Dylan O’Brien Dating History

The ‘Teen Wolf’ movie actor, who is known to be the most eligible bachelor in town amongst the younger generation, has certainly given us something to gossip about when it comes to his relationships. Dylan left many of his fans heartbroken when he officially announced his relationship with Britt Robertson back in 2012, where later the news of the couple being engaged also took over the media.

Despite the actor trying his best to keep his personal life, we all know that the paparazzi are always on the hunt to chase the latest updates on the private lives of Hollywood celebrities.

To know more about Dylan O’Brien’s dating history and the number of women he has been with till now, stay with us and keep reading,

where we will also tell you about whether the Hollywood star is currently seeing someone or simply waiting for the perfect woman to arrive.

Let’s have a quick peek at the names of the ladies O’Brien has dated over the years before going into further details of their relationship.

NamesYears Together
Britt Robertson2012-2018
Chloe Grace Moretz2018
Sarah Ramos2020
Chloe Bennet2022
Sabrina Carpenter2022

1. Britt Robertson

Britt Robertson 

The two met for the first time on the sets of ‘The First Time’ in 2012, but it was not a case of love at first sight. As a matter of fact, the two actors even had trouble building their onscreen chemistry and were not at ease when working together as each other’s love interest. Luckily with time, the actors got to know more of one another and eventually started dating at the end of 2012.

It was not until 2013 that fans got the news that their heartthrob Dylan O’Brien is involved with Britt Robertson. However, the actor did not confirm the relationship but was spotted visiting Robertson on the sets of ‘Tomorrowland’ where he was not cast, which led to the obvious that the two were involved.

By 2015 the couple had already been together for nearly 3 years and were going stronger than ever, also labeled as ‘couple goals’ for their tight-knit relationship. But we all know for a fact that no matter how much in love one is, there are always little things that make each uncomfortable in a relationship. With this being said, both actors admitted in an interview how uncomfortable it was for them to work on set in front of one another. Robertson said that she became nervous working in front of O’Brien and coincidentally he felt the same and avoided working in front of Robertson.

Nevertheless, the actress also mentioned that no matter how busy she and O’Brien were, at the end of the day, they always found time to spend with each other.

2017 was quite a year for the couple as there was a picture on Instagram in June from Robertson’s account saying that they were engaged, but before fans could react to the news, the picture was taken down as the actress confirmed that her account had been hacked who had posted the engagement rumor.

Sadly, three months later, in September, O’Brien had an accident on the sets of the ‘ Maze Runner’ where he was injured severely and in a very bad state both physically and mentally. The actor couldn’t help but tell the media how his girlfriend, Britt Robertson, was nothing less than a saint to have stood by his side every step of the way during his recovery process.

Unfortunately, the famous proverb, ‘all good things must come to an end,’ proved to be true once again when the couple split up after being in love for 6 years, marking the longest relationship of Dylan O’Brien’s dating history. Although the duo didn’t announce anything publicly, they were seen hanging out with other people. That’s when we knew that the two had chosen different paths.

2. Chloe Grace Moretz

Chloe Grace Moretz 

In 2018 after the breakup with Robertson, O’Brien was spotted spending quality time with his longtime crush Moretz in Los Angeles. Sources have mentioned that the duo was seen at the ‘Nice Guy Restaurant’ two nights back to back where they didn’t arrive together to avoid attention from the media. But upon the couple leaving the restaurant together, the paparazzi managed to take a few clicks and also reported that the two stars were flirty and all over each other, which led to rumors being speculated about their dating.

Unfortunately, their relationship was kept out of the limelight for good, and we still don’t know whether the two were into something serious or just passing the time as good friends.

Just for the record, in 2011, O’Brien said in an interview that he had a crush on Mortez after watching her perform in the movie ‘ Kick Ass’. But the actor soon had to withdraw his remark as he found out from Wikipedia that Moretz was only 14 years old when the movie came out, after which O’Brien commented that Morterz is a very cute and talented girl and he most definitely does not have a crush on her!!

3. Sarah Ramos

Sarah Ramos

Ramos and O’Brien were the talks of the town when a video of the two actors went viral on social media back in 2020, where they recreated a scene from ‘ The Social Network’. Even though this sounds pretty normal, the video raised many questions among fans as a majority of them thought that the actors were quarantining together, causing suspicions to arise of a secret affair between the duo.

But as we know, our suspicions do prove us wrong at times, and this was one of those times, honestly speaking, the two friends were just having a laugh trying to keep us entertained. Besides that, Ramos has been romantically involved with Matt Spicer since 2013, with whom she tied the knot later on at the end of 2020.

To conclude we can say that O’Brien and Ramos are simply the best of friends who enjoy each other’s company. Also, according to sources, Dylan has been spotted hanging out with Ramos and her husband Matt quite a few times, as the trio is on excellent terms with one another.

4. Chloe Bennet

Chloe Bennet 

Chloe Bennet is another name that can be associated with Dylan O’Brien’s dating history. In June 2022, the two were seen having lunch together at Potato Chips in Los Angeles, where outsiders commented that both actors seemed to be flirting with one another and enjoying each other’s company, yet again spreading rumors of the couple dating.

O’Brien and Bennet have been asked multiple times about the rumors and their relationship, but both of them prefer to avoid answering, leaving us in a hanging situation.

5. Sabrina Carpenter

Sabrina Carpenter 

O’Brien and Sabrina Carpenter, the actress plus singer, have kept on confusing us as to whether they are an item or just share a flirty relationship as good friends.

The rumor started in September 2022 when multiple fans claimed to have seen the duo to be intimate a couple of times in two different bars, one located in New York City and the other one in Manhattan.

The age difference between the two is 8 years, leading to people passing remarks about Carpenter being too young for O’Brien. But then again, the two have not given any clarification regarding their relationship, so we cannot say anything for certain.


After dating Britt Robertson for six years, it is quite obvious that O’Brien has not been able to find someone to stick with for a long. Dylan O’Brien’s dating history tells us that he has been seen with many stars and associated with several rumors, to which none he admitted.

From this, we can conclude that O’Brien likes to keep his private life a secret. However, the current rumor about the actor is that he could be dating Sabrina Carpenter.

Whatever the case, all we can do is wait and see if we get any confirmation about the actor’s current relationship status, as we are more than curious to know which lucky lady gets to date the all-in-one Dylan O’Brien.

Previous articleLisa Marie Presley’s Death Cause Remains Still Unknown: Further Investigation to Take Place
Next articleMichelle Williams Dating History: Love Life, Boyfriend, Fiancee, Marriage, Divorce (American Actress)
Al Amin Sagor is simply a movie freak who is passionate about writing entertainment content. He loves to watch web series, and movies and write on celebrity gossip or trendy movie news. He also covers media and entertainment news on various online platforms. He is one of the "Jewel" of The News Titan.


Please enter your comment!
Please enter your name here