A bunch of pre-teens sit around in a circle playing spin-the-bottle. Whoever the bottle lands on must go with the spinner into a closet and stay there 7 minutes. ("Seven Minutes in Heaven") A wooden chair blocks the closet door so the couple cannot leave before time is up. Charlie Logan is there with his best friend, Stu. Stu spins the bottle and lands on a pretty girl who wants nothing to do with him. After explaining the "three bases" (and getting them completely wrong) to Charlie, Stu goes into the closet. The girl tells him to just say we kiss, but Stu wants to say that he touched her "boobie". She refuses, but he still insists, never dropping the subject of her breasts. Next, Charlie spins and hoping it lands on a beautiful girl looking at him. Instead, it lands on a Goth girl wearing all black, black lipstick and all. They go into the closet, and she confesses his love for him, and is eager to have sex. She takes off her shirt, unbuttons his, and scratched his chest, saying she read her mom's Cosmo magazine, which said that it increases pleasure. He screams in pain and she pinches his nipples. He refuses to have sex with her, doing everything in his power to get away from her. The angry girl finally throws him through the closet door. Her shirt still off, she vows that he will never find love and be in pain forever. The hex is set on him.
About twenty years later, Charlie Logan (Dane Cook) is at the beach with a beautiful girl making out. They lay on the sand and she licks sand off his balls and tells him she loves him. He tells her that's nice, and she is upset that he did not tell her he loved him too. He replies with his thought that the "L-word" shouldn't be thrown around like that. Even more upset, she asks if he is eight years old and leaves.
Later, Charlie is talking to his best friend, Stu (Dan Fogler). They are both doctors, Charlie is a dentist and Stu is a cosmetic surgeon specializing in breast enlargement. Stu hears Charlie's tragic tale and complains that he should just lie to keep the relationship going, explaining that relationships are based on lies and gives numerous examples of common lies told to girlfriends and wives. Charlie says that he is not comfortable saying something he doesn't really feel. Women come out of the Cosmetology office and Stu gawks at them. Right then, Charlie's overweight receptionist comes out of his office telling him his agenda for the day. She yells at Stu for supposedly looking at her breasts, saying she is more than happy with what the good lord gave her. He denies having looked. The two men look at their patients, Charlie's are a bunch of old people, and Stu's are young beautiful women.
Later, Charlie walks into Stu's office, and quickly closes the door when he sees a patient topless. Stu yells for him to get back in, that he needs his opinion on whether the patient's breasts are symmetrical. Stu knows they are, but is just "doing his friend a favor so he doesn't have to pay for a lap dance".
Stu and Charlie are at a wedding; Charlie's ex-girlfriend is getting married. It seems that every girl Charlie dates gets married to the next guy she meets. The surrounding women snicker about him and he is oblivious to what they are saying. All of a sudden, Charlie sees a beautiful brunette (Jessica Alba) walking his way. She runs into a waiter and glass flies everywhere. No one is hurt, and she apologizes, saying she didn't mean to. She walks to Charlie and sits down. They ask what the other does for a living, and she jokes saying she is a serial killer, killing people she meets at weddings. In return, he jokes that he is an FBI agent, and she is under arrest. Actually, he is a dentist, he explains, and gives her his business card. The woman's name is Cam, and she accidentally spills hot soup on his lap and splashed cold water on it to cool it down.
Cam is feeding fish to penguins at a zoo-type facility. Her brother, Joe comes up to her, having just smoked marijuana. She tells him that if they find him with pot, he's fired, regardless of him being her brother. He asks how they will know, and she tells him he smells like he's been bathing in bong water and there is a pipe hanging out of his pocket. He is overjoyed; having been looking for that pipe and know finds it. She is now carrying his buckets of fish for the penguins, and falls backwards into the water, and chips a tooth. Joe jokes and asks if he is really the one looking wasted. She calls Charlie, who is having sex to help a woman find her true love.
He gets hundreds of messages from women and men wanting to have sex with him so they can find a husband, not because they are actually interested in him. He drinks mountain dew to keep himself energized in between sex- sessions. When Cam calls, he thinks it is just an excuse to see her, and says she can just say she wants to see him if she does. She assures him she really chipped a tooth and explains how she chipped it. He doesn't believe her, but they meet in his dentist office, and he fixes her tooth. He refuses to let her pay, and offers to let her pay for dinner instead. She refuses, saying she is emotionally unavailable. He does, however, help jump start her car, give her a ride to her house, and back to her car to get her extra key from her home to unlock her car, because she locked the keys in her car, and has to break a window with a brick to get into her house, because her house key is on a key ring in her locked car. Cam explains that her brother calls her "Murphy" because of Murphy's Law: Everything that can go wrong will.
Charlie surprises Cam at work one day where she is talking about penguins. He talks her into going on one date with her. On their date, she hits her head on a pole, they kiss, and he tells her she is a good kisser. One date turns into three, and he is scared that she will dump him for another guy after sleeping with him. He avoids sleeping with her on the basis of Stu calling him on his emergency dental line, Charlie assuring Cam that she looks great but he has to go.
