Cassie is currently dating hip hop star/mogul/CEO of Bad Boy Entertainment Sean Diddy Combs.Cassie is currently dating hip hop star/mogul/CEO of Bad Boy Entertainment Sean Diddy Combs. Born Cassandra Elizabeth Ventura on 26th August, 1986 in New London, Connecticut, she is …Her best friend Michelle Richardson (April Pearson) arranges for her to take Sid Jenkins (Mike Bailey) virginity at a party. Cassie Ventura has been in relationships with Ryan Leslie (2004 - 2007). Cassie, born Cassandra Ventura, is an American model, singer-songwriter, dancer, and actress.It is revealed that Sid did indeed find her and that the pair spent several years travelling around America,  although she does not mention him by name. She was born and raised in New London, Connecticut.She works as a waitress in a cafÃ©, and later discovers a website titled Oblivion , filled with candid shots of her.very interesting because she has a lot of problems, and she s very troubled, and she s anorexic and completely lacking in self-esteem and self-belief, but along with that she s sort of quite smart.Cassie is briefly referred to by Doug in series 6 when he mentions to Liv that he once danced for a girl to help her get through an exam, referring to Cassie s centric episode in the second series.There, she meets a kind young Iowan named Adam (Stephen Michael Kane), with whom she forms a strong platonic friendship when he offers her a place to stay in his apartment.
Cassie is definitely putting something on Diddy and he likes it enough to give her a second chance.
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The show s producers and writers described her centric episode in an interview with The Independent as being about how she gets through her day without eating.
Where before she was bubbly, cheerful and unashamedly quirky, she is now a shadow of her former self, appearing tired and withdrawn, living in a shared flat in London and working as a waitress in a cafÃ© to make ends meet.
she seems to be the only one who he has been spotted with on numerous occasions.