Dylan O’Brien rocketed into the pop culture spotlight as the hilarious, sharp-tongued Stiles Stilinski on MTV’s “Teen Wolf,” winning over fans with a blend of perfect comedic timing and disarming vulnerability. What many might not realize is that, before landing the life-changing role, O’Brien was practically a newcomer – his only acting credits were a handful of self-made comedy videos uploaded to YouTube.
Growing up in New York and New Jersey, a young O’Brien had his eyes set on sports broadcasting, not acting. But after his online skits caught the right kind of attention, fate threw him onto a completely different track – one that led from web videos to Hollywood film sets in a matter of a few eventful years.
Breaking out on television, O’Brien quickly took a gamble by signing on as the lead in “The Maze Runner” film series. Not only did the dystopian blockbuster trilogy rake in a staggering $900 million worldwide, but it also cemented O’Brien’s place as a bankable star. His momentum nearly came to a halt in 2016 after a serious accident during the filming of “The Death Cure” left him hospitalized and sidelined for months – a setback that could have derailed a lesser career. Instead, O’Brien made a steady and determined return, diving into diverse projects like “Love and Monsters” and “The Outfit,” proving his resilience and expanding his range along the way.
The Private Side of Dylan
As his career has blossomed, O’Brien has insisted on keeping at least one thing out of the spotlight: his private life. He avoids Instagram altogether and keeps his personal world close to the vest, rarely venturing into tabloid territory or oversharing in interviews. Ironically, it’s this mystique that seems to make fans all the more intrigued by who he is off camera.
One of his longest relationships was with actress Britt Robertson. The two met while filming “The First Time” in 2011 and spent several years together, quietly navigating their romance away from red carpets and social media posts common among other Hollywood couples. By the time they reportedly split in 2018, they had never been staple tabloid fodder – a reflection of O’Brien’s no-nonsense approach to fame.
Most recently, O’Brien was linked to model Rachael Lange after the two were seen hand in hand at Paris Fashion Week in January 2023. True to form, neither has spoken publicly about the relationship – if there even is one.
The rumor mill has swirled around O’Brien before. At different times, he’s been spotted with or rumored to be involved with several industry names, including:
- Chloë Grace Moretz (with whom he shared the screen in “The Maze Runner”)
- Britt Robertson (confirmed relationship from 2011-2018)
- Sabrina Carpenter (seen together at a club in 2022)
Still, genuine glimpses into O’Brien’s personal philosophy are rare. On a 2018 podcast, when pressed about romance, he simply said, “The older I get, the more I value authenticity over everything else. That’s true for work, friendships, and especially dating.”
If there’s a through-line to O’Brien’s story – from his rise as an unlikely YouTube star to a leading man in Hollywood – it’s his grounded nature. Friends and castmates repeatedly emphasize how little fame has changed him. As “Teen Wolf” co-star Tyler Posey once put it to Entertainment Weekly, “Dylan’s the same guy now that he was when we started – just with better clothes and more people asking for his autograph.”
Past Relationships
Rachael Lange
Sabrina Carpenter
Chloe Bennet
Gracie Abrams
Chloë Grace Moretz
Britt Robertson
In recent years, O’Brien has taken on projects that challenge him in new ways – including an acclaimed role in Taylor Swift’s “All Too Well” short film – while continuing to guard his personal life. He seems perfectly content to let his work do the talking, keeping the rest of his life exactly where he likes it: out of the spotlight.