… a flashback episode slated to air in late April will feature the stories of how each of the New Girl gang lost their virginity. In that episode, O’Brien will play Jess’ (Zooey Deschanel) prom date, a gorgeous, romantic, guitar-playing 18-year-old who promises a memorable “first time” for Jess, who wants to lose her virginity to someone special. But will he be able to actually seal the deal? (x)