- Actor-Inspired Element: It was Julia Stiles's idea for Patrick to sing "Can't Take My Eyes Off Of You" on the football field.
- Actor-Shared Background: They worked in Heath Ledger's Australian background to be an actual part of the character, including having Kat ask him if the accent was real or faked.
- The Cast Showoff:
- Dawson Casting: One of the most notable aversions, all of the main cast was between 18 and 20 during the filming of the movie playing high schoolers (Krumholtz was the oldest, and he was barely 21 when the movie premiered). Some of the supporting cast were a little older, though - Gabrielle Union (Chastity) and Susan May Pratt (Mandella) were 27 and 25, respectively.
- Deleted Role: Gil Junger wrote a part for himself as a teacher, but the scenes were deleted.
- Follow the Leader: This is a Setting Update of a classic work of literature, set in an American high school, following the lead of Clueless.
- Missing Trailer Scene: Kat rejecting Patrick at the lockers then the camera zooms in on his grinning face *swoon*.
- Old Shame: Averted, a lot of people expected Heath Ledger to continue in the teen comedy genre but he instead refused a lot of similar roles until he started to get the parts he wanted like in The Patriot and A Knight's Tale. Despite this, he didn't consider this film to be an old shame, just not where he wanted to take his career.
- One-Take Wonder: The then-17 year old Julia Stiles slowly broke down into tears while reading the poem on the very first take, an acting cue that was not in the film's script. First-time director Gil Junger was so moved, he called a wrap to the shoot after that.
- Reality Subtext: Kat gets accepted to Sarah Lawrence College. Larisa Oleynik (Bianca) went to Sarah Lawrence.
- Recycled: The Series
- Romance on the Set:
- Joseph Gordon-Levitt dated both Larissa Oleynik and Julia Stiles after filming... not at the same time. The main cast apparently became fairly close friends, regardless.
- Julia Stiles and Heath Ledger were briefly involved too.
- Star-Making Role: Both for Julia Stiles and Heath Ledger.
- Throw It In!:
- Stiles's tears during the poetry reading scene were apparently unscripted, as was the brief shot of Ledger playing with the Bunsen burner near the opening of the film.
- Karen McCullah claims the title was based off a diary entry she made during high school about a boyfriend she hated. When she and Kirsten Smith were writing the script, they looked over the entry and went "that's our title".
- Tuckerization: Cameron James is named after James Cameron.
- Unintentional Period Piece: As mentioned under The '90s, the film is a parodic time capsule of the decade.
- What Could Have Been:
- The original script had a much darker tone. Mandella would make several references to suicide attempts for instance.
- Julia Stiles had auditioned to play Bianca and got cast as Kat instead. Larisa Oleynik, who played Bianca, apparently really wanted to be Kat.
- Kate Hudson was approached to play Kat, but her mother Goldie Hawn hated the script and forbade her to do it.
Trivia / 10 Things I Hate About You