If you ask a casual fan about the The First Time movie Dylan O’Brien project, they usually point to one of two things: the fact that he met his long-term ex-girlfriend Britt Robertson on set, or the vibes of that one specific GIF where he’s looking incredibly stressed in a car. It’s funny. We think of Dylan now as the guy from The Maze Runner or the dude who absolutely carried Teen Wolf as Stiles Stilinski, but back in 2011 and 2012, he was just a kid from YouTube trying to figure out if he could actually lead a film.
Most people assume The First Time was his very first movie. Technically? It wasn't. That honor goes to an indie called High Road (2011), which was basically entirely improvised. But The First Time was the one that felt like a real introduction. It was the first time—pun absolutely intended—that he was the "guy." The lead. The romantic interest who wasn't just there for comic relief.
Why The First Time Still Matters in 2026
Honestly, the teen rom-com genre is usually pretty trash. It's full of tropes that make you want to roll your eyes into the back of your head. But there’s something weirdly grounded about this movie. Directed by Jonathan Kasdan, it doesn't try to be Superbad or a John Hughes rip-off. It’s just two kids, Dave (Dylan) and Aubrey (Britt Robertson), talking.
The plot is thin, but that’s the point. They meet in an alleyway behind a party. They spend a weekend together. They deal with the awkward, fumbling reality of losing their virginity. It’s not flashy. It’s actually kinda painful to watch in some parts because of how real the social anxiety feels.
Dylan’s performance here is the blueprint for everything we love about him now. You see that frantic, fast-talking energy he brought to Stiles, but filtered through a lens of genuine vulnerability.
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The Chemistry That Wasn't "Instant"
There is this massive misconception that Dylan and Britt Robertson had this "love at first sight" moment.
If you look at old interviews, Britt has been pretty open about the fact that their first kissing scene was actually a disaster. She told Hollywire years ago that she felt so bad about it they had to re-film it the next day. They weren't an instant match. They had to work for that chemistry. Of course, they ended up dating for several years after, which became a huge part of the movie's legacy for the fans, but on set? It was just two actors trying not to be awkward.
Breaking Down the "First Time" Era
To understand why this movie is a cult classic for O'Brien fans, you have to look at where he was in his career.
- 2010: Lands Teen Wolf after four auditions. He originally was supposed to read for Scott, but he liked Stiles better. Smart move.
- 2011: High Road comes out. He plays a runaway named Jimmy. It’s his technical debut.
- 2012: The First Time premieres at Sundance. This is where the industry realized he could lead a movie.
- 2013: A small role in The Internship (the Google movie with Owen Wilson).
- 2014: The Maze Runner changes everything.
What People Get Wrong About His "First" Roles
A lot of people think Dylan was a "theatre kid" or went to some fancy acting school. He didn't. He was a cinematographer hopeful who made YouTube videos where he lip-synced to the Spice Girls and did comedy sketches.
When he filmed The First Time movie Dylan O'Brien was still learning the ropes of a professional set. In the film, his character Dave is obsessed with Jane (played by Victoria Justice). He's the "nice guy" who's stuck in the friend zone. It’s a trope, yeah, but O'Brien plays it without the typical "nice guy" bitterness. He makes Dave feel like a real human who is just deeply, deeply confused by his own emotions.
The Sundance Factor
It’s easy to forget that this was a Sundance film. It wasn't some massive blockbuster release. It only made about $92,000 at the box office because it had a very limited theatrical run. Most people found it later on DVD or streaming.
If you go back and watch it now, the dialogue is surprisingly sharp. Jonathan Kasdan (who later wrote for Solo: A Star Wars Story and the Willow series) has a specific way of writing teenagers that feels slightly more articulate than they actually are, but O’Brien and Robertson make it sound natural.
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Real Talk: Is It Actually a Good Movie?
If you’re looking for a plot with high stakes, you’re going to be bored. Nothing really "happens" in the traditional sense. It’s a "walking and talking" movie.
But if you want to see the exact moment a star was born, it’s worth a watch. You can see the gears turning in Dylan’s head. You can see his "thing"—that ability to look like he’s having a minor internal crisis while trying to remain cool.
Some quick facts about the production:
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- It was filmed in about 20 days.
- The script was heavily dialogue-focused, requiring long takes.
- Dylan was balancing the shoot with his Teen Wolf schedule.
Actionable Steps for the Dylan O'Brien Completist
If you've only seen him in The Maze Runner or Love and Monsters, you're missing the foundation of his career. Here is how to actually dive into his early work without wasting time on the fluff:
- Watch the YouTube Archive: Search for "movie_manic" on YouTube. That’s his old channel. It’s cringey, it’s 2000s-coded, and it’s essential to see his comedic timing before he had a script.
- Double Feature: Watch High Road and The First Time back-to-back. You’ll see the jump from pure improvisation to disciplined, character-driven acting in the span of one year.
- Check the Commentary: If you can find the DVD of The First Time, the commentary tracks are gold. They reveal just how much of the "awkwardness" was actually just the actors being genuine.
The transition from a YouTube kid to a Sundance lead isn't common. Most "influencers" fail miserably when they try to act. O'Brien succeeded because he didn't try to be a "personality"—he just tried to be Dave.
To see the full evolution, move from this film directly into his guest spot on New Girl (Episode: "Virgins"). It’s basically the comedic, R-rated version of the same character type, and it proves that by 2013, he had completely mastered the art of being the "awkward but charming" lead.