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Sean ‘Diddy’ Combs and Ex Cassie’s Relationship Timeline on November 18, 2023 at 5:54 am Us Weekly

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Nicholas Hunt/Getty Images

Sean “Diddy” Combs and ex-girlfriend Cassie weathered many ups and downs during their romance before parting ways for good in 2018.

While Cassie (real name Cassandra Ventura) has since married Alex Fine and become a mother, her relationship with Diddy hasn’t stopped making headlines. The New York Times reported in November 2023 that Cassie filed a lawsuit against Diddy claiming the music mogul had a history of abuse while they were together.

Cassie alleged in court documents obtained by the outlet that Diddy urged her to take drugs, beat her and forced her to have sex with “male sex workers” while “filming the encounters.” She further claimed that Diddy “forced her into her home and raped her” in 2018.

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Related: Hollywood’s Sexual Misconduct Scandals

While Hollywood may appear to be all glitz and glam on the surface, the industry has seen its fair share of scandals through the years. The New York Times and the New Yorker first published investigative pieces in 2017 that accused disgruntled movie producer Harvey Weinstein of decades of sexual assault and harassment. Soon after, Weinstein stood trial and was […]

Diddy “vehemently” denied the allegations at the time, calling them “offensive and outrageous” in a statement to The New York Times.

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Scroll down to see Diddy and Cassie’s relationship highs and lows:

2007

The pair first met in 2005 and two years later they were romantically linked. Diddy and Cassie’s relationship began after the “I’ll Be Missing You” rapper split from Kim Porter, with whom he shares four children: stepson Quincy, son Christian and twin daughters D’Lila and Jessie. (Diddy also shares son Justin with his high school sweetheart Misa Hylton-Brim and daughter Chance with ex Sarah Chapman.)

Jamie McCarthy/WireImage

2012

Cassie and Diddy publicly confirmed their relationship by attending several events together, including Kanye West’s Paris Fashion Week runway show that March.

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February 2014

“Baby do you like it? I just want to get you wat you Like! I just wanna Mk you smile #takeDat!” Diddy captioned an Instagram photo of a diamond ring, sparking engagement speculation. Cassie was later seen wearing the rock, but neither party ever confirmed an engagement.

Related: On-Again, Off-Again Celebrity Couples

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Some couples just need a break every now and then! Click through to see which of your favorites couples — like Jessica Biel and Justin Timberlake — couldn’t help splitting and rekindling year after year.

December 2015

Rumors that the pair called it quits surfaced after Cassie posted a photo of a sleeping baby meme on Instagram that read, “How I sleep … knowing that I’m single and nobody cheating on me.” She quickly deleted the post.

August 2016

Following a headline-making argument in Beverly Hills, the couple once again sparked breakup rumors. However, Us Weekly exclusively confirmed at the time that Cassie and Diddy were still together and the altercation was just an argument.

Larry Busacca/Getty Images

January 2018

“I love children. I’m trying to get 10,” Diddy revealed during an appearance on Power 105.1 FM’s The Breakfast Club. “Whatever is supposed to happen in the future is going to happen, but that’s something that I want. I would only have it with my girl [Cassie], of course.”

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John Shearer/Getty Images for The Hollywood Reporter

October 2018

Less than one year later, news broke that Cassie and Diddy had parted ways for good. “They are indeed no longer together and haven’t been for months,” Cassie’s rep said in a statement to LoveBScott at the time. The split announcement came one month after Diddy was spotted with model Jocelyn Chew in Miami.

January 2019

Cassie moved on with personal trainer Fine, which a source told Us was a blow for Diddy, who originally hired Fine to work with the singer. “Diddy’s ego wasn’t just shot,” the insider claimed to Us. “This is their realest breakup … They were in love for many years. They were in a very real relationship for over a decade. They broke up and always got back together.”

