Nina Dobrev Stuns Fans As She Celebrates With Ex-Boyfriend Glen Powell After Shaun White Split

The holiday season often brings ex-partners back together, though rarely in circumstances as graceful and genuinely joyful as what unfolded on the Caribbean island of St. Barts over New Year's Eve. Nina Dobrev, the actress best known for her role in The Vampire Diaries, spent the festive period celebrating with her former boyfriend Glen Powell—and his current rumoured girlfriend, Michelle Randolph.

What could have been awkward instead became the stuff of modern celebrity friendship goals, with the trio posting videos of themselves dancing, laughing, and genuinely enjoying one another's company amongst a wider circle of A-list friends.

For Dobrev, the getaway marked a significant moment: her first major public celebration following her September 2025 breakup with professional snowboarder Shaun White, with whom she had been engaged.

The trip to St. Barts, shared across social media on 6 January 2026, showcased not merely a vacation but a deliberate statement about how former romantic partners can evolve into genuine friendships.

Dobrev and Powell had briefly dated in 2017, a relationship that ended amicably as both focused on their respective careers. Nearly a decade later, they've clearly maintained the warmth that originally drew them together—just in a different context.

Nina Dobrev And Glen Powell: How Exes Become Best Friends

The video recap Dobrev posted to Instagram revealed far more than typical holiday footage. Clips showed the trio engaging in activities that require genuine comfort and ease with one another: dancing together, playing pickleball, working out, and swimming.

These aren't the activities people typically document if they're merely being polite. They're the moments people share when they're actually enjoying one another's company.

Dobrev's caption reflected this authenticity: '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.'

That sentiment carries particular weight given Dobrev's recent romantic upheaval. Her engagement to Shaun White, the legendary Olympic snowboarder, ended in September 2025 after several years together.

The breakup was undoubtedly difficult, yet here she was just months later, celebrating publicly with her ex and his new romantic interest, appearing genuinely happy in every photograph and video clip.

The vacation itself was something of a who's-who of entertainment and influencer culture. The group included Top Gun: Maverick actor Miles Teller and his wife Keleigh Teller, Glee alum Chord Overstreet, and influencer Alix Earle—who herself made headlines during the trip after being spotted getting close with Tom Brady during New Year's Eve celebrations.

The extended friend group numbered well beyond the core trio, suggesting this was less a romantic getaway and more a genuine celebration of friendship and connection.

Michelle Randolph And Glen Powell: New Love, Established Friendship

Michelle Randolph's presence at the trip is worth noting. Dating rumours about Randolph and Powell had circulated since November 2025, yet here she was, comfortable enough with Dobrev to document their time together publicly.

Rather than creating tension or awkwardness, Randolph's inclusion seemed natural, suggesting she and Powell had likely discussed the trip beforehand and that everyone involved understood the emotional maturity required to make such a dynamic work.

This approach to post-breakup friendship is increasingly common among younger celebrities and public figures, yet it remains noteworthy enough to attract attention and, inevitably, scrutiny.

The fact that it unfolded so successfully—with genuine smiles, laughter, and what appears to be authentic joy—suggests something important about how relationships can transform rather than simply end.

Dobrev's own words captured the essence of the trip best. In a subsequent Instagram post on 3 January, she reflected on the experience: 'The perfect way to ring in the new year.'

For someone navigating the emotional landscape of a broken engagement, celebrating with friends—old and new—appears to have been exactly what she needed as she moves forward into 2026.