Winter Break

At her 25th high school reunion, Peggy Sue faints and awakens in 1960—back in her senior year, before her marriage and all her regrets. Given a second chance to relive her youth, she must decide whether to change the choices that shaped her life or embrace the past that made her who she is.

In 2008, during the last month of summer before high school begins, an impressionable 13-year-old Taiwanese American boy learns what his family can't teach him: how to skate, how to flirt, and how to love your mom.

When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, who's not entirely sold on the idea. Plunging headlong into the campus experience, the increasingly outspoken Deanna – now Dee Rock – embraces freedom, fun, and frat boys on her own terms, finding her true self in a senior year no one ever expected.

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.