Why is Nina Dobrev vacationing with ex Glen Powell after her Shaun White split? Inside the friendship turning heads
Nina Dobrev and ex Glen Powell. Image Credit: Jason Merritt/Getty Images
Nina Dobrev has once again captured public attention, this time not for a new film or television role, but for a headline-making New Year’s getaway that redefined modern celebrity friendships.
The Vampire Diaries star rang in 2026 on the Caribbean island of St. Barts alongside her former boyfriend Glen Powell and his rumored girlfriend Michelle Randolph, just months after ending her high-profile engagement to Olympic snowboarder Shaun White.
What might have been an awkward reunion instead unfolded as a widely praised display of maturity, emotional growth, and genuine camaraderie, drawing widespread attention across social media and entertainment circles.
Nina Dobrev’s First Public Celebration After Shaun White Split
The vacation marked Dobrev’s first major public appearance following her September 2025 breakup with Shaun White, whom she had been engaged to after several years together.
Rather than retreating from the spotlight, the actress appeared confident, relaxed, and joyful, sharing glimpses of the trip on Instagram on January 6, 2026. The posts showed Dobrev laughing, dancing, swimming, and celebrating with a tight-knit group of friends.
Her decision to celebrate openly, especially with a former romantic partner, was widely interpreted as a clear signal that she is moving forward on her own terms.
How Nina Dobrev and Glen Powell Turned Exes Into Friends
Dobrev and Powell briefly dated in 2017, ending their relationship amicably as both prioritized their rapidly growing careers. Nearly a decade later, their friendship appears not only intact, but thriving.
Videos shared from the trip showed the former couple engaging in everyday, intimate activities, from pickleball and workouts to group swims and late-night dancing, suggesting a level of comfort rarely seen between celebrity exes.
In a caption that quickly went viral, Dobrev wrote:
“Some old friends, some new friends… now all best friends. Haven’t laughed, been in awe or smiled this much in my life. The perfect way to ring in the new year.”
The message resonated with fans who praised her emotional maturity and openness.
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Nina Dobrev & Shaun White split after 5 years: What to know
Michelle Randolph’s Role in the Dynamic
Adding another layer to the story was the presence of Michelle Randolph, Powell’s rumored girlfriend since November 2025.
Rather than fueling speculation or tension, Randolph appeared fully integrated into the group, posing comfortably with Dobrev and sharing her own memories from the trip. Her inclusion suggested that all parties had communicated clearly and set boundaries rooted in respect.
Randolph later shared photos from the vacation, captioning them with reflections on new friendships and fresh beginnings, reinforcing the narrative that the trip was about community, not romantic entanglements.
A Celebrity Getaway Filled With A-List Faces
The St. Barts vacation wasn’t limited to the trio. The extended group included:
- Miles Teller and wife Keleigh Teller
- Chord Overstreet
- Influencer Alix Earle, who drew attention for being spotted with Tom Brady during New Year’s Eve celebrations
The presence of such a large, diverse group underscored that the getaway was a social gathering rather than a romantic reunion.
What This Moment Says About Nina Dobrev’s Next Chapter
For Dobrev, the timing of the trip carries deeper significance. Ending an engagement is rarely easy, especially under public scrutiny. Yet just months later, she appeared emotionally grounded, surrounded by supportive friends, and visibly optimistic about the year ahead.
Entertainment analysts note that Dobrev’s approach reflects a broader shift among younger Hollywood stars, where relationships are allowed to evolve rather than end in conflict.
By celebrating openly and authentically, Dobrev seems to be reclaiming her narrative as she steps into 2026 with clarity and confidence.
FAQ
Why did Nina Dobrev and Shaun White break up?
The couple ended their engagement in September 2025. While no specific reason was publicly disclosed, sources indicated the split was amicable.
Is Nina Dobrev dating Glen Powell again?
No. Nina Dobrev and Glen Powell are not romantically involved. They dated briefly in 2017 and have remained friends since.
Who is Glen Powell’s current girlfriend?
Glen Powell has been romantically linked to actress Michelle Randolph since November 2025, though neither has formally confirmed the relationship.
Why were Nina Dobrev and Glen Powell vacationing together?
They were part of a larger friend group celebrating New Year’s Eve in St. Barts, emphasizing friendship rather than romance.
How did fans react to Nina Dobrev’s vacation posts?
Fans largely praised Dobrev for her maturity, emotional strength, and positive approach to post-breakup life.
What does this trip mean for Nina Dobrev’s career and public image?
The trip reinforces her image as emotionally grounded and self-assured, qualities that resonate strongly with modern audiences.
Are Nina Dobrev and Michelle Randolph friends?
Based on shared photos and public interactions, the two appear friendly and comfortable with one another.