2007: Cassie becomes the spokesmodel for Diddy's fashion label Sean John.
The pair met after Cassie became the official model for Diddy's burgeoning clothing line, but it wasn't until Cassie was signed to Diddy's Bad Boy Records that the relationship rumors began circulating. The two publicly denied any romantic connection, mostly because Diddy was still on-and-off with ex-girlfriend Kim Porter before they officially split in 2009.
2012: Cassie & Diddy go public with their relationship.
The pair began attending various events together, but especially sparked the public's interest after they were seen at Kanye West's Paris fashion week show that year.
2013: Cassie opens up about their romance in Madame Noir.
In an interview with Madame Noir, Cassie describes her relationship with Diddy by saying that "just being around him is a completely inspiring experience." She also mentioned how honesty and communication were huge factors in their romance.
2014: The couple sparks engagement rumors after Cassie is spotted wearing a ring.
Diddy posted a huge diamond ring on his instagram with the caption: "Baby do you like it? I just want to give you what you like!" Although Diddy's rep had denied the engagement rumors, photos of Cassie wearing the ring still had fans speculating.
2015: Breakup #1
According to Page Six, the power couple split but got back together shortly after. In an interview with The Breakfast Club, Diddy shared his 25/75 relationship rule. "If I’m in a relationship with you, like 25 percent of your time, you’re gonna just feel like, 'Aw man, I hate being here, this guy, aw man, he cheated on me, he lied on me,'" Diddy said. "But then there’s 75 percent of 'I'mma make you the happiest woman in the whole wide world,' and I promise you’ll smile the most.”
2016: Breakup #2
Reports from TMZ detail the explosive argument in which Diddy took Cassie's phone but later returned it. When the police were called to Cassie's home, no crime was charged, but a domestic incident report was filed. The two split once again but reunited shortly after the incident.
2018: Cassie & Diddy call it quits
The last post on Cassie's instagram of the two was from the Met Gala in May, while Diddy's last post was from her birthday in August, captioning the post "Go BEST FRIEND ! ITS YOUR BIRTHDAY -- HAPPY BIRTHDAY to MY LOVE ?? @cassie LOVE YOU 4eva #CassieDay" Since then, sources close to the couple admit that the two have officially split and have not been together for months.