- Creator's Favorite Episode: Drew Barrymore's favourite film of her own.
- Creator's Oddball: Raja Gosnell, a director known for over-the-top gross-out children's comedies and live-action adaptations of cartoons, directs a straightforward romantic comedy.
- Dawson Casting:
- One of the reasons Drew Barrymore as Josie blends in at high school; most of the other actors playing high school students were also in their mid twenties. David Arquette stands out in particular — he plays Josie's younger (age 23) brother, but is actually 3 years older than Drew Barrymore.
- Though Josie still doesn't quite pass for eighteen; in fact she looks even older as a supposed "student" than she does when she's working at the newspaper.
- Averted, however, by Jessica Alba as one of the school's most popular girls ("Nuh-uh, I'm Disco Barbie!") and Leelee Sobieski — the movie was released just over a fortnight before Jessica's 18th birthday, and Leelee turned 16 a few months later.
- One of the reasons Drew Barrymore as Josie blends in at high school; most of the other actors playing high school students were also in their mid twenties. David Arquette stands out in particular — he plays Josie's younger (age 23) brother, but is actually 3 years older than Drew Barrymore.
- Real-Life Relative: When Garry Marshall's character is speaking to his employees at the Chicago Sun-Times board room, he says, "I don't even know my own kids." His real life daughter, Kathleen Marshall, is sitting to his right when he's speaking.
- What Could Have Been: Chloƫ Sevigny was considered for the role of Aldys.
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