How Did Cassie & Diddy Meet? The Notoriously Private Couple Has Mixed Business & Romance

There are few Hollywood relationships that have remained relatively under the radar, despite being made up of two big public figures. One of these is the relationship between Cassie Ventura and Sean "P. Diddy" Combs, the latter of whom hasn't exactly been known for shying away from the spotlight. A lot of times I forget that the two are even a couple, aside from the moments when they quietly pop up on a red carpet or, you know, when Cassie is allegedly at the center of a brawl between two of hip hop's biggest artists. We have already looked into how long the two have been dating, but how exactly did Diddy and Cassie meet?

This wasn't an easy answer to uncover considering the two have been a notoriously secretive couple, especially in the earlier years of their relationship. But I found out that they met initially for business and was set up by her first producer, Ryan Leslie, back in 2007. In a 2012 interview with The Urban Daily, before they had openly acknowledged anything romantic going on between them, Cassie shared how she met Diddy, saying,

Through Ryan [Leslie]. He heard “Me and You” in the club and he was trying to find out who the artist was. A lot of people heard the song before they saw my face... I made a Myspace November 2005 and that’s when I originally put “Me and You” out. It had finally ran its course where it was on everyone’s page.

In the same interview, Cassie went on describe how he was a mentor for her and agreed to release her debut album with Bad Boy Records. She said, "He always gives great advice. In the beginning with the first album, everything was moving so quickly and I was moving around so quickly and bouncing from country to country, I never had the opportunity to really talk to him." Well, that seemed to change quickly. She was also asked of the rumors about a romantic relationship with Diddy in the interview and responded that she would not talk about her personal life.

In August 2008, Cassie released her single "Official Girl" which most people took as a hidden message about her rumored relationship Diddy, considering he was already publicly linked with some other women around that time. Diddy defended Cassie when rumors of her being dropped from Bad Boy started to come out and told MTV, "Cassie’s definitely not dropped from Bad Boy ... People really understand that she does have some talent and it takes some time to mold it. Everybody’s not perfect. I think she had some rough shows, just being nervous. Sometimes people have to break out of that."

When it comes to Diddy, he has actually never spoken directly about any sort of romantic relationship with Cassie. He was on The View in October 2013 and explained that he was not ready for marriage, telling the hosts,

It definitely would be a dream come true for me to just one day be ready for that ... I’m not really looking because I know the responsibility that comes with that and I think that a lot of people, they jump into that and they’re not honest with themselves. I’m brutally honest with myself. I don’t want to get married and not make that woman be the best.

But, just a few months later, Diddy seemed to propose to Cassie on Instagram, which pretty much confirmed that they have been a thing for all of those years.

Since that proposal post, they have gone all out on their social media, proclaiming their love for each other constantly, so it's safe to assume it's the real deal now. The couple recently appeared in a steamy video for his newest fragrance, 3 AM, which is essentially them having sex, so... whatever their set up is, it works for them, they're clearly in love, and that's all that really matters.

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