Joshua Jackson's Summer of Second Acts: New Romance, Old Flames, and Fresh Starts

Joshua Jackson is having quite the month. The 48-year-old actor has been spotted multiple times in New York City with model Olivia Burgess, most recently on June 26 when the pair were photographed hanging out together in casual-but-put-together style—he in jeans and a layered button-down, she in a denim skirt and brown tank top. But here’s where it gets interesting: this is the second public outing in as many weeks, following a June 7 hand-holding stroll through the Big Apple that had everyone paying attention.

What makes Jackson’s romantic life particularly compelling right now isn’t just the new connection with Burgess, a 37-year-old model who’s walked runways for Jean Paul Gaultier. It’s the timing and the context swirling around it. Just two days after that first June 7 sighting, Jackson made headlines for something entirely different: publicly praising Katie Holmes, his former Dawson’s Creek costar, after they reunited professionally on the film Happy Hours. His Instagram post dripped with genuine warmth and gratitude, calling Holmes a core relationship in his personal and professional life. He even held her hand at the Tribeca Film Festival while reflecting on their shared history.

That reunion carries particular weight because Jackson and Holmes have been orbiting each other’s lives for nearly three decades. They played Pacey and Joey on Dawson’s Creek and briefly dated offscreen around 1998-1999—back when both were young and the show was defining a generation’s television habits. The fact that they’re working together again for the first time since the show ended in 2003 is significant enough; Jackson’s public appreciation post elevates it further. He wasn’t just thanking a colleague—he was honoring a friendship that clearly matters to him deeply.

For Jackson, all of this arrives on the heels of major personal shifts. His marriage to actress and producer Jodie Turner-Smith ended publicly in 2023 and was finalized in May 2025. They share a 6-year-old daughter, Juno. So in the span of just a few weeks this June, Jackson appears to be threading multiple needles: exploring new romance with Burgess, publicly celebrating a meaningful old friendship with Holmes, and navigating co-parenting after divorce. It’s a lot, and yet he’s doing it with the kind of grace and intentionality that suggests he’s genuinely working through what’s next.

The real story here might not be about who Jackson is dating, but about a man in his late 40s being thoughtful and present across different chapters of his life simultaneously. Whether it’s holding hands with someone new or holding hands with an old friend at a film festival, he seems to be moving through this season with both openness and respect for the people involved.