Reality Bites or Kicking and Screaming are initial pairing choices.
Say Anything works as a Seattle high-school prequel to post-college Singles.
Action Jackson is a joking double-feature suggestion.
Love Jones is an appealing alternative with a similar vibe.
Vanilla Sky is proposed and immediately withdrawn as a joke before the Jerry Maguire choice.
Jerry Maguire completes a Crowe progression from high school through post-college life to professional adulthood.