The start of 2026 saw actress Nina Dobrev ringing in the new year with a sun-soaked Caribbean getaway, but it was her company that truly set the internet abuzz. The 'Vampire Diaries' star shared a video montage from her holiday, which notably featured her ex-boyfriend, actor Glen Powell, and his current rumored girlfriend, Michelle Randolph.
A St. Barts Reunion Captivates Fans
In the cheerful video posted by Dobrev, the trio was seen sharing remarkably relaxed and upbeat moments together on the island of St. Barts. The scenes quickly captured fan attention, showcasing the group engaged in various lively activities. They were spotted dancing at a nightclub, playing pickleball, working out, and swimming in the pristine Caribbean waters. The overall vibe suggested a comfortable, friendly dynamic rather than any lingering awkwardness from past relationships.
One particular image that drew widespread notice featured Nina Dobrev posing cheerfully between Glen Powell and Michelle Randolph. According to a report by Mandatory, the ease displayed by all three individuals stood out, highlighting a mature and cordial friendship.
Star-Studded Guest List and Heartfelt Caption
The vacation was a celebrity-filled affair, with the guest list including actors Miles Teller and his wife Keleigh Sperry, Chord Overstreet, and social media influencer Alix Earle. Prior to the viral video, Dobrev had hinted at the special nature of the trip in a social media post on January 3. She captioned it, “Some old Friends, some new friends… now all best friends. Haven’t laughed, been in awe, or smiled this in my life, The perfect way to ring in the new year.”
From Past Romance to Present Friendship
Nina Dobrev and Glen Powell dated briefly in 2017 before amicably parting ways. Both have since moved on in their personal lives. Powell, renowned for his role in 'Anyone But You,' is currently linked to actress and model Michelle Randolph. Their appearance together on this trip seems to confirm their relationship status.
For Dobrev, the holiday comes a few months after a significant personal chapter closed. In September 2025, she and Olympic snowboarder Shaun White mutually ended their engagement. The couple had been together for five years and got engaged in New York City in October 2024, with White presenting a 5-carat diamond ring. A source told People magazine that the split was “a mutual decision, and wasn’t an easy one, but it was made with love and a deep respect for one another.”
The 2026 vacation footage has successfully shifted the narrative, demonstrating that former flames can indeed reunite as genuine friends, surrounded by a supportive social circle, to celebrate new beginnings.
