Vanessa Hudgens And Zac Efron
Ya gotta root for high school sweethearts... especially when they're High School Musical sweethearts. Vanessa Hudgens and Zac Efron 4ever.
Rachel McAdams and Ryan Gosling
Both Rachel McAdams and Ryan Gosling are conveniently single at the same time, which means a reconciliation is inevitable at this point. Next step: The Notebook 2?
Angelina Jolie and Billy Bob Thornton
She may have found her soul mate in Brad Pitt, but Angelina Jolie seemed perfectly (and weirdly) matched with Billy Bob Thornton circa 2001.
Adam Brody and Rachel Bilson
Adam Brody and Rachel Bilson dated while playing a couple on 'The OC,' and their characters Seth and Summer eventually got married. C'mon, it's not too late for that ending!
Cameron Diaz and Justin Timberlake
Cameron Diaz and Justin Timberlake seemed like a fun, goofy pair—luckily, there's always that faux-sex scene in 'Bad Teacher' to remember their relationship by!
Chili and Usher
Chilli and Usher were adorable together, and she recently admitted on Twitter that she'll love him forever.
Jake Gyllenhaal and Kirsten Dunst
Jake Gyllenhaal and Kirsten Dunst loved themselves some PDA, which made us love them even more.
Amy Poehler and Will Arnett
Amy Poehler and Will Arnett may have just broken up, but it's never too early to start campaigning for their reunion.
Jennifer Lopez and P Diddy
Jennifer Lopez has had loads of celebrity boyfriends, but our favorite is P. Diddy. If only that whole night club shooting hadn't happened...
Kim Kardashian and Reggie Bush
We're really happy about Kanye West's new baby with Kim Kardashian, but Kim's first boyfriend on 'Keeping Up with the Kardahians,' Reggie Bush, was one of the cutest boyfriends of all time.
Hilary Duff and Aaron Carter
From approximately 2000-2003, everyone wanted to be and/or date Hilary Duff and Aaron Carter.
Reese Witherspoon Ryan Phillippe
The love that 'Cruel Intentions' built: Reese Witherspoon and Ryan Phillippe ruled the early '00s.
Rebecca Romijn and John Stamos
We often still refer to Rebecca Romijn as Rebecca Romijn Stamos, and with good reason. She and John Stamos were perfect together.
Chad Michael Murray and Sophia Bush
Proof that dating your co-star isn't always the best idea? Sophia Bush and Chad Michael Murray, who started dating (and later divorced) while working together on One Tree Hill. We still miss these guys so much though.
Carson Daly and Tara Reid
Tara Reid recently admitted to just getting over her ex, Carson Daly, whom she split with in 2001. He's engaged with a baby now but it's not too late to reconcile!
Joe Jonas and Demi Lovato
Joe Jonas and Demi Lovato are still friends even though they broke up on weird terms. Friends make the best boyfriends, Demi! Just sayin'...
Julianne Hough and Ryan Seacrest
Julianne Hough and Ryan Seacrest's split was rather recent, making it even more of a possibility that these two are not over for good. Right?
Blake Lively and Penn Badgley
The best thing ever was when Serena and Dan dated on-screen and in real life. But Gossip Girl's over now, Blake Lively. Ditch your hubby Ryan Reynolds and call up your old friend Penn Badgley!
Nick Lachey and Jessica Simpson
While now Nick Lachey and Jessica Simpson are both parents and happily in new relationships, we'll always hold a special place for the couple that basically invented MTV reality shows.
Nina Dobrev and Ian Somerhalder
Vampire Diaries fans are not happy that Nina Dobrev and Ian Somerhalder broke up and, frankly, neither are we.
Sarah Jessica Parker and Robert Downey JR.
Sarah Jessica Parker and Robert Downey Jr. dated for seven years before they broke up in 1991, apparently due to his drug use. He's sober now, SJP! Let's make this happen.
Courteney Cox and David Arquette
Coco Arquette definitely wants her parents, Courteney Cox and David Arquette, back together. Do it for the kid, guys.
Gwyneth Paltrow and Ben Affleck
After three turbulent years of dating, Gwyneth Paltrow and Ben Affleck split for good in late 2000. They were the "it" couple of the late 90's though and we'll never forget it.
Heidi Klum and Seal
They share four kids and so much love between them! Heidi Klum's new boyfriend just doesn't compete with the hotness that is her ex husband, Seal.
Kris and Bruce Jenner
And lastly, we can all agree that Kris and Bruce Jenner announcing their split was the most depressing thing, right? Here's to hoping it's not for good.