NOTE: This spoiler was sent in by LiliRoze who says... "One of the best romantic comedies I have seen in years.  The chemistry between the stars is excellent.  I do not watch Grey's Anatomy, but I now understand Patrick Dempsey's ‘McDreamy’-ness."

The movie opens at a college party in 1998, with the camera following a man dressed in a Bill Clinton mask.  He walks through the crowd and spots a girl dressed as Monica Lewinsky.  After some obvious Clinton oral sex references, "Bill" is invited by "Monica" to meet her in her dorm room.

Cut to "Bill," a little drunk, stumbling to the room and reaching up on the door ledge, searching for the spare key "Monica" had told him would be there.  Entering, he strips to the waist (leaving on the mask) and crawls into bed with "Monica," who proceeds to scream.  The woman in the bed turns out to be the roommate, who was supposed to be away for the evening.  After some pummeling from the roommate, "Bill" removes his mask and tries to explain the situation quickly -- how he had met "Monica," she had told him about the key, and had promised him her roommate would not be there for the evening, because the roommate is a boring bookworm who would be studying somewhere else.

Jump to the two of them in a common room, having a somewhat guarded, introductory conversation. The roommate quickly reveals herself to be intelligent and quick-thinking, and he introduces himself as Tom (Patrick Dempsey).  When she says her name is Hannah (Michelle Monaghan), he quickly mentions her name is a palindrome.  She admits that she knows him by reputation -- since he has slept with half the freshman on her floor.  Tom answers by saying that is only because half the floor happens to be female.

Hannah goes to the coffeepot and pours some coffee into a disposable paper cup.  She almost drops the cup when it quickly gets too hot to hold.  Tom mentions he has an idea to prevent that from happening, an invention he will call "the coffee collar."

Tom finds her attractive, and starts to turn on his charms.  They continue to chat easily, with Hannah mentioning she is an art major.  When Tom admits he is trying to see if she is attracted to him, she manages a quick dressing-down of his manners, his facial features, and his ego.  Tom is obviously impressed that she is so un-impressed by him, and there is a spark between them.

Fast forward 10 years.  Tom wakes up in bed with a pretty blonde who asks if she can see him again that night.  He immediately reminds her of one of his rules – “no back-to-backs,” meaning he never dates the same woman two days in a row.  Tom is quickly revealed over the next 10 minutes of the movie to have many dating rules, all carefully contrived to prevent a serious attachment forming between him and any of the many women he dates.  We also learn that he prides himself on his honesty.

Tom stops at a Starbucks and immediately focuses on a beautiful woman in line ahead of him.  Within moments she seems to sense his attraction.  Tom orders 2 coffees (one very simple coffee, one very specific and complicated).  The beautiful customer and a little old lady are both waiting for their coffees together with him. Tom leans over to the little old lady and very sweetly helps her slide a “coffee collar” (heavy paper ring) onto her cup to protect her hand from the heat.  He mentions to the older woman as he helps her, “I hear the guy who invented these things gets 10 cents for every one used.” In the meantime, with almost no encouragement from Tom, the beautiful customer helpfully hands Tom his own cup, and we later learn that she has written her name and phone number on his coffee collar.

Following Tom through the city of New York (fabulous use of scenery throughout the movie!) He enters a building where a woman is restoring a large painting (obvious sight gag reference to oral sex here).  Turning, we see the woman is Hannah, and Tom hands her the coffee.  She is pleased to see he ordered it just the complicated way she likes it.

They spend the day together, and we learn that throughout the years they have become very comfortable with each other.  Tom orders food for her in the restaurant, and Hannah plays a game of guessing the dessert Tom wants to order at an exclusive bakery.  Hannah teases Tom about the woman’s name and number on his coffee cup, and Tom mentions a rule about not being able to call her for 24 hours so he doesn’t appear eager.  Hannah mentions some of his other rules – coupled with a slightly sarcastic reference to the fact that at least Tom is always honest.  Tom agrees with her, obviously thinking it is his best quality, and it prevents the women he dates from being hurt or led astray by his advances.

