Cassie and Kid Cudi’s Relationship: How Long Did it Last?
Kid Cudi, a rapper best known for hits like “Day ‘N’ Night” and “Pursuit of Happiness,” will take the stand in Sean ‘Diddy’ Combs’ sex trafficking and racketeering trial. Cudi’s testimony is expected on May 21, more than a week after testimony in the case initially began. Despite not yet taking the stand, the hip-hop artist’s name has been bandied regularly in the months before the trial and during testimony from other witnesses. Kid Cudi is tied to the case through Cassie Ventura, whom he dated briefly. Do you know exactly when they were hooking up?
When did Kid Cudi Date Cassie Ventura?
Cassie Ventura and Kid Cudi’s romance has come up a lot during Diddy’s trial. Their liaison has been openly discussed in the lead-up to the trial, too. In fact, Kid Cudi’s name has come up so often that you would think he and Cassie were deeply involved with each other over a long stretch of time. In actuality, their romance was incredibly short-lived.
According to her testimony, Cassie Ventura and Kid Cudi only dated for a few months in 2011. While they began seeing each other while she and Sean ‘Diddy’ Combs were taking a break from their relationship, insiders claim there was, in fact, some overlap between the two relationships. The romance was a well-kept secret until 2023, when Kid Cudi’s name was mentioned in Cassie Ventura’s lawsuit against Diddy. Diddy and Cassie settled the lawsuit in just 24 hours for $20 million.
Cassie Ventura and her mother both mentioned the rapper during their testimony
Kid Cudi and Cassie Ventura’s relationship has been over for more than a decade, and was incredibly short-lived even back then. Still, it remains an essential aspect of the case against Diddy. While he has yet to take the stand, both Cassie and her mother, Regina Ventura, have mentioned the rapper while testifying against Diddy.
During her time on the stand, Cassie revealed that Combs became infuriated upon discovering her involvement with Kid Cudi. She said he physically assaulted her and threatened her life. According to Cassie, Combs threatened to blow up Cudi’s car during his tirade over the relationship. While Diddy was not charged in any explosion, Cudi’s vehicle did, in fact, explode in his driveway. According to Rolling Stone, Kid Cudi’s car, a Porsche, was set on fire in January 2012 by an “incendiary device.”
Regina Ventura also took the stand to testify against Diddy. Cassie’s mother recalled how Diddy blackmailed her for $20,000, insisting that if she didn’t pay up, he would release explicit photos of Cassie. The elder Ventura testified that the threat came as retaliation for her daughter’s relationship with the younger artist. While Regina Ventura said she paid Diddy, he later returned the cash.
Who is he seeing now?
Despite being wrapped up in Diddy’s legal drama, Kid Cudi no longer has ties to Cassie. While their short-lived romance has come under scrutiny in recent years, they have both very much moved on. Cassie is currently expecting her third child with her husband, Alex Fine. Kid Cudi is in a relationship, too.
Kid Cudi has had several notable relationships over the years, but he’s ready to make things official with Lola Abecassis Sartore, a fashion designer. The couple went public with their romance in April 2024 by announcing their engagement. It’s unclear how long they were seeing each other before he popped the question. They have not announced a wedding date.
