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.

Since Joshua Jackson and Holmes actually dated in 1997, the once-inconceivable pairing of Pacey Whitter and Joey Potter on Dawson's Creek will always pack an extra punch.

"I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always," Holmes told Rolling Stone in 1998, without naming names. "And that I feel so fortunate because he's now one of my best friends."

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 Josie and the Pussycats actress only dated Jackson off and on for about a year, starting in 2002, but they remained good friends.

The German actress agreed to drinks but not dinner with Jackson after they met in 2006, but he made reservations anyway.

"I felt really bad because he looked very eager and he put on a clean shirt," Kruger recalled on Conan in 2013. "And so I was like, 'OK, fine. Let's go.'"

The reluctant supper turned into a decade-long relationship, the couple splitting their time between his native Vancouver, her beloved Paris, New York and L.A.

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.

However, they split up in 2016, amid rumors that Kruger had fallen for Norman Reedus, her costar in the 2015 film Sky. She and the Walking Dead star remain together, welcoming daughter Nova Tennessee in November 2018.  

No hard feelings, though, as Jackson congratulated Kruger when she was honored at the 2017 Cannes Film Festival, writing on Instagram that he was "over the moon" for her.

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.

"We had a one-night stand," Turner-Smith told Seth Meyers in May 2021, recalling how she was instantly attracted to the actor but let him make the first move. "We're in a two-, three-year one-night stand now."

Or, as Jackson put it to Entertainment Tonight that July, "There is nothing…better off than being married to her and having that baby. It's everything."

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."

Finalizing a custody arrangement threatened to get messy, but, days before they were due to go to trial in October 2025, the exes resolved to work it out.

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.

But they went their separate ways, Nyong'o telling Harper's Bazaar U.K. in an interview published in October 2024, "My love for my cat is singular. If I'm ever so lucky to be in a romantic relationship again, it'll be because of him."

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.

Perhaps Jackson is just a gentleman, but he sparked romance rumors once again by holding the model's hand on a June 2026 outing in New York.