These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Deader Than Disco: Used to be a very popular film, but the end of the 90s and increasing parodization have reduced it to prime Snark Bait.
Fridge Logic: Dean's inspired choice for the bet. A girl who looks like Laney as opposed to people who weren't single, deeply unattractive or you know lesbian. Any number of girls would have presented a greater challenge.
Hollywood Homely: Granted, Zack's major concern was over Laney's personality, but a lot of emphasis is put on her physical makeover. WHO could possibly think Rachael Leigh Cook was unattractive? This has since become the most famous part of the movie, and an infamous example of this trope at work.
Beautifully parodied in Not Another Teen Movie: "Glasses? And a ponytail? Ugh!". Made funnier by the fact the Dean expy skips over all the actual challenging choices, such as an albino guitarist, a hunchback, and conjoined twins.
Karma Houdini: Taylor is mean to Laney, especially in competition for prom queen, and she wins.
Meaningless Villain Victory: She wins prom queen, but loses the respect of the whole school (which she never actually had in the first place) by publicly insulting everyone who voted for Laney after being crowned. The last time we see Taylor in the film, she's being given a wide berth at graduation — sort of her classmates unconsciously saying "Wait, high school's over! We don't have to put up with your shit anymore!"