I'll Be Seeing You

Amy Andrews is a highly organized senior associate at a patent-acquisition firm who is pursuing a major promotion. Her work-driven lifestyle leaves little room for spontaneity, and even her promising first date turns awkward when she tries to schedule their next meeting weeks in advance. Meanwhile, Mark, an adventurous interim Activities Director at Summerville Meadows and a former park ranger, is being urged to make his position permanent, but he worries that settling down will limit the adventures still ahead of him. Amy's grandmother Vivien remains energetic and bold, while her close friend Sue is facing her first wedding anniversary since her husband George's death. Amy's boss, Phyllis, asks her to deliver a confidential patent contract in person to eccentric inventor Alan Vespertine in Eureka, California. Although Amy has promised to spend the weekend with Vivien, the promotion depends on getting Vespertine's signature. When Amy's car breaks down on the way, Mark arrives in his grandfather's van, Mabel, and spontaneously joins Amy, Vivien, and Sue for the coastal trip. The group makes an unsuccessful detour to see the world's largest ball of twine before continuing to Keystone, a town that holds special memories for Vivien. In Keystone, Vivien reveals that she fell in love there in 1975 with Teddy Robertson, a young man she met after he accidentally hit her with a penny from a wishing fountain. Their brief romance lasts only five days, but it changes how Vivien understands love and spontaneity. While revisiting their old meeting places and dancing to the song I’ll Be Seeing You, the group discovers a bottle hidden in a tree containing a letter Teddy left in 1979. The note asks Vivien to find him, and an address and a series of clues lead the travelers into Oregon in search of the life-changing romance she thought was long over. The search becomes increasingly complicated as Amy's work deadline forces the group to split up. Vivien and Sue take a train while Amy and Mark drive toward Eureka, but Vivien and Sue impulsively board an earlier train and leave Amy and Mark together. The two share a mistakenly booked romantic hotel package and begin to understand each other, with Amy learning about Mark's grandparents and his belief that life should be lived in the present. Their pursuit of Teddy first leads them to the wrong Teddy Robertson, a much younger vineyard owner, and then to an engagement party where Amy must retrieve the lost briefcase containing Vespertine's contract. The party's theme of finding love unexpectedly reinforces the lessons Amy is resisting. The pressure peaks when Sue faints and Mark leaves to keep the promise he made to George to look after her. Amy reaches Vespertine's home, but he delays signing while asking detailed questions about the agreement. When he receives a call about his granddaughter Izzy's ballet recital, Amy encourages him to attend rather than miss another important personal moment. She leaves without the signature and tells Phyllis that she needs to put her life first, although Vespertine ultimately signs the contract. Amy also takes time away from work to reconsider the promotion and whether the career path she has planned is actually the life she wants. With help from the traveling musicians Clyde and Pepper, Amy reaches Star Valley in time for Vivien's reunion with Teddy. Teddy explains that he built a loving life with his late wife Muriel, just as Vivien built one with her late husband Charlie, but both are grateful that their brief first romance shaped the people they became. They agree to stay in touch. Vivien tells Amy that the journey was about more than finding Teddy. A later conversation urges Mark to stop hesitating about his next step. Amy encourages Mark to recognize how deeply he cares for Summerville Meadows, and Mark finally decides to accept the permanent Activities Director position. Mark says that he needs a better place to live if he is staying and asks Amy to help him look. They arrange to start on Tuesday; the dialogue does not establish a decision to move in together.