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Workaholic Ally Wilson, who has made it to the final two on the dating reality television show "Happily Ever After," was convinced to sign up for the show if only to promote Swans Hotels, where she works in Marketing at the Los Angeles corporate office, although she does admit that Tanner Dillon, the bachelor who will choose between her and the other finalist for the last series of five dates, does proverbially check off all the boxes in a potential mate. Because she has been more than obvious about her motivations, she is nonetheless surprised that Tanner does choose her. She may be less prepared that those five dates will be held in her hometown of Winterland, a Vermont ski resort where she has not been since she left for college after high school in her plan to climb the corporate ladder away from small town Winterland. While she is looking forward to Tanner meeting her parents, Tom and Molly Wilson, she is less excited about running into some people, such as her childhood rival "Mean" Helene. But she is especially not looking forward to running into her high school sweetheart Brett Hollister, who broke her heart when he didn't follow her when she moved to Southern California for college. Brett, who has never left Winterland, now runs what was his family's resort hotel, the Winterlight Inn, where Ally got her start in the hotel business. Ally, who finds that the more things change, the more they stay the same especially when it comes to the now struggling Winterland Inn which is facing shorter and shorter tourist seasons due to climate change, may also find the same applies to Brett. What happens in this triangle is affected by the show's producer Lauren Burns, who not only wants good TV but also wants what's best for the contestants with regard to love. Thanks to her objective "camera" eye, Lauren is able to see more clearly the guy with whom Ally should end up.