NOTE: This spoiler was sent in by Caleb who confesses... "It has been a few weeks so I definitely won't be spot on, but the movie was a total flop so it isn't like anyone will know anyways."
The film starts with artistic opening credits depicting things that are lucky and things that are unlucky. A four-leaf clover is labled as being "lucky" whereas a black cat is deemed "unlucky". After going through a series of items including right-side up horseshoes (lucky), upside-down horseshoes (unlucky), the number seven (lucky), and the number thirteen (unlucky), and so on, the film opens with an introductory shot of Ashley Albright (Lindsay Lohan) who is tagged as "lucky". We meet Ashley as she steps out of her apartment building in New York City. She is dressed very chic despite the fact that it is raining heavily. When the doorman comments on her lack of an umbrella, Ashley says "do you really think I need one?" Suddenly, the rain stops, the clouds part, and the sun comes out to provide beautiful weather. Ashley smiles and gets into a cab. She gives the driver her destination and asks him to get there in four minutes. The driver makes a comment along the lines of "yeah right, in your dreams". As he gets going, however, he is amazed to find that his path is devoid of traffic and every stoplight is green. Ashley smiles smugly and calls a friend on her cell phone, saying that she's running early and will be able to pick up some breakfast and coffee.
As the cab goes down the street, it sends a jet of water right onto Jake Hardin (Chris Pine) who gets the label of "unlucky". On this particular occasion, however, Jake has caught sight of a special opportunity as he spots recording mogul Damon Phillips (Faizon Love) walking a dog through the park. Jake digs out a CD from his backpack and goes after Phillips, shouting and waving to attract attention. Unfortunately, Jake trips over his own feet and snaps his belt, which results in his pants dropping around his ankles. Jake pulls them up and awkwardly continues pursuit. Phillips has been temporarily detained because his dog had left a brown present in the middle of the park walk. The park policeman has his eye on Phillips, so the rich man pulls out a five-dollar bill, picks up the dog dropping with it, tosses it into the trash, and continues on his way. Jake runs up, desperate to catch up to Phillips, but not quite desperate enough to pass up a five-dollar bill in the trash that he suddenly glimpses. Unfortunately, it's a poo dollar and Jake gets feces all over his hands. Grossed out, Jake runs to a nearby pond to wash his hands. As he gets back up, he knocks over a female jogger and falls on top of her. At the same time, his pants fall down. Seeing her attacker in his boxers freaks the woman out, so she starts screaming rape, attracting the attention of everyone in the vicinity including the policeman, who gives chase. Jake heaves himself up and races after Phillips, but is tackled to the ground by the policeman. Phillips is getting into his limo at this point, so frenzied Jake takes the CD and throws it. Unluckily, the CD misses the door and goes under the hind wheel instead; it is crushed as the limo heads off. Defeated, Jake requests that the policeman take him to a certain precinct that is a bit nicer to him than others.
Back to Ashley arriving at her workplace, breakfast in hand. She just misses getting on an extremely crowded elevator, which seems unlucky until a split second later, we hear a ding and a completely empty one opens up next to her. Ashley gets in and holds the door for David Pennington (Chris Carmack), the son of some rich guy who owns a sports team. By the time she gets to her floor, Ashley has a date with David. As she exits the car, we see that the crowded one that she missed earlier has reached the same floor but is malfunctioning, with the doors opening two inches and then slamming shut on the unlucky people trapped inside. Ashley walks into her company and greets her best friends Maggie (Samaire Armstrong) and Dana (Bree Turner). All three girls are interns at the same PR firm. Ashley tells her friends about her future date with the handsome son of a multi-millionaire, maybe even billionaire, and they all squeal over her luck. Ashley then grabs a typewriter iand goes to take notes at a meeting, but when she arrives at the conference room, it's empty. It turns out that the meeting is for the firm's most important client, record mogul Damon Phillips, who arrives and waits impatiently for the presentation to begin. Unfortunately, Ashley's boss Peggy Braden (Missi Pyle) is still stuck on the elevator with malfunctioning doors. Phillips is enraged at the tardiness and gets up to leave; thinking fast, Ashley decides to try and save the account by coming up with a pitch herself.
Cut to the elevator doors being pried open as Ms. Braden rushes out. She enters the firm just in time to bump into Phillips, who is leaving. Ms. Braden frantically tries to explain about the elevator, but Phillips informs her that Ashley made a pitch ahd he loved it. Phillips departs, and Ashley explains that in order to save the client, she improvised a pitch that involved a fancy masquerade ball. Impressed, Ms. Braden puts Ashley in charge of the big party and also promotes her, giving her an office.
We return to Jake, who has been released from the police station and is back at his shabby apartment. His Aunt Martha and young cousin Katy (Makenzie Vega) apparently live in the apartment unit across the hall. We find out that bad luck runs in the family as evidenced by a toy car glued to Katy's face. Jake dislodges the toy as Katy relates the tale of that day's misfortunes. Then he heads off to his job as a custodian at a nearby bowling alley. Jake is also the manager of a British band called McFly (an actual band playing themselves) that he is very dedicated to, as we saw earlier when he tried to introduce the band demo to Phillips. Jake has managed to get some record executives to come to the bowling alley and check out the band, so everyone is excited. Things are going great until Jake leans too far back in his seat, falls over, and kicks off the sound equipment. Sparks fly as Jake tries to fix the damage, but the record executives leave. The band is thoroughly disheartened, and inform Jake that they want to return home to England since they haven't had any luck in The States. Jake convinces McFly to give him one more week to make something happen.
Meanwhile, Ashley has nothing to wear for her date with David Pennington, despite having a large walk-in closet full of clothes and shoes in her beautiful apartment. Dana and Maggie are commenting on how lucky Ashley is when the doorbell rings; it's Ashley's charming neighbor Antonio who received some misdelivered dry-cleaning. Ashley thanks him, and then on a second thought invites Antonio to the masquerade ball as a date for Ms. Braden. Antonio agrees, mentioning something about his "fees" which Ashley laughs off as a joke. It also turns out that the misdelivered dry-cleaning is a Dolce & Gabbana dress that doesn't belong to Ashley, but Sarah Jessica Parker. Ashley decides that she'll return the dress after she wears it on her date with David. She laughs gleefully as Dana and Maggie once again exclaim about the luck. Ashley tells her friends that she doesn't believe in luck, so Dana challenges Ashley to take a luck test. They purchase a scratcher but Ashley declares that "it isn't fair because I'm really good at these". Maggie laughs at the idea of being good at lottery scratchers, but Ashley immediately wins twenty-five bucks. Then she keeps winning on subsequent scratchers. Dana and Maggie are convinced that Ashley has some sort of magic luck, but Ashley still isn't buying it.
Later, Ashley goes on her date with the young heir; it involves private helicopters, a beautiful restaurant, and perfection. There is also a scene where Ashley leads her boss through the big empty hall she has rented for the party, describing her vision and what she has planned. Ms. Braden is impressed but also a bit curt, as if to remind Ashley that this is a big event that better not go wrong.
Finally we get to the night of the masquerade ball. All of the decorations are perfect and Phillips is aggressively promoting his record label. Ms. Braden is totally charmed by Antonio and happily congratulates Ashley on a job well done. At the same time we see desperate Jake trying to get into the party but to no avail. He dejectedly walks away, but happens upon a side entrance where an usher mistakes him for a dancer. Jake grabs the opportunity and poses as the dancer in order to gain entrance to the ball. He changes into the performance outfit and heads onstage with the other dancers. As the number starts, the dancers around Jake try to get him to follow the choreography, which he awkwardly attempts all the while trying to get off the stage. He finally manages to break away and heads to the VIP area to see Phillips; unfortunately, he is stopped by Dana who asks him why he's abandoning the dance routine. At that moment, Ashley walks up and Jake says that he wanted to ask Ashley for a dance. Ashley chides Jake for "sucking up to the boss" but then, with a little help from Maggie and Dana, convinces herself that she deserves a treat. Ashley and Jake dance together and eventually kiss, which magically transfers all of Ashley's luck to Jake. As the kiss ends, Jake sees Phillips heading outside, and rushes after the record producer. As they both get outside, a driver loses control of his car, which careens toward the crowd. Jake shoves Phillips out of the way and is hit by the vehicle. Miraculously, he isn't hurt at all. Phillips is amazed at Jake for having saved his life; he offers "if there's anything I can do, just name it". Jake tells Phillips about McFly, and Phillips tells Jake to bring the band to his studio the next day. Jake is elated for his luck has changed.
