Fans have been waiting for years for Diddy to pop the question to his longtime love Cassie, but it looks like the romance has hit the skids. The former couple's relationship had been rocky for months prior to their split Credit: Rex Features. Cassie was in a long-term relationship with Diddy from 2007 to 2018. In August 2019, they announced their engagement. Diddy seemingly approved the new relationship by liking the photos. The pair announced their split in October 2018. CASSIE & DIDDY'S RELATIONSHIP. Diddy and Cassie reportedly started dating in 2007 but, for a long time, the duo remained tight-lipped about their relationship. Cassie, born Cassie Ventura, and her former beau P Diddy, also known as Sean "Diddy" Combs, were in an off-and-on-again relationship for more than a decade. As many know, Cassie was in a decade-long relationship with music mogul Diddy. For the longest time, Cassie and Diddy were the ultimate hip-hop couple, and it even seemed they were headed to the altar in 2014 when the rapper posted a pic of an engagement ring on his Instagram page. 22 October 2018, 10:52 | Updated: 22 October 2018, 10:58. In December 2018, Cassie made her relationship … Diddy, who a year ago filed to legally change his name to Sean Love Combs, was rumored to be dating Lori Harvey last year after breaking up with longtime love Cassie. The news of her pregnancy comes a few months after she and Fine began dating. Cassie has some thoughts after she and Diddy’s breakup made headlines.. Cassie Breaks Silence Following Diddy Split With Savage Instagram Post. Shortly after, Cassie began dating Fine … Cassie and … Cassie entered into a relationship with bull-rider/fitness trainer Alex Fine in late 2018. "Diddy wants happiness for Cassie and her new chapter. In June 2019, she and Fine announced that they were expecting their first child together. Cassie and Alex met in 2018 after Cassie got out of a 11-year relationship with Diddy; Cassie and Diddy, 51, were together from 2007 until 2018.