As the story unfolds, we dive deep into a heartfelt narrative of love interwoven with deception. At its core is Tom Leezak, portrayed by Ashton Kutcher, a relatable everyman who finds himself caught in a whirlwind romance with the enchanting Sarah McNerney, played by Brittany Murphy. Their fateful meeting on the beach ignites a passion that leads to a whirlwind courtship, defying the disapproval of Sarah's affluent family. Ultimately, this culminates in a dreamlike wedding, yet lurking beneath the surface of their seemingly perfect romance are soon-to-be-unraveled secrets.
As they set off on their European honeymoon, Tom and Sarah's endeavors to consummate their marriage unfurl amidst a series of unfortunate incidents filled with hilarity and miscommunications. Their struggle to join the elusive mile-high club is just the tip of the iceberg, as they face numerous unexpected challenges: a generous cognac gift from Peter Prentiss, Sarah's childhood friend harboring unresolved feelings; and a mischievous sex toy from Tom's buddy Kyle, which inadvertently casts a shadow over their experiences.
The tension escalates when their romantic journey hits a snag. An unfortunate car accident leaves them stranded in a snowbank, while their attempts to secure accommodations result in a string of disastrous hotel experiences. A rundown pensione suggested by Tom’s father turns into a vermin-infested horror, prompting the couple to seek the refuge of an opulent Venetian hotel.
Yet, even within the comforts of luxury, the cracks in their bond deepen. Tom's growing indifference leads him to abandon Sarah in favor of sports at a local bar, which leaves her contemplating the future of their union. When Sarah unexpectedly reunites with Peter, a cascade of hidden truths begins to unravel: Tom's accidental role in the death of Sarah's beloved dog, and her own affair with Peter during the early days of their relationship.
As the couple begins to drift apart, they embark on their separate paths. Tom finds his attention drawn to American tourist Wendy, while Sarah wanders the enchanting canals of Venice, burdened by her secrets. Wendy attempts to entice Tom with her playful flirtations, prompting him to make a hasty retreat through a hotel bathroom window, leaving her bewildered. Upon returning, Tom discovers Sarah had spent an evening with Peter, intensifying his confusion and frustration.
The evening quickly spirals as Sarah, under the influence, finds herself in Peter's company once more. Their kiss elicits a jarring slap, serving as a stark reminder of Sarah's marital vows to Tom. Unbeknownst to her, Tom witnesses this moment and is soon confronted with a shocking discovery—Wendy's bra in their hotel room—which ignites a fierce argument with Peter. Their squabble eventually leads the couple behind bars, yet they remain unable to consummate their union. However, with Peter’s assistance, they are released and decide to return to Los Angeles, mirroring the story's initial moments.
Months later, Sarah has moved on while Tom continues to yearn for her presence. In a desperate bid for reconciliation, he seeks guidance from his father and attempts various antics to win her back, including a comical failed attempt to crash through the gates of her family estate. But when Sarah hears Tom express his heartfelt feelings in front of the camera, her heart softens, leading her to open the gates. They reunite in a passionate embrace, solidifying their love and ultimately winning over Sarah’s family as they recognize the depth of Tom’s affections for their daughter.
