While Chris Pine is best known for his leading roles in Star Trek, Wonder Woman and 2022's Don't Worry Darling, the actor's leading ladies have also made headlines over the years.
Pine has dated a handful of famous faces, from Zoë Kravitz to Olivia Munn. The actor most recently split from British actress Annabelle Wallis after four years together. Their breakup was announced in March 2022, following a low-profile relationship.
The actor has worked to keep his love life out of the spotlight over the years, telling The Hollywood Reporter in January 2014 that his romantic relationships are "something I don't really want to talk about."
The year prior, he told Cosmopolitan that the best dating advice he'd ever received was from his mother. "My mom always told me to take my elbows off the table, so that if I ever had dinner with a queen, I would know how to eat properly. But she also taught me basic things about being a gentleman, like opening car doors. Especially in Los Angeles, I think people lose those small gestures that harken back to a different time but are still mutually appreciated by men and women. Those little things are just nice."
Prior to his relationship with Wallis, Pine dated a number of actresses and models. Here's a look at Chris Pine's dating history.
Stefanie Keenan/Getty ; George Pimentel/WireImage
Pine's romance with Wallis first made headlines in March 2018, when they were spotted together at London's Heathrow Airport. The following month, they were seen at a dinner event in Malibu.
Over the course of their relationship, the actors stayed largely out of the spotlight, avoiding red carpet appearances together. A model and actress, Wallis is best known for her roles in The Mummy and Peaky Blinders.
After four years of dating, however, the Wonder Woman actor and the Malignant actress split in March 2022, PEOPLE confirmed.
David M. Benett/Dave Benett/Getty
Pine and his Star Trek Beyond costar Sofia Boutella first hinted at a romantic relationship in September 2016, when Boutella showed support for Pine at the premiere of his Oscar-nominated film Hell or High Water.
"With this special special human dear to me at Hell Or High Water London premiere," she captioned a black-and-white photo of them. "So proud of him!"
Another source said Pine was acting "chivalrous" with Boutella and added that the two were "flirty" throughout the event. But despite the affectionate sighting, their relationship was never confirmed. An insider also told PEOPLE that the costars were "friends but not dating" at the time.
Alberto E. Rodriguez/Getty ; Chelsea Lauren/WireImage
In May 2015, Pine was spotted with TV actress Vail Bloom, who is best known for her turn as Heather Stevens on The Young and the Restless, for which she earned a Daytime Emmy nomination.
The pair were seen cuddling up during a romantic lunch date in Hollywood and were photographed sharing a kiss al fresco.
Afterward, they were spotted taking a stroll and shopping around town together. Pine's rep didn't comment on the pair's relationship status at the time.
BILLY FARRELL/Patrick McMullan
Before stepping out with Bloom, Pine was linked to Batwoman actress Zoë Kravitz. The pair were first spotted together in September 2014 at a Coldplay concert. A few months later, they spent the evening partying at Tao Nightclub during the Sundance Film Festival.
The actors were last seen out together at a pre-Oscar dinner party at Madeo restaurant in Beverly Hills, where the duo were photographed arriving together.
Iris Björk Jéhannesdéttir
David M. Benett/Getty
Pine also dated Icelandic model Iris Björk Jéhannesdéttir. The couple were first spotted sharing a kiss during a romantic getaway to Paris in November 2013, as seen in photos published by Daily Mail. Two months later, they were spotted in LAX airport. The couple were linked until early 2015, PEOPLE previously reported.
The actor had a brief romance with model Amanda Frances before dating Jéhannesdéttir. Pine and Frances were photographed holding hands and walking to a car together in 2013.
The actor and South African model Dominique Piek dated for two years, from September 2011 until spring 2013. Pine even made a rare red carpet appearance with his girlfriend, marking their official debut as a couple at the 2012 Cannes Film Festival.
Bryan Bedder/WireImage ; Paul Drinkwater/NBCU Photo Bank/NBCUniversal
In 2010, Pine entered into a romance with another high-profile star, Olivia Munn. He briefly dated the X-Men: Apocalypse star and kept their months-long romance private. While the pair never officially confirmed their relationship, they were photographed together on a handful of occasions, including a dinner date in January 2010.
The same month, the pair enjoyed a "playful" night out at The Woods in Los Angeles. "They looked like they were having a lot of fun," an onlooker told PEOPLE. "They were really playful, and it seemed like they couldn't stop touching each other."
Franziska Krug/Getty ; Jon Kopaloff/FilmMagic
During a May 2021 appearance on the Hollywood Raw podcast, The Hills alum revealed that she and Pine briefly dated in 2009 after meeting him at the ShoWest Awards, where she was being honored with her Sorority Row castmates for the horror film.
"[Chris] came up to me and introduced himself to me and gave me his number," the reality star shared, admitting that she didn't know who the Just My Luck star was at the time.
"And all the girls were kicking me under the table like, 'Oh, my God. You don't know who that is?' I'm like, 'No.' They're like, 'That's Chris Pine.' I was like, 'Oh, he's hot,' " she said.
In her 2022 memoir, Choices: To the Hills and Back Again, she shared more details, revealing that Pine first told her "that he'd seen me onstage and thought that I was really beautiful. He asked if he could take me out sometime."
After going out "more than a few times," the pair's lifestyles began to clash. "He didn't like the whole paparazzi side of it. That was my life, was going out and I was followed by paparazzi. So being on The Hills, our lives completely opposite and just so different with my lifestyle and filming," she continued. "He was more a real actor, theater actor and loved to read books and jazz music and didn't really like to go out to clubs or anything like that."