After his huge breakthrough into acting through his leading role in the beloved teen drama Teen Wolf, Dylan O’Brien went on to develop a pretty impressive career. From starring in The Maze Runner series to returning to the screen in Not Okay, O’Brien garnered a lot of public attention throughout his career.
Related: Everything Dylan O'Brien Has Said About Appearing In The Teen Wolf Movie
Despite his huge public presence, O’Brien has famously preferred to keep a large part of his life away from the public eye. This includes anything to do with romance and his romantic life. While his long-term romance with fellow young actor Britt Robertson was made known to fans globally, it turns out that O’Brien has actually had a far more interesting and longer dating history than many may know. So let’s take a look at the actor's list of past and current romantic partners.
8 He Met Britt Robertson In 2012
Despite the actor’s preference to keep his private life away from the public eye, his most known relationship to date was that with The Longest Ride star, Britt Robertson. The pair of young actors first met in 2012 when they starred alongside each other in the Jonathan Kasdan romcom The First Time. In the film, O’Brien and Robertson played young lovers Dave and Aubrey, who embark on a relationship that sees them experience a series of firsts together.
7 The Pair Went On To Have A Long-Term Relationship
Following their first meeting, it seems as though their incredible on-screen chemistry translated far beyond the screen as the pair began to date. The next 6 years saw the pair develop a heartwarming relationship together. Both Robertson and O’Brien didn't shy away from directly addressing the relationship to the public and made things work despite their busy schedules and budding careers. During an interview with Clevver [via Elite Daily] Robertson detailed the way that the pair respected each other’s professional boundaries yet still found time for each other.
The actress mentioned, “When I go visit him I don’t even go on set. And, when he visits me it’s very rare that I’ll go on set.” Before later adding, “You know, you just find the time to be with one another.”
6 But They Broke Up In 2018
However, despite the fairytale romance between the pair, the young actors ultimately called it quits after 6 years in 2018. As it was reported, sources speculated that the reasoning behind the breakup was due to the pair wanting different things from the relationship. While O'Brien gave off signs of wanting a spontaneous kind of love, Robertson was seemingly in the market for something different.
Related: The Accident That Changed Everything For Dylan O'Brien
5 A Rumored Fling With Chloë Grace Moretz
After the shocking breakup, it seems as though O’Brien was more than ready to put the heartbreak behind him and start up a new adventure with a different, yet equally talented, lady. According to People, O’Brien and Kick-Ass star Chloë Grace Moretz were spotted together at The Nice Guy in Hollywood during the summer of 2018. While neither of the pair ever spoke up about the rumored fling, O’Brien had previously admitted having a crush on the actress during a 2011 interview with Hollywire.
The actor stated, “I wanna give a special shout out to Chloe Moretz because she is the most badass little chick that I’ve ever seen,” He then added, “What she did in Kick-Ass is amazing, and I have a crush on her.”
4 His Long-Time Crush On Selena Gomez
While on the subject of O’Brien’s celebrity crushes, the most notable mention must go to the actor’s infatuation with the Grammy-winning singer and actress Selena Gomez. Throughout the years, the actor has never been shy to directly state that his all-time celebrity crush was the Disney Channel icon. However, due to the wild fan reaction that the admission of the crush brought around, O’Brien went on to retract the statements.
He stated, “I kinda have no freedom now changing my celebrity crush at all because four years ago I said this, and it’ll follow me I think until I die. I think I’m done with celebrity crush names because it kind of just follows me around.”
3 Another Speculated Fling With Sarah Ramos
While not much was heard about the actor’s romantic life from 2018 onwards, in 2021 rumors sparked of his involvement with Parenthood star Sarah Ramos. The speculation came after the pair recreated the iconic “laptop scene” from the Oscar-winning 2010 film, The Social Network. However, despite the public’s interpretation of the pair’s relationship, O’Brien himself went on to clarify the true nature of the relationship and even labeled the actress as “one of his best friends”.
2 His Rumored Relationship With A Mystery Woman
Despite his relationship with Ramos being purely platonic, it seems as though 2021 didn’t go without romantic flair for O’Brien. Back in June 2021, O’Brien was speculated to be dating a mystery girl referred to as “the girl in the purple hoodie” by fans. The rumors came after a source at Deuxmoi revealed that the actor’s new girlfriend was a sweet non-famous girl from the same neighborhood as him. However, O’Brien never publicly addressed the relationship or the mystery woman.
Related: How Sadie Sink Really Felt Working With Dylan O' Brien in Taylor Swift's All Too Well
1 Thought To Be Dating Chloe Bennet
Whether O’Brien dated the mystery “girl in the purple hoodie” or not, it seems as though the speculated romance was short-lived anyway. In June 2022 rumors began to circulate that O’Brien was romantically linked with Agents Of S.H.I.E.L.D star Chloe Bennet. The rumors came after TMZ spotted the pair sharing a cute lunch at Potato Chips Deli In LA. According to the report, the pair’s interactions were very flirty. Despite the news surfacing, neither of the pair confirmed nor denied the romance.
