Nina Dobrev has always been more than just the girl from The Vampire Diaries. She’s a magnet for headlines, mostly because her love life feels like a high-stakes drama that actually has a heart. If you’ve been scrolling through social media lately, you’ve probably seen the photos of her ringing in 2026 in St. Barts. It wasn’t just the beach vibes that got people talking; it was the fact that she was hanging out with her ex, Glen Powell, and his rumored girlfriend, Michelle Randolph. Honestly, it’s a masterclass in how to be an "evolved" ex.
But how did we get here? To understand her current "newly single and thriving" energy, you have to look back at the guys who actually made the cut. We aren't just talking about the rumors; we're talking about the relationships that defined her time in Hollywood.
The Shaun White Era and the 2025 Breakup
For a long time, it really looked like Shaun White was the one. They met at a Tony Robbins event in 2019, and the story goes that Shaun didn't even know who she was. Can you imagine? One of the biggest TV stars of the decade, and he’s just giving her social media tips like she’s a random attendee. They survived the 2020 lockdowns together, sharing those hilarious videos of Shaun’s hands pretending to be Nina’s while she washed groceries. It was wholesome. It was steady.
Then came the 5-carat Lorraine Schwartz diamond.
Shaun proposed in October 2024 at The Golden Swan in New York. Nina was in total shock. She even posted "RIP boyfriend, hello fiancé." But by September 2025, the dream ended. The breakup was a massive shock to the system for fans who thought they were "endgame."
While some sources told People it was a mutual decision made with deep respect, other whispers suggested they were on different pages about the future. One insider claimed Nina was ready for the marriage and kids phase, while Shaun wasn't quite there. Whatever the truth, by the time she showed up at the Toronto International Film Festival for the premiere of Eternity without her ring, the writing was on the wall.
The Ian Somerhalder Years: More Than Just On-Screen Heat
You can't talk about who has Nina Dobrev dated without bringing up the Ian Somerhalder years. This wasn't just a fling; it was a cultural phenomenon. From 2010 to 2013, "Nian" was everything. They tried to keep it professional at first—Nina even told Seventeen she never wanted to date a co-star—but that chemistry was impossible to ignore.
They did the music festival circuit, traveled to Paris, and even rushed their cat to the hospital together. When they split in 2013, the internet basically broke. But here’s the thing that confuses people: they actually stayed friends. Like, real friends. Nina even called Ian’s marriage to Nikki Reed "beautiful." It’s rare to see that kind of maturity in Hollywood, but Nina seems to make a habit of it.
The Men Between the Big Romances
Nina hasn't always been in years-long commitments. Sometimes, it’s just a few months of fun or a "time apart" situation that quietly fizzles out.
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- Glen Powell (2017): These two were the "it" couple for a minute after being spotted at the Golden Globes. They were super cute at Julianne Hough’s wedding, but by November, they decided to "slow things down." Seeing them together in St. Barts in early 2026 proves there’s zero bad blood.
- Grant Mellon (2019): This was a bit more "hush-hush." He’s a screenwriter, and they were seen at Lakers games and Paris Fashion Week. It lasted about six months before they went their separate ways right before she met Shaun White.
- Austin Stowell (2015): This was a solid seven-month run. They went to the Bridge of Spies premiere together and looked very much in love in Saint-Tropez.
- Derek Hough (2013): This was a quick one. Only six weeks! He’s her best friend’s brother, so it probably felt a little too close to home, or maybe the timing was just off.
The "Secret" Prequel: Rob Mayes
Wait, who? Most fans don't realize Nina dated Rob Mayes before The Vampire Diaries even started. This came out in the 2025 book I Was Feeling Epic. Apparently, they both auditioned for the lead roles in the show—Rob was gunning for Damon Salvatore. They kept their relationship a secret because they didn't want it to hurt their casting chances. Nina got the part; Rob didn't. That made things awkward, and they split in 2009. Imagine how different the show would have been if he had won the role!
What We Can Learn From Nina’s Dating History
If there is one takeaway from Nina Dobrev’s history, it’s that she doesn't do "messy." Whether it’s a five-year engagement or a six-week spark, she manages to keep her dignity intact. She’s the queen of the "friendly ex."
Actionable Insights for Your Own Dating Life:
- Prioritize the Friendship: Nina’s ability to stay close with Ian and Glen suggests that if the foundation is respect, the breakup doesn't have to be a disaster.
- Professionalism Matters: If you date a colleague (like she did with Ian and Rob), keep the drama off the clock.
- Don't Rush the Next Step: Even with a 5-carat ring, she was willing to walk away when the alignment wasn't right. Never settle for a "maybe" when you want a "yes."
Check back for more updates on Nina's 2026 adventures, as she seems to be enjoying the single life to the fullest right now.