The search for the woman who changes everything for Jake Gyllenhaal and Kevin Costner may have found its star. Sarah Pidgeon, who is captivating audiences as Carolyn Bessette-Kennedy in FX’s Love Story: John F. Kennedy Jr. & Carolyn Bessette, is officially in negotiations to join the high-profile Amazon MGM Studios feature ‘Honeymoon with Harry.’ The film, which has spent over two decades in “development hell,” is finally moving toward a production start this spring under the direction of the Crazy, Stupid, Love creative team.
A Heartbreaking Catalyst for a Reluctant Duo
Sarah Pidgeon is set to portray the fiancée of Jake Gyllenhaal’s character, a woman whose sudden and tragic death just two days before her wedding serves as the emotional anchor of the film. While her screentime may be centered on the beginning of the story, her character’s influence looms large as her grieving groom-to-be decides to go on their pre-planned honeymoon anyway. In a twist of fate, he finds himself accompanied by his late fiancée’s overprotective and prickly father, played by Kevin Costner.
A Legacy of “Development Hell” Finally Finds its Cast
The road to ‘Honeymoon with Harry’ has been one of the longest in modern Hollywood history. Based on the 2012 novel by Bart Baker, the project was originally set up at New Line Cinema back in 2004. Over the last twenty years, a revolving door of A-list talent has been attached, including pairings like Vince Vaughn and Jack Nicholson, and later, Bradley Cooper and Robert De Niro. With Gyllenhaal and Costner now firmly attached and Pidgeon in final talks, the project has finally secured the multi-generational star power it needs to make it to the finish line.
Reunited Behind the Camera
The film marks a significant reunion for its creative leads. Dan Fogelman (This Is Us) penned the script, while the directing duo of Glenn Ficarra and John Requa are set to helm the project. This trio previously collaborated on the 2011 hit Crazy, Stupid, Love and more recently on the Hulu series Paradise. Fogelman has described the tone of the movie as a throwback to the “human dramedies” of the 1970s, citing influences like Terms of Endearment and Jerry Maguire for its balance of humor and devastating emotional weight.
Production Sets Sail for Sydney
According to the latest industry production listings, filming for ‘Honeymoon with Harry’ is scheduled to begin on April 1, 2026, with locations primarily set in Sydney, Australia. The Australian coast will stand in for the tropical island honeymoon destination where Gyllenhaal and Costner’s characters will be forced to confront their mutual grief and their deep-seated dislike for one another. Producers include Fogelman, Mike Karz, and Amazon MGM’s Jennifer Salke, who is making her producing debut under her Sullivan Street Productions banner.
