As Cassandra “Cassie” Ventura revealed in her lawsuit against Sean “Diddy” Combs, she was in a brief relationship with rapper Kid Cudi in 2011. Before the lawsuit, however, there wasn’t much known about the couple’s romance.
In 2012, rumors were circulating that Ventura and Cudi potentially had a fling, as noted by Yahoo! At the time, no one knew that Ventura and Combs were on a break, so many claimed the “Me and You” singer cheated on the producer with Cudi. Regardless of how Ventura and Cudi connected, fans seemed even more convinced something was going on after the rapper tweeted cryptic messages. In a since-deleted tweet, Cudi shared: “Do you guys want to know [whose] girl found me intriguing.” Although Cudi didn’t explicitly say Diddy, many believe he was talking about his fellow musician.
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Although it was all rumors, speculation of Ventura and Cudi’s fling grew after the rapper and Combs got into an altercation. According to Bossip, in 2012, Cudi and Combs happened to be in the same club and had a heated exchange. A source shared, “The club owner didn’t know that the two had beef over Cassie and decided to sit Diddy down next to Cudi. The two then exchanged some heated words to the point where the entire club was watching — creating a huge scene.” While the two went their separate ways, this wasn’t the last time Combs confronted Cudi.