In the meantime, Ashley's luck has also changed as the heel of her shoe breaks, causing her to trip and rip her dress. Mortified, Ashley starts to leave the crowded dance floor but is stopped by the police, who arrest her, Ms. Braden, and Antonio. Phillips returns from his near-death experience outside just in time to witness his PR team being led off in handcuffs. It turns out that Antonio is a male prostitute, unbeknownst to Ashley. Unfotunately, since she was the one who set the guy up with Ms. Braden, all three of them get jailed for solicitation. Ashley can't believe her bad luck, and starts thinking that she is the victim of a candid camera prank type show. This is too much for Ms. Braden, who makes bail and leaves, telling Ashley that she is fired and will never work in public relations again. Miserable and pissed, Ashley gives attitude to another jailmate and earns a punch in the face.
The next day, Ashley leaves the police station with a black eye; too-large, shabby borrowed clothes; and running, smeared make-up. On the way home she gets splashed by cars driving through puddles, pooped on by birds, and is unable to hail a taxi. Things get worse at her apartment, however, because the place is completely flooded and has been declared unlivable. Ashley asks if she can at least get some clothes, but the crew member laughs, "hey everybody, she wants to retrieve her clothes" as all the other workers share a chuckle. The crew member tells Ashley that he was able to save some stuff, and hands her a sad little cardboard box full of miscellaneous items. A stunned Ashley gets back on the elevator; as the doors close the bottom of the box gives out, spilling the pathetic remainder of her possessions all over.
Ashley moves in with Maggie and Dana; she thanks her friends and promises not to overstay her welcome. Although the apartment has only one modest room, Maggie and Dana have managed to make the place home. Ashley is touched by her friends' positivity and optimism, but the deep moment is ruined when she finds out that she has to sleep on a recliner.
Not everything in Ashley's life had gone to hell, however, as rich, handsome David Pennington was still calling her for a second date. Ashley is a bit hesitant because of the wave - or rather, tsunami - of bad luck that she'd been recently crushed under. Dana and Maggie remind Ashley that she isn't supposed to believe in luck; Ashley is about to respond when her hair gets caught in the blow-dryer. She rips it off, but the resulting jolt causes her to smash the bathroom mirror. Ashley barely has time to lament her newly accumulated seven-years bad luck when the blow-dryer catches on fire. Like an idiot, Ashley throws the machine into the bathtub and turns on the water. This results in the entire apartment building getting shorted out and a lot of angry neighbors.
At the other end of the luck spectrum, McFly is playing for Phillips as his studio. Jake nervously watches, and after a few minutes Phillips gets up and leaves. Frantic, Jake pleads for Phillips to give the band a chance, saying that he believed in McFly because they were talented and made good music. Phillips reveals that he is actually going to sign the band, saying "I wouldn't give them ten minutes of my time if I wasn't going to sign them". He then instructs an assistant to move Jake and the band into one of the studio's penthouses. The assistant flirtaciously congratulates Jake.
