Will You Merry Me? (2008)

In the heart of New York, young lawyer Henry Kringle and the captivating Rebecca Fine find themselves drawn together in an enchanting tale of love at first sight. Their lives intertwine as they compete for an apartment, leading to a charming agreement to share their new found home and sparking an unexpected romance. Hailing from an opulent, contemporary Jewish family in Los Angeles, Rebecca's world is about to dramatically collide with Henry's humble, tradition-steeped Midwestern upbringing. As the snow gently falls upon Madison, Wisconsin, a pre-Christmas proposal sets the stage for a holiday season of momentous revelations and clashes of cultures. The couple plans to introduce their families, hoping to surprise them with their engagement news amidst the harmonious blend of Hanukah and Christmas festivities. However, the tranquil Midwestern town is anything but calm as tensions rise and traditions tangle. Henry's father, deeply rooted in family tradition, harbors hopes of his son continuing the family law practice, while Rebecca's family had envisioned a glamorous Aspen getaway. Despite their differences, the fathers find common ground, but the mothers become embroiled in a subtle tug-of-war, each attempting to undermine the engagement in their own crafty ways. As the couple navigates the choppy waters of familial disagreements and cultural disparities, they begin to realize that their impending marriage might be more challenging than they'd anticipated - especially when dealing with in-laws. But the true test comes in the form of Henry's old flame, Kristy, who his parents still view as the ideal match, stirring the pot of uncertainty and making the lovers question their commitments. "Will You Merry Me?" is a delightful comedic roller-coaster, filled with warmth, humor and a healthy dose of reality. It explores the fascinating dynamics of family relationships and cultural diversity, all while keeping the magical spirit of the holiday season at its heart. This film promises a wild, whacky ride of good intentions and missteps, as two distinct families strive to respect each other's traditions in the face of love, rivalry and the looming question - will this engagement truly last?

Will You Merry Me? is a comedy movie featuring Cynthia Stevenson and directed by Nisha Ganatra.

It is possible to buy Will You Merry Me? on Amazon Video, Apple TV and Vudu.