Jeff was born sometime in the mid-1970s to William and Doreen Winger, although they divorced when Jeff was still young. This divorce would have two essential impacts on Jeff's life because it meant that he grew up without a father — which is a part of several of his more important storylines — and it would inspire him to become a lawyer.
In the season 2 episode "Accounting for Lawyers," Jeff describes his earlier encounter with a lawyer that helped steer his career goals. He explains that his parents' divorce ended in a messy custody battle, in which he met one of the first people he ever admired, the lawyer who left the courtroom in a "great-looking suit and a sky-blue Mercedes SLK." While viewers don't get to learn much more about Jeff's childhood throughout Community, there is one other moment the show explores — his childhood encounter with a bully named Big Cheddar, who he eventually realizes was his friend Shirley (Yvette Nicole Brown). In "Foosball and Nocturnal Vigilantism," a competitive game of foosball causes them to realize their younger encounters, in which a particularly embarrassing foosball loss ultimately caused a 10-year-old Jeff to switch schools.
Likewise, much of Jeff's time in high school is left unexplored, although viewers do get a chance to see a teenaged Jeff auditioning for The Real World: Seattle. During the second season episode "Intro to Political Science," Annie (Alison Brie) plays a tape of Jeff singing a cover of George Michael's "Faith" while wearing aviator sunglasses and a leather jacket with his name spelled out in tape on the back.
