1. Britney Spears and Justin Timberlake
Ah, what a perfect romance this could have been, if only it had lasted. Thankfully, both Britney and Justin finally seem healthy and happy in their respective relationships.
2. Michael Jackson and Lisa Marie Presley
Most would have thought that the Prince of Pop and the King of Rock ‘N’ ‘Roll’s daughter would be a perfect match, but it’s not surprising the romance was short lived when you look at shots of the couple like this one.
3. Jennifer Lopez and Sean Combs
Back when Jenny was still “from the block” and Puffy was P. Diddy? or was it Puff Daddy? We lost track a long time ago.
4. Marilyn Manson and Rose McGowan
Fans may have forgotten about this romance but there’s one thing we know we’ll never forget: the indelible image of Rose’s inexistent outfit burned into our brains.
5. Ashlee Simpson and Pete Wentz
When Ashlee Simpson and Pete Wentz showed up to the 2008 VMA’s together, showing off Ashlee’s baby bump - everyone had high hopes. But despite their adorable son together, it seems these two just couldn’t make it work.
6. Drew Barrymore and Hole’s Eric Erlandson
Honestly, we just kind of miss Drew Barrymore’s more punk rock days - even if hanging with Courtney Love doesn’t seem like the most advisable of activities.
7. Jessica Simpson and Nick Lachey
Another Simpson sister, another sad divorce. These two were simply too cute to be true - plus, we suspect Nick might’ve been dipping into Jessica’s makeup too much. Look at those glossy lips!
8. Travis McCoy and Katy Perry
For before there was Russell, there was your boy Travie, front man of Gym Class Heroes. However cute they might’ve seemed together back in the day, these two ended up duking it out in public by taking thinly-veiled jabs at each other through songs.
9. Axl Rose and Stephanie Seymour
Remember attractive Axl Rose? That’s all.
10. Pamela Anderson and Kid Rock
What can we say, they just seemed perfect for each other!
11. Nas and Kelis
Her milkshake brings all the boys to the yard, but looks like it wasn’t enough to keep Nas there! (sorry)
12. Taylor Swift and Joe Jonas
Oh sweet Taylor, don’t give up hope, you’ll find your dream man someday!