As 35-year-old Bev Donofrio (DREW BARRYMORE) and her 20-year-old son, Jason (ADAM GARCIA), set out to overcome one last hurdle to her publishing her life story, "Riding in Cars With Boys," we see a series of flashbacks that lead them up to this point in 1996.
Back in 1965, 15-year-old Bev lives with her parents, Theresa (LORRAINE BRACCO) and Leo (JAMES WOODS), a local cop, but spends time chasing boys with her friends, Fay (BRITTANY MURPHY) and Tina (SARA GILBERT). While at a party doing just that, 18-year-old dropout Ray Hasek (STEVE ZAHN) defends her honor and the two quickly become an item.
One thing leads to another and Bev, like Fay, finds herself unexpectedly pregnant, greatly disappointing her parents. After weighing her options, Bev decides to marry Ray. After having Jason, she works as hard as she can so that she can win a scholarship to attend college to pursue her dream of writing. Unfortunately and unbeknownst to her, one thing after another - particularly motherhood and Ray's deadbeat ways -- ultimately derail her plans.
As the years pass, however, and Jason (LOGAN ARENS & CODY ARENS) gets older and Ray and his friend, Lizard (DAVID MOSCOW) create more unexpected challenges in her life, Bev finds herself questioning her potential, future and her ability to be a good mother. From that point on - in both the past and present -- she does what she must and can to get on with life and overcome the various setbacks and challenges thrown her way.