The story centers on Tom Stansfield (played by Ashton Kutcher), a hardworking but clumsy young man who works for his tyrannical boss, Jack Taylor (played by Terence Stamp). Tom has a crush on his boss’s daughter, Lisa Taylor (played by Tara Reid), but is too shy to act on his feelings.
One day, Jack asks Tom to housesit for him while he goes on a business trip. Tom sees this as an opportunity to impress Lisa and finally confess his feelings to her. However, things quickly spiral out of control when Tom’s best friend, Paul (played by Andy Richter), and his girlfriend, Audrey (played by Molly Shannon), show up uninvited and throw a wild party at the house.
As the party gets increasingly chaotic, Tom struggles to maintain order and prevent any damage to his boss’s property. Meanwhile, Lisa unexpectedly returns home early from her trip, catching Tom and his friends in the act.
In the climax of the film, Tom must race against time to clean up the mess and win back Lisa’s trust before Jack returns home. With the help of his friends and some creative problem-solving, Tom manages to set things right and earn Lisa’s forgiveness.
In the end, Tom confesses his feelings to Lisa, and she admits that she has feelings for him too. The two share a romantic kiss, finally cementing their relationship.
“My Boss’s Daughter” is a lighthearted and silly comedy that relies on slapstick humor and wacky antics to entertain audiences. While the film received mixed reviews from critics, it has developed a cult following over the years for its charming performances and zany plot twists.