Charlie doesn't believe that he is really a "lucky charm", so in order to disapprove the theory, he sleeps with an obese woman named Courtney. Known for laying on the side of the pool eating donut holes out of her bag, and having full body acne, Charlie pays her $1000 to date her. At their date, Charlie gets himself very drunk in preparation to sleep with her. He showers extensively after sleeping with her.
During that time, Charlie does not call Cam. She is going crazy waiting for him to call. Joe consoles her by saying that there is madness in love, but there is also reason in madness. He knows all this by using pages from a philosophy book as rolling paper, and smokes the philosopher's thoughts. Charlie pretends to be sick to avoid seeing Cam in person. Instead, they talk on the phone and on the computer. Stu was supposed to ask Courtney on a date to see if he is really a lucky charm, but instead he just asks her the time. He does not reveal this to Charlie until after he sleeps with Cam. Charlie is furious after seeing Courtney on the TV news, married. At that point, he has also slept with his receptionist after her pleading with him to.
Charlie vows not to lose Cam. He pampers her, making her breakfast in bed with everything from coffee to fruit to waffles and pancakes, sending her flowers and balloons galore at work, and even showing up there dressed in a penguin suit. Cam is disgusted, especially at her car, which is decorated with "Almost married signs" and hearts drawn on the windows. He has decided to take the day off to hang out with her, promising he won't get in the way.
After seeing "George at 8" written on Cam's calendar, Charlie is sure that it is her date, and that is the guy who she will marry. But George turns out to be her hairdresser. Too late, and Charlie has already traveled to her work, planning on proposing, and attacks the man he thinks is George with a giant blow-up penguin. He is taken away by security, and Cam tells him that their relationship is over, even after begging her not to say that.
Stu takes Charlie's nameplate off his wall, and puts it where is own was, to convince people that he is "Good Luck Chuck" to get girls to sleep with him. He is kissing and licking a beautiful girl when the real Charlie comes in, and tells the girl that he is the real Charlie Logan, and shows her his identification card. She slaps Stu and leaves his office.
Charlie sits in the rain thinking, when a homeless man takes glass bottles out of a bin to put in his own bag when a bottle falls on the floor and spins, pointing at a Goth woman sitting on a bench. Charlie remembers the Goth girl from when he was ten years old at the party, and the hex that she put upon him. He finds her house and goes to it, being driven by Stu in his hummer. Her daughter answers, wearing the pentagram silver pendant that she wore at that age. Charlie describes himself, begging her to take off the hex, offering to show her his penis and pulls down his pants and underwear at her doorstep. She tells him that she didn't know what she was doing, she was only a girl, and also had the hots for a guy named Scott. She goes on to say that if two people are meant to be together, nature will bring them together. She is married herself, and shows Charlie the family portrait on the wall. The daughter's blazing blue eyes match her own.
Charlie takes that to mean he is not meant to be with Cam and calls the "penguin guru" that Cam idolizes who wrote a book Cam loves. They meet for lunch and really hit it off. Charlie is emotionally crushed and pigs out while playing video games at his house. Stu comes and visits him with his new girlfriend, a woman with three breasts who came to him to have one surgically removed, but Stu loves them and convinces her to keep them. She lifts up her top to show Charlie her chest. That's not the reason they came, however. They convince Charlie to go find Cam at the airport on her way to Antarctica with the penguin guru Charlie thinks she will marry, but ends up being married himself. In order to catch her before leaving, he has to buy tickets to the two flights going there, not knowing which one Cam is on, and the airport employee will not tell him. It ends up costing him tens of thousands of dollars because the only available tickets are first-class. He pays with a credit card and runs through the airport. He goes through a tough time in airport security, but makes it out okay.
He eventually finds Cam, and gives her an engagement ring box, which contains a round pebble. She had explained earlier in the movie that for penguins to find a mate, they scan the beach for a pebble to give to another. She is touched and calls his name. They run to each other and make out, the whole airplane watching them. She tells him that she is coming back Wednesday and he gets off the plane.
The Goth girl takes a pin out of her Charlie Logan voodoo doll, which has a picture of his face when he was a little boy. The pin was in his heart, and she puts the voodoo doll back in the box that she got it out of.
Stu and his girlfriend are housesitting while Cam and Charlie are in Antarctica. Stu asks what good is it housesitting if they don't look for homemade porn. They find it, and watch Charlie licking and kissing a penguin stuffed animal while Cam gets turned on and yells at him how hot it looks, dictating at him what to do to the penguin next. The camera angle is reversed, and the audience can now see Stu's girlfriends' three breasts as they lay on Charlie and Cam's bed.
*CUT TO THE CHASE*
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Charlie sleeps with his receptionist and an obese woman named Courtney, and both find love. He goes back to the Goth girl who put the hex on him and she, without telling him, reverses it, and Charlie gets married to Cam. Stu also find love, a woman with three breasts.
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