While window-shopping at a fun thrift store filled with old clothes and some antique items, Tom tells Hannah that his father is getting married for the 6th time.  Hannah sympathizes with Tom over the fact that his father is a serial groom, and doesn’t seem to know how to just “date” a woman (in obvious contradiction to his son).  The wives are all young gold diggers, because Tom’s father turns out to be well off financially (Tom, of course, is very wealthy due to the coffee collar invention.  In fact, it is never revealed that he has any type of profession, and he seems to just enjoy his New York life.) 

Tom tries desperately to convince Hannah to attend his father’s wedding with him.  Hannah jokingly asks why he won’t take another woman (knowing full well why) and Tom reminds her of the “no weddings or family events” rule for women he dates.  Hannah is tired of being his “safe” date, but she agrees.

Jump to the wedding.  Tom’s father, Thomas Sr., (a fantastic-looking Sydney Pollack) is in his tux, standing in the church vestibule, negotiating business into a cell phone with his lawyer at his side.  We learn that the person he is doing business with on his wedding day is his young, hot bride Christie (played by an over-tanned Kelly Carlson of Nip/Tuck fame), who is outside in the limousine on her cell phone, with her attorney at her side.

Tom Sr. alternates between negotiating terms with the bride (more oral sex references here) and fawning over how much he loves his son Tom -- who is standing at his side trying to help his father see the ridiculousness of the entire wedding, and reminding him that wife number 6 will only lead to divorce number six. 

Finally, negotiations complete, Tom Sr. marries the girl, and the reception party begins with a loud rendition of Kanye West’s Gold Digger.  We see Hannah and Tom at the bar, enjoying the party, and more conversation regarding Tom Sr.’s penchant for marrying young women.  Suddenly, Tom panics when he sees a woman with a strange hairstyle walk into the reception.  He grabs Hannah and begs her to dance with him to hide him from the girl, who he reveals to be the “psycho blogger” – someone infatuated with him who follows his every move, and even wrote a two-page blog that very morning all about Tom’s face. 

Dancing easily together (when he is not dodging the blogger) Tom reminds Hannah of their first conversation the night they met – how Hannah had made fun of his facial features, whereas the blogger seems fascinated by them.  Hannah admits she was joking, that she really thought he was hot, and Tom admits he was only interested in bedding her that night.  Hannah then asks why he stopped trying, but they are interrupted by the psycho blogger (played quite well by Christine Barger).  Tom introduces Hannah as his girlfriend, which instantly upsets the blogger, and he playfully snuggles in to Hannah in an attempt to convince the blogger he is sincere, and the blogger leaves in a huff, promising to update her website. 

Hannah begins to feel quite comfortable in Tom’s arms, and her face shows it.  But just as quickly as she relaxes into him, Tom pulls away and drags her off the floor, because the blogger has left.  Next they are eating dessert, with Hannah eating a slice of white cake, and Tom with chocolate.  Tom reaches over and gets a forkful of her cake, saying he should start copying her, because she always orders the best desserts.  Hannah tells him not to, because she likes to share his chocolate, as she reaches over and takes a bite of his cake.

Later, they are strolling through the park together and he thanks her for being his date. Hannah tells Tom that she is taking a business trip to Scotland for 6 weeks.  Tom pretends to be devastated at the thought of not seeing her for 6 full Sundays (implying that the Dinner/Bakery/Thrift Shop day they shared is a regular Sunday routine for them).  Hannah laughs it off, saying he will be fine.

Sometime during these scenes, they come across a stranger’s dog while strolling the streets.  Tom approaches the dog and talks lovingly to it, petting and using a baby-talk voice, saying “I love you,” over and over.  Hannah asks why he can say it to a dog, and not a human.  Tom observes that Hannah has the opposite problem, that she says “love you” too casually.  (This dog petting ritual of Tom’s is repeated with different dogs throughout the film.)

The next day Tom joins his three best friends (Kadeem Hardison, Chris Messina & Richmond Arquette) for a regular basketball game at a gym.  They talk about women, with one guy being married, and others revealing various details about their love lives.  Tom says he has the best of both worlds –he can date a wide variety of women, and still have his steady friendship with Hannah.  One of the friends questions if that is fair to Hannah, and Tom doesn’t seem to realize the implication.

