The early 2000s were a strange time for romance. It seemed like a very small pool of pop culture icons were continuously hooking up with one another. Whether it was the Hilary-Lindsay-Aaron love triangle (iconic!), or Wilmer Valderrama hooking up with everyone for some reason, something must have been cosmically up because love matches were bizarre in the early aughts.

While some only lasted a few months, some lasted for years — but all were a bit mismatched. So get ready for a bizarre stroll down memory lane, because here are 18 celebrity couples that are completely emblematic of the 2000s.

18. Justin Timberlake and Britney Spears

Of course, we had to start with everyone’s favorite 2000s couple, Justin Timberlake and Britney Spears. Let us not forget the matching denim outfits heard ‘round the world. This duo was almost too good to be true. Both were of Mickey Mouse Clubhouse fame, and both were undeniably at the top of their game musically. Granted, JT had a huge comeback post-*NSYNC, but this was during the days when both were teen pop sensations. Basically, you couldn’t turn a corner without seeing them on the cover of every Tiger Beat magazine.

17. Kirsten Dunst and Jake Gyllenhaal

TBT to when Kirsten Dunst and Jake Gyllenhaal were the 2000s couple to be spotted. After being introduced by Jake’s sister, Maggie, the two became pretty serious pretty quickly. Jake is definitely a bit of a player. In case you forgot, he kind-of recently dated Taylor Swift and was definitely the inspiration to a few of her songs. Regardless, we were all totally rooting for these two to work out. Especially since they even lived together and adopted a puppy togeher! Sadly, they did not.

16. Rachel McAdams and Ryan Gosling

UGH. There is nothing more beautiful than when a beautiful on-screen couple becomes a beautiful IRL couple. Thank god for Rahel McAdams and Ryan Gosling. Not only did they share multiple memorable kisses throughout the filming of The Notebook, who could forget their kiss at the MTV Movie Awards? It was every teenage girl’s dream to see the couple from their favorite Nicholas Sparks novel come to life with these two.

15. Jessica Simpson and Nick Lachey

Granted, this 2000s couple ended up being kind of a disaster, but when they were good — they were great. Everyone loved seeing Nick Lachey and Jessica Simpson together. In fact, the married couple’s dynamic was so popular that they even had their own reality show, Newlyweds: Nick and Jessica on MTV. A classic. They were pop stars in love, and it was love at first sight. Simpson even publicly discussed losing her virginity to Lachey on their wedding night. Unfortunately, it turns out that a reality show about the details of your intimate life may not be the best thing for a marriage and the two divorced. They are now both happily married — to other people.

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14. Brad Pitt and Jennifer Aniston

This one hurt a whole lot, TBH. Not only were Brad Pitt and Jennifer Aniston everyone’s favorite 2000s couple, their breakup was probably the most infamous of all time. After Pitt allegedly cheated on Aniston to end up with Angelina Jolie, people even wore T-shirts that said “Team Jen” or “Team Angelina.” Remember that? Yikes. Everyone was rooting for Jen. She was Hollywood’s good girl, and Brad was an internationally-adored bad/kinda good boy. Although we won’t ever forgive him for breaking her heart, it was probably for the best considering she and Justin Theroux are kind of perfect.

13. Rachel Bilson and Adam Brody

This early 2000s couple is another example of how being in love on-screen can turn into the real thing. All over the world, fans of The O.C. rejoiced when Adam Brody and Rachel Bilson (aka Summer and Seth) began dating. They were photographed everywhere they went, and who could deny that they looked straight-up adorable together? Luckily for them, they managed to maintain a low profile and broke up amicably, which is definitely no easy feat in the spotlight. We still ship these two, though.

12. Jennifer Lopez and Diddy

Can you even imagine how powerful this early 2000s couple would have been if they had stayed together? We can all agree that Jennifer Lopez has somehow found the fountain of youth, and manages to look better the older she gets. Diddy is a multi-millionaire mogul and rap legend, but unfortunately the two didn’t work out. You may remember their claim to fame as a couple — when they appeared at the Grammys and J-Lo wore a now-legendary green Versace dress. The two were unstoppable. That is, until they broke up after Diddy’s alleged infidelity. Sigh.

11. Paris Hilton and Nick Carter

As soon as this relationship started, pretty much everyone knew it was destined for disaster. The early 2000s were a wonderful and strange time when all we seemed to care about was who Paris Hilton was dating. So, when she paired up with Backstreet Boys frontman, Nick Carter, we couldn’t wait to see what would happen next. The blonde pop culture icons were all over the tabloids (remember when they got each other’s names tattooed?), but the relationship must have been disastrous.

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10. Hilary Duff and Aaron Carter

OKAY — can we just talk about how getting to see Hilary Duff and Aaron Carter become an early 2000s couple was like a dream come true for every tween? Let’s not forget when Aaron had a cameo on Lizzie McGuire, causing every viewer to aggressively ship them. The two shared an on-screen mistletoe kiss, and the relationship developed from there. Granted, it turns out that Hil was way too good for Aaron, and their break up was highly publicized amidst rumors that he had cheated on her with Lindsay Lohan.

