Casandra “Cassie” Ventura and her husband, Alex Fine, have become the source of major headlines amid Diddy’s ongoing federal criminal trial. As The Shade Room previously reported, Cassie dated Diddy for about ten years. This was before she filed a bombshell lawsuit against him in November 2023. In the civil lawsuit, Cassie alleged that their relationship began when she was 19 years old and he was 37. Per Cassie, Diddy allegedly pursued a romance with her. Their relationshipp would ultimately, allegedly, be plagued with abuse, sexual assault, rape, and sex trafficking.
The suit would note that the singer was seeking “justice for the decade of her life that Mr. Combs took away from her with threats of violence, excessive use of drugs, physical and psychological abuse, and sexual slavery.” Furthermore, her suit would shock millions and arrive amid her being married to Fine for about four years, having given birth to two children.
As Cassie and Alex Fine are now in court, testifying against Diddy for his alleged abuse and assault of the singer and other women, The Shade Room is taking a look back at the singer and her husband’s romance and growing family over the years.
201?: The Pair Meet
According to Vogue, in October 2019, the singer revealed to Vogue that she met Fine at the gym. However, she did not note a specific date or time period. Per the outlet, Fine was a wellness consultant who initially worked with Diddy and then added Cassie to his list of clients.
“They hit it off, and she started to open up to him. Alex wanted to be with Cassie,” a source told PEOPLE in November 2023.
October 2018: Cassie Hard Launches Her Romance With Alex Fine
Per US Magazine, in September of 2018, Cassie and Diddy’s relationship came to an end.
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Two months later, the singer took to Instagram to seemingly hard-launch her romance with Fine into the public eye.
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June 2019: The Pair Reveal They're Expecting
In June of the following year, Cassie took to Instagram to reveal that she and Fine were expecting a baby girl.
“Can’t wait to meet our baby girl 💗 Love You Always & Forever,” she wrote at the time.
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August 2019: Alex Fine Proposes To Cassie
In August of 2019, Cassie took to Instagram to share footage from Alex Fine’s cowboy-themed proposal to her. The clip revealed that the pair’s engagement was adorned with flowers and a gleaming, romantic sunset, which showed off the shadows of the singer’s growing baby bump.
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“I love you best friend. I can’t wait to spend the rest of my life with you,” Cassie wrote in a separate post shared via Instagram.
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“When he got down on one knee, everything just stopped. I felt like I lost my sense of hearing,” she later told Vogue. “I saw just his mouth moving, and he said, ‘I want to spend the rest of my life with you. I will never forget how special Alex made me feel that night.”
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September 2019: The Pair Tie The Knot!
According to US Magazine, in September 2019, Cassie and Alex Fine tied the knot in an intimate backyard wedding in Malibu, California, that featured 14 guests.
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October 2019: The Pair Celebrate Their Union & Baby Shower
In October of that year, Cassie would share photos from her wedding via Instagram.
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Additionally, she would also take to the platform to share photos from her baby shower in California.
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December 2019: Cassie & Alex Fine Welcome Their First Child
In December 2019, Cassie gave birth to her and Alex Fine’s first child, a baby girl they named Frankie Stone Fine.
“She’s just different. Frankie Stone Fine. My BFF,” Cassie wrote on Instagram on December 12, 2019, alongside a shot showing a peek of the infant.
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December 2020: The Pair Reveal They're Expecting Their Second Child
On December 10, 2020, Cassie took to Instagram to share a clip showing herself, Frankie, and Alex at an apparent doctor’s visit. Furthermore, the clip showed Cassie lying down as her growing baby bump appeared for the camera to see.
“Coming soon,” she wrote in the clip’s caption.
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March 2021: The Pair Welcome Their Second Child
On March 27, 2021, Cassie took to Instagram to share that she and Fine welcomed their second child, a baby girl, on March 22, 2021. Additionally, she revealed that they named her Sunny Cinco Fine.
“On Monday March 22nd, 2021 @ 10:22am our hearts got bigger. Welcome to the world baby girl! We love you so much Sunny Cinco Fine!” she wrote.
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February 2025: The Singer Reveals She's Expecting Her & Alex Fine's Third Child
In February 2025, Cassie returned to Instagram to share that she’s expecting her third child with Alex Fine, per The Shade Room.
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The following month, she revealed that she and Fine are preparing to welcome a baby boy, per The Shade Room.
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Per the New York Post, Cassie is reported to be eight months pregnant.