At some point, Ashley thinks back to when her life stopped being perfect and realizes that everything changed when she kissed Jake. "That dancer stole my luck from me," she angrily declares. Unfortunately, she doesn't know who the guy is or even what he looks like since they were all wearing masks at the masquerade ball. Ashley reasons that if the mystery man stole her luck with a kiss, then she can take it back with another one. Maggie and Dana get the pictures of all twenty male dancers hired for the ball, and we then get a montage of the girls hunting down each of the guys and having Ashley french them. Maggie runs up to a guy jogging in the park, holds up a photo to compare, and nods as Ashley attacks the guy from the other side with a kiss. Dana holds up a picture next to the face of a performance artist on the street and gives Ashley a thumbs up at which point she grabs his face and locks lips. The girls crash a dance class and Ashley swaps spit with a bewildered student. Dana is standing by and notices that the dance instructor is actually one of the twenty as well, and Ashley pounces on the guy. After each kiss Ashley attempts to win on a scratcher, but fails every time. Finally, the girls are feeling frustrated after having found nineteen of the dancers without any luck. Ashley is livid at guy number twenty, who is the only one left and thus, sure to be the luck thief.
Meanwhile, David Pennington continues calling Ashley and asking for dates. Maggie and Dana take this as a sign that Ashley's luck is still good, and convince her to go on the date. Determined to defeat her unlucky streak, Ashley agrees. Right before the date, however, she drops a contact in the kitty litter box, fishes it out, and puts it back in her eye to the disgust of her friends. Thus, Ashley's eye gets injured and she arrives on the date with an eyepatch. David has invited her to an exclusive museum exhibition, and the art seems to consist of heaps of wet mud. A severe looking woman approaches David as Ashley comments on how the mud heaps are grotesque and disgusting. She also compares the works to fecal matter and questions "who would call this 'art'?" An embarassed David clears his throat and introduces the severe looking woman as his mother, and the artist. Ashley is mortified, but snaps out of it when she spots the twentieth dancer serving drinks. Jumping on the opportunity to get her luck back, Ashley excuses herself and makes a beeline for the final guy that she had to kiss. It turns out, however, that all of the waiters at the exhibition were actually performers. The performance starts with all the lights dimming. A voice comes on and talks about mud and the origin of humans as one by one the waiters strip off their uniforms to reveal caveman outfits as spotlights focus on each of them. Oblivious to all this, Ashley is trying to take advantage of the sudden darkness in order to kiss the dancer, who is trying to fight her off because he has to participate in the act. Ashley manages to lock lips just as the spotlight reveals the two of them. Everyone gasps, and Ashley tries to recover by saying that the guy needed CPR. She continues frenching him and then makes a big act of pounding on his chest; the guy is flailing around this entire time, clearly conscious and not in need of any medical attention. Finally satisfied that she has her luck back, Ashley gets up and declares the dancer to be okay. She confidently struts back toward a flabbergasted David, but trips over her own dress and falls right into a big mud pile, which sadly, is also a piece of art worth thousands. Ashley is thrown back in jail, shouting "this is ridiculous, it was just mud!" She then turns, only to come face to face with the same woman she gave attitude to last time. Ashley tries to save herself with a quick, "oh you must have met my twin sister; she's the bitch, I'm the nice one". Unfortunately, it doesn't work and the tough jailbird gets to give Ashley a second black eye.
The next morning, a crestfallen and filthy Ashley is walking down the street. She enters a restaurant and asks for a glass of water, but the waiter tells her to get out because they only serve customers. Jake happens to be eating breakfast a few tables down and looks over to see what the commotion is about. Ashley snaps and starts shouting at the people eating in the restaurant, telling them to stop pitying her and that she wasn't always so pathetic. Terrified, a man offers her his half-eaten meal. Ashley is disgusted and shouts at the man for his insulting offer, but then hunger defeats pride and Ashley decides to take a few pieces of bacon as the other customers gasp in disgust and disbelief. While reaching for the food, Ashley accidentally spills some salt. Having enough bad luck heaped on her already, she follows the old adage and throws some salt over her shoulder... right into the eyes of a waiter who falls and causes the breaking of many plates. At this point Jake stuffs the rest of his food into a napkin, grabs Ashley, and hauls butt out of there. Ashley thanks him, and they walk to a nearby park where she sits on a bench and eats the food that Jake gives her. Ashley asks Jake why he's being so nice, and he tells her that he knows what it's like to be SOL (shit outta luck). Offended, Ashley asks "what makes you think I'm SOL?" Jake motions for Ashley to turn around; she does and finds a "wet paint" sign on the bench and paint stripes on her clothes. Ashley groans, and a sympathetic Jake tells her that he knows of a job opening. After being reassured several times that Jake wasn't promoting his church, Ashley agrees to his help.
