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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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Advice

How to Secure Profitable Indie Film Deals

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When it comes to distributing your independent film, smart negotiations are key to ensuring you maximize your return on investment. Crafting a well-structured deal can help you not only recoup production costs but also earn profits. Here’s how to approach these negotiations with confidence and strategy:

Know Your Costs and Set Clear Goals

Before entering any negotiation, have a firm grasp of your film’s production costs and financial objectives. Knowing your break-even point will give you leverage in negotiating terms that cover your investment and align with your profit goals.

Do Your Homework: Research Industry Standards

Familiarize yourself with the going rates and typical deals for films similar to yours in genre and budget. Understanding standard industry terms gives you a benchmark to assess offers, ensuring you’re entering into a fair deal. Knowledge is power—walk into negotiations with the confidence of someone who knows their worth.

Focus on Recouping Your Investment First

Prioritize structuring your deal to recover your initial investment as quickly as possible. You might negotiate a higher percentage of the revenue until you break even, allowing for a more favorable split with the distributor once your costs are covered. This ensures you’re not taking unnecessary financial risks.

Negotiate Fair Profit-Sharing Terms

Once your investment is recouped, it’s time to focus on profit-sharing. Whether it’s a percentage of net profits or a tiered revenue structure, ensure the terms are fair and transparent. Aim for a structure that rewards both the distributor and you based on your film’s success.

Ask for Minimum Guarantees

If possible, negotiate for a minimum guarantee—an upfront payment from the distributor. This gives you immediate cash flow, reduces financial pressure, and mitigates risk in case your film underperforms. A minimum guarantee can be a game-changer for indie filmmakers.

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Get Specific About Deductible Expenses

Distributors often deduct marketing, distribution, and other costs from the gross revenue before calculating your share. Be specific about which expenses are allowable, capping them if necessary. This will protect your share of the profits and prevent hidden fees from eating into your earnings.

Strategize Rights and Territories

Consider how to leverage different rights—such as theatrical, streaming, and physical media—across various territories. Instead of bundling all rights into one deal, explore the option of making separate agreements for different platforms or regions. This diversified approach can increase your revenue streams.

Include Performance Benchmarks

Protect yourself by including performance clauses in your contract. These can allow you to renegotiate or even terminate the deal if the distributor fails to meet agreed-upon milestones—whether that’s related to marketing efforts, audience reach, or sales targets.

Get Legal Advice—It’s Worth It

Always consult an entertainment lawyer experienced in film distribution. They’ll help you navigate legal complexities and spot any red flags in the contract. Legal expertise can save you from costly mistakes and ensure your interests are fully protected.

Be Ready to Walk Away

The ultimate power in negotiation lies in your willingness to walk away if the deal doesn’t meet your needs. Don’t feel pressured into accepting unfavorable terms. There are always alternative distribution models—such as direct-to-consumer or hybrid approaches—that may offer more control and financial upside.

Explore Alternative Distribution Models

Traditional deals aren’t your only option. Hybrid distribution, crowdfunding campaigns, or self-distribution through platforms like Vimeo On Demand can offer greater control and potentially higher returns, especially for niche films or filmmakers with a dedicated fanbase.

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Final Thoughts: Turn Negotiations into Win-Win Partnerships

Negotiating a distribution deal isn’t just about getting the best terms for yourself—it’s about finding common ground that benefits both you and the distributor. A fair, well-negotiated deal sets the stage for a successful partnership, leading to greater exposure for your film and, ultimately, a more profitable outcome.

Approach each negotiation with clarity, confidence, and an understanding of your film’s value. By doing so, you’ll not only recoup your investment but also ensure that your film’s distribution reflects the hard work, passion, and creativity that went into its creation.