Johnny Nunez/WireImage

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June 2019

After Cassie announced she was expecting her first baby with Fine, Diddy sent his well-wishes via social media. “Congratulations @Cassie and Alex,” Diddy captioned a photo of the pair via Instagram. “I wish you all nothing but love and happiness. God bless L O V E.”

September 2019

Diddy shared a cryptic message via Instagram after news broke that Cassie and Fine tied the knot. “Keep Going. I’ve got you. – The Universe,” the quote read. Three months later, Cassie welcomed her and Fine’s first daughter, Frankie. The couple expanded their family in March 2021 with the arrival of daughter Sunny.

Jeff Vespa/Getty Images For GQ

November 2023

“After years in silence and darkness,” Cassie said in a statement to The New York Times after filing a bombshell lawsuit against Diddy for alleged abuse and assault. “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.”

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Diddy, meanwhile, issued a statement of denial via his legal team that same day. “Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail,” his lawyer Ben Brafman said in a statement to the outlet. “Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday.”

Cassie’s legal team, for its part, claimed that Diddy offered her “eight figures to silence her,” which she rejected. Instead, she sued her ex-boyfriend for allegedly harming her in the past both physically and sexually.

She alleged in the lawsuit that when she dated rapper Kid Cudi in 2012, Diddy got so angry he threatened to blow up the musician’s car. “Around that time, Kid Cudi’s car exploded in his driveway,” the documents state. Cudi told the NY Times that Cassie’s account of the story was “all true.”

One day after filing the lawsuit, Cassie confirmed to Us that she and Diddy had reached a settlement.

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“I have decided to resolve this matter amicably on terms that I have some level of control over,” the singer said in a November 17 statement distributed by her attorney Doug Wigdor. “I want to thank my family, fans and lawyers for their unwavering support.”

Diddy also released a statement through Wigdor, sharing that they had decided to resolve the matter “amicably.”

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).

Nicholas Hunt/Getty Images Sean “Diddy” Combs and ex-girlfriend Cassie weathered many ups and downs during their romance before parting ways for good in 2018. While Cassie (real name Cassandra Ventura) has since married Alex Fine and become a mother, her relationship with Diddy hasn’t stopped making headlines. The New York Times reported in November 2023 

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Entertainment

Jay-Z Locked In Tyla. The Industry Is Shaking.

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By Bolanle Media | July 2, 2026


Photo: Tyla at the 2026 Met Gala in custom Valentino — days before making the biggest business move of her career.


There are career moves, and then there are statements. Tyla just made a statement that will be studied in music business classrooms for years.

The South African superstar — born Tyla Laura Seethal, 24 years old, and already the proud owner of two Grammy Awards — has officially signed a multi-million dollar global deal with Roc Nation, Jay-Z’s powerhouse entertainment company, walking away from Epic Records to align herself with the most influential roster in the music business. The signing was confirmed across social media with a major digital announcement this week, and the reaction from industry insiders was immediate — shock, admiration, and the quiet acknowledgment that someone just changed the trajectory of African music forever.

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From “Water” to a Global Phenomenon

Let’s not forget where this all started. In 2023, a 21-year-old from Johannesburg released a song called “Water” that nobody could quite categorize and everybody needed to hear. Within weeks, it had sparked one of the most viral TikTok dance challenges of the decade, charted simultaneously across the United States, the United Kingdom, and Africa, and earned Tyla a Grammy Award for Best African Music Performance — the first year that category even existed.

That win wasn’t just personal. It was a signal. African music — Afrobeats, Amapiano, and now what Tyla herself calls A*Pop — was no longer knocking at the door of the global mainstream. It had walked through it. And Tyla had handed it the key.

What followed was a whirlwind two years of sold-out shows, magazine covers, red carpet domination, and a growing reputation as one of the most stylistically fearless artists on the planet. She attended the 2026 Met Gala — her third consecutive appearance — wearing a custom Valentino gown dripping in diamond chains with a sweeping teal skirt, styled by the legendary Law Roach, with beauty by Pat McGrath. The look was breathtaking. But it was also strategic. Every Met Gala appearance, every fashion moment, every carefully placed interview has been building toward exactly this: the infrastructure to match the vision.


