Hilarie Burton as Winona Marshall 

17 // hard to sleep

Milo Manheim as Wally Clark

18 // matilda

Chase Crawford as Joshua Marshall

19 // elastic heart

Ruby Rose Turner as Jennifer Marshall

18 // here's to never growing up

Mallory James Mahoney as Amanda Marshall

11 // bigger than the whole sky

Adrian Grenier as Michael Ford

18 // how to save a life

Mila Kunis as Kimberly Nelson

18 // you missed my heart

ADDITIONAL CAST

Bart Johnson as Joseph Marshall

Rachel Blanchard as Melissa Marshall

Nick Pugliese as Charley 

Sarah Yarkin as Rhonda

RaeAnn Boon as Dawn

Jess Gabor as Janet

Josh Zuckerman as Mr Martin

Peyton List as Maddie

Miles Elliot as Yuri

Ci Hang Ma as Quinn