Sebastian Stan's Relationship History: From First "Serious Love" to Current Romance

Known for his role in the Marvel universe as Bucky Barnes, Sebastian Stan often leaves fans swooning with his good looks and charming personality. Understandably, many of his adoring fans often wonder what things look like for Sebastian in the romance department. Turns out, he has had a very star-studded list of girlfriends on his quest to find his happily ever after.

From his first “serious love” with Gossip Girl co-star Leighton Meester to his budding romance with Annabelle Wallis, Sebastian Stan’s relationship history is full of captivating chapters. Keep reading as we take a closer look at this charming actor’s relationship timeline.

Sebastian’s first high-profile romance was with his Gossip Girl co-star Leighton Meester. The two met in 2008 on the set of the hit TV show, where Sebastian played Carter Baizen and Leighton starred as Blair Waldorf. Their relationship quickly became a fan favorite. During an interview with Variety, Sebastian later referred to Leighton as his “first serious love.”

Despite their strong bond, the couple called it quits in 2010. Neither has publicly shared why they broke up, but the split appeared to be amicable. Fans still look back on their romance as one of Sebastian’s most memorable early relationships.

After his split from Leighton, Sebastian was linked to Glee star Dianna Agron in 2011. Their romance started with sparks but fizzled out by the end of the year. The couple briefly reunited in early 2012, but their connection didn’t last. Reports suggested long-distance challenges and trust issues contributed to their final breakup. Though short-lived, this chapter in Sebastian’s dating history kept fans and tabloids talking.

In 2012, Sebastian started dating Jennifer Morrison after they met on the set of ABC’s Once Upon a Time. Sebastian guest-starred as the Mad Hatter, while Jennifer played Emma Swan. Their on-screen connection quickly grew into a real-life romance.

The couple appeared happy, often attending events and supporting each other’s careers. However, their relationship ended in mid-2013 after about a year together. Both Sebastian and Jennifer stayed silent about the reasons behind their breakup, keeping things private.

One of Sebastian’s longest relationships was with Margarita Levieva. The two first crossed paths while filming the 2009 movie Spread, but their romance didn’t begin until 2014. The couple kept things low-key, occasionally sharing glimpses of their life together on social media.

Fans loved seeing Sebastian post travel photos featuring Margarita, but the pair parted ways in 2016 after two years together.

In 2020, Sebastian sparked dating rumors with Spanish actor Alejandra Onieva. The couple kept their relationship mostly under wraps, rarely appearing in public together. Sebastian gave fans a peek into their romance in 2021 with a playful birthday tribute on social media. By late 2021, however, their relationship had quietly ended.

Sebastian’s most recent relationship is with British actor Annabelle, known for her roles in Peaky Blinders and The Mummy. The couple was first spotted together in May 2022 at Robert Pattinson’s birthday party. Since then, they’ve attended several high-profile events, including the Cannes Film Festival in 2024.

Annabelle has shown her support for Sebastian’s career by frequently celebrating his achievements on social media. Though the couple values privacy, fans have occasionally caught glimpses of their sweet connection.

Sebastian’s relationship history is as intriguing as his Hollywood career. From his first love with Leighton to his current relationship with Annabelle, Sebastian’s journey through love reflects the challenges of balancing fame and personal life.