The early 2000s were such a different time, especially in the world of Hollywood. It’s hard to believe all that has changed since then. Sure, there are plenty of celebs who were famous back then who are still on the A-list now, but there are some who have retired completely, some who have moved on to new industries, and some who aren’t making feature films anymore. Some of your favorite wild reality TV stars have settled down to start families and work on more mature projects, some of your favorite shows from that decade probably ended years ago, and some films from that time have gotten multiple sequels by now! It’s crazy how things change over the course of just a few years.
You know what else is really funny to look back on? The celebrity couples who are no longer together. Some of them were super cute together, too! But we all know that relationships in Hollywood can go from sweet to sour very quickly, so it’s no surprise that many of these couples moved on a long time ago. But it’s fun to reminisce about them! Here are 20 power couples from the 00s we wish were still a thing.
20 Britney Spears & Justin Timberlake
Who could forget those golden years when Britney Spears and Justin Timberlake were happily together? They were such a pop star power couple! Honestly, we’re still a little sad that they ever broke up. But according to Nicki Swift, things might not have been so romantic behind the scenes.
Apparently, these two had some serious trust issues, and they were both concerned about loyalty.
In the world of Hollywood, we can totally see how that would be a huge problem for any couple—it’s tough to deal with those issues even when you’re not in the spotlight all the time!
19 Jennifer Lopez & Ben Affleck
Jennifer Lopez and Ben Affleck were so adorable together. We know that both of them have had their fair share of rocky relationships since then—who knows, maybe things would have been different if they had stayed together! But sometimes, it’s just not meant to be. According to US Magazine, Jennifer says that the split was very painful for her. She said that it took her about two years to feel like she was confident in herself again. We had no idea she ever felt this way—it just goes to show that breakups are super difficult, even for strong women.
18 Aaron Carter & Hilary Duff
Sometimes it’s hard to believe it’s been so long since Hilary Duff and Aaron Carter broke up. Even though both of them have long since moved on, it’s fun to look back on the days when they were together.
They were both teen idols, and any girl would have loved to be in Hilary’s place at the time!
According to E! Online, Aaron’s feelings for Hilary definitely lingered after the breakup. They were only thirteen when they dated, so it’s been quite a while, but it seems like Aaron hasn’t quite forgotten about his true love for Hilary Duff!
17 Nick Lachey & Jessica Simpson
Oh my gosh, we could go on forever about how much we miss Nick Lachey and Jessica Simpson! They just seemed so perfect together, and everyone was so shocked when they announced that they were ending their relationship. Hearts broke everywhere. It was definitely a sad time for fans. According to US Magazine, there was tension between the two of them before they finally divorced. It probably didn’t help that they had their own reality show and had to go through all of the things that normal newlyweds do in front of a camera instead of in private! That’s rough!
16 Jake Gyllenhaal & Kirsten Dunst
Who doesn’t love Jake Gyllenhaal? We’re definitely in his fan club. Back in the early 2000s, he actually dated Kirsten Dunst for a while, and the two of them really looked so happy together!
However, maybe they split because Jake doesn’t really seem like the type who wants to settle down.
According to Diply, Kirsten said that she and Jake weren’t really compatible from the beginning. She said that she liked to go out and spend time at events, while Jake was always happier staying home and just hanging out! However, Kirsten did say that she truly loved Jake at the time.
15 Scarlett Johansson & Josh Hartnett
We’re pretty sure that Scarlett Johansson could be with any man that she wanted, whether he was a guy on the Hollywood A-list or a guy who had no interest in Hollywood at all. She’s just that beautiful! Back in the early 2000s, Scarlett and Josh Hartnett were a serious power couple—it seemed like they were on the cover of every tabloid. But it wasn’t all sunshine and rainbows. According to The Star, Josh says that he regrets dating his former movie costars—and yes, that would include Scarlett! Ouch! Well, maybe they just weren’t super compatible together.
14 Brody Jenner & Kristin Cavallari
Wow, remember the days when Brody Jenner and Kristen Cavallari were together? According to US Magazine, these two caused quite a bit of drama when they were together, and it definitely stirred up some controversy on the famous reality TV show The Hills. However, Kristen recently told US Weekly that Brody is one of the few costars from The Hills that she does still keep in touch with.
She did admit that she wasn’t invited to his wedding—which is understandable!
After all, having an ex at your wedding could probably make things quite awkward, so it’s for the best.
13 Rachel McAdams & Ryan Gosling
Okay, Rachel McAdams and Ryan Gosling were truly the cutest company in Hollywood while they were together. After filming The Notebook, they fell in love for real—and honestly, it just seemed like it was fate! Just look at the two of them—it really seemed they belonged together. They had so much chemistry on screen, so it just seemed natural that they would have the same chemistry off-screen, too. But according to an interview in GQ, Ryan said that their busy schedules were the downfall of the relationship. They were both spread too thin to make time for each other.
12 Paris Hilton & Nick Carter
Honestly, we kind of can’t believe that Paris Hilton and Nick Carter dated—sure, looking back it makes sense, but both of them have faded from the spotlight since then. It just feels like it was forever ago! According to Hello Giggles, their relationship was pretty much doomed from the beginning.
These two were just never meant to last.
Nick said that dating Paris was a bad idea for him—he ended up going out and partying much more than he would have normally, and it distracted him from his work. They also got into fights over some silly things.
