Chris Pine’s Mystery, Longtime Girlfriend Is Allegedly a Designer 15 Years His Junior, Sources Claim

Chris Pine might be one of Hollywood’s most private leading men, but even he can’t entirely keep his romantic life under wraps. The 44-year-old Star Trek actor has been quietly dating 29-year-old Keana Sky Wenger, a former hostess at an LA restaurant who reportedly caught his eye while on the job sometime in late 2022 or early 2023. 

Cut to August 2023, and the two made headlines as they were spotted on a dreamy boat ride in Portofino, Italy. Since then, they haven’t been seen together often, but their rare sightings speak volumes. Just last Thursday, the couple attended an exclusive Brunello Cucinelli dinner party at the iconic Chateau Marmont, per Daily Mail.

Naturally, Keana’s background has sparked quite a bit of interest — after all, who hasn’t fantasized about their Hollywood crush strolling into their workplace and whisking them away across the globe? (It’s not impossible; just ask Matt Damon’s wife Luciana Barroso, who was also working in a restaurant when she met her now-husband).

Once a hostess at Saffy’s, an LA hotspot, Keana reportedly said goodbye to the job shortly after making a splash as Pine’s plus-one at the Ralph Lauren Purple Label Spring 2025 show in Milan last June. Now, she’s believed to be exploring a career as a designer — a move that seems perfectly on-brand given her growing appearances at high-fashion events by Pine’s side.

Pine, known for his low-key approach to dating, has a history of keeping his relationships under the radar. His previous romance with actress Annabelle Wallis lasted nearly four years and followed a similarly private pattern, with no bold red-carpet debuts or gushy social media posts. The pair split in early 2022. Before Wallis, Pine was linked to Sofia Boutella, two years his junior, and Zoë Kravitz, eight years younger — making his 15-year age gap with Wenger his most significant yet.

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