Bolanle Media is excited to announce our partnership with The Newbie Film Academy to offer comprehensive courses designed specifically for aspiring screenwriters. Whether you’re just starting out or looking to enhance your skills, our resources will provide you with the tools and knowledge needed to succeed in the competitive world of screenwriting. Join us today to unlock your creative potential and take your first steps toward crafting compelling stories that resonate with audiences. Let’s turn your ideas into impactful scripts together!

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Advice

How to Distribute Your Independent Film

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In independent filmmaking, finding the right distribution strategy is essential to your film’s success. With multiple avenues available, choosing wisely can determine whether your film reaches its audience or fades into obscurity. Here’s a guide to understanding key distribution options and selecting the path that aligns with your film’s goals and audience.

Streaming Platforms: Reach the Masses

Streaming services like Netflix, Amazon Prime, and Hulu have revolutionized film distribution, offering indie filmmakers access to massive audiences. However, standing out in a sea of content can be tough.

Pros:

  • Wide audience reach
  • No need for physical distribution
  • Potential for lucrative licensing deals

Cons:

  • Fierce competition
  • Limited control over marketing and presentation
  • Revenue sharing models that may not favor filmmakers

Theatrical Releases: The Power of the Big Screen

While traditional theatrical releases are often out of reach for indie films, alternative approaches—such as on-demand screenings or local theater partnerships—can still offer a way to showcase your film on the big screen.

Pros:

  • Provides a communal viewing experience
  • Can generate press coverage and reviews
  • Builds buzz for future digital releases

Cons:

  • Expensive and logistically complex
  • Limited reach compared to digital platforms
  • Requires robust marketing to fill seats

Direct-to-Consumer: Taking Control of Your Film’s Fate

Selling your film directly through your website or platforms like Vimeo On Demand allows you to retain full control over distribution, pricing, and presentation.

Pros:

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  • Higher profit margins and control
  • Direct connection with your audience
  • Ability to set your own marketing and release timeline

Cons:

  • Requires significant effort to promote
  • Limited reach compared to major platforms
  • You’ll need to handle technical distribution details yourself

Film Festivals: Building Buzz and Opening Doors

Though not a distribution platform itself, film festivals provide critical exposure and can lead to distribution deals or offer an ideal launchpad for your film.

Pros:

  • Potential for awards, critical acclaim, and exposure
  • Networking opportunities with industry professionals
  • Can lead to distribution deals or funding for future projects

Cons:

  • Highly competitive submission process
  • Can be expensive to submit and attend multiple festivals
  • No guarantee of securing broader distribution

Educational and Institutional Distribution: Tapping into a Niche Market

For documentaries or films with educational appeal, targeting schools, libraries, and other institutions can be a profitable and less competitive distribution path.

Pros:

  • Great for niche topics with educational value
  • Long-term revenue potential
  • Less crowded marketplace than consumer-focused channels

Cons:

  • Limited to specific genres or subjects
  • Requires specialized marketing efforts
  • Slower sales cycle

Hybrid Approaches: Mixing It Up for Maximum Reach

Many indie filmmakers find success by combining different distribution strategies. For example, you might launch at film festivals, follow with a limited theatrical run, and then transition to streaming or direct-to-consumer sales.

When deciding on your distribution approach, consider:

  • Your target audience: Where do they consume content?
  • Your film’s genre and style: Is it festival-worthy, best suited for niche audiences, or primed for a streaming debut?
  • Your marketing and distribution budget: Can you afford a theatrical release, or should you focus on digital platforms?
  • Your goals: Are you aiming for maximum revenue, critical recognition, or audience-building for future projects?
  • Control vs. exposure: How much say do you want in how and where your film is seen?

Final Thoughts: Charting the Right Course

There’s no one-size-fits-all when it comes to distribution. Each film is unique, and the strategy that works for one project might not be right for another. The key is to research your options thoroughly, network with fellow filmmakers, and remain flexible as you navigate the ever-evolving world of indie film distribution.

By carefully selecting and blending the right distribution methods, you can maximize your film’s reach, revenue, and overall impact—ensuring that your story finds its audience and leaves a lasting impression.

