Associated people:

Matt Dillon

Natalie Portman

Beautiful Girls (1996)

Barely helpful plot summary:

A musician heads back to his hometown for a high school reunion. Then he kind of falls in love with teenage Natalie Portman. His friends are pretty fucking weird, too. 

Similar films:

Grosse Pointe Blank (1997)

High Fidelity (2000)

Just Friends (2005)

Kicking and Screaming (1995)

Late Night Shopping (2001)

Nobody's Fool (1994)