Dylan O’Brien had a New Girl cameo in season 2, but which character did he play? Created by Elizabeth Meriweather, Fox sitcom New Girl follows quirky middle school teacher Jess Day (Zooey Deschanel) after learns her live-in boyfriend is cheating on her and subsequently moves into a Los Angeles loft apartment with three new male roommates. They are lovable slacker Nick Miller (Jake Johnson), ladies’ man Schmidt (Max Greenfield) and prankster Winston Bishop (Lamorne Morris).
New Girl ran for seven seasons and chronicled the misadventures of the gang – plus Jess’s best friend Cece Parikh (Hannah Simone) – as they navigated life in their thirties, earning plenty of praise for its offbeat humor and cast chemistry along the way. The sitcom boasted an impressive roster of cameos during its run too – from recurring New Girl guest stars like Jamie Lee Curtis and Rob Reiner as Jess’s divorced parents Joan and Bob to one-off appearances from the likes of pop legend Prince, celebrity chef Gordon Ramsay or Happy Days star Henry Winkler.
In its second season, New Girl featured appearances from Brenda Song (as Winston’s love interest Daisy), Dermot Mulroney (as Jess’s ex Russell) and Taylor Swift played Elaine – the former lover of Cece’s almost-husband Shivrang (Satya Bhabha) who memorably interrupted their wedding to declare her love for him. Maze Runner star Dylan O’Brien also appeared in a New Girl season 2 episode titled “Virgins” as a character credited simply as “The Guy.” In this flashback-heavy episode, Jess receives a text from an old flame named Teddy which prompts the gang to reminisce about how they lost their virginity in an unofficial contest to determine who had the worst first time
A flashback to Jess’s teenage years reveals she first attempted to get romantic with her prom date (Superstore and Son Of Zorn actor Johnny Pemberton) who she co-founded her high school’s Gender Equality Society with. The pair took to their post-prom hotel room, but Jess soon got frustrated by her date being a tad too courteous and dejectedly retreated to the hotel hallway. There she met Dylan O’Brien’s New Girl character “The Guy,’ a guitar-strumming teen dream who Jess is instantly infatuated with after they sing one-hit-wonder Lisa Loeb’s classic ’90s track “Stay (I Missed You)” together.
Unfortunately, Jess and O’Brien’s The Guy’s meet-cute in the New Girl season 2 episode was interrupted when her prom date had a medical emergency, but the pair eventually reconnected by chance a few years later when Jess – still a virgin – moved to Los Angeles and bumped into him at the bar that would become the gang’s main hangout. They tried to hook up but because neither had their own place, they ended up in a tiny castle in a kid’s playground where the pair ended up wedged and half-naked. Jess and The Guy (whose real name is never revealed) part ways on bad terms, but on the upside, she did end up losing her virginity the following day to Teddy (Christopher Wallinger, American Crime Story) – one of the firemen who rescued Jess and The Guy from their rather embarrassing predicament.
Dylan O’Brien wasn’t the only New Girl guest star in “Virgins.” The episode also featured cameos from Merritt Wever (Nurse Jackie) as Schmidt’s first-time love Elizabeth, Mad Men actor Joseph Culp as Mick Jagger – who Cece lost her virginity to – and Looking’s Lauren Weedman as the woman Winston first had sex with who he finds out in the present-day was a sex worker paid to deflower him. For any New Girl fans wondering, it was Winston – not Jess – who ended up winning the “worst first-time” contest.
