Will You Merry Me (2008)

It's the December holiday season. What starts as a planned six month anniversary celebration for transplanted New Yorkers, lawyer Henry Kringle and commercial decorator Rebecca Fine, who began as roommates but fell in love in the process, turns instead into a somewhat impromptu proposal of marriage from Henry, which Rebecca, who sees their future as clearly as Henry, accepts. Not knowing what they were going to do for the holidays, they decide for their two sets of parents - Marilyn and Henry Kringle, and Suzie and Marvin Fine - to convene in the Kringles' hometown of Dunstan, Wisconsin so that Henry and Rebecca can meet their respective future in-laws before Angelenos Suzie and Marvin head to Aspen for their planned holidays. While the Christian Kringles and the Jewish Fines had never restricted their offspring from dating outside their faith in not being fundamentally religious, their different religious backgrounds are just one of the many sticking points, especially concerning the holidays and the wedding, in a Kringle-Fine union of families. The Kringles are conservative and traditional, while the Fines are more liberal. The Kringles are Midwest small town, while the Fines are west coast big city. These difference become most apparent between Marilyn and Suzie. But what emerges is that in the short time they have known each other and the impromptu nature of the engagement, Henry and Rebecca have never really talked about their future, they having different visions, partly spurred by their families and their upbringing. Added to the mix causing Henry and Rebecca's engagement potentially to fall apart is Henry's childhood friend, Kristy Easterbrook, she and Marilyn who may have always thought that she and Henry were meant to be together.