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Charles is a charming but gaffe-prone thirtysomething whose friends are getting married one after the other, with him as the most likely candidate to be best man. He has come to find attending weddings unbearably tedious, and he himself remains single (or, as an ex-girlfriend of his puts it, a "serial monogamist"). One day, at yet another wedding, he meets Carrie (Andie MacDowell), and he has a one-night stand with her.
When he meets her again at another wedding, he begins to think she might be the right one. Unfortunately, she's now engaged to someone else...
Contains examples of:
- Author Appeal: Oh, Richard Curtis, with your clumsily adorable Hugh Grant characters and your alluring American women and your quirkily awkward dialogue and your minor social crises.
- Babies Ever After: Charles and Carrie, in the Where Are They Now? Epilogue, as well as the couple married at the first wedding, seen briefly at Charles'
- British Accents: A nice sampling of them, from posh to Scottish brogue.
- Bury Your Gays: Guess who gets the funeral?
- But Not Too Bi: Fiona. "Well, I was a lesbian once at school, but only for fifteen minutes, so I guess it doesn't count."
- The Cameo: The bumbling priest at the second wedding is played by Rowan Atkinson.
- The Casanova: Inverted. The one who happens to have done the most sleeping around (and is quite casual about it) is Carrie rather than Charles.
- Cluster F-Bomb: Dropped rather... curiously by Charles. See the main article.
- Defrosting Ice Queen: Fiona, to some extent.
- Disposable Fiance
- The Ditz: Scarlett.
- Dreadful Musician: The amateur duo at the first wedding. They're even listed as "Frightful Folk Duo" in the credits.
- Exactly What It Says on the Tin: There are four weddings and a funeral.
- Fairytale Wedding Dress
- Foreshadowing: At the fourth wedding: "When someone asks you a question, just say "I do"
- Friendship Moment: Several of those take place among Charles's circle of friends.
- Hollywood Heart Attack: Gareth.
- Insatiable Newlyweds: Bernard and Lydia.
- It Always Rains At Funerals: Played straight.
- Last-Second Word Swap:
"-Bit of a poor show you not having a stag night. -We did! We did... We didn't think it was a very good idea in this day and age."
- Life of the Party: Gareth.
"I remember the first time I saw Gareth dancing. I feared lives would be lost."
- Lost Wedding Ring: At the first wedding, Charles, as the best man, realizes at the last minute that he's forgotten to bring the rings.
- Malaproper: The priest at the second wedding makes a number of verbal blunders ("awful wedded wife" for "lawful wedded wife", etc.).
- Psycho Ex-Girlfriend: All of Charles' former girlfriends.
- Running Gag: Charles oversleeps and shows up late at every wedding he's invited to. His friends make absolutely sure he's on time for his own.
- Speak Now or Forever Hold Your Peace: Played straight by David at his brother Charles's wedding. David is actually mute and Charles must translate for everyone else what he says in sign language. Cue an Armor-Piercing Slap from the spurned bride.
- Upperclass Twit: Tom.
- Wedding Day: Four of them, three hilarious in one way or another.
- No rings, trainee vicar, groom having second thoughts
- Weddings for Everyone: Everyone, interestingly, but Charles and Carrie.
- Where Are They Now? Epilogue