A Guide to Joshua Jackson's Stacked Romantic History

Joshua Jackson Sparks Romance Rumors With Model Olivia Burgess During NYC Outing

Suffice it to say, Katie Holmes wasn't the only one who liked the idea of she and Joshua Jackson coupling up for good.

Her recent endorsement of the sentiment came in the form of tapping the heart on several Instagram comments shipping the Dawson's Creek costars, whose reunion in Holmes' latest directorial effort Happy Hours—the first in a planned trilogy of films about, as the synopsis put it, the "pursuit of love"—has their fans in a nostalgic frenzy.

But even though she and Jackson are both technically available, the actors are perfectly content being dear friends, almost 30 years after they did date in IRL. And while their chemistry at the film's Tribeca Film Festival premiere June 6 did nothing to quell that WB-era longing, Holmes and Jackson have long since moved on, multiple times over.

In fact, barely 24 hours after the premiere, Jackson's romance journey took a new turn, with the 47-year-old and model Olivia Burgess sparking dating speculation thanks to a hand-in-hand walk they took around Manhattan.

Not that they even needed to hold hands to generate a romance rumor, such is the way being famous goes—and Jackson, who shares 6-year-old daughter Juno with ex-wife Jodie Turner Smith, is an old pro when it comes to the world being interested in every move he makes.

But, as he noted on The Ellen DeGeneres Show in 2019, dating itself had changed by the time he was single again after the end of his decade-long relationship with Diane Kruger.

"Maybe it was there, but I don't remember it. I mean, everything's on your phone now, right?" Jackson said. "There's no more talking to people anymore. You talk to somebody and they're like, 'Ugh! No, no, no, no, no! We don't do that anymore.' So, yeah, it's been quite a big change."

Yet the Doctor Odyssey alum still managed to meet people, somehow, some way. And now that he may be embarking on a new relationship, we didn't want to wait to delve into Jackson's complete romantic history.

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