Dylan O'Brien's Dating History Includes Only One Confirmed Girlfriend

While he rarely talks about his love life in public, actor Dylan O'Brien's girlfriend, or if he has one, remains an enigma to fans. The "Teen Wolf" star was once linked to a married woman and even rumored to be engaged.

Recently, Dylan O'Brien was linked to singer and actress Sabrina Carpenter after an alleged photo of the pair spending time together went viral. The image was shared via a popular gossip site by an anonymous witness that claimed they saw the actors being more than friendly with each other.

The sighting garnered mixed reactions, with some fans worrying about the age gap between the two and others supporting the rumored romance. It remains to be confirmed or denied, and the same goes for many of O'Brien's supposed former flames.

Dylan O'Brien is pictured at the 2022 MTV Video Music Awards at Prudential Center on August 28, 2022, in Newark, New Jersey | Source: Getty Images

Several years ago, he was in a confirmed long-term relationship with his former co-star Britt Robertson. After the lovers separated, O'Brien spent time with many other actresses, fueling more curiosity about his dating life. Still, he never entertained the speculations.

The actor has received much acclaim for his impressive portrayal of his characters. While he is aware of the fame they brought him, he seems to harbor no attachment to his celebrity status. During an interview in July, O'Brien said he found the likelihood of losing that fame quite "freeing."

When it came to generally accepted dating expectations, the "All Too Well" co-star rejected most of them, saying they were "entrenched in dated misogyny." Rules such as the guy being expected to initiate everything, including texts or dates, or "making the first move" seemed silly to O'Brien.

Dylan O'Brien poses at A24's "Bodies Bodies Bodies" New York Screening on August 02, 2022, at Fort Greene Park in New York City | Source: Getty Images

While he wasn't entirely against being the one to initiate any kind of romance, he explained that if a woman offered to pay or took the initiative, he wouldn't feel "emasculated." However, a rule that did repulse O'Brien was about "making the first move," in which case some form of physical affection took place.

O'Brien thought the expectation of making the first move caused discomfort because of the lack of communication. He noted that one could never know if the other person would be comfortable with something like a spontaneous kiss. Sometimes the moment can be misread. Explaining his preference, he said:

"I much prefer to ask if I want to kiss somebody. You know what's sexy? Communication. [Laughs.] Clear communication. Not surprising someone with a kiss when maybe they don't [...] want to or they're not ready or not feeling it."

Dylan O'Brien poses on the red carpet at the "Not Okay" New York Premiere at Angelika Film Center on July 28, 2022, in New York City | Source: Getty Images

Moreover, the "Maze Runner" alum joked that he didn't trust most men to "read the room" after rejecting the idea of surprising women with kisses. Interestingly, he made exceptions for special cases, such as when his crush kissed him "mid-sentence."

Dylan and Sabrina Carpenter Reportedly Spent Time Together

In September this year, O'Brien and Carpenter were allegedly spotted spending time together in New York City. An anonymous witness sent a photo of the pair to the gossip outlet DeuxMoi on Instagram, depicting them dressed casually in the city's streets.

The reports immediately swirled on the internet, and romance speculations soon ensued. Another social media user claimed to have seen O'Brien and Carpenter sharing a kiss in a local bar, fueling the rumors; yet when fans asked for proof of the kiss, none was submitted.

The reports of this meeting garnered mixed reactions from the public, with many fans worrying about the eight-year age gap between the 31-year-old O'Brien and 23-year-old Carpenter. Others didn't seem to mind it since they were both considered adults and even supported the possibility of Carpenter being Dylan O'Bryan's girlfriend.

On the other hand, O'Brien and Carpenter's meeting coincided with the New York fashion week, and some fans thought they were only in the city to attend the shows. Another social media user claimed that the woman in the viral picture looked nothing like Carpenter. Still, their romance remains to be confirmed nor denied.

Sabrina Carpenter poses for a photo at the Teen Vogue Summit 2022 at Goya Studios on November 12, 2022, in Los Angeles | Source: Getty Images

Dylan and Sabrina Have a Friend in Common

While it remains unclear if Carpenter is indeed Dylan O'Brien's girlfriend, they share a mutual connection with singer-songwriter Taylor Swift. Carpenter's connection to the "Wildest Dreams" hitmaker began in 2009 when she performed a cover of Swift's "Picture To Burn." The "Girl Meets World" actress was only ten at the time.

The following year, she attended one of Swift's concerts and raved about how much she enjoyed herself in a touching tweet. Carpenter then expressed her hopes someday to have a world tour as successful as Swift's, citing two of the singer's sold-out shows.

In August 2020, Carpenter sat down with Apple Music following the release of Swift's album "Folklore," where she admitted that Swift influenced how she navigated her musical career. The year after, Carpenter received a Red Taylor Version Package from the artist and shared the moment on her Instagram story.

