Drive Me Crazy was released in the year 1999, and it shows. Within five minutes of the film, you know who's ending up with whom. As many of the reviews have stated, the two leads have chemistry to spare. They're funny, sweet, charming, and most importantly, adorable together. We know they're going to be sharing some big kiss and slow dancing before the credits roll. The movie doesn't try to throw any relationship curve balls but instead follows the standard script - but that's not the point. It's not about shocking endings or twists you didn't see coming. It's a relationship drama with a comedic twist, not a murder mystery action flick. So the movie sticks to the predictable, fluffy approach.
The movie tackles issues that we've seen done a thousand times, but it only really succeeds by giving no solid answers. The jocks make fun of the outcasts and vice versa. When Chase calls out how the popular kids are all willing to make fun of Dave and we get prepared for the standard "popular kids are jerks" speech, Nicole cuts him off, pointedly asking, "can you honestly tell me you've never made fun of those [popular] people over there?" Instead of trying to put the blame on one social group, the movie shows that relationships are complicated, and there is no clear, definitive answer. We see outcasts be shallow and popular jocks be welcoming. Just like how Nicole and Chase start to get confused on where exactly their feelings lie as they get more invested in their fake relationship, the audience gets the line between in-crowd and counter-culture, along with all the stereotypes associated with them, blurred.
Furthermore, the female lead Melissa Joan Hart pulls off her role phenomenally and so does her co-lead Adrian Grenier. We never really know when the two start to fall for each other because they're always putting on a show. Just when we think we know Nicole has fallen for her neighbor, she turns around and tries to get Chase's ex to see things from his perspective. Nicole is always planning and scheming to the point where it's hard to tell when the act stops and her true feelings begin. Chase meanwhile is easier to read. Since he's following Nicole's lead, we know he's in love by the time he's taking initiative in their "relationship." Regardless of whether the two characters do a good job of acting, the two leads certainly give a wonderful performance.
So yeah, Chase ends up with Nicole, the two semi-loser friends of our protagonists end up together, and the parents have been in a relationship since the beginning of the film. Chase helps Nicole cut loose and she cleans him up a little bit. It's predictable and familiar, but in the way you know the layout of your childhood home - maybe it's not the most exciting place you've ever been but you definitely had fun there.