Joshua Jackson and Diane Kruger: From 1st Date Fail to 10 Years of Love

Joshua Jackson and Diane Kruger really seemed like they were in it for the long haul —but after a decade as one of the most stylish couples in Hollywood, they were sadly no more.

With the Dawson’s Creek star, now 47, firmly back in the spotlight following a long-awaited Capeside reunion, a high-profile divorce from Jodie Turner-Smith and those tantalizing on-set shots with Katie Holmes that almost broke the more millennial quarters of the internet, we thought it was time to figure out why this seriously cool couple didn’t last the course.

How It Began

Kruger, now 49, was finalizing her divorce from first husband Guillaume Canet when, in 2005, Jackson — only a year or so out from Dawson’s Creek coming to an end —asked her out. But things didn’t go well, as both parties confirmed in separate interviews many years later.

“Our first date was a miserable one,” Jackson told Us Weekly in 2012. “I took her to an Italian restaurant, and there was some flower that was blooming. She was allergic to it so she sniffled and sneezed the entire time. And when I get nervous, you might have noticed I talk a lot.”

Kruger elaborated further to Conan O’Brien in 2013, revealing that she didn’t even realize they were on a date. “He thinks he asked me out on a date, which is not true, because I did not agree to that,” she said. “I agreed to have drinks with him. I actually had plans with someone else for dinner, so I know I didn’t say yes to dinner. We were sitting at the bar, and it’s nine o’clock, and I’m ready to leave. And he was like, ‘Let’s go, we have dinner reservations.’ And I felt really bad because he looked very eager and he put on a clean shirt. And so I was like, ‘OK, fine. Let’s go.’”

That’s when her allergic reaction to the flowers kicked in — but Jackson was undeterred. “I thought he might say, ‘Let’s call it a day. I’ll bring you home,’” said Kruger. “And of course not. He talked about himself for an hour and a half. Nonstop. He took me back to my hotel in his car, which was a piece of s**t. Excuse me, but it was. The door was eaten by his dog, it smelled so bad. If you know Josh, you know he was not the tidiest of guys, so trust me, it was not cute.”

Despite this, Jackson still went in for a kiss. “I swear to God, at the end, I was like, ‘Should I slap him?’” she said.

The next day, Jackson sent Kruger flowers and a box of Kleenex “because we’d had such a miserable date and I figured I was never gonna hear from her again.” But Kruger told him the flowers would die because she was leaving town the next day.

Jackson was, in his own words, “deep in the friend zone” … until 2006, when they reconnected and things went a little more smoothly.

How Long It Lasted

These two kept going for 10 whole years! And Jackson went through quite the glow-up thanks to Kruger’s stylish credentials —the couple were frequently photographed together looking impeccable on and off the red carpet, and Jackson admitted his love had secretly disposed of some of his more well-loved Adidas sneakers (but didn’t mention if she’d also discreetly had his car cleaned!)

“When you are in a relationship, you want the other person to appreciate the things you like,” Kruger told Glamour of her man’s suave new look. “It sounds superficial, but it’s nice.” And Jackson told The Hollywood Reporter in 2015 that he appreciated the makeover. “I certainly pay more attention to how I dress now than I did a decade ago before we started dating,” he said.

After around nine years of dating, they officially moved in together. “That’s a big step into adulthood for me, to allow that time for someone else out of my time,” Kruger told Net A Porter at the time.

Related: Diane Kruger and Norman Reedus’ Relationship Timeline

Diane Kruger and Norman Reedus’ romance has hooked fans in for years, beginning with their onscreen chemistry in 2015’s Sky. The duo met on the set of the drama while Kruger was still dating Joshua Jackson. Kruger and Jacksonsplit in July 2016 after 10 years together, and shortly after the breakup, Kruger was linked to […]

However, tellingly, both parties said that marriage just wasn’t a talking point for them. “No paper you have signed will keep you around,” Kruger told Allure in 2010, while Jackson told Us Weekly two years later, “Marriage is important for the people it’s important for, but neither one of us is particularly religious, so I don’t think there’s any particular push.”

How It Ended

In 2016, they issued a statement confirming they had separated but were still good friends. The world was shocked: it had seemed like babies were imminent.

In 2017, Kruger told Vulture that the split had actually been “a long time coming.” She said, “You don’t break up overnight after 10 years. It wasn’t like an urgent, ‘Oh my god, I can’t sleep at night’ thing.”

And it seemed that the “remaining friends” line was actually true for these two; in the months following the split, they were spotted together a number of times, taking walks and sharing a hug.

What They Said About Each Other

These two had a gorgeous dynamic in public, with Jackson frequently helping out his fashion-forward girlfriend on the red carpet, which Kruger particularly appreciated when she wore a dress with a huge hoop to 2012’s Inglourious Basterds premiere.

“Once I finished dinner, I had to go to the bathroom, and it became so tight that I couldn’t breathe anymore,” Kruger told People. “Josh had to come with me to the ladies room and cut me out of it. He literally had to help me remove the dress to help me go to the bathroom. It was crazy! That’s real love, isn’t it, to have someone like him help me in the weirdest situations. He’s great and he’s like my hero.”

Jackson was equally gushy about Kruger in an interview with The Hollywood Reporter in 2015. “One of the most attractive things to me about Diane is how confident she is in herself as a woman and in her beauty, and how much self-respect she has and the way that manifests itself in the way she dresses,” he said. Swoon.

What They Say Now

Both consummate professionals — or just nice people —they have both been kind and respectful about each other in the years since, with Jackson even celebrating his ex’s win at Cannes Film Festival in 2017 with a celebratory Instagram post. “Yes she Cannes,” he wrote. “Having witnessed the integrity and dedication that you bring to every job, I’m over the moon to see you getting the recognition you deserve.”

However, some eagle-eyed fans noticed that Kruger had deleted all evidence of the relationship from her own Instagram feed. But that’s just normal post-breakup clean-up stuff, right?

In 2023, Kruger hinted at one of the problems in the couple’s seemingly perfect relationship: they wanted kids together, but it sadly didn’t happen for them. “I was in a very serious relationship at the time, and we tried very hard to have a child, which didn’t work out,” she said on the “Divorced Not Dead” podcast.

Happily, both Jackson and Kruger have since become parents to little girls. Jackson shares daughter Juno, born in 2020, with Turner-Smith, while Kruger and partner Norman Reedus, who she got serious with not long after her split from Jackson, welcomed daughter Nova into the world in 2018, when the actress was 42.

Key Relationship Takeaways

This one nearly didn’t get off the ground but we’re so glad it did: for a good few years there, these two were red carpet royalty and clearly learned a lot from each other. Plus, of course, the obvious glow-up Kruger gave Jackson was a gift to the world, with the actor’s TV credentials and heartthrob status only going up and up ever since.

Kruger, meanwhile, has found happiness in motherhood —and in her relationship with The Walking Dead’s Reedus. “I thought it wasn’t going to happen, and she came into my life when I was ready,” she told People in 2022. “I’m grateful that happened for me and our family. She’s changed my world and the way I look at everything.”