Overnight Delivery

Overnight Delivery is a 1998 straight-to-video romantic comedy. The main arc of the film is a highly formulaic Road Trip Romance, made watchable mainly by a pair of highly likeable leads, both of whom are probably more recognizable now than when the movie was made.

Paul Rudd plays Wyatt Trips, a smart and driven college student who spends most of his time pining over his girlfriend, who goes to a different school a thousand miles away. One night, he becomes convinced his girlfriend is cheating on him, gets drunk, and has a chance encounter with an impressively canny stripper (Reese Witherspoon) who convinces him to write a particularly nasty breakup letter and send it by an overnight delivery service.

The next day, Trips realizes his mistake, and enlists the help of said stripper to get the package back before it gets to his girlfriend. A series of misadventures later and they find themselves on a road trip across the country, and wondering if he's racing toward the right girl.

"Sniper: I have a bead on him, sir. Police Captain: Do not fire until the hostage is clear. Sniper: But he's only an undergrad, sir. Police Captain: Nevertheless."
 * Acceptable Inevitable Targets: Several scenes poke fun at college students. Including one during a hostage situation.

"Driver: (while driving away in a flaming truck) As God is my witness, you will not stop this package! Not on my watch!! Ivy: That is one dedicated professional."
 * Berserk Button: She may play by her own rules when it comes to relationships, but NOBODY calls Ivy a slut.
 * Betty and Veronica: Kind of inverted. The sweet, blonde, virginal Kim turns out to be lying and manipulative, while the streetwise, brunette stripper turns out to be both nicer and more sensitive than she appears.
 * Dawson Casting: Paul Rudd plays an undergrad, and was 29 when the movie was made. Averted with Reese Witherspoon, who 22 at the time.
 * Disposable Fiancé: Not quite a fiancee, but Tripps does plan on marrying his girlfriend before Ivy comes along. In the end, she turns out
 * Dumb Blonde: While not especially dumb, Kim is a pretty blonde, former cheerleader who's presented as being notably dimmer than the two leads.
 * Good Bad Girl: Ivy works as a stripper and is evidently sleeping with one of her professors. Despite that, she's shown to be kind, highly intelligent and entirely moral.
 * Irrevocable Message: The break-up letter is the driving force of the plot.
 * Nerds Are Sexy: Not nerds, exactly, but both Wyatt and Ivy are shown to be pretty smart and well-read. Wyatt's girlfriend, by contrast, is implied to be a little dumber.
 * Last Girl Wins: Trips starts out willing to do anything to marry his high school sweetheart. By film's end, things have changed.
 * Obstructive Bureaucrat: The clerk for the delivery company turns out to be someone Tripps had accidentally offended the previous day. She makes quite sure that he won't be able to get the package back through the proper channels.
 * Poor Communication Kills: Trips starts worrying about his girlfriend cheating on him, and when he tries to call her, her roommate tells him she's "out with The Ricker" and stars ranting about how much noise The Ricker was making last night. Tripps naturally takes this as confirmation of his fears. Turns out that The Ricker is a dog she's taking care of.
 * A Simple Plan: Once Trips realizes he can't get the letter back, he decides to go to Memphis to intercept it. Sounds easy enough...
 * Unstoppable Mailman: The Global Express driver is very committed to his job. He's absolutely determined to make sure the package gets to its destination on time: