Diddy and Cassie's Relationship Timeline Paints a Complicated Picture

Diddy and Cassie had a complicated relationship over the years. With a lawsuit against Diddy filed, we take a look at their relationship timeline.

Allison Hunt - Author

Nov. 16 2023, Published 10:42 p.m. ET

Cassie and Diddy at CAN'T STOP WON'T STOP: A BAD BOY STORY premiere in 2017
Source: Getty Images

If you or someone you know is experiencing domestic violence, call the National Domestic Violence Hotline at 1-800-799-7233.

The Gist:

  • Cassie and Diddy met when she was signed to Diddy's label, Bad Boy Records.
  • They dated officially from 2012–2018.
  • In November 2023, Cassie filed a lawsuit against Diddy alleging rape and years of abuse.
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Sean "Diddy" Combs and singer Casandra Ventura, known professionally as "Cassie," had an up-and-down relationship spanning over a decade. But years later it comes out that it was more down than up.

On Nov. 16, 2023, The New York Times reported that Cassie filed a lawsuit against Diddy for "rape and years of abuse."

What led to the lawsuit? Let's take a look back at their relationship timeline.

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Cassie and Diddy's relationship timeline is long and complicated.

Cassie and Diddy at Clive Davis and Recording Academy Pre-GRAMMY Gala in 2018
Source: Getty Images

Cassie and Diddy first met in 2005, and the singer eventually released her first album, "Cassie," under Diddy's record label, Bad Boy Records. At the time, Diddy was with his longtime partner, and mother of his children, Kim Porter.

2007: Cassie and Diddy are romantically linked.

In 2007, Cassie became a spokesmodel for Diddy's well-known clothing brand, Sean John. At the time, rumors were going around that the pair were in a relationship, but Diddy was still on again, off again, with Kim until 2009.

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2012: Cassie and Diddy attend multiple events together.

Cassie and Diddy at the GQ Men of the Year Party at Chateau Marmont on Nov. 13, 2012
Source: Getty Images

Although Cassie and Diddy never publicly discussed their relationship, the pair arrived together at multiple public events including Kanye West's Paris Fashion Week show in March of that year. This basically told us that they were together, without telling us that they were together.

February 2014: Cassie and Diddy spark engagement rumors.

The engagement rumors started flying when Cassie was seen out and about wearing a huge rock on her finger. Diddy further stirred the pot when he posted a picture of a diamond ring on Instagram and captioned it, “Baby do you like it? I just want to give you what you like!" (via Billboard).

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December 2015: Cassie and Diddy break up but then get back together.

Break up rumors started when Cassie posted a baby meme on Instagram writing, "How I sleep … knowing that I’m single and nobody cheating on me," (via US Weekly). There were reports that Cassie was seen flirting with another man, but that the pair quickly got back together.

August 2016: Cassie and Diddy had a big fight sparking break up rumors once again.

Cassie and Diddy at the Boys & Girls Harbor Salute To Achievement at David H. Koch Theater, Lincoln Center on Sept. 26, 2016
Source: Getty Images

Cassie and Diddy got into a huge argument in a car. The fight escalated and Diddy jumped out of the car, but not before taking Cassie's phone from her. Cassie told her mom what happened, and her mom called the cops. The cops then filed a domestic incident report.

Despite the fight, it was confirmed that the pair didn't break up.

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January–August 2018: Diddy gushes about Cassie publicly.

Multiple times throughout 2018, Diddy publicly talked about Cassie. One time with with popular radio show, The Breakfast Club. He stated that he wants kids but "would only have it with my girl [Cassie], of course,” (via US Weekly). Diddy also posted on Cassie's birthday on Instagram captioning, "Go BEST FRIEND ! ITS YOUR BIRTHDAY — HAPPY BIRTHDAY to MY LOVE ?? @cassie LOVE YOU 4eva #CassieDay," (via Billboard).

October 2018: Diddy and Cassie officially break up for good this time.

Cassie's rep confirmed that Diddy and Cassie broke up. The rep said, "They are indeed no longer together and haven’t been for months," (via US Weekly.)

Just a year later in 2019, Cassie was married to her personal trainer, Alex Fine.

November 2023: Cassie files a lawsuit against Diddy.

As stated earlier, on Nov. 16, 2023, The New York Times reported that Cassie filed a lawsuit against Diddy for "rape and years of abuse." Cassie told The New York Times, “After years in silence and darkness, I am finally ready to tell my story, and to speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships.”

Diddy reps responded and said, “Mr. Combs vehemently denies these offensive and outrageous allegations."

If you need support, call the National Sexual Assault Hotline at 1-800-656-4673 or visit RAINN.org to chat online one-on-one with a support specialist at any time.

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