Jump to Hannah on the airplane to Scotland.  Before she shuts off her cell phone for takeoff, she looks wistfully at the photo on the screen – it is a close, smiling photo of her and Tom.  She sighs resolutely and shuts the phone.

Later, Tom calls Hannah when it is 3am her time.  He is so self-absorbed, he doesn’t seem to realize he has woken her, he confuses England and Scotland, and then wants to discuss mundane details like the filling of the pothole in front of his building, with no regard for the fact that she is exhausted.  She is not irritated with him, though.  She takes it in stride as part of his personality.  When the call ends, she says, “love you,” which seems to be normal for her.

The next time Tom’s phone rings, it is the middle of the night for him, and Hannah is in a pub, talking about her activities in Scotland.  They seem to have a hard time getting in sync with each other . . .

On another call, Hannah is in a small car, in the middle of a rainstorm, stuck on a muddy back road and surrounded by a herd of longhorn cattle.  She is complaining to Tom about her situation as her phone cuts in and out.  From a distance, you can see a man approaching on horseback.  The call then abruptly drops, and we see Tom flop back on his bed, yelling, “I hate Scotland!”

The next montage of scenes shows each of them trying to place calls to the other, with nothing more than static and frustration.  Tom gets increasingly desperate to hear from her, including diving for the phone at one point.  When he next meets his friends for b-ball, he casually admits he might possibly be developing feelings for Hannah.  The boys take this is stride, figuring he is just missing his routine with her.

Tom then tries spending time doing his “Hannah” things with various other women – he takes one to the thrift store, and she complains about everything in the store being old.  He takes another to the bakery, and she complains about the long lines, and doesn’t understand how to play the “guess what I’m going to order” game.  At the restaurant, the third woman orders all the fried food, which Tom doesn’t like.  Tom begins to realize there is no replacement for Hannah.

The next time he sees Kadeem Hardison’s character, he confesses that he is ready to begin dating Hannah, and he plans to tell her when she returns.  He makes sure to note that he doesn’t want it to be too serious, but they can give it a try.

Soon the call comes from Hannah that she is back in NY, an excited message saying she wants to meet him for dinner, and she has a lot to tell him.  Tom spends the evening trying on different shirts, trying to get the right look for her.  He stops and buys her just the right flowers, and goes happily to the restaurant.  When he sees her, both their faces light up.

In slow motion, Hannah jumps up to go to him, but then stops and turns, grabbing the arm of a tall, strawberry-blonde man.  She introduces him to Tom as Colin McMurray (Kevin McKidd), a man she met in Scotland, and she eagerly shows him a massive engagement ring.

Tom is so shocked he knocks into a waiter and has a disastrous pratfall, with flowers and food flying everywhere.  When Hannah tries to help him up, she asks about the flowers, and Tom denies they are his.

Over dinner, Hannah excitedly goes on and on about meeting Colin, revealing that he had rescued her on the muddy road that day, approaching her on horseback.  They met and spent all of the next 4 weeks together.  Colin’s family is quite wealthy and owns a whisky distillery.  She then reveals they are getting married in two weeks at his family’s castle in Scotland, and since Tom is her best friend, he is the obvious choice for her maid of honor.  Tom stands up in fake enthusiasm and smacks into the same waiter, who almost starts a fight with Tom over his clumsiness.

The next day Tom meets Hannah for lunch, where he learns who will be the other bridesmaids.  Stephanie (Whitney Cummings) a friend of Hannah’s who Tom really likes, Hilary (Emily Nelson), who Tom does not know, and Melissa (Busy Phillips), who Tom is desperate to avoid, because he used to date her and he broke her heart, because she couldn’t get used to “the rules.”  Hannah also mentions that Melissa will especially hate Tom now, because Melissa has wanted to be Hannah’s Maid of Honor since they were kids.

During lunch, Hannah gets a phone call from Colin and excuses herself from the table.  Stephanie senses the tension between Tom and Melissa and tries to get everyone to remember that they are there to make Hannah’s wedding special.  They all agree, and begin to explain to Tom the various details and responsibilities he will need to remember about being a “MOH,” and Tom seems undaunted by the tasks.

