I Want What They Have, Colleagues-to-Lovers-to-Colleagues Edition: Katie Holmes and Joshua Jackson

Vogue

23-07-2025

Love is a many-splendored thing, especially when you're gawking at it from the outside. In this new column, we'll be examining the celebrity couples—or, occasionally, friend pairs—who give us hope for our own romantic futures as we try to learn what we can from their well-documented bonds.
I've only wanted the best for Katie Holmes since my inaugural viewing of the iconic 2004 rom-com First Daughter (is it effectively the same movie as Chasing Liberty, which was released that same year, presumably because studio execs don't communicate with each other? Absolutely, but how lucky were we to have a spare?), so it follows that I'm extremely dialed in to her various projects—the latest of which is a new film trilogy called Happy Hours. Also featured in it? None other than her former Dawson's Creek costar and real-life ex, Joshua Jackson.
Obviously, Holmes is a fashion icon and screen legend and alumna of the Tom Cruise Sham Hollywood Marriage Program, class of 2012, so there is a lot to say and appreciate about her at any given moment. But…am I extremely washed for caring so much about her reunion with Jackson? The plot of Happy Hours allegedly revolves around 'two people navigating their relationship within the challenges of careers and family responsibilities and the pursuit of love, despite life's inevitable obstacles' (likely thing for them to do!), and I, for one, can't wait to see Holmes and Jackson as those selfsame two people.
'Working with Josh after so many years is a testament to friendship,' Holmes wrote on Instagram after news of the project broke. 'We can't wait for everyone to see what we make.'
Holmes and Jackson c. 2000.
Holmes and Jackson's relationship was decades ago, at this point; it also took place in the late 1990s (a decade teeming with romantic regret) while they were filming Dawson's Creek, and yes, Holmes did say that she and Jackson became 'best friends' after breaking up in 1998. But I can't help it; when I look at these two laughing it up on a park bench, I want them to be in love! Is that so wrong?
As far as we (okay, I; I don't know who the royal 'we' was meant to refer to) know, Holmes and Jackson are possibly both single right now; Jackson split from his wife and co-parent Jodie Turner-Smith in 2023 and Holmes ended her relationship with Grammy-nominated musician Bobby Wooten III the year before. Still, just because two adults are both single and look good as hell on a bench doesn't mean they're necessarily destined to find romantic love. In fact, I kind of love the fact that Holmes and Turner are back in each other's lives as colleagues. I mean, who knows you better than your ex-onscreen-boyfriend, who just happens to also be your ex-boyfriend, who also just so happens to be your bestie? Counting down the moments until Happy Hours is my new Before Sunrise!