Where do the horny tweens go when a teen idol disappears? When Dylan O’Brien vanished five years ago, I went to Tumblr, then Twitter, then a liberal-arts college. I turned Teen Wolf microblogging into social-media-management experience, outfitting résumés with conversions from horny reblogs to ad dollars. I got an entry-level salary and a Rent the Runway membership and started calling Oscar Isaac “daddy.” I lost my Tumblr password and grew up. All the while left to wonder, where have all the funny, werewolf-adjacent, brunet Mets fans in Jeeps gone?
Following a hiatus from the limelight, O’Brien is back and harnessing the horny power of the internet for good. To the tune of a heartbreak anthem and in the un-showered meta-shoes of Jake Gyllenhaal, the original “internet boyfriend” is ready to reboot.
While his early fame predates the term internet boyfriend, he bore all the markings of the breed. His role as Stiles Stilinski, lead human and comedic relief in MTV’s Teen Wolf, earned O’Brien “breakout star” status and began our virtual love affair. He was absent from Instagram, which passed for mystery. He was a genuinely talented actor not known for romantic roles, allowing fans to write their own fantasies. He was progressive without the “I’m a male feminist” energy, and if my previously mentioned Teen Wolf microblogging didn’t give it away, he was god-tier GIF fuel. The internet lore around him eclipsed his commercial fame, and his celebrity was a fault line that separated two eras of celebrity crush: the poster on the wall and the anonymous internet smut. His fans had imagination and the internet, forces they wielded to invite absolute sexual chaos. They obsessed over every detail, down to his favorite baseball team and the broken-down blue Jeep his character drove. Wattpad and Tumblr “imagines” bred some of the most creative erotica you’ve ever seen written by hormone-riddled tweens, and Dylan O’Brien was their muse.
In a move toward mainstream fame, he went on to lead the Maze Runner movies, riding the “dystopian future” wave of content that held an iron grip on society around 2015. His fans followed him to the maze, but after a traumatic on-set injury in 2016, our internet boyfriend was MIA. In the years of silence, we moved on.
Then, unlike our other ex-boyfriends, politics brought us back together. After years in the recesses of my mind, O’Brien reentered the conversation, turning to Twitter to deliver swoon-worthy content about impeaching Trump, getting vaccinated, and supporting women’s rights in Texas. He achieved what many men before him have found impossible: championing women without the ick. Where the Brads, Chads, and state legislators let us down, our first internet boyfriend was there to pick us back up.
Onscreen, art began to imitate tweet as O’Brien slowly reemerged as a leading man, embracing the internet’s obsession with him. When we measure the past week against his ten-year career, we see he’s at his best when he exists online in our stories. The appeal of this O’Brien (Taylor’s Version) is his willingness to perform on stages set by female artists. And like before, internet culture is making him famous.
In May 2020, the internet was a dark place, having recently been ravaged by the “Imagine” music video. Actor Sarah Ramos had been steadily making quarantine a funnier place with her “quaranscenes” when she found herself viral once again. Twitter was abuzz over her Social Network spoof with Eduardo Saverin played by none other than our absent king DOB in his hoodie and his fuck-you flip-flops.
The short video made a massive splash and caught the attention of Andrew Garfield, who praised O’Brien’s portrayal of the character he had played years ago. O’Brien told The Hollywood Reporter the one minute, 27-second clip generated “more clout in this industry than I’ve gotten in a decade.” I guess my quarterly search for “who is dylan o’brien dating” wasn’t quite delivering.
Then came August 2021, when O’Brien returned looking like that guy you dated in Bushwick, complete with temporary tattoos, Gen-Z streetwear, and a fresh bleach and tone. He was promoting his upcoming film Not Okay, written and directed by Quinn Shephard, which follows a young woman (Zoey Deutch) who takes a trip to Paris seeking social-media fame but gets caught up in a “terrifying incident.” With just a few photos and a new lady-powered project, he woke his sleeping fandom and expanded it to the money-piece community.
Come November 5, Taylor Swift’s Instagram teaser video for All Too Well: The Short Film nearly broke the internet, racking up over 8 million views in the days preceding the release and breeding countless headlines nodding to the casting. Dylan stars alongside Stranger Things alum and future Oscar winner Sadie Sink, both having been handpicked by Swift.
The surprise casting reminded the world of what we had been missing: our funny, brunet, vaccinated, pro-choice Mets fan in a Jeep.
Written and directed by Swift, the short film dropped Friday night and garnered 1.2 million views in the first 30 minutes, passing another million every hour. The video itself is ripped from vintage “aesthetic” Tumblr, marked by fall foliage, fairy lights, and wire headphones. Bearded, buzzed, and beanied, O’Brien gives a painfully convincing portrayal of your last non-internet boyfriend alongside Sink’s hopelessly romantic Swift. Together, the two tell a story of heartbreak bred from immaturity with a sprinkle of pumpkin spice and gaslighting.
Last weekend, All Too Well dominated every boozy brunch conversation and every other tweet in my timeline, all echoing the same sentiment: the perfect casting for a perfect video for the best song Swift has ever written.
Today, O’Brien’s fan-base potential goes far beyond retired fanfic writers; he has reemerged earnestly as an artist. Just weeks ago, he starred as a more Hollywood version of himself in an episode of Curb Your Enthusiasm, reintroducing himself as a legitimate comedic actor who can hold his own opposite an industry legend. Call it kismet or call it a genius agent, the cameo amplified O’Brien’s rock-solid return to relevance. As the 30-year-old reunites with a ten-year-old fandom, we have to ask: Did the love affair maim you too?
The teenagers who once crushed on O’Brien were the same teenagers overplaying All Too Well, feeling the song’s lyrics more deeply than a 14-year-old should, but that’s the true Taylor Swift effect. Your vintage celebrity crush meets the first song to truly break your heart, a perfect partnership rooted in nostalgia.
