9. Kristen Stewart and Robert Pattinson
Many Twi-hard hearts were broken when K-Stew and R-Pats finally called it quits after a good four Twilight movies together. Team Jacob can mark this one down as a win.
8. Justin Bieber and Selena Gomez
We really beliebed this one was going to work out!
7. Miley Cyrus and Liam Hemsworth
After meeting and dating after filming The Last Song together, Miley and Hemsworth announced their engagement. We were surprised but figured, hey, she’s just being Miley. Post break-up Miley stars in a racy video for her song “Wrecking Ball” about Hemsworth that makes us hope this is the last song we’ll hear from her for a while.
6. Reese Witherspoon and Ryan Phillippe
During Witherspoon and Phillippe’s marriage from ’99-’07, we imagined their relationship was just like Heaven. But when the couple broke up in 2007 amidst rumors of Phillippe’s jealousy of his wife’s success, as well as an affair, we realized maybe he had cruel intentions the whole time.
5. Rachel McAdams and Ryan Gosling
Any girl who says she doesn’t love The Notebook is lying. The same goes for any girl who says she wasn’t even a little sad when Gosling and McAdams broke up. We can only hope that Ryan will channel his inner Noah and win her back somehow.
4. Nick Lachey and Jessica Simpson
If there’s one thing we learned from Nick and Jessica, it’s not to turn your marriage into a reality show. While Newlyweds on MTV made us love the couple more with each episode, these two felt the opposite. When they announced their split in 2005, we couldn’t help but wonder what a relief it must have been for Nick not to have to explain the difference between chicken and tuna one more time.
3. Chris Brown and Rihanna
While Breezy and Ri-Ri played coy about their flirtatious friendship for years before announcing their relationship in 2008, it was only one year until these two celebrities had one of the most publicized break-ups in Hollywood. When they crawled back to love in early 2013, we had mixed feelings about the reunion. Luckily, Brown threw the deuces up to Rihanna within a few months.
2. Brad Pitt and Jennifer Aniston
Brad Pitt and Jennifer Aniston were like the Barbie and Ken of Hollywood. That all changed, however, when Pitt took his role as Angelina Jolie’s husband in Mr. and Mrs. Smith a bit too literally. But while we sat in bed eating bon-bons and cursing Brangelina, Jen kept quiet about the breakup for three years until finally admitting in a 2008 Vogue interview that she thought Angelina’s actions were “uncool.”
1. Justin Timberlake and Britney Spears
Every nineties girl is still waiting for the day JT and Britney get back together. When these two broke up in 2002 after three years of pop-music bliss, we were the ones crying a river.