The next day Hannah asks Tom to spend the day with Colin, playing b-ball with his friends.  Tom reluctantly agrees.  When they arrive at the gym, the friends are taken aback that Tom would bring “competition” into their game, and Tom tells them not to worry – his plan is to emasculate Colin by beating him senseless in basketball.  When he asks Colin if he has ever played, Colin admits that “netball” is mostly a women’s sport in Scotland.

Tom and friends pull out all the stops in a 2-on-2 game, and Colin is not faring well.  The men tease him about this not being a “girl’s game,” and Tom is enjoying that he is proving himself to be a better man.  Suddenly, Colin gets his hands on the ball near the net, and manages a killer slam-dunk.  When all the men stop and stare, Colin apologizes, thinking it was an illegal move.  When the friend on Colin’s team gets excited, Colin asks why they all don’t do it . . . and they sheepishly admit that they would if they could.  Colin proceeds to then dominate the game.

Tom later sulks to the locker room, headed for the shower.  He is stopped cold by the sight of Colin in the shower, and each friend in turn stops and stares, as it is implied Colin is a very (cough) “manly” man.  Tom becomes more disappointed over how perfect Colin seems to be.

Colin must return to Scotland to get permission for the marriage from a special council, so Hannah asks Tom to accompany her to the church to meet the minister that will fly with them to Scotland to perform the ceremony.  When Tom asks why Colin needs permission to marry her, Hannah admits that Colin is actually royalty – a Duke.  Tom waits for Hannah to enter the church before screaming in frustration over Colin’s further perfection.

Upon meeting the minister, Tom decides on a different tactic – playing up the fact that Hannah and Colin don’t have a history together, and have only known each other a very short time.  When the minister presses Hannah for details of their relationship so he can work them into the ceremony, Hannah is tongue-tied.  Sensing an opportunity, Tom jumps up and begins to speak on the importance of really knowing someone, and as he speaks, he looks around the room and finds an art book, and remembers (in great detail) a time many years ago when Hannah had spoken of a specific artist, and how that artist had painted a beautiful portrait of a particular woman, and that Hannah had commented about how that painting represented love to her – how she would wish that someone would one day love her that much -- as that woman had been represented in that painting.  The minister is impressed by this and scribbles it down.  Hannah is surprised that Tom remembers the conversation so well.

Tom plans the bridal shower, and wants to impress Hannah that he has matured (thus ready for a mature relationship), and can throw a wonderful, appropriate, sophisticated shower for her.  He invites the boys over for poker and announces they can’t play until all the gift baskets are made and the apartment decorated (Tom is obviously quite well-to-do – the apartment is very large and very impressive). 

At the shower, Hannah is very impressed.  Tom throws a few digs in at the culture clash of marrying a Scot – playing loud bagpipe music, serving haggis-type hors d'oeuvre, and pointing out various other mismatches in their tastes.  Things seem to be going well in general, until the entertainment arrives.  Instead of being the “psychic” Melissa had promised would be great fun at the shower, she had tricked Tom into getting a woman who turns out to be a sex-aid sales person.  Tom can’t believe this blow to his credibility, and Hannah is furious, thinking he would do such an immature thing at her shower.  Melissa is happy to think Tom will have to step down and she will get to be the MOH.

Tom gathers his friends together and they come up with a scheme to make Tom the perfect MOH, and Tom rents videos and crams all night over magazines and etiquette books.  The next time he and Hannah go shopping, Hannah is very impressed by his sudden change – he is educated, suave, and secure as he suggests different china patterns and linens.  Hannah then playfully takes him to shop for lingerie, and Tom cannot bear the thought of Colin seeing her in the sexy outfit, and he becomes flustered and frustrated by the sexual tension.

Back out on the street, Hannah again praises him on how much help he was, and she feels she is seeing a side of him she had not seen before . . . then she tells him what she has been putting off – that today is her last day in New York, and she will be living in Scotland after the wedding.  He puts her in a cab and says goodbye, stunned.

Devastated, Tom walks the streets.  He sees a beautiful woman walking two dogs, and he doesn’t even try to hit on her, but he does pet her dogs, getting disgusted when he finds out one is a Scottie.  He meets his father, saying he is ready to give up Hannah.  He can’t win.  Tom Sr.  tells Tom he is getting another divorce already, and then admits to Tom that he used to play the field like Tom did, and never realized until it was too late that Tom’s mother (his first wife) was the perfect woman for him. Tom is surprised by this news.  He  encourages Tom to not give up on Hannah (there is a great joke here about “Bogy” (Humphrey Bogart) that not a single person under age 25 laughed at in the theater.)

