Although she has traveled all over the world, flight attendant Montana Moore has yet to find a man with whom she wants to settle down. However, with her sister's upcoming wedding and pressure from her oft-married mother, she's determined to get engaged in the next 30 days. In that time, her best friends (and fellow flight attendants) conspire to help her re-encounter her exes as she flies all over the country.

When a naïve entertainment reporter is assigned to produce a special segment, exposing the decadent lifestyles of her celebrity friends, she is torn between accelerating her career and preserving their images.

Everything Adam knows about love, he learned from the movies. Unfortunately, Adam is no Cary Grant, and the closest he's come to experiencing true romance is one drunken night with his unrequited love, Kate. But that evening failed to live up to Adam's expectations, so he casts himself and Kate in a movie recreation of their one night, hoping for a better ending. It's a total flop, and Adam is forced to cast a new Kate when she no longer wants any part of her part. But re-casting Kate leads to an ending that even Adam never saw coming, in this playful comedy about love, movies, and how our love of movies affects how we love.