A Look Back At Cassie And Kid Cudi's Short, Drama-Filled Fling

It seems that every "Day 'n' Night," Cassandra "Cassie" Ventura and Kid Cudi's relationship was filled with drama. Many of you may not have known that the two even dated because, for years, Ventura had been in a very public relationship with producer Sean "Diddy" Combs.

It wasn't until 2023, when Ventura filed a lawsuit against the "I'll Be Missing You" singer, that she revealed that she had a brief fling with Cudi in 2011. Before the suit, neither Ventura nor Cudi ever spoke about their romance or what had happened between the two. However, the "Pursuit of Happiness" singer has talked about past relationships, which fans now know included Ventura.

In 2019, he tweeted an apology to all his ex-girlfriends for the way he treated them. He wrote, "I apologize to all my girlfriends in my 20s and early 30s I let down and treated like s**t because I wasn't right. All of my relationships didn't work out because of me. I had to accept that and find peace and be better." While no one knew at the time that this list of ex-girlfriends included Ventura, they do now. And now that people are aware of their romance, many are curious about the details of their relationship. While the information on their fling is scarce, what has bubbled up paints Cudi and Ventura's romance as a hotbed of drama.

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.

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.

Back in 2012, it was reported that Kid Cudi was worried Sean "Diddy" Combs would retaliate for the musician having a fling with his long-time girlfriend, Cassandra "Cassie" Ventura — and it seems like Cudi had every right to be fearful.

In 2023, Ventura filed a lawsuit against Combs and shared some bombshell claims against the producer, including that he allegedly blew up Cudi's car, according to Entertainment Weekly. The documents explained that the "Me and You" singer revealed she had a brief fling with Cudi during a difficult period in her and Comb's relationship. When the producer learned about the relationship between Cudi and Ventura, he attacked her. That wasn't it. In February 2012, the singer alleges that Combs told her "that he was going to blow up Kid Cudi's car." What's more, he was intent on making sure Cudi was at home with his friends when it all went down. Not long after their conversation, Cudi's car exploded.

Combs shot down everything Ventura claimed in her lawsuit, but Cudi's crew backed her up, saying she wasn't making up the attack on the "Pursuit of Happiness" singer. One of Cudi's reps told The New York Times straight up, "This is all true," backing Cassie's side of the story. So, even though Cudi and Ventura weren't together for too long, their relationship definitely caused a whole lot of drama.