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Cassie & Diddy: See Photos of Them Over the Years

By:
July 1, 2025 9:35AM EDT
NEW YORK, NY - MAY 07: Cassie Ventura and Sean "Diddy" Combs attend the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. (Photo by John Shearer/Getty Images for The Hollywood Reporter)
Getty Images

Cassie gave a powerful and emotional testimony against Diddy during his 2025 sex trafficking trial. Look back at their past relationship here.

Cassie and Diddy had an on-and-off romance from 2007 to 2018. The couple met when Cassie modeled for the rapper’s clothing brand, and they went Instagram Official in 2012. Cassie even signed to Diddy’s Bad Boy Records at one point in their relationship. The pair’s on-and-off romance sparked many rumors, including some engagement speculation in 2014. The pair had a few breakups and reunions especially before they eventually split up for good in 2018.

About five years after their split, Cassie filed a lawsuit against Diddy, claiming that he had subjected her to physical and sexual abuse. After the filing, Diddy’s lawyer released a statement saying that he denied all of the allegations. However after they settled the lawsuit in 2023, a video of Diddy assaulting Cassie surfaced in 2024. One year later, Cassie appeared as the government’s star witness against Diddy in his sex trafficking trial. 

Look back at Cassie and Diddy’s photos from their past relationship in the gallery below. 

1 of 8

Diddy & Cassie

Diddy & Cassie
Broadimage/REX/Shutterstock

Cassie and Diddy pose together at the Metropolitan Museum of Art’s Costume Institute Benefit celebrating the opening of Heavenly Bodies: Fashion and the Catholic Imagination in New York in May 2018. Diddy wore a white suit with white shoes and a cross necklace and Cassie wore a black suit with a white undershirt and black shoes. 

October 17, 2018, 10:43AM
2 of 8

Diddy & Cassie at a 2018 Pre-Grammy Party

Diddy & Cassie at a 2018 Pre-Grammy Party
Efren Landaos/REX/Shutterstock

Cassie and Diddy posed for photos at a Pre-Grammy Gala thrown by Clive Davis and The Recording Academy in New York on Jan. 27. 2018. She wore a black and white dress, while he went in a full black tux with a matching coat. 

October 17, 2018, 10:42AM
3 of 8

Diddy & Cassie at a Film Screening

Diddy & Cassie at a Film Screening
James Shaw/REX/Shutterstock

Cassie and Diddy used to do very fancy date nights. Here, they attended the ‘Can’t Stop, Won’t Stop: A Bad Boy Story’ film screening in London on May 16, 2017. 

October 17, 2018, 10:42AM
4 of 8

Diddy & Cassie at a 2017 Met Event

Diddy & Cassie at a 2017 Met Event
Kevin Tachman/Vogue/REX/Shutters

Cassie and Diddy turned heads at The Costume Institute Benefit celebrating the opening of Rei Kawakubo/Comme des Garcons: Art of the In-Between inside the Metropolitan Museum of Art in NYC on May 1, 2017.  The singer sported a long black gown with an intricate design along the floor. 

October 17, 2018, 10:42AM
5 of 8

Diddy & Cassie at a 2017 Film Premiere

Diddy & Cassie at a 2017 Film Premiere
Broadimage/REX/Shutterstock

Diddy and Cassie went on another date to another premiere event for ‘Can’t Stop, Won’t Stop: A Bad Boy Story’ in Los Angeles on June 21, 2017. Here, she wore a bright red gown and stole the spotlight. 

October 17, 2018, 10:42AM
6 of 8

Diddy & Cassie at ‘The Perfect Match’ Film Premiere

Diddy & Cassie at ‘The Perfect Match’ Film Premiere
Matt Baron/REX/Shutterstock

Diddy and Cassie smiled big for photos at ‘The Perfect Match’ film premiere in Los Angeles on March 7, 2016. She wore a gold and black sparkly gown, while he looked dapper in a three-piece suit with a tie. 

October 17, 2018, 10:42AM
7 of 8

Diddy & Cassie at a 2016 Benefit

Diddy & Cassie at a 2016 Benefit
Andrew H. Walker/WWD/REX/Shutter

Cassie and Diddy at the Boys & Girls Harbor ‘Salute to Achievement’ benefit in NYC on Sept. 16, 2016. She wore a gorgeous dress, and he went in all-black. What a cute couple they were!

October 17, 2018, 10:42AM
8 of 8

Cassie and Diddy at the 2015 Met Gala

Cassie and Diddy at the 2015 Met Gala
Matteo Prandoni/BFA/Shutterstock

Cassie Ventura and Sean Combs are seen seated at the 2015 Met Gala. The singer sported a beautiful, plunging black dress, while Diddy sported a simple black tux. 

November 17, 2023, 9:32AM