Connor Mead (McConaughey) is a famous photographer and serial womanizer. He attends his brother Paul's wedding, where he becomes reacquainted with Jenny Perotti (Garner), Connor's childhood friend and the only girl who's ever captured his heart. After Connor delivers a drunken speech at the rehearsal dinner where he says that love isn't real, he's met in the bathroom by the ghost of his uncle Wayne (Douglas), the man who taught Connor everything he knows about seducing women. Wayne informs Connor that, over the course of the evening, he will be visited by three ghosts who will lead him through his romantic past, present, and future.
As one can notice from this synopsis, the plot is based on Charles Dickens' A Christmas Carol, featuring a wedding day and the day before, rather than the familiar Christmas and Christmas Eve from A Christmas Carol. The three ghosts share similar appearances with the original descriptions, and the film shares the traditional plot points from the book.
This film features examples of:
- Bouquet Toss: Being set around a wedding, the film ends with the bride tossing the bouquet. It's caught by Keiko, the Asian archer who hasn't shown up since the beginning of the movie, who shoots it out of the air.
- Brick Joke: That Asian archer who appeared at the beginning of the movie doing some William Telling and then seeminly disappeared? She reappears at the end of the movie shooting the wedding bouquet out of the air.
- Bridezilla: Sandra, the fiancée of Connor's brother Paul. She is racked with wedding jitters, has a minor panic attack when the salad served at the rehearsal dinner is wrong, and calls off the wedding, complete with throwing decorations into the fireplace, when she finds out Paul slept with her bridesmaid when they were dating.
- The Casanova: Connor is a serial womanizer. His Uncle Wayne was where he learned it from.
- Childhood Friend Romance: Connor has known Jenny since they were little kids, and has been in love with her ever since.
- Dad the Veteran: The fact that Sandra's father is a sergeant and a Korean War vet is brought up a lot. He runs the wedding rehearsal a bit too much like a military operation, and even his toast at the reception involves a gory recollection about tending to a wounded member of his unit.
- Gone Horribly Right: The back story of Connor Mead involves him suffering a minor romantic disappointment. He then gleefully accepts his uncle's advice on womanizing so that he'll never feel vulnerable to a female ever again. It works to the point of him becoming a womanizing Jerkass whom everyone hates.
- Race for Your Love: A rare case where the chaser is not after his Love. In the climax, Connor Drives Like Crazy down a hill in Uncle Wayne's old car to stop Sandra from leaving Paul.
- Rom Com Job: She's a wedding planner, he's a photographer.
- The Unfair Sex: The protagonist Connor Mead is portrayed as needing a lesson in respecting women. The problem is, not only is he given a sympathetic backstory (a childhood love hurt his feelings, and he turned into a player to avoid such pain again), but they show the bridesmaids pretty much engaging in the same bed-hopping behavior (even competing to bed the protagonist) with no negative consequences. There is even a scene where it is discovered that one of them slept with the groom (Connor's brother). When Connor makes the logical arguments that 1) this was years before his brother even met his fiancé and 2) they were comforting the bridesmaid, when she was the one he slept with and she didn't tell the bride either, he is treated as scum and even his own brother tells him off for it.
- William Telling: This happens in involving an arrow, a rising pop star, and the 6th place Japanese archery champion."She didn't even medal!"
- Yet Another Christmas Carol: The film is a variation on this, where the ghosts (even though at least one isn't actually dead) show the main character his romantic past, present, and future in order to make him give up his womanizing ways.