Teenaged nerd Hewitt's older self appears before him in a dream and advises him to take a girl to tonight's school dance. When he wakes up, Hewitt decides to take his dream's advice and embarks on a quest to find a girl to take to the dance before the school day ends.
- The Bully: Sean, who keeps stealing Hewitt's food until he can find a way to get rid of him.
- Exact Words: Kathy promises to go to the dance with Hewitt if he does a favor for her. When he does it, she just gives him her hair lace. She never specified which part of her would go with him.
- Foreshadowing: Upon examining Anastasia, Hewitt remarks on the classmates' rumors that anyone who touches her turns to ash. Turns out she's the one who turns to ash when she touches water.
- Goth Girls Know Magic: Anastasia is rumored to be a witch.
- Guide Dang It!: Building the corsage is this to some, as the game won't let you combine the required items unless you're in Mary Beth's area.
- Laxative Prank: The solution to getting rid of Sean is to put eye drops on the food, and they will act as a laxative when Sean takes it.
- Locked in the Bathroom: Skippy hangs out in the bathroom all day in order to avoid girls, even skipping class to do so.
- Lockpicking Minigame: Required to open Room 21.
- Notice This: Smaller items that you have to pick up occasionally flash.
- Noodle Incident: When you try to use anything unusable, Hewitt might remark that he's keeping his hands to himself this time.
- NPC Roadblock: The hobo behind the school.
- Older Than They Look: Hewitt appears to be no older than 14. He is actually a high school student and old enough to drive.
- Onion Tears: Hewitt does this to Mary Beth in order to get her eye drops.
- Protagonist Title: The game is named after Hewitt, the protagonist.
- Shout-Out: To The Wizard of Oz. When Hewitt sprays Anastasia with the water fountain, she screams, "I'M MELTING! I'M MELTING!" and turns to ash because she's a witch.
- Ungrateful Bastard: Kathy, who goes back on her promise to go to the dance with Hewitt after he retrieves her files and laughs in his face if he tries to talk to her again.