What Roc Nation Actually Means

To understand why this deal matters, you have to understand what Roc Nation actually is — because it is not simply a record label.

Founded by Jay-Z in 2008, Roc Nation is a full-service entertainment company with divisions spanning artist management, touring, brand partnerships, film and television, sports management, and philanthropy. Its roster has included Rihanna, Alicia Keys, J. Cole, Big Sean, Lil Uzi Vert, and Megan Thee Stallion — artists who didn’t just sell records, but built multi-decade cultural empires that extended into fashion, film, business, and beyond. The through-line isn’t genre. It’s scale.

For Tyla specifically, the Roc Nation deal unlocks a completely different level of access. We’re talking about premium budgets for music videos and live production, top-tier brand partnership pipelines with luxury and lifestyle companies, film and television placement relationships that most artists spend a decade trying to build, and the kind of media weight that gets you on the cover of VogueTime, and Billboard in the same calendar year. Roc Nation doesn’t just manage artists — it engineers icons.

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On the African music side, Tyla joins fellow Roc Nation signee Ayra Starr, the Nigerian pop star who inked her deal in 2025, deepening the label’s clear and deliberate strategic investment in African pop as the next dominant global genre. Jay-Z is not betting on a trend. He is betting on a generation.


The Album That Could Rewrite the Playbook

The timing of this signing is not accidental — it is surgical.

Tyla’s highly anticipated sophomore album, A*POP, is officially set to drop July 24, 2026, just three weeks away — a 14-track project that she has described as unapologetic, globally ambitious, and deeply rooted in her South African identity while simultaneously reaching for something universal. The lead single “She Did It Again” features Swedish pop titan Zara Larsson, a collaboration that announces in no uncertain terms that Tyla is not staying in any lane she didn’t build herself.

With Roc Nation’s full machine now behind the album rollout — promotional infrastructure, media relationships, tour routing, brand activations — A*POP arrives with a runway that Epic Records simply could not have provided at this scale. The industry is already paying attention. For music supervisors, film and TV executives, brand marketers, and entertainment investors reading this right now — put A*POP on your radar immediately. This is the kind of release that shapes culture, not just charts.

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The Bigger Picture Nobody Is Talking About

Here is what gets lost in the excitement of a big announcement: the systemic significance of what Tyla just did.

The music industry’s historical relationship with African artists has been, at best, transactional — major labels slow to invest, quick to cash in on a viral moment, and consistently reluctant to build the kind of long-term infrastructure that turns an artist into a brand. Tyla has navigated that system with remarkable intelligence, refusing to be reduced to a trend, building her artistic identity on her own terms, and now — at 24 — arriving at the negotiating table with enough leverage to choose Roc Nation on her terms.

That matters. Not just for Tyla, but for every African artist watching this unfold from Lagos, Accra, Nairobi, Cape Town, and Houston. It is proof that the path from regional phenomenon to global superstar is not only possible — it is being paved right now, in real time, by a young woman from Johannesburg who refused to shrink.

For media companies, content platforms, entertainment executives, and brand strategists operating in the African diaspora space — this is your data point. African pop is not a niche. It is not a trend. It is not a moment. It is a movement, and Tyla just secured the most powerful co-sign available in the global music business to lead it.

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Watch this space. Very closely.


Follow @bolanlemedia on Instagram for real-time music, film, and entertainment industry news. Read more at bolanlemedia.com

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Entertainment

DJ Shinski Brings AfriqueFest To Life

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AfriqueFest: Pan-African Musical Experience — World Cup Edition is set to take over Noto Houston on Sunday, June 28, bringing together East, South, and West African sounds in one immersive celebration of music, culture, and connection. Presented by Experience Noir and Bolanle Media, the event is designed as a cinematic night for the culture, blending global energy with Houston nightlife in a way that feels elevated, intentional, and deeply rooted in African creativity.

Spotlight on DJ Shinski

At the heart of this year’s experience is DJ Shinski. Born and raised in Nairobi, Kenya and now based in Houston, DJ Shinski has built an international name off high-energy sets that move effortlessly across Afrobeats, Amapiano, hip‑hop, dancehall, reggae, and electronic sounds.

He has also become Africa’s most‑subscribed DJ on YouTube, crossing the 2‑million‑subscriber mark and turning his mixes into a global destination for music lovers.

DJ Shinski’s style is precise but unpredictable: one moment it’s classic Afrobeats, the next it’s East African anthems, then a run of throwback hip‑hop or R&B that still feels fresh. That ability to read a room and connect multiple worlds in a single set is exactly why AfriqueFest is building so much of the night’s energy around him.

At AfriqueFest, DJ Shinski helps drive the Safari Grooves segment, representing East and Central Africa from 4 PM to 6 PM. Expect a journey that moves from Nairobi to Dar es Salaam, Kampala, Addis, and beyond, all filtered through his signature “vibes on vibes” approach behind the decks.

DJ Tunez and the rest of the night

Supporting that energy, DJ Tunez leads the Gold Coast Beats chapter from 8 PM to 10 PM, bringing his own Nigerian‑American Afrobeats pedigree to the stage. Together with the Diamond Rhythms segment (South) and a curated roster of DJs, the night stretches across the continent in three distinct musical chapters, all connected by a single dance floor.

Hosted by @chris_gone_crazy, @kingdrewwskyy, @roselynomaka, and @samsnewleaf, AfriqueFest is positioned as more than a party—it’s a celebration of sound, style, and Pan‑African identity in Houston, with DJ Shinski anchoring the experience from the moment doors open.

Brought to you by Bolanle Media & Experience Noir

Brought to you by Bolanle Media and Experience Noir, this World Cup edition of AfriqueFest is crafted as a night where global DJs, storytellers, and music lovers collide and create a shared cultural memory. With DJ Shinski front and center—and DJ Tunez helping close the night—guests can expect a show that reflects both the future of African nightlife and the power of the diaspora to create unforgettable live moments.

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If you want to experience DJ Shinski live at AfriqueFest, now is the time to lock in your spot. Purchase your tickets now at AfriqueFest.com and get ready for a night of music, movement, and culture at Noto Houston.

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Entertainment

STREAMING PREMIERE · JUNE 13, 2026

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Laughter Meets Inspiration: Our Ladies Show Lands on The Roku Channel

A bold new sketch comedy series for women premieres June 13 across the U.S., U.K., and Canada — arriving on the back of a festival-winning run that has critics and audiences already paying attention.

It isn’t every day a brand-new comedy arrives already wearing a row of trophies. Our Ladies Show does. The seven-episode inspirational sketch comedy series — created, written by, and starring Christin Jezak — begins streaming on The Roku Channel on Friday, June 13, 2026, available free to viewers in the United States, United Kingdom, and Canada.

Produced in partnership with global media services leader Encompass Digital Media, the series sets out to do something rare in today’s streaming landscape: make women laugh out loud and leave them lifted. In a media moment crowded with noise and cynicism, Our Ladies Show is a deliberate counterweight — comedy with a conscience, built for women of every age and background.

A Show Built Around Real Life — and Real Laughs

Each of the seven episodes opens with a monologue from one of the cast members introducing the theme, then rolls into three or more sketches that hit the subject from every comedic angle. The series tackles the things women actually carry: holding grudges, comparison, beauty, patience, gift giving, the importance of community, and dealing with anxiety.

