A 2008 romantic comedy film directed by Paul Weiland, starring Patrick Dempsey and Michelle Monaghan.
Tom Bailey Jr. (Dempsey) is a commitment-phobic Casanova who for the last ten years has also been in love with his best friend Hannah (Monaghan). Hannah goes to Scotland for six weeks and falls in love with a Scotsman named Colin (Kevin McKidd). She announces to Tom that she and Colin are engaged and asks Tom to be her maid of honor. Tom is determined to stop Hannah from getting married to Colin before it's too late.
Contains examples of:
- Abhorrent Admirer: Tom Sr.'s secretary, who has a crush on Tom Jr.
- Best Woman: When Hannah tells Tom she's engaged, she tells him she would have expected to be his "best man" were he the one getting married, and promptly asks him to be her "maid of honor".
- Big Applesauce: Where Tom and Hannah live and where the first half of the movie takes place before the action moves to Scotland.
- Bigger Is Better in Bed: Implied about Colin, given Tom and his friends' reaction to seeing him in the shower.
- Covers Always Lie: Neither of Hannah's wedding dresses nor the bridesmaids' dresses match the ones seen on the poster.
- Disposable Fiancé: Poor Colin.
- Fat Comic Relief: Poor Hilary, who seems to exist for no other reason. First there's her insistence on a dress size that's too small, and her equal insistence that she'll be able to fit into it. Then there's her unhealthy liquid crash diet, during which she almost faints. Then she actually faints after she's squeezed into the dress, and finally it rips when she sits down.
- Fourth-Date Marriage: Hannah is engaged to Colin within six weeks of meeting him and planning to marry him within another two.
- Friendship as Courtship: We don't know how much time passes between Colin and Hannah's aborted wedding and Tom and Hannah's, but it's likely that they took this step, having been friends for a decade and therefore already knowing everything about each other.
- Gender Flip: To My Best Friend's Wedding, following an almost identical plot—person realizes they're in love with their opposite-sex friend just as said friend announces their engagement and engages in Relationship Sabotage while helping them plan their wedding.
- Gold Digger: Tom Sr.'s latest wife (and the others too, it's implied).
- Happily Married: Felix and his unseen wife, as implied by his dialogue. The other guys tease him about supposedly being a Henpecked Husband, but he makes it clear that (a) he's not, and (b) even if he were, he's okay with that.
- Heart Is Where the Home Is: Helen is Tom's best friend from college. He realizes he is in love with her only when she's on sabbatical in Scotland. Predictably, she returns to New York with Colin, a Scottish duke who wants to marry her. Colin isn't portrayed as a jerk (except when it comes to sharing cake) but he just turns out to be wrong for Helen.
- Heroic BSoD: Tom, after Hannah rebuffs his declaration of love.(whispers tearfully) "I can't be your maid of honor. I can't give you away."
- Ladykiller in Love: As well as Tom realising how he feels about Hannah, Tom's father reflects that despite his multiple marriages, he's only been genuinely in love once with Tom's mother, but at the time he was young and stupid and made so many mistakes that by the time he realised he was ready to fight for her she had already moved on and left him.
- Love Epiphany: Tom has this about Hannah when she goes away for six weeks.
- May–December Romance: Tom Sr. has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting it off with Melissa, one of Hannah's friends.
- Mistaken for Gay: Tom gets this a few times, as a man serving in a traditionally female role.
- "Mister Sandman" Sequence: The opening sequence set in 1998 is abundant with pop-culture references such as people dressed as then-President Bill Clinton and Monica Lewinsky.
- One True Love: Tom Sr. describes Tom's mother as this.
- Popping Buttons: Hilary's dress rips up the side when she sits down.
- Psycho Ex-Girlfriend: Melissa is a complete bitch to Tom throughout most of the movie, having been one of his many discarded flings, even as Tom truthfully points out that he never misled her to think he wanted more.
- Pun-Based Title: A play on "maid of honor", obviously.
- Serial Spouse: Tom Sr, who's been married so many times that his lawyer needs to remind him that this is his sixth wedding, and when he appears to be hitting it off with Melissa, has to be reminded that it will be his seventh.
- Speak Now or Forever Hold Your Peace: Tom crashes Colin and Hannah's wedding at precisely this point.
- Surprisingly Realistic Outcome: The generic plot aside, there are a few moments where Hannah realizes that as wonderful as Colin is, there are things she doesn't know about him that could prove problematic as time goes on. She also rebuffs Tom when he tries to tell her how he feels and is actually angry that he waited until the last minute to do this.
- Token Black Friend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.
