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:
- Back-to-Back Poster: The poster has main characters Connor Mead and Jennifer Perotti in this setup, with Perotti holding the end of a scarf that's around Mead's neck like a leash. Perotti is Mead's childhood friend and first crush, and who he finally pairs up with.
- 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.
- My God, What Have I Done?: Connor's silent reaction when he recalls abandoning Jenny.
- 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.
- Never Be Hurt Again: Connor became a womanizer after failing to get Jenny in highschool. At the end of the movie he acknowledges that he became so afraid of being hurt again he broke things off with her even when they got together as young adults a few years later.
- He also realizes this is the real reason that Sandra called off the wedding. Pointing out that while she’s mad at his brother she’s still friends with the bridesmaid, that she actually got over it once she heard it and she became afraid of being hurt later because she actually loves him very much.
- Rom Com Job: She's a wedding planner, he's a photographer.
- 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.