11 Brad Pitt & Jennifer Aniston
It seems like all of Brad Pitt’s high profile relationships weren’t the right fit for him in the end: we all know that Brangelina is no longer, and if we rewind a few years, we can relive how Hollywood basically crumbled when he broke up with Jennifer Aniston. It was a sad time—it was clear that Jen was very unhappy with the way everything ended, and we really did feel bad for her at the time. According to Vanity Fair, Jen just wished that she didn’t have to go through that difficult breakup so publicly. She said it was very difficult.
10 Mariah Carey & Nick Cannon
Who could forget when Mariah Carey and Nick Cannon were together? Yes, Mariah may have a reputation for being a diva, but it’s clear that she did love Nick, even though the marriage didn’t last.
For a while, they were THE power couple in Hollywood—Mariah was always at the top of the charts, and it was like everything she touched turned to gold.
But sadly, their marriage wasn’t meant to be. According to E! Online, the two of them still love each other and care deeply about each other. Nick says that Mariah is the strongest woman he knows.
9 Ryan Reynolds & Alanis Morrissette
Now, this is one of those couples that you never really expected to see together. Ryan Reynolds and Alanis Morrissette? Really? Well, once upon a time, before Ryan married Blake Lively, these two were happy as can be. It’s surprising, but there was definitely a spark there! According to Zimbio, the two were even engaged at one point! It just goes to show that sometimes, opposites can attract. Alanis said that Ryan was always very supportive of her, but it seems like since their split, they have probably dropped all contact. After all, they are both married to other people now.
8 Wilmer Valderrama & Mandy Moore
Wilmer Valderrama has been involved in a few high profile relationships during his time in Hollywood. Of course, we all know that he dated Demi Lovato for a few years, but before then, he dated Mandy Moore! According to People, things did not end on a positive note between the two of them.
She has gotten upset about a few things he has said about her in the press since the relationship ended.
It’s shame that this is the way things turned out—it’s always nice when you can stay friends with an ex, but it doesn’t always work out.
7 Rachel Bilson & Adam Brody
Rachel Bilson and Adam Brody always looked like they were having so much fun together! They were costars on the popular TV show The O.C. When they got together off screen, fans were so happy! They were excited to see that two of their favorite actors had fallen in love in real life. But according to PopSugar, the two just couldn’t make it work—unfortunately, this seems to be the case for many costars who end up dating each other. They began dating in 2003, but they eventually broke up in 2006. It was such a shame to see it end!
6 Will Arnett & Amy Poehler
Okay, we’ve got to admit, this breakup was really upsetting. Will and Amy were comedy’s most incredible power couple. They are both so funny and talented that we really thought they were 100% perfect for each other—the thought of them going their own separate ways was unthinkable!
But sadly, sometimes even the best couples realize that they simply can’t make it work.
According to Huffington Post, Will and Amy separated in 2012. Amy has opened up about the divorce and said that the process was extremely difficult, but luckily, she had a good support system to help her get through it.
5 Tim Burton & Helena Bonham Carter
Tim Burton and Helena Bonham Carter truly seemed like they were just made for each other. It’s really no secret that Helena was basically Tim’s muse for so many of his movies throughout the early 2000s. She just had that aesthetic that he admired, and of course, she is super talented too. But even this marriage wasn’t quite right. According to US Magazine, Helena opened up and said that she was basically grieving after they split up. They really were an artistic match made in heaven—it is sad that things did not work out between them romantically in the end.
4 Sophia Bush & Chad Michael Murray
Another costar couple that just couldn’t make it work out! Sophia Bush and Chad Michael Murray were sweethearts, but things did not end well between these two. These two actors appeared on the TV show One Tree Hill together, and they fell in love when the cameras weren’t rolling. But according to US Magazine, Sophia has since revealed that perhaps they were not as happy together as they seemed.
She said that her costars and the producers of the show really wanted them to get married because it would bring so much good publicity!
Imagine dealing with that kind of pressure?
3 Orlando Bloom & Kate Bosworth
Orlando Bloom doesn’t hang around Hollywood much anymore—he does way more work in theater these days—but remember when it seemed like every single had a huge crush on him? Yup, we’ve all been there! Unfortunately for all of the girls who were in love with him, he was married to Kate Bosworth. But this relationship wasn’t going to last forever. According to Female First, while the two of them get along just fine today, Kate originally broke up with Orlando because she didn’t like his friends! Well, she is not the only woman out there who's done that.
2 Matt Damon & Winona Ryder
It might seem like Matt Damon and Winona Ryder wouldn’t have much in common, but surprisingly, they actually dated for a while! According to PopSugar, the way they got together is just as surprising—Winona used to be best friends with Gwyneth Paltrow, who introduced them!
They started dating in 1997, and they stayed together until 2000 when they finally decided to call it quits.
Although the relationship didn’t work out, Winona says that she has no regrets. She says that Matt is a really good guy, and she is glad that they have been able to remain friends over the years.
1 Jared Leto & Cameron Diaz
Whoa! Sometimes we actually forget that Jared Leto and Cameron Diaz dated because it feels like so long ago—and because Cameron had actually retired from acting since then. But they were together for several years, and they were quite happy during that time. According to PopSugar, Jared and Cameron were actually together from 1999 until 2003. In fact, at one point there was even a rumor swirling around that they were engaged! However, it was never confirmed whether or not this rumor was true, and it didn’t matter in the end anyway—they went their separate ways 15 years ago.
References: etonline.com, vanityfair.com, people.com, huffingtonpost.com, popsugar.com