9. Lindsay Lohan and Aaron Carter

And of course, we had to mention one of the most controversial couples from the early 2000s. After his public breakup with Hilary Duff, Aaron Carter got together with everyone’s favorite redheaded diva, Lindsay Lohan. There were tons of rumors that Aaron had cheated on Hilary with Lindsay for a few months, and teen gossip magazines were constantly trying to pit the two girls against each other. While Aaron is the obvious villain in this love triangle, Lindsay took every opportunity to bad mouth Hillz and it was not cute.

8. Mila Kunis and Macaulay Culkin

While Mila Kunis is now lovingly married to her That ’70s Show co-star, Ashton Kutcher, there was a time when she was a part of another iconic early 2000s couple with Home Alone child star, Macaulay Culkin. The two had a very low-key and super long-term relationship of eight years, which is basically a lifetime in Hollywood years. At the time, Kunis didn’t believe in marriage, but she seems to have changed her tune, and is now happily married with a new baby. Macaulay, on the other hand, is looking hot as ever, so they’re both up to great things.

7. Jared Leto and Cameron Diaz

Talk about a seriously badass early 2000s couple. It feels like everyone seems to have forgotten about the romance between Jared Leto and Cameron Diaz. The two dated for three years but managed to keep their relationship fairly private. However, they sparked engagement rumors in 2003, when Diaz was spotted wearing a diamond ring at the Golden Globes. Unfortunately, any rumors were quickly squashed when they officially split in 2003. At least we’ll always be able to cherish the memory of this super cool couple.

6. Lindsay Lohan and Wilmer Valderrama

Another classic LiLo relationship for the books. Looking back, it seems like Lindsay managed to be a part of more than one 2000s couple doomed to failure. If you don’t remember, That ’70s Show star Wilmer Valderrama seriously managed to make his way around young Hollywood. The dude came out of nowhere, dating the likes of Lindsay, as well as Mandy Moore, Mischa Barton, Mila Kunis and Ashlee Simpson. Dating Wilmer was kind of the beginning of Lindsay’s breakdown, so it’s probably a good thing the two separated.

5. John Mayer and Jessica Simpson

John Mayer is a notorious bad boy and heartbreaker. So it was pretty confusing when he briefly dated everyone’s favorite good girl (and ex-wife of Nick Lachey), Jessica Simpson. Unfortunately, the early 2000s couple ended less-than-amicably after Mayer’s controversial (and really classless, TBH) Playboy interview, in which he said some seriously pretty intimate and unnecessary things about the “With You” songstress. Since the split, Jess hasn’t forgiven the crooner, and he’s gone on to break other Hollywood hearts, including Katy Perry, Jennifer Aniston, Taylor Swift, and countless others.

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4. Ashlee Simpson and Ryan Cabrera

Oh, you thought we’d have Ashlee Simpson and Pete Wentz on this list? Sorry, but her relationship with Ryan Cabrera was WAYYY more emblematic of this decade than her relationship with the Fall Out Boy singer. We first started shipping Ash/Ry during his frequent appearances on The Ashlee Simpson Show on MTV. They insisted they were just friends at the time, but we were not stupid. He wrote the song “Photo” about Jessica’s lil sis. He later dated Audrina Patridge — so pretty much everything about him reminds us of the 2000s.

3. Ryan Gosling and Sandra Bullock

In what may be one of the most often-forgotten relationships, we have early 2000s couple, Ryan Gosling and Sandra Bullock. That’s right, the two briefly dated after falling in love on set of their movie, Murder by Numbers. Their relationship was pretty monumental since older women dating younger men is still (somehow) a huge taboo in Hollywood. This duo had an age difference of 16 years which sent some people’s heads spinning. While they didn’t last more than two years, their split was pretty low-profile and the two ended on good terms.

2. Matt Damon and Winona Ryder

The best thing about this early 2000s couple is probably the fact that they had matching haircuts. Can we, for a second, talk about Matt Damon and Winona Ryder? The two met after being introduced by another iconic couple, Ben Affleck and Gwyneth Paltrow. Ben and Matt were BFFs, and so were Gwyneth and Winona. So cute. Either way, the couple broke up after two years amidst constant rumors of arguing and breaking up. However, the two ended on great terms and remember the relationship fondly.

1. Hilary Duff and Joel Madden

After Hilary and that f*ckboi Aaron Carter split, we were all pretty happy to hear she was dating someone new — even if the pairing was completely unexpected. A Disney Channel good girl dating a bad boy rocker? It was scandalous. Hilary has even has since suggested she lost her virginity to the Good Charlotte guy. We’ve got to admit that we shipped it hard. But alas, all good things must come to an end and so did the Hilary/Joel mashup. Joel started dating Nicole Richie soon after and the two have been together ever since. If you need anymore proof these two were sooooo early-aughts, just check her outfit.

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