Before Kimye, Kanye was engaged to someone else. The rapper had planned to wed designer Alexis Phifer when he popped the question over a lobster and pasta dinner in Capri in August 2006. While it was his late mother Donda’s wish that they marry, a year and a half into the engagement they split in April 2008.
In September 2013, Miley Cyrus and Liam Hemsworth confirmed they had ended their engagement. Despite trouble actually making it down the aisle, the two have been on-again off-again since then and are a couple once again—with no plans to marry just yet.
Simon Cowell is now with his baby’s mom, Lauren Silverman, and they haven’t married yet. Cold feet Simon? In January 2012, he was engaged to Mezhgan Hussainy. They then went “on a break” (Hey Ross, hey Rachel) and eventually called the whole thing off.
Ah, Bennifer. Ben Affleck and Jennifer Lopez started dating in 2002, and were supposed to wed in September 2003. But the media circus surrounding them contributed to their downfall and they called off their wedding right before the big day. In January 2004, they were done.
Gwyneth Paltrow and Brad Pitt once rocked the same hairstyle and that was enough to keep them together for a while. After meeting on the set of the 1995 flick, Seven, the two called it off in June 1997, after two and a half years together. Gwyneth admitted years later she may not have been completely faithful. Beautiful people problems.
Before Blake Lively and their two children, Ryan Reynolds had a different type. Alanis Morisette was once the object of his affections, and the two were engaged in 2004 after dating for two years. They ended things in 2006 and everyone lived happily ever after—just not with each other.
Nick Cannon planned a Jumbotron proposal in Times Square, but eventually called it quits with model Selita Ebanks. They ended things in October 2007, then Nick moved on to Mariah Carey.
Weeds star Mary-Louise Parker and actor Jeffrey Dean Morgan got engaged in February 2008. After dating on and off since December 2006. They called it quits in April 2008.
Katie Holmes and Chris Klein hooked up pre-Tom Cruise marriage. Katie and the American Pie actor dated for five years before getting engaged in 2003. In 2005 they ended things.
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