High school sweethearts Wyatt Trips (Paul Rudd) and Kimberly Jasney (Christine Taylor) are dealing with a long distance relationship as they attend different colleges. He phones her but her roommate seems to suggest that Kimberly has a new guy. Heartbroken and angry, he goes to a strip club and gets involved with dancer Ivy Miller (Reese Witherspoon). She convinces him to write her a Dear John letter. They send it overnight delivery with a fake used condom and photo. Hal Ipswich is the overly dedicated new delivery man.

The rom-com road trip is a long standing movie tradition. First, his friends need to be the ones who drag him to the strip club. This is led by two future comedic movie stars early in their careers along with a couple of interesting supporting actors. Rudd and Witherspoon have many of their future moves. I think Witherspoon would blame it on her hair color and being blonde could have helped to accentuate her personality. It needed something and it's so close to being actually good. The two future stars keep almost connecting. They do get somewhere by the end and that does save it. I notice her hair is a little lighter in the sunshine done up in a ponytail at the end. Hmmm... I wonder.

... such, are so-called "wacky teen comedies" really only for teens, or are they iconic in theme and execution, and can be enjoyed by any viewer regardless of age..? Which reminds me, oddly, of WHEN HARRY MET SALLY, not only one of the greatest films of all time; not only (possibly) the best thing Billy Crystal ever did; but in fact a movie which enjoyed an audience far outside what the producers expected and indeed a film which has over the years become part of the cultural gestalt. "I'll have what's she's having" is as much a punchline as it is a test of one's filmic credentials. So, to answer my own question, I think the answer is, yes, a good film can easily transcend its genre. In fact a good film can not only transcend its genre but it can in fact loop around (permit me the metaphor),pick up a bunch of viewers from other demographics, and then come full circle back to where it started. (This was the case with High School Musical, an innocent attempt to expose an entirely new, and sceptical, generation, to the many joys of the MGM musical template, which not only succeeded, but has captured the imagination of other viewers of other ages, while still being a breakout film in its own class.) As for OVERNIGHT DELIVERY, I always believed it was under-rated and under-appreciated. If you liked Witherspoon as June Cash (and you must have, because she got an Oscar),well, keep in mind she was 22 here and cute as the proverbial button. Rudd made his chops on network TV and showed how his low-key underhanded approach makes him a perfect foil in a romantic com -- like a tennis player, he has a knack for picking up a line, or an emotion, and tossing it back. The story at first glance seems dated, the idea of a young man so obsessed with what he is losing (and may have never had to start with) that he does not see what is right in front of him. However, if you do the math, most of the knockoffs came AFTER this tale, not before, suggesting it was a lot more original than it seemed. Highly recommended.

Man! I watched almost by mistake this movie on cable on a Saturday afternoon several years ago. (Maybe 1998 after it came out).

It caught my attention quickly with it's dynamic love story and the charming characters.

I felt sympathy for Reese's character because she was tender, naive, but also faithful, clever, and pretty.

Paul Rudd's character was the highlight of the movie because of his dialogs and on screen charisma.

Christine Taylor portrays the bitchy girlfriend everyone has to hate but cannot help but fall in lust with her.

Overall, the movie delivers a positive message for those avid romantic movie fans who want more from the plot and dialogs rather than watching the typical love story.

I like the dynamic manner of telling the "overdrive" love story.