The pair first dated during the early Dawson's Creek years in 1998–1999 and later reunited professionally. They walked the red carpet together on April 14 at a New York screening, and Happy Hours — written, directed and starring Holmes — premieres at the Tribeca Film Festival on June 6. The cast also includes Mary-Louise Parker, Joe Tippett and Constance Wu.
Both actors are 47. Jackson, who praised Holmes for creating the part on the Today show, was married to Jodie Turner-Smith in 2019 and shares a daughter, Juno; they split in 2023. Holmes, who was married to Tom Cruise from 2006 to 2012, shares daughter Suri with him. Happy Hours has no theatrical release date yet.