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Long divorced workaholic Olivia Pershing née Phillips, a Long Island stager, is getting remarried, to her pseudo business partner, equally workaholic Josh Johnson, a high end real estate agent. If they had their way, they would get married in a simple civil ceremony, however they are letting Olivia's daughter, Grace Pershing, arrange a small weekend getaway wedding for them, no major questions asked on their end. Grace believes they are unromantic, epitomized by the fact that her mother desentimentalizes spaces for a living, hence the reason why Grace wants to arrange something special for them. Grace chooses to hold the festivities at the Willow Lake Inn, a lakefront Vermont country property, Julie Turner, on behalf of the Inn, making most of the arrangements locally. When the band that Grace chooses to perform at the ceremony cancels at the last minute, Julie even arranges for an alternate, namely her father, the Inn owner who has always had music in some form in his life, it which he does solely for his own pleasure now. The weekend starts off with a bang when Olivia arrives at the Inn to discover the owner is former pop star Mick Turner, her college sweetheart, they who were each other's first love. Olivia performed in and wrote songs for his band at the time. Without Olivia, Mick and the band left when they got their first tour and a record deal, Mick and Olivia never having reconnected after that based solely on the circumstances of the time leading to a misunderstanding of the situation on both their parts, all this happening thirty years ago. Based on the way their relationship ended, their reunion is an uncomfortable one. One other person who will not be happy to see Mick is Olivia's judgmental oft-married but currently single mother Nora Winters, who never thought Mick was devoted enough to Olivia, he focused too much on the music. Grace knew nothing of this past life of her mother's, while Julie knew only of a woman her father dated in college. Recently widowed Mick, largely seen as the catch of the area of the middle aged set, has only recently felt ready to reenter the dating pool. Soon to be an empty nester and alone with only the memories, Mick is thinking about selling the Inn, which he has troubles telling Julie as it's the only home she's ever known. Grace, Julie and Duke, the Inn's chef who was the band's drummer, see a spark between Mick and Olivia, Duke who knew them as a couple. Although Grace likes Josh, she sees him more as a business partner than a husband for her mother. As such, Grace, Julie and Duke hope that the course of true love happens for Olivia and Mick to have a happily ever after, even if it's thirty years later than when it should have.