Encouraged, he makes a sophisticated game plan with his friends, who by now are encouraging him with the rally cry to “steal the bride!”  He heads to Scotland a few days before the wedding with the plan that no matter what it takes, he will steal her away.

Upon arrival of all the bridesmaids in Scotland (the scenery alone for the rest of the picture is worth seeing the movie on the big screen – many will recognize landmarks from the movie Highlander), Hannah is very excited to meet everyone, especially Tom.  Tom spends the day trying to get Hannah alone to talk to her.  He learns they will be playing some traditional Highland games, where the groom has to prove he is worthy of the bride by winning.  Tom sets out to beat Colin, and after a neck-and-neck race to the very last, Colin finally pulls out and wins.

At dinner that night, Hannah learns that Colin is a hunter (she is against it) and that he practices the bagpipes every night (she winces), and when Hannah tries to reach for a bite of Colin’s chocolate cake, he stops her.  Some comedic cultural clashes occur between the Americans and the Scots at the table.

That night, Hannah’s mom Joan comes to her room to give her a photo album she can keep with her in Scotland, and they reminisce over old photos, including newer ones of Hannah and Tom together.  Hannah admits to missing her late father, and Joan (played by a beautiful Karen Quinlin) reveals to Hannah that her father had always hoped Hannah would marry Tom.  Joan then (semi-reluctantly) expresses her happiness for Hannah’s marriage, and leaves the room, with Hannah in deep thought.

The next day, Hannah is getting a practice hairstyle for the wedding – a hideous updo that the girls convince Tom to lie about, because this is for Hannah’s big day and they should be supportive.  Colin’s mom also insists on draping a heavy wool tartan sash across the front of Hannah’s dress, which clearly makes Hannah uncomfortable.

Finally managing to get her alone for a walk in the evening, Tom can’t get a word in as Hannah goes on and on about the vows, how she can’t decide what to say.  Tom, overcome with feelings for her, says something to the effect of, “I want to spend the rest of my life with you.  You make me happier than anyone ever has.” He is obviously speaking from his heart directly to her, and not reciting vows, but Hannah thinks the opposite, and laughs them off as “too generic and obvious.”

Tom digs deeper and grabs her hands, facing her, and says something like, “I can’t live without you.  You are my best friend, the best friend I have ever had.”  He is looking at her so intensely that she seems to wonder if he is talking about the vows.  The moment is interrupted by the bridesmaids coming to meet them to announce another Scottish tradition – they will go to the local pub, where Hannah will carry a pot full of salt, and they will sell her kisses to the local men for donations dropped into the pot.

Tom is upset at the interruption, and goes to the pub, where Hannah, shy at first, is met by many burly Scotsmen who sweetly kiss her full on the mouth in exchange for dropping money in the pot.  When the third man announces to the whole bar that she has “the breath of an angel,” all the men cheer and Hannah begins to relax and enjoy the tradition as the money begins to pile up in the pot.

When she finally sees Tom in the back of the room, they greet each other with a casual kiss, as usual.  Tom then apologizes for only having a few coins to put in the pot.  He drops them in, then proceeds to kiss her on the lips.  This turns into a second and third kiss, then finally Hannah drops the pot and they begin to passionately kiss.  No one in the bar seems to notice (the ‘maids are getting shots at the bar) except for Joan, the mom, who simply swigs her drink and looks away.  Once they finally break the kiss, both are surprised and flustered, and drop to their knees to begin picking up the salt and coins spilled when Hannah dropped the bowl.  They part in silence.

That night, Hannah and Tom pace in their respective rooms in the castle, thinking of each other.  Finally, Hannah, still in her pajamas, heads for Tom’s room.  Tom, in just his boxers, is still pacing when there is a knock at the door.  When he opens it, it is a very drunk Michelle, who removes her robe to reveal sexy lingerie, and throws herself at him.  When Tom reminds her that she hates him, she doesn’t care and proceeds to pin him on the bed.