The next scene is at the bowling alley, where Jake has an argument with his former boss while Ashley stands by. The argument ends, and Ashley assumes that she didn't get the job. Jake informs her that she did get the job, but not the one Jake wanted her to have. Jake was trying to get her a job as a waitress, but instead Ashley gets Jake's old custodial job. We get a musical sequence of her at the bowling alley dropping trays of glasses, knocking over people, cleaning out the disgusting bathroom, wrestling with the floor waxer, and getting smacked by the pinsetter. She has a hard time adjusting to her new bad luck, but doesn't give up.
A while later, Jake comes to check on her, and as an experienced former bad luck guru he watches Ashley going about the bowling alley attracting accidents. As Ashley climbs up a ladder to change a fluorescent bulb, Jake munches on fries and gives commentary. "Hmm, she should have placed the bulb on top of the ladder first because now she'll be juggling" Jake observes as Ashley precariously climbs the ladder and nearly drops the bulb. "Oh, she should have turned off the power because now she's going to be electrocuted" Jake predicts as Ashley does indeed get electrocuted and falls back off the ladder. Fortunately, Jake is there to catch her. He also gives her his Be Prepared Backpack, which has a gamut of just-in-case items from Bactine to extra socks. Ashley is touched.
One day, Ashley delivers food to Jake at the studio, knocking over several things as she enters. After making some great saves, Jake invites her to stay and hear McFly play. They hang out and bond, and Jake speaks affectionately about his cousin Katy. Ashley assumes Katy is Jake's girlfriend and becomes jealous. Later on, it's raining heavily as Ashley gets off work. She starts walking home but her umbrella flips. At that moment, Jake pulls up in a car and offers Ashley a ride; she tosses her umbrella and accepts. As the car pulls away, lightning strikes Ashley's trashed umbrella. They end up at Jake's luxurious penthouse, where Jake gives Ashley some dry clothes so that she can wash her rainsoaked ones. Unfortunately, Ashley spills half a box of detergent in the machine, which ends up spewing foam and bubbles all over the laundry room as the klutz tries desperately to stop the process and only makes things worse. Finally, Jake comes in and shuts everything off; the two of the laugh and then have a tender moment. They are just about to kiss when Katy interrupts. Ashley is delighted to find out that Katy is Jake's kid cousin, not girlfriend. Katy relates another tale of her bad luck. She recognizes Ashley as another sufferer and says that "Jake calls us 'special'".
Over the next few weeks, Ashley and Jake grow closer as McFly's first single soars on the music charts. Phillips has been pressuring McFly to come up with a second hit, and he tells the band that they are going to perform their first preview concert at the huge Hard Rock Concert Hall. Jake is jubilated but also nervous, wondering if McFly would be able to fill such a large venue. He is also anxious because the band is having trouble coming up with a good new song. He tells Ashley about his stress and she decides to help. It turns out that Maggie is a songwriter. Maggie comes to the studio and performs one of her pieces on the guitar. The band loves it, and after a few tweaks and an increase in tempo, they decide that it's a perfect second single. Maggie is thrilled, and Phillips walks in towards the end of the session and likes what he hears. He commends Jake for doing such a great job and also informs the group that they have sold out the Hard Rock. After some more happiness, Phillips mentions that Jake has been having unbelievable luck since the masquerade ball. Ashley snaps to attention at this tidbit and figures out that Jake was the one who took her luck. Dana tells Ashley to go take it back, which she does with a big kiss. Jake is momentarily stunned, but then goes in for another kiss which Ashley stops. She leaves, smiling because she has her luck back: "hello easy fabulous life".
