Rihanna and Chris Brown dated for two decent chunks of time, the first of which ending after he beat her senseless. Never a good sign. Nor was taking him back after that, but she's moved on with Drake ... thank goodness. Good luck, Karrueche!
Perhaps the most lethal of any love we've ever seen, Amy Winehouse and Blake Fielder-Civil abused drugs so fervently that she could never recover from that viscious cycle, passing away at age 27. He, meanwhile, ended up locked up for a long time.
Justin Bieber and Selena Gomez had a long love affair that involved him taking her virginity and a whole lot of partying and frequent breakups, fights and general emotional turmoil. It's possible it wasn't meant to be. And by possible we mean obvious.
Jenelle Evans and Courtland Rogers, who are still technically married, were only together as a couple for a few months ... during which she aborted his baby and both were arrested for heroin possession and assault. They also feuded on Twitter a lot - even by her standards. Not healthy.
Britney Spears and Kevin Federline were married two years and had sex at least that many times, as evidenced by their two sons. How in the world did these two ever get married? Okay, we can grasp why K-Fed married her (see photo). Just not the reverse ...
Ray J hit it first, and he filmed it. The XXX-rated Kim Kardashian marked the end of the duo's relationship, though it catapulted her to fame, making it a net positive, we suppose. Ray then relased a song CALLED "I Hit it First," which is just hilarious.