Tom tries desperately to avoid her advances, trying to also keep her loud drunk blabbering quiet.  Hannah approaches the door and witnesses Michelle on top of Tom, both scantily clad, and runs back to her room.  Tom sees her and throws Michelle off, running after Hannah.

Hannah makes it to her room and slams the heavy wooden door and locks it.  Tom presses himself against the door, desperate to talk to her.  Hannah refuses.  When Tom asks why she came to his room, she admits it was to talk about the kiss. (She doesn’t seem to need an explanation about Michelle, which may be because she “knows” Tom and accepts who he is, or doesn’t care at this point?  It’s not clear.)  In probably the most touching scene in the film, the camera switches back and forth between them on opposite sides of the door, each pressed against it, as Tom begs her to “let me in, please let me in,” and Hannah refusing.  She finally tells him that she can’t wait for him anymore – that Colin loves her, and that is what she wants, for a man to love her as Colin does (it becomes clear here that all this time it didn’t matter to her if she doesn’t love Colin as much as she could love Tom, or that she and Colin have little in common.  She simply wants to marry a man who she knows loves her).  She is sobbing.

Dejected, Tom walks away and says he has to leave.  He cannot bear to “give her away” tomorrow at the ceremony.

The next day Tom gets in a car to go, and Colin and Hannah watch from the window.  Colin tells her he is sorry that the two of them got in a fight, and Hannah calmly replies that Tom is her best friend, and he will get over it.

As Tom rides away from the castle, he seems ready to live his life without her.  When the driver has to stop for a herd of sheep crossing the road, Tom sees a dog sitting on the side of the road.  He sees it as a sign – it is the same dog he first saw upon arriving in Scotland, a dog who (of course) received his “love you” ritual greeting.  Upon seeing the dog, he steps out of the car and approaches the dog, who is harpy to see him.  He suddenly realizes something, and tells the driver to go back.  In the meantime, Hannah is shown leaving for the church, big silly hair and tartan too.

Heading to the church, Hannah’s car drives on to a ferry to cross a large lake.  A few minutes later, Tom’s car just misses it.  Desperate for a way to get to the church, he learns it will take too long to drive on the road around it, and he spots a man with a horse on a trailer.  He jumps atop the horse, and offers the man “3 cents for every coffee collar sold – do you know how much money that is?” and the man agrees, not having any idea what a coffee collar is.

Quickly getting directions to keep to the shoreline, Tom races off on the horse, and as he approaches the church, they show the ceremony in progress, with the minister telling the story about the artist and the painting, and Hannah looks wistful at the memory.  Tom tries to slow the horse as they approach the church doors, but instead it stops galloping abruptly and throws him head first into the heavy oak door.  Bursting through, he lands face down on the stone floor.

Hannah sees him and leaves Colin at the altar, running down the aisle.  When she gets to him he is unresponsive as she kneels down and strokes his hair, saying his name again and again.   Finally, he comes around, and manages to stand and he says he will be truthful with her, and proceeds to tell her the hairdo is terrible, and the tartan sash is ugly, and he then mentions how the night they first met – how he had crawled into bed with the wrong girl, who actually ended up being the “right” girl . . . and that although he prides himself on always being totally honest, he had been lying to himself about her all along.  He finally says “I love you.” She says something similar, and they embrace and passionately kiss.

When they part, two of Colin’s biggest kilt-wearing friends block the door, and Tom realizes he is in trouble.  Colin comes to Hannah, and she gives him back the ring, saying gently that she is sorry – that he is the perfect man, just not perfect for her.  Colin is upset, but understanding.  He approaches Tom and shakes hands.  One of Colin’s relatives says something in an unintelligible  thick brogue accent, and Tom asks for a translation.  Colin says that the relative thinks Colin should punch Tom, which he then does.

The next scene shows the same minister, back in New York, presiding over a beautiful outdoor ceremony for Tom and Hannah.  Michelle is finally the MOH.  That night Hannah is in bed, pulling back the covers for Tom as he approaches.  Before jumping in beside her, he turns on the light, saying he wants to make sure it’s really the right girl.  He crawls in beside her as they kiss.