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* HeartIsWhereTheHomeIs: 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.
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* LadykillerInLove: 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.



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trope was cut/disambiguated due to cleanup


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 (Creator/KevinMcKidd). She announces to Tom that she and Colin are engaged and asks Tom to be her [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

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Tom Bailey Jr. (Dempsey) is a commitment-phobic {{Casanova}} [[TheCasanova 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 (Creator/KevinMcKidd). She announces to Tom that she and Colin are engaged and asks Tom to be her [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.
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* TestingTheLoveInterest: Tom asks his date what kind of cookie she thinks he'd order as a test because his best friend Hannah (who he's UnknowinglyInLove with) would be able to guess right instantly:
-->'''Tom:''' OK, guess what I'm going to order.\\
'''Random Date:''' ...Why?\\
'''Tom:''' Just do it, it's a game, it's fun.\\
'''R.D.:''' OK... a cookie?\\
'''Tom:''' No, be more specific, what kind of cookie?\\
'''R.D.:''' [[ComicallyMissingThePoint A really big cookie?]]

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* SurprisinglyRealisticOutcome: 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.

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* SurprisinglyRealisticOutcome: 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.
**
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.
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* TestingTheLoveInterest: Tom asks his date what kind of cookie she thinks he'd order as a test because his best friend Hannah (who he's UnknowinglyInLove with) would be able to guess right instantly:
-->'''Tom:''' OK, guess what I'm going to order.\\
'''Random Date:''' ...Why?\\
'''Tom:''' Just do it, it's a game, it's fun.\\
'''R.D.:''' OK... a cookie?\\
'''Tom:''' No, be more specific, what kind of cookie?\\
'''R.D.:''' [[ComicallyMissingThePoint A really big cookie?]]
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They Do is now a disambig page


* TheyDo: Tom and Hannah.
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* BigApplesauce

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* BigApplesauce BigApplesauce: Where Tom and Hannah live and where the first half of the movie takes place before the action moves to Scotland.
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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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

to:

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=]).(Creator/KevinMcKidd). She announces to Tom that she and Colin are engaged and asks Tom to be her [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

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** 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.


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** 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.

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* RealityEnsues: 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.


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* SurprisinglyRealisticOutcome: 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.
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Okay, that is complainingy and also an oversimplication of both plots.


* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.

to:

* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.
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* PunBasedTitle: A play on "maid of honor", obviously.
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Tom (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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

to:

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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.



* AbhorrentAdmirer: Tom Sr's secretary, who has a crush on Tom Jr.

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* AbhorrentAdmirer: Tom Sr's Sr.'s secretary, who has a crush on Tom Jr.

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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also been in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

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Casanova
A 2008 romantic comedy film directed by Paul Weiland, starring Creator/PatrickDempsey and Creator/MichelleMonaghan.

Tom (Creator/PatrickDempsey) (Dempsey) is a commitment-phobe commitment-phobic {{Casanova}} who for the last 10 ten years has also been in love with his best friend Hannah (Michelle Monaghan).(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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late. \n

----



* TokenBlackFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.

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* TokenBlackFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.man.

----
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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also been in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.
----

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also been in love with his best friend Hannah (Michelle Monaghan), Monaghan). Hannah goes to Scotland for six weeks and falls in love with a Scotsman named Colin (Kevin [=McKidd=]), she [=McKidd=]). She announces to Tom that she and Colin are engaged and asks Tom to be her [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.
----



* CoversAlwaysLie: Neither of Hannah's wedding dresses nor the bridesmaids dresses match the ones seen on the poster.

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* CoversAlwaysLie: Neither of Hannah's wedding dresses nor the bridesmaids bridesmaids' dresses match the ones seen on the poster.



* FatComicRelief: Poor Hilary, who seems to exist for no other reason--first with her insistence on a dress size that's too small, and her equal insistence that she'll be able to fit into it. Then her unhealthy liquid crash diet, during which she almost faints. Then actually fainting after she's squeezed into the dress and finally having it rip when she sits down.

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* FatComicRelief: Poor Hilary, who seems to exist for no other reason--first with 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 fainting faints after she's squeezed into the dress dress, and finally having it rip rips when she sits down.



* OneTrueLove: Tom Sr. describes his Tom's mother as this.

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* OneTrueLove: Tom Sr. describes his Tom's mother as this.



* SpeakNowOrForeverHoldYourPeace: Tom crashes into Colin and Hannah's wedding at precisely this point.

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* SpeakNowOrForeverHoldYourPeace: Tom crashes into Colin and Hannah's wedding at precisely this point.

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tropes were renamed


Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also been in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.



* BiggusDickus: Implied about Colin, given Tom and his friends' reaction to seeing him in the shower.
* BlackBestFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.

to:

* BiggusDickus: BiggerIsBetterInBed: Implied about Colin, given Tom and his friends' reaction to seeing him in the shower.
* BlackBestFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.
shower.



* TheyDo: Tom and Hannah.

to:

* TheyDo: Tom and Hannah.Hannah.
* TokenBlackFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.
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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle 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 [[TitleDrop maid of honor]]. Tom is determined to stop Hannah from getting married to Colin before it's too late.

