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Aaliyah was engaged to former Roc-A-Fella CEO Damon Dash. They were planning on being wed in the spring of 2002. But unfortunately she was killed in a horrific plane crash on August 25, 2001. Ironically 3 and a half years later he was married to singer Rachel Roy on January 15, 2005 ironically a day before Aaliyah would have hit her 26th birthday if still alive.

But even in his pictures with Rachel Roy, he never has looked nearly as happy and satisfied and content as he did when he was with Aaliyah.

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15y ago

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