Overnight Delivery - Plot

Plot

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. Trips loves Kim, even though they have never consummated their relationship.

One day when Trips 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 Trips that he get back at Kim by sending her an abusive letter and a topless picture of himself with Ivy. Trips complies by sending the package through Global Express, an overnight delivery service.

The next morning, Trips discovers that "The Ricker" is, in fact, Kim's girlfriend's dog whom Kim had to dogsit. Regretting his mistake, he realizes he has 24 hours to retrieve the package before it gets to her. Trips and Ivy go to the Global Express office where, by chance, they encounter a spiteful classmate of Trips' (Sarah Silverman) who refuses to help them. Trips tries to talk the deliveryman (Larry Drake) into giving him the package, but he thinks Trips is a spy for the company, and refuses to break the rules.

Trips 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. Trips escapes and runs into Ivy on the road. Fearing that if he went back to the airport, 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. Trips 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 Trips 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, Trips 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. Trips and Ivy then steal a drunk's car and drive to Kim's campus.

After saying goodbye to Ivy, Trips gives chase to the delivery man and stops him in time. But after meeting Kim, Trips 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 gifted to him long back. Trips 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.

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