Added: 24

Changed: 114

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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan), Hannah goes to Scotland for six weeks and falls in love with a Scotsman named Colin (Kevin McKidd), she

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan), Hannah goes to Scotland for six weeks and falls in love with a Scotsman named Colin (Kevin McKidd), she
[=McKidd=]), she announces to Tom that she and Colin are engaged and asks Tom to be her [[TitleDrop maid of honor]]. Tom
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!! Contains examples of:
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* HappilyMarried: Felix and his unseen wife, as implied by his dialogue. The other guys tease him about supposedly being a HenpeckedHusband, but he makes it clear that (a) he's not, and (b) even if he were, he's okay with that.
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* FriendshipAsCourtship: 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.


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* SerialSpouse: 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''.
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* SpeakNowOrForeverHoldYourPeace: Tom crashes into Colin and Hannah's wedding at precisely this point.

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* AbhorrentAdmirer: Tom Sr's secretary, who has a crush on Tom Jr.



* FatComicRelief: Poor Hilary, who seems to exist for no other reason--first with her insistence on a dress size that's too small, and her equal insistence that she'll be able to fit into it. Then her unhealthy liquid crash diet, during which she almost faints. Then actually fainting after she's squeezed into the dress and finally having it rip when she sits down.



* PsychoExGirlfriend: Melissa is a complete bitch to Tom throughout out most of the movie, having been one of his many discarded flings, even as Tom [[JerkassHasAPoint truthfully]] points out that he never misled her to think he wanted more.

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* PoppingButtons: Hilary's dress rips up the side when she sits down.
* PsychoExGirlfriend: Melissa is a complete bitch to Tom throughout out most of the movie, having been one of his many discarded flings, even as Tom [[JerkassHasAPoint truthfully]] points out that he never misled her to think he wanted more.more.
* RealityEnsues: 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.

Added: 506

Changed: 9

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* CoversAlwaysLie: Neither of Hannah's wedding dresses nor the bridesmaids dresses match the ones seen on the poster.



* HeroicBSOD: Tom, after Hannah rebuffs his declaration of love.
--> ''(whispers tearfully)'' "I can't be your maid of honor. I can't give you away."



* MayDecemberRomance: 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 one of Hannah's friends.

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* MayDecemberRomance: 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.


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* PsychoExGirlfriend: Melissa is a complete bitch to Tom throughout out most of the movie, having been one of his many discarded flings, even as Tom [[JerkassHasAPoint truthfully]] points out that he never misled her to think he wanted more.
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* MistakenForGay: Tom gets this a few times, as a man serving in a traditionally female role.

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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan)

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan)
Monaghan), Hannah goes to Scotland for six weeks and falls in love with a Scotsman named Colin (Kevin McKidd), she



* BiggusDickus: Implied about Colin, given Tom and his friends reaction to seeing him in the shower.

to:

* BigApplesauce
* BiggusDickus: Implied about Colin, given Tom and his friends friends' reaction to seeing him in the shower.



* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.

to:

* GenderFlip: To ''Film/MyBestFriendsWedding'', following an almost identical plot--person realizes they're in love with their opposite sex opposite-sex friend just as said friend announces their engagement and engages in RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.



* MayDecemberRomance: Tom Sr. has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting if off with one of Hannah's friends.
* OneTrueLove: Tom Sr. describes his Tom's mother as this.

to:

* MayDecemberRomance: Tom Sr. has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting if it off with one of Hannah's friends.
* MisterSandmanSequence: The opening sequence set in [[TheNineties 1998]] is abundant with pop-culture references such as people dressed as then-President Bill Clinton and Monica Lewinsky.
* OneTrueLove: Tom Sr. describes his Tom's mother as this.this.
* TheyDo: Tom and Hannah.

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* FourthDateMarriage: Hannah is engaged to Colin within six weeks of meeting him and planning to marry him within another two.



* GoldDigger: Tom's father's latest wife (and the others too, it's implied).

to:

* GoldDigger: Tom's father's Tom Sr.'s latest wife (and the others too, it's implied).



* MayDecemberRomance: Tom's father has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting if off with one of Hannah's friends.
* OneTrueLove: Tom's father describes his mother as this.

to:

* MayDecemberRomance: Tom's father Tom Sr. has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting if off with one of Hannah's friends.
* OneTrueLove: Tom's father Tom Sr. describes his Tom's mother as this.

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* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.

to:

* BestWoman: 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".
* BiggusDickus: Implied about Colin, given Tom and his friends reaction to seeing him in the shower.
* BlackBestFriend: Felix to Tom. When Tom and Hannah marry, he's serving as the best man.
* DisposableFiance: Poor Colin.
* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.wedding.
* GoldDigger: Tom's father's latest wife (and the others too, it's implied).
* LoveEpiphany: Tom has this about Hannah when she goes away for six weeks.
* MayDecemberRomance: Tom's father has a succession of short-lived marriages to much younger women, and at the film's conclusion, appears to be hitting if off with one of Hannah's friends.
* OneTrueLove: Tom's father describes his mother as this.
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Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan)

to:

Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan)Monaghan)

* GenderFlip: To ''Film/MyBestFriendsWedding'', 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 RelationshipSabotage while helping them plan their wedding. True to form, the girl is viewed as a villain and doesn't end up with the guy, while the guy is viewed as a hero and the film concludes with ''their'' wedding.
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[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/2nr5rxlrzuye6sskloxrxsogqu.jpg]]
Casanova Tom (Creator/PatrickDempsey) is a commitment-phobe who for the last 10 years has also in love with his best friend Hannah (Michelle Monaghan)

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