The comedy comes from a place of warmth rather than mockery — a “laugh at ourselves” spirit that runs through a gallery of unforgettable characters: a nosey neighbor, an overwhelmed mom, relentlessly optimistic flight attendants, beauty pageant winners past their prime, and a crew of unruly campers with a counselor who simply cannot hold it together.

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Then the show does something most sketch series don’t. In the final segment of every episode, the cast gathers in a living-room setting and invites the audience in — sharing real inspiration drawn from the theme, the sketches, and their own personal stories. It’s the moment the laughter turns into something that stays with you.

The Women Behind the Show

Our Ladies Show brings together three performers with serious range:

  • Christin Jezak — creator, writer, and star (Miracle at Manchester, Raising Hope, Jimmy Kimmel Live!)
  • Hillary Hawkins — (Primal, Nick Jr.’s Play Along, Gullah Gullah Island)
  • Sarah Hernandez — (Nefarious, Unplanned, House of Payne)

“In a world with so much division and depression, I hope women of all ages and backgrounds will watch this show, laugh, be reminded of how beautiful, unique, and loved they are, and remember how much we need each other.”— Christin Jezak, Creator & Star

Already a Festival Favorite

The series’ recurring long-form sketch, Neighborhood Watch, didn’t arrive quietly. Originally released as a web series and revamped for Our Ladies Show with new footage, sound, and music, it has been sweeping the festival circuit:

  • 🏆 Best Webseries — 2026 New Media Film Festival (Los Angeles)
  • 🏆 Best Web/TV Series — Paris Film Awards
  • 🏆 Best Web Series — Dallas Movie Awards
  • 🏅 Additional wins at the London Movie Awards, Florence Film Awards, and Hollywood Gold Awards
  • 🎬 Official Selection — 2026 Harvard Divinity School Film Fest
  • ⭐ Finalist — Houston Comedy Film Festival
  • 📣 Three nominations — 2025 Content Christian Media Conference, including Best Actress in a TV and Web Series nods for both Christin Jezak and Sarah Hernandez

Where and When to Watch

Our Ladies Show premieres Friday, June 13, 2026, streaming on The Roku Channel — the home of premium and free entertainment — in the U.S., U.K., and Canada. All seven episodes deliver the series’ signature blend of sharp sketch comedy and genuine encouragement.

Click Here To Get Tickets

Watch the trailer now on your platform of choice:

For more information, visit www.ourladiesshow.com and follow @ourladiesshow on Facebook, Instagram, and TikTok.


About Christin Jezak

Christin Jezak has worked for over 15 years in the entertainment industry. She created and stars in Our Ladies Show and the award-winning web series Neighborhood Watch. She produced the EWTN TV program For the Sake of the Gospel and the all-women web series Ladies Keepin’ It Real, played Dr. Sam in Miracle at Manchester (starring Dean Cain, Daniel Roebuck, and Eddie McClintock), and voices Agnes in the podcast Confessions of a Catholic Single. She held a lead role in a short film for NTT Data directed by Academy Award–winning cinematographer Janusz Kamiński, has co-starred on Raising Hope, and appeared in Jimmy Kimmel sketches and a Grubhub Super Bowl commercial.

About The Roku Channel

Roku pioneered streaming on TV and is the #1 TV streaming platform in the U.S., Canada, and Mexico by hours streamed (Hypothesis Group, Dec. 2025). The Roku Channel is the home of premium and free entertainment, alongside Roku’s Howdy and Frndly TV services. Roku is headquartered in San Jose, California.

About Encompass Digital Media

Encompass Digital Media is a global managed services company — technology-driven, software-defined, and people-powered. Trusted by world-leading broadcasters, networks, sports rights-holders, and OTT platforms, it processes over 25,000 hours of content daily, serves 850 channels to 84 countries, distributes over 243,000 live events annually, and reaches 400 million radio listeners weekly worldwide. Learn more at www.encompass.tv.

Media & Interview Requests: To interview creator Christin Jezak or the cast, contact Christin at cjezak@p2ptheatre.com.

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