My Boss's Daughter

Tom Stansfield (Ashton Kutcher) is a researcher at a publishing company who works under the tyrannical Jack Taylor (Terence Stamp). Tom has a crush on his boss' daughter, Lisa Taylor (Tara Reid), who is completely controlled by her overprotective father. She reveals to Tom that her father is making her housesit on the night of a party she wants to attend. He convinces her to stand up to her father and go to the party anyway. Lisa then asks him to come to their house, leading Tom to think that she invites him to the party. In reality she just wants him to fill in for her and he reluctantly agrees. A comedy of errors ensues including the return of Lisa's older brother, Red, who's on the run from drug dealers. Red throws the drugs into the toilet and gives the drug dealer a bag of flour. One of Tom's tasks is to guard their owl, O-J, which lives in an open cage for not being able to fly after a depression with its prior mate. After the bird drinks off the toilet, that the drugs were poured into, it flies away. Jack Taylor's ex-secretary Audry goes to the house to try to earn her job back. After fighting with her boyfriend, she stays over at the house. Lisa returns home after finding out that her boyfriend Hans is cheating on her. Tom hides from her everything that happened and she spends some time with him thinking he is homosexual. He clarifies to her that he's a heterosexual and she starts to like him. Audry's friend thinks she has breast cancer and asks Tom to feal her breasts. Lisa comes in on them and is disgusted by the situation.

T.J., the drug dealer, finds out about the fake drugs and threatens to kill Tom if he doesn't return him his money. The drug dealer tries to open a safe and steal it. However, Tom gives him sleeping pills mixed with alcohol which sends him into a coma. Because they think he is dead, Audry and her friends bury him. Later, T.J. rises from the grave and threatens to kill Lisa. Tom rescues her with the help of Red and she falls in love with him. He then goes to get her father, but on the way back the owl gets into the car making Tom lose control of the car and crash into the house. They find police officers in the house looking for T.J. who is caught. Jack Taylor is enraged by the damages done to the house and throws Tom out. The next day, Jack Taylor hears his son explaining to Lisa how she should stand up to their father and goes back to Tom. Jack realizes his mistakes and gives Tom a promotion.