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Bolanle Media is excited to announce our partnership with The Newbie Film Academy to offer comprehensive courses designed specifically for aspiring screenwriters. Whether you’re just starting out or looking to enhance your skills, our resources will provide you with the tools and knowledge needed to succeed in the competitive world of screenwriting. Join us today to unlock your creative potential and take your first steps toward crafting compelling stories that resonate with audiences. Let’s turn your ideas into impactful scripts together!

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Advice

How to Build Excitement for Your Indie Film

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Launching your marketing efforts early can significantly influence your film’s success. By generating buzz during production, you create a loyal following and ensure that your audience is buzzing with excitement as the release date approaches. Here’s how to effectively market your film right from the outset:

Begin Marketing During Production
One of the most powerful strategies for indie filmmakers is to start their marketing campaigns while still in production. This proactive approach allows you to share behind-the-scenes content, teasers, and updates that actively engage potential viewers. Social media platforms are perfect for this, providing a direct line of communication with your audience. Regularly posting content keeps followers informed and builds anticipation for your film’s release.

Share Behind-the-Scenes Content
Behind-the-scenes footage offers a unique glimpse into the filmmaking process, making it relatable and engaging for audiences. Share candid moments from the set, interviews with cast and crew, and insights into your creative process. This transparency fosters a personal connection with viewers, encouraging them to invest in your project and follow along as it develops.

Utilize Teasers and Trailers
As production progresses, consider releasing short teasers or trailers that highlight key elements of your film. These visually appealing snippets should evoke curiosity about your story and characters. A well-crafted teaser can generate excitement and prompt viewers to share it within their networks, amplifying your reach.

Engage Directly with Fans
Building a loyal audience requires direct engagement. Take the time to respond to comments on social media, participate in discussions, and share user-generated content related to your film. This interaction fosters a sense of community and encourages followers to become advocates for your project, spreading the word organically.

Create Momentum Early
Starting your marketing efforts early creates momentum that can carry through to your film’s release. By consistently sharing content and engaging with fans, you lay the groundwork for a successful launch. When audiences feel involved in your film’s journey, they’re more likely to support it upon release—whether through ticket purchases or by sharing it with their networks.

Leverage Influencers and Collaborations
Consider collaborating with influencers or other filmmakers who share a similar audience. These partnerships can help expand your reach and introduce your film to new viewers. Influencers can create buzz by sharing their thoughts on your project or participating in promotional events, such as live Q&A sessions or social media takeovers.

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Build an Email List
Creating an email list allows you to communicate directly with interested viewers. Use this list to send updates about production milestones, exclusive content, and important release information. An engaged email list can be a powerful tool for driving ticket sales or streaming views when your film is released.

Monitor Feedback and Adapt
As you share content and engage with your audience, pay attention to their feedback. Understanding what resonates with viewers can help you refine your marketing strategy. Be open to adapting your approach based on audience reactions; this flexibility enhances your connection with fans and improves overall engagement.

Seize the Opportunity: Start Early and Engage

Early marketing and buzz generation are essential components of a successful release strategy. By beginning your marketing efforts during production, sharing behind-the-scenes content, engaging directly with fans, and leveraging collaborations, you can build anticipation for your film long before its premiere. This proactive approach not only fosters a loyal audience but also increases your film’s chances of success when it’s time to hit the screen.

Remember, in indie filmmaking, every moment counts—start early to make the most of your opportunity!

Bolanle Media is excited to announce our partnership with The Newbie Film Academy to offer comprehensive courses designed specifically for aspiring screenwriters. Whether you’re just starting out or looking to enhance your skills, our resources will provide you with the tools and knowledge needed to succeed in the competitive world of screenwriting. Join us today to unlock your creative potential and take your first steps toward crafting compelling stories that resonate with audiences. Let’s turn your ideas into impactful scripts together!

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