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The movie starts out with Dan Foreman (Dennis Quaid) waking up early in the morning to go to a meeting with a client. He works for a magazine called Sports America and is the vice president of the sales department. On his way out of the house, he notices a pregnancy testing device's empty box in the trash can, he thinks its his daughter's, Alex (Scarlett Johansson).
He meets the client, Kalb, who seems to be an old friend of Dan's. They talk a bit, and Dan doesn't try to make a sell pitch to him. He merely leaves Kalb a copy of Sports America, and tells Kalb to call him if he is interested in ad space. Dan comes home late at night, and he checks on his daughters. The younger one, Jana, is asleep, but Alex is still up. Dan thinks Alex is pregnant, so he tells her that if she needs someone to talk to, he's there for her. Alex just says shes tired, and they say good night. Dan goes back to his bedroom, and his wife is up. Dan is about to tell her that he thinks Alex is pregnant when his wife, Ann, tells him that she is pregnant. Dan is shocked to find out that when this child is 21, he'll be 72.
We next see a sales meeting held by GlobeCom, where Carter Duryea (Topher Grace) is doing a presentation on dinosaur cell phones, targeting the market for kids that are under 5 years old. When he's done, Steckle, who is Carter's friend and superior, tells him that GlobeCom just bought out Sports America, and they are looking to send someone over to be in charge of business. Carter wants the job, but before he even said anything, Steckle said he already dropped in a good word for him to Teddy K, who is the head of GlobeCom, and that Carter will most likely get the job. We next see Carter at home in bed, telling his wife (Selma Blair) how excited he is to get this new job. It's clearly shown that his wife is not interested, and just wants to go to sleep.
Next morning, Dan is at work and is told by one of his co-workers that GlobeCom just bought out Sports America, and that there would be a lot of layoffs. We then see Dan's daughter, Alex, walking to Dan's office building to play tennis with him. Carter is also entering because this is the first day of his new job. They get in the same elevator. Carter notices that Alex presses the 47th floor, and they make small talk. As Carter gets out of the elevator, he gets escorted to see people and his office, etc. He accidentally bumps into Dan, who is running out to meet Alex for tennis. Dan and Alex go out to play tennis, and Alex is whooping Dan's butt, because he's thinking about the buyout by GlobeCom and the upcoming baby. Alex sees that Dan isn't really focused on the game, Dan tells her that he is just letting her win. They take a break, and Alex tells Dan that she successfully transferred into NYU from SUNY, and she wants to study creative writing at NYU. Dan says that's great, but really expensive. Nevertheless, he tells her that he would support her because its her education, and that's important. At the same time, Carter is told that he would have a new office, which is Dan's current one. Just as Carter is looking around, Dan comes back, and they are now properly introduced to each other. As a first impression, Dan thinks that Carter is young and inexperienced.
Carter goes to a Porsche dealership and buys a 911 Carrera, he's all psyched up about driving it that he didn't notice another car as he was pulling out, and smashes the front of the car right away. He goes home just in time to find out that his wife is leaving him, apparently their marriage didn't work out after only 7 months. Carter falls asleep in his car.
Next day at work, we see Carter moving into Dan's old office, and Dan's moving to the office next door. Carter gives a pep talk at their first company meeting, he's chugging down coffee as he is really nervous. But as soon as he gets into talking about advertising, he becomes very confident. He starts talking about working as a team and this thing called Synergy, putting sports factoids onto cereal boxes, etc. The employees, including the janitor, are psyched up, only Dan seems a little skeptical.
Carter invites Dan out to lunch. They go to a sushi restaurant, it's apparent that Dan doesn't like raw fish, but Carter still wants him to try one. Dan reluctantly eats it and almost throws up. Carter then gets down to business by telling Dan that they need to increase the ad pages in Sports America by 20 pages, or they would have to fire a lot of people. He says he likes what Dan's been doing, and that Dan can be his wingman. Dan does not like the idea, but if he didn't accept it, he would be unemployed, so he takes the job.
We next see Carter at his home. Since his wife left him, he's been pretty lonely, only with a fish to keep him company. Carter then calls Dan up to tell him to get the workers together, and they'll have a meeting on Sunday. After the Sunday meeting, everyone is pretty mad at Carter. As they leave, Carter is asking everyone of them if they wanted to go out and have a drink, because he just wants some company, they all said no. When he asked Dan, Dan said he has to go home and eat dinner with his family, and Carter won't want that. But Carter says he does, and pretty much invites himself over.
They drive to Dan's house, Carter is introduced to Ann. He tells her how thankful he is that they "invited" him over and that he is looking forward to a home cooked meal. Ann then tells Dan privately in the kitchen that Carter is so young and he is so old. As Ann is getting the baked ziti out of the oven, she says she is nauseous and Dan tries to take the tray from her, but it is too hot so he drops the entire tray on the floor, they then called Domino's instead.
Carter is wandering about the living room when Alex comes in, they recognize each other from the elevator. Jana comes in as well, and they both comment how young Carter is to be Dan's boss. Alex then asks if Carter wanted to play Foosball, Carter agrees. They play in the garage and they talk about themselves. Alex explains how she is always seen as a jock, because she plays tennis, and that some people thinks that she is a lesbian, because she doesn't have a boyfriend. The pizza comes and Dan goes to the garage and accidentally yells "kids, come on in" to his boss. At the dinner table, Carter is trying to explain that he and Dan are really just colleagues, but Dan says that Carter is the bossman, and he's the wingman. Carter then spills water over Dan's lap, as Carter is trying to dry him off, Dan says no one touches him there except for Ann. After dinner, as Carter is leaving, Alex is seen watching him from upstairs.
