abroad essay. The process has been a struggle for Nick who just learned that among all the other work the program requires, he must sign a contract, committing him to finish the program. Nick worries that the contract leaves him no easy out if things get tough. And, if he is able to leave early, everyone, including his father, will know he can’t hack it. Grace agrees to proof read the essay and sends Nick on his way. As he walks away another student approaches and points out that Grace is wearing a t-shirt with an image of the Globe Theatre on the front. Katie, it turns out, lived in London with her family for several years. As they talk Grace realizes the two are in the same biology class. Katie tells Grace that she’s been struggling with the course and even failed the last quiz. Sensing an opportunity to reach out, Grace offers to help tutor Katie and the two head off together.
The night of Martha’s party, Greg and Abigail are busy unloading arrangements. As they do, Greg drones on and on about his amazing travels and adventures. He’s so entranced with his stories that Abigail can’t get a word in edgewise. As they work it becomes clear to Abigail that despite his good looks, Greg lacks any charm and is completely self absorbed…even more so than Abigail.
At the bistro, Stephanie and Ben prepare to take the food to Martha’s party. As they pack up the trays, Stephanie tells Ben that she’s decided to move forward with the catering business. What’s more, she’s decided not to bring on Ben’s investor and instead, she’s decided to invest in herself. If she keeps her costs low and uses some of the bistro profits, Stephanie’s sure she can make both businesses work. Ben likes the plan and tells Stephanie that he “loves her when she’s like this.” He then carries a tray outside, leaving Stephanie to wonder what he just said.
Back at the party, Cassie escorts the still unaware Martha to her surprise. Cassie keeps the ruse going right up until she and Martha walk into the ballroom. Cassie and Martha turn the corner just as the crowd of Martha’s friends yell “Surprise!” Cassie wishes Martha a happy anniversary just as Martha finds Tom standing and waving in the crowd. Stunned, Martha moves through the crowd towards Tom, still in awe that Tom and her friends kept the surprise from her for so long. As she takes it all in, Tom looks down and realizes Martha has a gift for him. In the box, to commemorate their 30th, Martha had one of the wedding photos framed in a beautiful pearl inlayed frame.
As Cassie wanders through the party she finds Abigail, slumped alone in a corner. After several hours of Greg’s incessant boasting, she’s sent him to get drinks while she enjoys a much needed break. She admits that Cassie was right and that Greg is totally wrong for her. Having acknowledged her error Abigail now heads off to fake a migraine and bring this date to an early end.
Later in the evening, John makes an unexpected appearance at the party. Cassie is glad he came, but surprised that he’s not clearing his mind and trying to select his new field supervisor. It’s then John reveals that he’s made his choice, but he’s unsure if the candidate will take the job. Cassie remarks that the job is the opportunity of a lifetime. John agrees that it is the opportunity of a lifetime, then asks Cassie if she will take the job. Cassie is stunned and flattered, but she has two businesses and a family to think of. John understands, but he also knows that if Cassie puts her mind to it, she can make anything happen.
A short time later, Sam arrives at the party in a celebratory mood. Not only did he get the lake house, Hillcrest hospital offered him the chief of staff job, while granting him the leeway to spend time with Nick and to keep his practice in Middleton. This spate of good news came about curiously at the same time Sam met Cassie. Sam confides that Cassie’s opinion really matters to him and that it has, ever since they first met. As they stand together Cassie tells Sam that John asked her to be the field supervisor on his trip to the Maldives. The news leaves Sam stunned.