When: September 2007 - 2010
Cassie is possibly Diddy’s highest profile relationship since he ended things with Kim Porter in 2007. Relative to some of his past relationships, Diddy has been rather modest about directly addressing his relationship with Cassie. Of course, modesty isn’t one of Diddy’s strongest attributes, and the public displays of affection between these two can be seen all over the Internet. And sure, Cassie denied dating Diddy when we interviewed her (twice!), but we don’t believe her for a second. Why? Well in August 2009, Diddy and Cassie seemingly outed themselves as a couple with a few TMI Tweets. Diddy (who previously tweeted during tantric sex) tweeted about how he loved eating turkey sandwiches after sex, and later that night Cassie tweeted that she was eating a turkey sandwich. Coincidence? We think not. By January 2010, there were rumors that Cassie was pregnant with Diddy’s baby which she denied (via Twitter, of course). So these two can deny it all they want but if you ask us, a rumor isn’t a rumor if it never dies and a picture is worth a thousand words.
Smash Probability: