Nina Dobrev and Glen Powell's fans did a double-take after seeing the former lovers ringing in 2026 together. The duo, both 37, enjoyed a sun-soaked vacation in St. Barts alongside Powell's rumoured new partner, Michelle Randolph. Needless to say, photos and videos from the fun-filled getaway have prompted renewed curiosity about where the ex-couple stands after a long-closed romantic chapter.
The curiosity arose when Nina, in her early January 2026 Instagram posts and Stories, shared heartfelt moments of the trio having the time of their life, as they swam, danced, laughed, and played games. The moments were all from a group trip that also included Miles Teller, Keleigh Teller, Chord Overstreet, and Alix Earle.
As the Vampire Diaries star enjoys her newly single life to the fullest after the split from her ex-fiance, Shaun White, it looks like she and Powell are on amicable terms. Here's a look back at Nina and Glen's romance and why they broke up.
Nina Dobrev and Glen Powell's brief romance
Nina was one of Glenn's earliest-known celebrity girlfriends. The dating rumours began in January 2017 after the two were spotted together multiple times, and they posted cute moments on their social media, including a popular photo where they recreated a popular scene from La La Land. From award shows to red carpet events and high-profile parties, the pair was inseparable, and fans also started shipping them together.
However, the romance didn't last long. In November 2017, sources close to the former couple confirmed that they were "taking time apart". An insider told E! News:
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"There hasn't been an official 'split' but Nina and Glen have been taking time apart. Nina just wrapped on a project and is about to start another and her schedule has been a huge part of it. They haven't been spending much time together since the end of the summer."
Neither Nina nor Glen openly addressed the breakup, but reports indicated that both were juggling demanding work schedules and spending less time together, which quietly cooled the romance. However, what did remain was a friendly bond that has grown stronger over the years. The breakup was one of the less dramatic and silent splits that didn't make sensational headlines.
After all these years, their platonic bond keeps showing up in small but meaningful ways. In 2018, the Dog Days actress was seen attending Powell's 30th birthday. Then again, in 2022, Nina walked the red carpet with her then-fiancé, Shaun White, at the 2022 premiere of Powell’s Top Gun: Maverick.
And now, the 37-year-old actress's New Year's celebration posts have reignited fans' interest in her personal life, and they are loving to see Nina's genuine smile after the heartbreak of her 2025 split from White.
Why Nina Dobrev and Shaun White broke their engagement
After a string of high-profile relationships, Nina found one of her longest and most serious partnerships with her former fiancé and Olympian, Shaun White. The two reportedly met in 2019 at a Tony Robbins event and kept their romance private before making it Instagram official in 2020. Over the years, Nina often shared cute moments with Shaun on social media, vacationing together and holding hands at red carpet events, where they appeared happy and deeply in love.
In 2024, Shaun proposed to Nina with a five-carat diamond ring. While fans had been eagerly waiting for the couple to announce their wedding date, it was suddenly reported that they had parted ways. PEOPLE confirmed the news, with sources claiming that though it was not an easy decision, it was a mutual one.
Who is the other woman who posed with Glen Powell?
The other woman seen posing with Nina and Glen in the New Year’s photos is actress Michelle Randolph, who has been linked to Powell in recent months. While the actor has not officially confirmed a romance, the two have been spotted together several times. On December 3, 2025, a source told Us Weekly that Glen and Michelle were casually dating, further fueling speculation about their relationship. The insider said:
"It's very new. They started seeing where things would go around October and have been trying to keep it under the radar for almost two months now.”
Speculation about Glen and Michelle surfaced online in recent months, and it continues to grow with each new appearance. The two were first spotted together in Austin in November 2025, where they were photographed dancing at a bar. In late December 2025, they were seen dining in Miami, staying at the same hotel, and leaving the city together.
Michelle is an American actress and model best known for essaying the character of 'Elizabeth Strafford' in the Paramount+ series 1923 and more recently as 'Ainsley Norris' in Landman. She is the sister of The Bachelor season 23 winner, Cassie Randolph. Michelle is quietly building her niche in acting and is expected to be seen in the upcoming 2026 release, Scream 7.
For now, there’s no indication of romantic rekindling between Nina Dobrev and Glen Powell. If anything, the St. Barts footage highlights how a brief, respectful breakup years ago allowed a friendship to survive. What are your thoughts on their bond?
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