A Guide to Joshua Jackson’s Stacked Romantic History

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It’s safe to say Katie Holmes wasn’t alone in wanting to commit to a long-term relationship with Joshua Jackson.

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.

Despite both being single, Katie Holmes and Jamie Foxx are happy remaining close friends, nearly 30 years after their brief relationship. Though their connection at the film premiere sparked nostalgia for their past, they’ve both moved on and had other relationships since then.

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.

Because Joshua Jackson and Katie Holmes were a real-life couple in 1997, their on-screen romance as Pacey Whitter and Joey Potter on Dawson’s Creek always feels particularly special.

Holmes described her first love as an amazing and unforgettable experience she’ll always cherish. She told Rolling Stone in 1998 that she felt lucky because the person is now a close friend, though she didn’t reveal their identity.

Jackson concurred that it was momentous while it lasted, telling The Times in 2023, “We were kids, so it was a full-on stars-moon-sky romance.”

And their chemistry endured, as evidenced by Holmes’ decision to recruit Jackson to costar in her film trilogy Happy Hours, about—as the synopsis put it—”two people navigating their relationship within the challenges of careers and family responsibilities and the pursuit of love despite life’s inevitable obstacles.”

Jackson was linked to the Sweet Valley High actress between 1999 and 2000.

The actress from Josie and the Pussycats and Michael Jackson had an on-again, off-again relationship for around a year beginning in 2002, and they stayed friendly afterward.

After meeting in 2006, the German actress accepted Jackson’s invitation for drinks, but declined to have dinner with him. However, he went ahead and made a dinner reservation anyway.

He remembered feeling terrible because the man seemed so excited and had even put on a nice, clean shirt. That’s when Kruger decided, ‘Okay, let’s do this,’ as he explained on Conan in 2013.

What started as an awkward dinner eventually blossomed into a ten-year romance. They spent those years traveling between his hometown of Vancouver and her favorite city, Paris, as well as New York and Los Angeles.

When it came to tying the knot, Kruger—who was previously married to Guillaume Canet for five years—told Glamour in 2011 that she believed “in a commitment that you make in your heart.” A few years later, Jackson told the publication he didn’t feel “any more or less committed to Diane for not having stood in front of a priest,” but they hadn’t ruled out swapping vows one day.

The couple separated in 2016, with reports suggesting Kruger had developed feelings for her Sky co-star, Norman Reedus. She and Reedus, known for The Walking Dead, are still together and welcomed their daughter, Nova Tennessee, in November 2018.

Despite their rivalry, Jackson happily congratulated Kruger when she received an award at the 2017 Cannes Film Festival, expressing his excitement in an Instagram post.

This wasn’t his first foray into dating after he and Kruger split up (we haven’t forgotten you, “Mystery Brunette”), but Jackson was linked to the Cheddar TV host in 2018.

Jackson and the English actress went public with their romance in October 2018 and got married in December 2019, four months before daughter Juno was born.

Okay, so basically, when I first met Janelle MonĂĄe, the chemistry was instant. I mean, seriously, electric! I totally crushed on her, but I played it cool and let her make the first move – I wanted to be respectful, you know? But then
 one night led to another, and another, and another! It’s been, like, two or three years of just
 amazing nights. It started as a one-night thing, but honestly, it never really stopped! I’m completely obsessed, and it’s the best ‘one-night stand’ ever!

As Jackson told Entertainment Tonight that July, he felt incredibly lucky, saying, “Being married to her and having our baby is absolutely the best thing ever. It’s everything I could ask for.”

Alas, they separated in September 2023, according to divorce papers Turner Smith filed the following month. The Queen & Slim star put a positive spin on one door closing and another opening, telling the Sunday Times in February 2024, “We obviously had such a beautiful moment together. And now it’s time for a new moment for both of us
The bravest thing in the world is to recognize when something’s not working and to make a move, and I always want to set that kind of example for my daughter.”

Their custody battle was heading towards a complicated court case, but the former couple managed to reach an agreement just days before their scheduled October 2025 trial.

Years after she caught him on Broadway in Children of a Lesser God, Jackson was spotted with the Oscar winner at a Janelle Monae concert in October 2023 and subsequent sightings included a PDA-packed trip to Mexico that March.

Nyong’o and her partner decided to go their separate ways, she shared in an October 2024 interview with Harper’s Bazaar U.K. She jokingly said her cat is the key to any future romantic relationship, stating her love for him is unique and special.

Be still all the hearts when Jackson was seen holding hands with the Bridgerton actress in August 2025, yet that may have just been a one-off episode, as the plot didn’t develop further.

Jackson fueled dating speculation once more when he was seen holding hands with the model during a New York outing in June 2026. While he may simply be a friendly companion, the gesture has led to romance rumors.

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2026-06-10 00:47