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The celebrity couple sparked rumors that they were heading for marriage in early 2014 when Combs posted a picture on Instagram of a diamond ring with the caption, “Baby do you like it? I just wanna Mk you smile [sic].” Although Cassie Ventura was spotted wearing the same ring on that finger, his rep denied that the celebrity couple was engaged; the ring was just an extravagant gift for his younger woman.

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Sean “Puff Daddy” Combs started his career as the founder of Bad Boy Records in 1993, which went on to sign rap icon Notorious B. That was just the beginning for this aspiring businessman.

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She began work on her second studio album in 2007 releasing three singles; "Official Girl" featuring Lil Wayne in August 2008, "Must Be Love" featuring Diddy in April 2009, and "Let's Get Crazy" featuring Akon in August 2009, which all failed to chart in the USA, in late 2009 Cassie signed a record deal with Interscope Records.

On April 11, 2013 Cassie released her debut mixtape Rocka Bye Baby, which was promoted with the release of "Numb" featuring Rick Ross and "Paradise" featuring Wiz Khalifa.

The celebrity couple ended their relationship the following year, and the breakup was anything but amicable.

While Kim Porter was pregnant with the twins, Sean “Puff Daddy” Combs fathered another woman’s baby—that child was born five months before the twins.

Apart from music, Cassie is signed to modeling agency Wilhelmina Models and One Management.