(L-R) Sabrina Carpenter, Taylor Swift, and Rosé are pictured at the 2022 Republic Records VMA Afterparty at The Fleur Room on August 28, 2022, in New York City | Source: Getty Images

She expressed her gratitude in the caption, affectionately referring to the artist as "blondie :’)." This year in August, Carpenter and Swift were pictured together at the Republic Records after-party at the Fleur Room alongside Rosé.

They also attended the American Music Awards ceremony this November and shared a sweet and humorous moment as Carpenter presented Swift with the Favorite Music Video award for "All Too Well." As she ascended the stage, Swift patted Carpenter on the head, making a subtle joke about their height difference.

Carpenter simply laughed before accepting a hug from the awardee. Her rumored beau also has a close relationship with Swift and regularly spends time with the "Blank Space" artist. O'Brien starred alongside "Stranger Things" actress Sadie Sink in Swift's rendition of "All Too Well."

(L-R) Taylor Swift, Sabrina Carpenter, and Gayle pose for a photo at the 2022 American Music Awards at Microsoft Theater on November 20, 2022, in Los Angeles | Source: Getty Images

Swift hadn't personally known O'Brien until she reached out to cast him, but she had always been a fan of his work. After the success of "All Too Well," the pair developed a bond and remained close friends. O'Brien even appeared on Swift's latest album "Midnights," released earlier this year.

He is credited as the drummer for the tracks "Snow On The Beach" and "Question…?" While O'Brien's connection to Carpenter remains unconfirmed, the "Emails I Can't Send" artist was romantically involved in a high-profile relationship with Joshua Bassett in August 2020.

Dylan O'Brien and Taylor Swift are pictured hugging accept the Video of the Year award for 'All Too Well (10 Minute Version) (Taylor's Version) (From the Vault)' at Prudential Center on August 28, 2022, in Newark, New Jersey | Source: Getty Images

Dylan Was Spotted Having Lunch with Chloe Bennet

Earlier this year, O'Brien and the "Agents of S.H.I.E.L.D" actress enjoyed a lunch date in Los Angeles at the Potato Chips Deli. Witnesses who also visited the restaurant claimed that Bennet and O'Brien were flirting with each other despite the seemingly casual outing.

The pair matched in white t-shirts, with O'Brien sporting a black cap, patterned shorts, and white sneakers, while Bennet wore cropped jeans and slip-on sliders. Outlets reached out to each party's team of reps to confirm the romance, but neither responded, and the speculations about Bennet being Dylan O'Brien's girlfriend soon fizzled out.

Chloe Bennet is pictured in Los Angeles on October 25, 2022 | Source: Getty Images

Fans Thought Dylan Was Secretly Dating Sarah Ramos

After Ramos and O'Brien recreated a scene from the film "The Social Network" and posted it on social media last year, rumors about the nature of their relationship arose. Fans of the two speculated if the video had been created in the same house. They also wondered if the pair had been quarantining together.

The rumors were fueled by Ramos's marital status, as she had been married to her longtime lover, Matt Spicer, since 2020. However, O'Brien cleared the air, saying that Ramos had always been his good friend, and the scene recreation was a friendly collaboration with scenes shot separately and discussed via FaceTime.

Sarah Ramos poses on the red carpet at the 2022 MTV VMAs at Prudential Center on August 28, 2022, in Newark, New Jersey | Source: Getty Images

Dylan Hung Out with Chloë Grace Moretz in 2018

Chloë Grace Moretz and O'Brien enjoyed a night out at The Nice Guy in Los Angeles with friends in August 2018. The pair reportedly stayed at each other's sides at the restaurant as they laughed and took pictures together. They exited the establishment separately but left for Avenue in the same car.

While romance speculations surfaced, sources maintained that the outing was casual as O'Brien and Moretz were joined by other people. Years before, in 2011, O'Brien had commended Moretz for her performance in "Kick-Ass," adding that she was his crush – a remark he later retracted due to her age at the time.

Chloë Grace Moretz poses for a photo at the Haider Ackermann + FILA show on November 17, 2022, in Manchester, England | Source: Getty Images

Dylan's Relationship with Britt Robertson Was the Longest

Robertson is, so far, the only woman confirmed to have been Dylan O'Brien's girlfriend. Their relationship began soon after they co-starred in 2012's "The First Time." The former lovers first met on the film set, and they dated for six years until they separated in 2018.

O'Brien and Robertson never confirmed the reasons for their split, but some reports suggested they'd already moved on to other people before breaking up. Others claimed that the former couple had relationship problems.

Britt Robertson and Dylan O'Brien are photographed as they arrive at "The First Time" Premiere during the 2012 Sundance Film Festival at Eccles Center Theatre on January 21, 2012, in Park City, Utah | Source: Getty Images

Still, they had many supporters, who were excited when they saw Robertson "announce" that she and O'Brien would marry in 2017 on Instagram. While the since-deleted post was well-received, its caption was still somewhat strange.

Eventually, it was discovered that Robertson's account had been hacked, and no such development had occurred in the actors' relationship. Fans were disappointed to see their romance end the following year and were especially crushed after it turned out the engagement announcement was false.

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