Mike (Omar Epps) tells the story of how he grew up in [[UsefulNotes/LosAngeles 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.
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!!Tropes:

* TheBet: 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. [[spoiler: Unfortunately, the reason why they didn't do it is because Alicia's brother Stacey is a Blood and will beat them up.]]
* ClusterFBomb
* DiegeticSwitch: Played with. Each flashback starts with a clip of the actual record of the song playing.
* TheEighties: The flashbacks take place from 1986 to 1989.
* EightiesHair: Mike and Roland have high-top fades, and Slim and Stacey have a Jheri curl.
* EverybodyHasLotsOfSex: What drives the boys to try and lose their virginity.
* {{Gangbangers}}: Stacey.
* HighSchoolDance: And middle school dance as well.
* HormoneAddledTeenager: 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.
* ItWillNeverCatchOn: Stacey says that he could be a rapper, but nobody would ever buy an [[SnoopDogg album about pot.]]
* {{Irony}}: The robbery that Stacey committed is what got them off the hook when the police pull them over.
* KnightTemplarBigBrother: Stacey, at first.
* NothingButHits: The soundtrack includes 80s rap songs.
* PetTheDog: Stacey, previously established as very protective of his sister, gives Mike advice on how to woo Alicia during the school prom.
* ThePlace
* PoliceBrutality: A mild version. The policeman makes them get out the car and gives them a pat down all because of a broken tail light.
* ShesAllGrownUp: [[spoiler:Alicia in the present day, played by Sanaa Lathan in a cameo role]].
* TheirFirstTime: Mike and Alicia. It leads to...
** SpeedSex: ...Mike not being able to keep going longer than a minute or so. Alicia takes it in stride [[TheyDo and accepts the idea of them being a couple]].
* TwoLinesNoWaiting: The storyline with them trying to get Roland to go to his wedding and meanwhile reminiscing about their childhood.
* VomitIndiscretionShot: Roland vomits all over everybody's suits in the car.
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