Next day at work, Dan tells Carter that he would be taking a client out to a Knicks game, but Carter interjects and says that they should take the client to a concert that day instead. Carter also tells Dan that there would be an upcoming company basketball game between the GlobeCom people and the Sports America people. After the concert, Dan and Carter go to a bar, Carter explains to Dan that they would have to fire two of Dan's best guys, one of which is Morty, because they aren't pulling their weight. Dan asks why don't they just fire him, but Carter makes Dan realize that he can't get fired because he has a family that needs him (a new baby, Alex going to NYU, etc). Dan realizes this and tells Carter that since he was the one who hired them, he'll be the one to fire them.
The next day, Dan calls the two guys in and tells them that they are being "let go". Morty seems sad but accepts it, and tells Dan its been an honor to work for him, but the other guy just curses at Dan and storms off. After this point, there is another series of layoffs, but they are done by Carter. We then see Dan helping Alex move in to her new dorm in NYU, and he tells her to take care of herself. We see Dan and Ann taking out a 2nd mortgage on their house to pay for the extra expenses. At the same time, we see Carter is signing his divorce papers.
At the company basketball game, we see Steckle, who is playing for the GlobeCom team, trash talking to Carter and Dan. We see there is a really athletic member on the GlobeCom team that is doing massive dunks, but he clearly is not working for GlobeCom. The game starts and the Sports America team is being schooled, but Dan gets a steal and he is about to dunk it, when the ball gets stuck between the hoop and the backboard, and Dan falls to the ground, injuring his arm slightly (really funny).
Carter is walking around NYC looking for an apartment when he runs into Alex at a cafe. He sits down and they talk. Afterwards, they walk around and go to dinner. Alex invites Carter to her dorm and they sleep together that night. Carter starts going out with Alex regularly now. For the next couple of days, we see Dan's got his arm around a sling, and he's making many calls to Alex, but always reachers her voice mail, and she never returns a call. Dan then asks Carter when he was in college, did he ever return phone calls, etc. Carter also asks Dan how he ever got such a good family.
It is Dan's 52nd birthday, and we see a lot of people are gathered at his house for a surprise party. As Dan is driving Jana home, he sees the people in the house and knows the people are waiting for him. He tells Jana to go in first and that he's gonna check the mail box. As everyone is waiting for him to come in, Dan walks in with nothing but his boxers on, and he turns around and moons everyone (hilarious). The party goes on, Carter and Alex slip out of the house and into his Porsche. Carter gives Alex a diamond necklace. As they walked out of the car, Dan sees them from a window and realizes that Alex has been dating his boss.
After work the next day, Carter hops in a cab to meet Alex, but he doesn't know that Dan is following him. Dan confronts Carter and Alex in the restaurant, and he only wants to know if Alex has slept with Carter. Alex indirectly admits it, and Dan punches Carter and gives him a black eye, just when Carter says he loves Alex. This is also the first time when Dan tells Alex that they have taken a 2nd mortgage on their house to pay for her tuition. That night, Carter apologizes to Alex, Alex says that its ok, but that they should break up. Dan got home and Jana tells him that Ann is in the hospital. Dan goes to the hospital to check on Ann, she is fine, just some minor bleeding. Alex comes to the hospital too, and she tells Dan that she broke up with Carter. She says that if they can't afford her tuition, she is fine to go back to SUNY. Dan agrees that since Alex is more independent now, he should also adjust himself to recognize that she is more independent. He also tells her that they would support her at NYU regardless.
The next day, the president of GlobeCom, Teddy K is coming to Sports America to give a talk. Dan walks in in the middle of it. As Teddy is talking about the idea of Synergy, Dan pipes up and says that he doesn't really see how that would work, and goes on to point out its fallacies. Teddy doesn't know how to respond to Dan, and makes a hasty exit. Afterwards, Steckle is really mad at both Dan and Carter, particularly Dan for his little outburst at Teddy K earlier. He promptly fires Dan and tells Carter to go to his office. But Carter tells Steckle that if he fires Dan, he'll have to fire him too. Steckle says fine, both Dan and Carter are fired. But then Dan says, Sports America will be really screwed now if they are gone, because they are just about to close in on a huge deal that would have saved the magazine. Steckle says that he is bluffing, but Carter says they are not. Steckle gives them 24 hours to straighten out the deal. After he leaves, we find out that they were bluffing, but Dan says he's got a plan.
We next see Dan and Carter meeting with Kalb. Carter goes on to talk about his idea of putting ads on cereal boxes, etc. But Dan signals for him to shut up. Dan asks Kalb what is holding Kalb back from closing the deal with Sports America. Kalb says that he is letting his son-in-law doing all these deals with TV companies, internet, etc and comes to the realization that he should be making the decisions himself. So he agrees right away to a deal with Sports America, which saves the company.
When they get back to their own office, we see Steckle sitting distraught at his desk. He says Sports America has just been sold back to its original company, and that both him and Carter are fired, but Dan gets his old job back. After a month, Dan calls in Carter for a meeting. He offers Carter a job, but Carter tells Dan that he doesn't know if this is what he really wants to do for the rest of his life, he appreciates the offer, but he'll have to decline. As he is walking out of the elevator downstairs, he runs into both Morty and Alex. Apparently, Morty is rehired by Dan. Carter asks Alex how she's been, she says she is writing short stories now. They smile and go their separate ways.
In the last scene, Dan is coming out of the delivery room, he tells Alex and Jana that they would have a baby sister. We cut to Dan calling Carter on his cell phone while Carter is jogging, he congratulates Dan.
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