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." Joshua Jackson's Dating History: Diane Kruger, Jodie Turner-Smith and More 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." Joshua Jackson and Diane Kruger in 2008 Marcel Thomas FilmMagic 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 Joshua Jackson and Diane Kruger in 2015 Amy Graves/WireImage 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. Joshua Jackson and Diane Kruger in 2013 Jim Spellman/WireImage 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. Diane Kruger and Norman Reedus' Relationship Timeline 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 Joshua Jackson and Diane Kruger in 2009 ustin Lubin/NBCU Photo Bank 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 The