Overnight Delivery
Wyatt Trips (Paul Rudd) is a student at Twin Cities College, Minneapolis, Minnesota. He is in a long-distance relationship with his high school girlfriend, Kimberly Jasney (Christine Taylor), who is currently a student at the University of Memphis. Wyatt loves Kim, even though they have never consummated their relationship.
One day when Wyatt calls Kim, her roommate's reply leads him to believe that Kim is cheating on him with some guy named "The Ricker". Heartbroken, he goes to a strip club, gets drunk and becomes acquainted with one of the club's dancers, Ivy Miller (Reese Witherspoon). She suggests to Wyatt that he break up with Kim by sending her a scathing letter and a topless picture of himself with Ivy. Wyatt complies by sending the package through Global Express, an overnight delivery service.
The next morning, Kim calls Wyatt claiming "The Ricker" is a dog who she had to dogsit. Regretting his actions, he realizes he has 24 hours to retrieve the package before it gets to her. Wyatt and Ivy go to the Global Express office where, by chance, they encounter a spiteful classmate of Wyatt's (Sarah Silverman) who refuses to help them. Wyatt tries to talk the deliveryman (Larry Drake) into giving him the package, but he thinks Wyatt is a spy for the company, and refuses to break the rules.
Wyatt buys an air ticket to Memphis, but his co-passenger turns out to be a serial killer, John Dwayne Beezly (Tobin Bell), who takes him hostage. Wyatt escapes and runs into Ivy on the road. Fearing that if he went back to the airport, the FBI would question him and he would not make it to Memphis in time, he begs Ivy to drive him all the way. They happen upon the Global Express delivery truck at a gas station. Wyatt breaks into the truck and locates the package, but the truck unexpectedly drives off. Ivy gives chase but despite their efforts they fail to retrieve the package.
At their next stop, Des Moines, Iowa, airport officials do not allow Wyatt to board the connecting flight. So they decide to travel to St. Louis, Missouri to board another connecting flight. En route to St. Louis they have an argument which leads to an accident which ends up with their vehicle falling into the river. They have dinner in a cowboy diner and then try to run out on the check, but get arrested. After posting bail, they are let off and once again happen upon the delivery truck outside a diner. While the deliveryman is having dinner, Wyatt decides to empty the truck's gas tank in order to stall him, but a carelessly flung cigarette butt sets fire to the gas and causes the truck to explode. But even that doesn't stop the deliveryman (who is clearly over the edge by now) and he drives off. Wyatt and Ivy then steal a drunk's car and drive to Kim's campus.
After saying goodbye to Ivy, Wyatt gives chase to the delivery man and stops him in time. But after meeting Kim, Wyatt suddenly realizes that he loves Ivy and not Kim. After breaking up with her, he runs into another guy who is wearing the same kind of locket that Kim gave him long ago. Wyatt correctly surmises that the guy is none other than "The Ricker" and Kim was cheating on him after all. He allows the delivery man to deliver the package, and confesses his love to Ivy, who kisses him passionately.
romantic