Right outside the studio doors, Ashley decides to test herself by hailing a cab. She raises her arm and three taxis screech to a halt in the street. Ashley blows them all off and starts walking down the block, where she bumps into the PR-boss-formerly-known-Braden, who is now married to Antonio. Ashley congratulates the two of them and gets an apology and a new job offer from her old boss. Ashley gleefully continues on her way.
When Ashley arrives back at Maggie and Dana's apartment that night, she is eager to tell them about her great day but finds her friends depressed. It turns out that Phillips requires all his new bands to play only songs that they write themselves, so McFly had to drop Maggie's song. Maggie is still optimistic despite the disappointment, and Ashley becomes pensive. The next night, Dana and Maggie decide to go to McFly's concert anyways because they have VIP tickets. Ashley is headed for a meeting at her new job. She has a change of heart in the cab, however, and heads for the concert instead.
\Meanwhile, at the concert, Jake's bad luck has come into play. Two of the band members are throwing up minutes before opening. Then the drummer drops his stick under the stage and goes down to retrieve it. Jake almost trips over the trapdoor and closes it because "someone could get seriously injured". Unfortunately, this also locks the drummer underneath. Ashley, Dana, and Maggie arrive backstage to greet Jake, who they find frantic because the concert is supposed to have started, but nobody can find the drummer. Phillips arrives and demands to know what's going on, angrily shouting that "the crowd wants to see the band, and I'm not going to be the one to tell them that they aren't getting what they want. You will". At this point, Ashley steps in and saves Jake with a kiss. The transfer of luck causes the drummer to activate a lift that carries him onstage as the crowd cheers. Ashley asks Jake to have the band play Maggie's song, and Jake agrees. The crowd loves it and Maggie is thrilled. Phillips isn't mad because he respects Jake for being "gutsy".
The concert is a huge success and at the after-party Ashley knows that she is in love with Jake. She wants him to keep the good luck, so she decides to leave and go stay with her parents for a while. Maggie urges Ashley to confess her feelings to Jake, but Ashley has made her decision to leave, saying "all of my feelings lead to me wanting to kiss him, and I can't do that". She says good-bye to Maggie and heads to Grand Central Station.
At the station, Ashley approaches the ticket booth and all trains immediately achieve a "delayed" status. Ashley rolls her eyes expectantly, but then she is surprised by Jake who had followed her. Jake tells Ashley that he figured out the luck thing and asks her not to leave, but Ashley tells Jake to go away because if he kisses her than he'll lose the luck. Jake admits that "yes, I won't have the luck, but I'll have you". Ashley has an "oh Jake!" *SWOON* moment and the two kiss. Then they kiss again and again and again. Then they take a two second breather and continue going at it. As they are macking, the status of the trains flip back and forth from "delayed" to "on time" and end up as a blur of spinning letters once Ashley and Jake really get into it. When they finally part lips, Katy is standing behind them with her hands on her hips. She starts yapping at Jake that "it isn't nice to leave a kid alone in a limo while you go and make out. I came to see if everything was all right but I popped a shoelace and swallowed my gum". Ashley and Jake look at each other mischievously, and then each of them kisses Katy on a cheek. Katy is grossed out, but Ashley hands her a scratcher and tells her that it's a fun game. Katy plays the slip and wins. She runs off delighted as Ashley and Jake smile at each other. On their way out of the station, Ashley asks Jake if he believes in karma.
Right outside the station, Jake grabs Ashley and spins her around for one more kiss. At that moment, the construction crew working behind them breaks a pipe and sends water squirting right at the couple. Jake and Ashley scream in horror and the movie ends on a freeze-frame.
*CUT TO THE CHASE*
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After getting her luck back, Ashley (Lindsay Lohan) blows off Peggy to help Jake (Chris Pine).
Jake wants Ashley as a part of his life, so they get together.
They each give little Katy a kiss on the cheek,passing on the luck to her.
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