5. Holiday In Handcuffs (2007)
Christmas-based romantic comedies may not be for everyone, but Holiday in Handcuffs is really something. On the surface, its premise is simple, but the closer you examine its story, the more insane it gets. It’s almost as though the film was created as an exercise in stretching reality without actually acknowledging how unrealistic it is.
It follows Trudi (Melissa Joan Hart), a waitress who is dumped by her boyfriend shortly before he was due to meet her parents for Christmas. Panicked, Trudi does the only thing someone in that situation would do: kidnap the nearest man (Mario Lopez) with an antique gun and hold him hostage over Christmas. Despite the most unhinged meet-cute ever, the pair begin to develop intense romantic feelings for one another.
Basing an entire romantic story around the idea of someone being kidnapped at gunpoint is beyond ridiculous. It’s an incredibly strange and convoluted premise that is stretched so insanely thin over the course of the film that it’s genuinely a wonder the filmmakers stuck with it at all. Still, there are a few surprisingly funny moments, and it’s weirdly sweet, so Holiday in Handcuffs isn’t a total bust.