Katie Holmes and Joshua Jackson are reportedly blurring the lines between fiction and reality. The former Dawson’s Creek co-stars, who famously dated briefly in the late ’90s, are said to be enjoying a low-pressure fling while filming their new movie Happy Hours in New York, and the timing couldn’t be more poetic.
According to a source, the pair are having some “no-strings fun” as they work together in New York, portraying former sweethearts who reconnect years after their breakup. For longtime fans, the parallels are hard to ignore. The idea of Joey and Pacey energy resurfacing decades later, this time in Manhattan instead of Capeside, feels tailor-made for pop culture nostalgia, per Star.
“Katie is enjoying the ride,” the source says of the casual romance. “She says spending time with Josh makes her feel alive again and she doesn’t want to shut that down just because she can’t possess him.” That mindset marks a noticeable shift for Holmes, who has kept her personal life relatively quiet in recent years.
Katie Holmes and Joshua Jackson’s New York Fling Is A Second Chance
Still not everyone in her circle is feeling relaxed about the situation. Friends of the 46-year-old actress are reportedly uneasy about where this could lead, especially given Jackson’s current outlook on relationships. The source notes that people close to Holmes are “worried that she’s going to get hurt” by the Doctor Odyssey alum, who finalized his divorce earlier this year.
“Katie does admit that she’s not immune to getting jealous,” the source reveals. “But she says it’s worth pushing herself out of her comfort zone, that’s how happy Josh makes her.” That willingness to lean into discomfort suggests Holmes is prioritizing joy over fear, even if it comes with emotional risk.
One factor working in Jackson’s favor is transparency. “Josh has always been upfront about what he is doing,” the source explains. “He’s told her that he’s not ready to be committed, so it’s not like he’s sneaking around, and Katie says she can respect that.” In an era where mixed signals are the norm, honesty might be what’s making this dynamic feel manageable at least for now.
Keeping It Casual…For Now
Since finalizing his divorce from Jodie Turner-Smith in May of 2025, Jackson has been spotted out with several women, including model Priya Jain and Bridgerton alum Simone Ashley. He shares a 5-year-old daughter, Juno, with Turner-Smith, and appears to be embracing a very open, very social chapter of his life.
For Holmes, the appeal seems less about labels and more about rediscovering excitement. “Fact is, Katie hasn’t had any romance in her life in a long time and what she has right now with Josh is so fun, it’s worth the risk,” the source says. “She insists that she’s strong enough to handle whatever happens, but that hasn’t stopped her friends from worrying. It’s obvious she’s playing with fire.”
Whether this New York fling between Katie Holmes and Joshua Jackson fizzles out or turns into something deeper remains to be seen. But for now, Holmes appears content, embracing the moment and letting life imitate art one scene at a time.
Kenna Raye 
Emma Taylor 
