It’s 1997. Alone in her computer lab, 13-year-old Jane finds her escape from the awkward throes of puberty by joining her sister and her unattainable high school crush in a covered wagon headed west on “The Oregon Trail.” Under the guidance of the all-powerful Voice of the Game, we watch “Then Jane” and her family navigate the deadly perils of 1850s frontier life, while present day Jane navigates the different but all-too-real dangers of high school, college, and eventually adulthood. Jane soon finds herself in her 20s, unemployed and battling an undefinable lifelong sadness, even as “Then Jane” continues to face the tribulations of the trail. With nearly two centuries between them, both Janes face hardships that seem impossible to overcome—until they find one another.