The young man in question is named Tom Stansfield, played by Ashton Kutcher. He is a hardworking employee at a publishing company who is head-over-heels for his boss's daughter, Lisa Taylor, played by Tara Reid. When Lisa's father, Jack Taylor (played by Terence Stamp), asks Tom to housesit for him while he goes on a business trip, Tom jumps at the chance to be alone with Lisa.
However, once Tom arrives at the Taylors' home, he immediately realizes that things are not going to be as easy as he thought. First, Lisa's younger brother Red (played by Andy Richter) is still at the house and is a bit of a nuisance. Then, a series of unexpected houseguests begin showing up, including Tom's eccentric coworker, a horny couple looking for a romantic getaway, and a group of tattooed ex-convicts.
To make matters worse, Lisa's older brother, who has been involved with shady drug dealers, shows up at the house looking for a place to stay. Tom must navigate all of these distractions while trying to win Lisa's heart and avoid getting hurt by the dangerous elements that are starting to converge on the Taylors' home.
The film is a raunchy comedy that features a number of comedic set pieces and slapstick gags. Along with Kutcher, Reid, Stamp, Richter, and a host of supporting actors, the film also features appearances by Carmen Electra, Molly Shannon, and Michael Madsen.