Chris Pine is having a weird year. And honestly? It’s probably exactly how he wants it.
If you’re looking for the guy who played Captain Kirk or Steve Trevor, he’s still around, but he’s basically traded in the spandex and the starships for a vibe that feels much more... well, Pine. Whether it’s his sudden pivot to the London stage or that "don't care" attitude toward his directorial debut being absolutely trashed by critics, Chris Pine now is an actor who has clearly stopped asking for permission to be himself.
He’s currently 45. He’s dating a designer named Keana Sky Wenger. He’s wearing Manolo Blahniks on red carpets and looking like he just stepped out of a 1970s Amalfi Coast fever dream.
It’s a far cry from the "Best Chris" debates of the 2010s.
The Pivot to the West End
So, what is he actually doing?
Right now, the big news is that Pine is heading to London. He’s set to make his West End debut in a new version of Chekhov’s Ivanov at the Bridge Theatre. Previews start July 4, 2026. If you follow theater, you know Ivanov isn't exactly a lighthearted romp. It’s a knotty, existential drama about a man in his mid-40s who feels like he’s lost his spark.
Director Simon Stone, who is handling the adaptation, recently mentioned that Pine is "uniquely sensitive and brilliantly intelligent." It’s a 11-week limited run. It feels like a deliberate move to distance himself from the "action hero" label that has followed him since 2009.
He hasn't been on stage in over a decade. The last time was The Lieutenant of Inishmore in LA back in 2010. For a guy who could easily just bank another $15 million check for a franchise sequel, choosing to spend a summer in a 900-seat theater in London says a lot about where his head is at.
The Poolman Fallout and Why He Doesn't Care
We have to talk about Poolman.
When Chris Pine decided to write, direct, and star in a sun-drenched, weirdo noir about a pool cleaner in Los Angeles, the industry expected... something else. What they got was a movie that premiered at TIFF and got, in Pine's own words, "f---ing panned."
It currently sits with a dismal 21% on Rotten Tomatoes.
Most actors would go into damage control. They'd hire a new PR team or pivot immediately to a safe, big-budget "comeback" role. Pine did the opposite. He went on podcasts and told everyone how much he loved the film. He called the failure "the best thing that ever happened" to him because it forced him to double down on what he actually enjoys.
"I was like, 'Maybe I did make a pile of s---,'" Pine admitted to Josh Horowitz. "But I went back and watched it. I f---ing love this film."
There’s something genuinely refreshing about that. In a town where everyone is obsessed with "tracking" and "brand management," Pine is out here making indie movies like Carousel—a dark romantic drama with Jenny Slate—and sci-fi comedies like Alpha Gang with Cate Blanchett and Dave Bautista.
He's chasing the weird stuff. The projects that probably won't win an Oscar but might actually be fun to film.
Life Outside the Spotlight
For a long time, Pine was the most private of the "Famous Chris" quartet. He famously didn't have a smartphone for a while, opting for a flip phone to stay off the grid. While he’s stepped back into the world of modern tech (mostly), his personal life remains pretty locked down.
His relationship with Keana Sky Wenger is the prime example. They’ve been linked since 2023, but they rarely do the red carpet thing. However, they finally made a rare public appearance together at the 2026 Golden Globes.
Pine was a presenter. Wenger was his plus-one. They didn’t do the big flashy "we're a couple" poses for the cameras, but they were spotted inside the Beverly Hilton looking very much in sync.
📖 Related: Finding Me: A Memoir and Why Viola Davis Had to Tell This Story
She's a designer who reportedly met him while she was working at a restaurant in LA. It’s a very un-Hollywood meet-cute. Before her, he was linked to Annabelle Wallis for a few years, but that ended back in 2022.
It seems like he's found a rhythm that works for him:
- Work on projects that interest him, regardless of the "career move" logic.
- Maintain a wardrobe that looks like a curated vintage shop.
- Keep the private life actually private.
The Star Trek 4 Question
Every time he does an interview, someone asks about Star Trek 4. It’s been years. Decades, almost.
The "Kelvin Timeline" crew has been in limbo for ages. While there are always rumors of a script being finished or a director being attached, the reality is that the project is still in development hell. Pine has always said he’d love to go back, but he’s also expressed frustration with how the franchise has been handled.
He recently pointed out that Star Trek shouldn't try to be Marvel. It’s a different beast. It’s about big ideas and character, not just $500 million box office returns. Whether or not we ever see him in the captain's chair again is anyone's guess, but he’s certainly not sitting by the phone waiting for it.
The Aesthetic and the "Vibe"
You can't talk about Chris Pine now without talking about the clothes.
The man has become a style icon for people who are tired of the standard "actor in a slim-fit navy suit" look. He’s wearing caftans. He’s wearing short-shorts. He’s rocking a silver beard that he refuses to dye.
At the Golden Globes this year, he was wearing Giuliva Heritage. He’s leaning into this "Intellectual Bohemian" persona that feels authentic to who he is. It matches his recent interest in film noir and his choice of stage roles.
He’s also been spending more time in Italy. He was spotted at a Como 1907 soccer match recently with Michael Fassbender. He’s even been to the Vatican—Pope Leo XIV invited him (along with a handful of other directors and actors) to discuss the "mission of human values" in cinema.
He's living a very specific, very curated life.
What’s Next for Pine?
If you want to keep up with him, you're going to have to look beyond the multiplex.
- Carousel: This indie romance with Jenny Slate is in post-production. It’s directed by Rachel Lambert, who did Sometimes I Think About Dying. Expect something quiet, moody, and likely a Sundance darling.
- Alpha Gang: This is the big one for sci-fi fans. The Zellner Brothers are directing. It’s about aliens who come to Earth to conquer it but get infected by human emotions. It sounds exactly like the kind of chaotic energy Pine is gravitating toward lately.
- Ivanov: If you’re in London this summer, this is the ticket to get. It’s Pine at his most raw, tackling Chekhov in a modern space.
Actionable Takeaways for Fans
If you're following Chris Pine's career in 2026, here is how to keep up:
- Look for the indies: Don't wait for a trailer during the Super Bowl. Pine is focusing on smaller distributors and streaming hits (like Poolman actually finding an audience on Hulu after the theatrical flop).
- Check the London Stage: If you can get to the Bridge Theatre, do it. This is a rare chance to see a Hollywood A-lister in a complex, non-commercial role.
- Ignore the "Career Advice": Pine is a case study in doing what you want once you've made your money. He’s proof that you can "fail" publicly (with a movie like Poolman) and come out the other side more respected for your honesty.
Chris Pine isn't trying to be the biggest star in the world anymore. He's just trying to be the most interesting version of himself. And honestly? That's way more fun to watch.