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Rapper Cassper Nyovest has reflected on perhaps his worst date ever, revealing that he once took a girl out in a beat up car and joked about being broke. The Doc Shebeleza hitmaker, who has had women swooning over him after his recent body transformation, told Tumi Morake on WTF with Tumi that he didn’t alway have his love life on lock.

“So, I was out there pushing (the car) and I was sweating by the time we got to the dinner. And then I try and crack a joke like, ‘yoh, I don’t have the money’. She was older and more mature and she just said, ‘come on, stop joking like that. That’s stupid’. It messed up my date. It was painful for me,” he said.

Cassper went on to have a few more successful relationships, including one with TV personality Boity Thulo. The pair dated twice but broke up in late 2015. Cassper also ended up writing about another one of his relationships, this time about a girl who he was interested in, who ended up choosing a businessman over him.

“This girl I was really digging, falling for, I was thinking of making her my girlfriend but she left me in the middle of writing this song. She told me she found a guy, some business dude that was willing to take care of her. And I’m broke. I am trying to invest in my craft, I can’t bless women like that,” he told Afternoon Express earlier this month.