''Overnight Delivery'' is a 1998 DirectToVideo romantic comedy. The main arc of the film is a highly formulaic RoadTripRomance, made watchable mainly by a pair of highly likeable leads, both of whom are probably more recognizable now than when the movie was made.

Wyatt Tripps (Creator/PaulRudd) is 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 Ivy Miller (Creator/ReeseWitherspoon), an [[GoodBadGirl impressively canny stripper]] who convinces him to write a particularly nasty breakup letter and send it by an overnight delivery service.

The next day, Tripps realizes his mistake, and enlists Ivy's help 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.

!!Tropes Associated With This Film Include:

* ArtisticLicenseGeography: The actual University of Memphis tower dorms were a ''lot'' less glamorous at the time, but the film needed a different physical setup for some of the final shenanigans. Everything in the movie was filmed in Minnesota instead.
* BerserkButton: She may play by her own rules when it comes to relationships, but NOBODY calls Ivy a slut.
* BettyAndVeronica: Kind of inverted. The sweet, blonde, virginal Kim turns out to be [[BitchInSheepsClothing lying and manipulative]], while the streetwise, brunette stripper Ivy turns out to be both nicer and more sensitive than she appears.
* DisposableFiancee: Not quite a fiancee, but Tripps does plan on marrying his girlfriend before Ivy comes along. In the end, she turns out [[spoiler: to have been cheating on him after all. Though he finds out after he dumps her.]]
* DumbBlonde: While not especially dumb, Kim is a pretty blonde, former cheerleader who's presented as being notably dimmer than the two leads.
* GoodBadGirl: 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.
* IrrevocableMessage: The break-up letter is the driving force of the plot.
* NerdsAreSexy: 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.
* LastGirlWins: Tripps starts out willing to do anything to marry his high school sweetheart. By film's end, things have changed.
* ObstructiveBureaucrat: The clerk for the delivery company turns out to be someone Tripps had [[DisproportionateRetribution accidentally offended the previous day.]] She makes quite sure that he won't be able to get the package back through the proper channels.
* PoorCommunicationKills: Tripps 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. [[spoiler: Then, at the end, that turns out to be a lie, and she actually ''is'' cheating on him.]]
* ASimplePlan: Once Tripps realizes he can't get the letter back, he decides to go to Memphis to intercept it. Sounds easy enough...
* UnstoppableMailman: The Global Express driver is very commited to his job. He's absolutely determined to make sure the package gets to it's destination on time:
--> '''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.