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Mike (Omar Epps) tells the story of how he grew up in Inglewood, California(nicknamed "The Wood"), with best friends Roland (Taye Diggs), who is getting married(and is currently missing) and Slim (Richard T. Jones), who scoffs at the idea of marriage, but is furious at Roland for disappearing. The story reminisces back to Mike's first encounters with Roland and Slim , his first real crush on a girl named Alicia (Malinda Williams), and the three young men's misadventures as teenagers.
- The Bet: How Mike meets Alicia. On his first day after moving from North Carolina, Roland and Slim bet him a dollar to slap Alicia's butt. Unfortunately, the reason why they didn't do it is because Alicia's brother Stacey is a Blood and will beat them up.
- Cluster F-Bomb
- Diegetic Switch: Played with. Each flashback starts with a clip of the actual record of the song playing.
- The Eighties: The flashbacks take place from 1986 to 1989.
- Eighties Hair: Mike and Roland have high-top fades, and Slim and Stacey have a Jheri curl.
- Everybody Has Lots of Sex: What drives the boys to try and lose their virginity.
- Foot Focus: Preceding Their First Time, Alicia invites Mike into her house one afternoon after school. They go to her room, where after she drops her book-bag, she proceeds to remove her shoes and socks. While watching this, Mike mentally urges "Down, boy!"
- Gang-Bangers: Stacey.
- High School Dance: And middle school dance as well.
- Hormone-Addled Teenager: Mike, Roland and Slim. Alicia knows this, which is why she gets so mad when Mike slaps her butt.
- Though she doesn't quite mind so much when Mike later reaches for her butt during their dance at the prom.
- It Will Never Catch On: Stacey says that he could be a rapper, but nobody would ever buy an album about pot.
- Irony: The robbery that Stacey committed is what got them off the hook when the police pull them over.
- Knight Templar Big Brother: Stacey, at first.
- Nothing but Hits: The soundtrack includes 80s rap songs.
- Pet the Dog: Stacey, previously established as very protective of his sister, gives Mike advice on how to woo Alicia during the school prom.
- Police Brutality: A mild version. The policeman makes them get out the car and gives them a pat down all because of a broken tail light.
- She's All Grown Up: Alicia in the present day, played by Sanaa Lathan in a cameo role.
- Their First Time: Mike and Alicia. It leads to...
- Two Lines, No Waiting: The storyline with them trying to get Roland to go to his wedding and meanwhile reminiscing about their childhood.
- Vomit Indiscretion Shot: Roland vomits all over everybody's suits in the car.