Chris Pine, one of Hollywood’s most reserved leading men, has managed to keep much of his personal life private, but his latest romance has drawn attention. The 44-year-old Star Trek actor is quietly dating 29-year-old Keana Sky Wenger, a former hostess at an LA restaurant. The two reportedly met while Wenger was working sometime in late 2022 or early 2023. Their relationship became public in August 2023 when they were spotted on a romantic boat ride in Portofino, Italy, sparking intrigue about the couple.
Since their Portofino outing, Pine and Wenger have maintained a low-profile relationship, making infrequent public appearances. One notable sighting occurred recently at an exclusive Brunello Cucinelli dinner party at the iconic Chateau Marmont, where they were photographed together. Despite their discretion, these rare appearances fuel public fascination, as Pine’s dating history is characterized by a similarly understated approach.
Chris Pine and Sky Wenger (@chrispinenut)
Wenger’s background has garnered significant interest, particularly because of her seemingly Cinderella-esque story. As a hostess at Saffy’s, a trendy LA restaurant, she caught Pine’s attention while working. The narrative recalls other Hollywood romances, such as Matt Damon meeting his wife, Luciana Barroso, under similar circumstances. Wenger left her job at Saffy’s after accompanying Pine to high-profile events, like the Ralph Lauren Purple Label Spring 2025 show in Milan, signaling a shift towards a new career path.
Now pursuing a career as a designer, Wenger appears to be making her mark in the fashion world, often accompanying Pine to high-fashion events. This transition aligns with her growing presence in the public eye, fueled by her association with Pine. The couple’s age gap—15 years—is noteworthy, especially considering Pine’s previous relationships, which include actresses Annabelle Wallis, Sofia Boutella, and Zoë Kravitz, each with smaller age differences.
Pine’s current romance with Wenger continues his trend of private, low-key relationships. His four-year relationship with Wallis ended in early 2022, and prior to that, he dated Boutella and Kravitz, maintaining a similar discretion throughout. With Wenger, Pine has managed to strike a balance between public interest and personal privacy, as their rare but notable outings keep fans intrigued while shielding much of their relationship from the spotlight.
