From Web Series to Podcast: How Situationships Creator Cylla Senii Turned Real-Life Dating Disasters into a Cultural Movement

Have you ever had a man who wasn’t your man, and you wanted to talk about it but didn’t know how because it felt weird or wrong to admit that you have feelings for your man who’s not your man? Sub in whatever gender preference, and almost all of us have been there—and Cylla Senii, tired of skirting around those uncomfortable topics, brought it to the public’s attention on multiple platforms.

By: Kiara Hurst

Photog: @adose.of.artes

HMU: @justshupier

Bouncing between Atlanta and New York in her early twenties, Senii and her friends found themselves swapping wild, hilarious, sometimes heartbreaking stories about modern dating. Ghosting. Being dumped over text. Boyfriends caught creeping on Craigslist. You name it, they lived it. It was the realization that she and all her friends were in situationshipsthat gave birth to Situationships, the web series turned TV show.

"We were always venting about how messy things were," she laughs. "At one point, I just thought, 'Yo, we're all literally in situationships. This could be a show.'"

Situationships arrived during a time when an influx of Black women were rising to fill the noticeable gap in representation. Inspired by web series pioneers like Issa Rae and the creators behind Black & Sexy TV, Senii set out to build her vision from scratch. Juggling a nine-to-five in advertising while scribbling down story ideas during her daily commute, she eventually teamed up with her producing partners, Brandon and Iris, both fresh out of college themselves.

"It was really just a lot of stumbling and figuring it out," she says. "We had no idea what we were doing, but we were determined."With her small crew and sheer perseverance, Senii set out to make Situationships a reality.

Lacking resources, Senii had to take on many roles herself while pursuing her dream. But wearing all the hats—creator, writer, director, producer, actor—took a toll. It wasn't long before Senii realized she had to learn one of the most crucial skills for any creative: delegation.

"I was right out of college leading a team of 50 people," she says. "Growing a team was necessary for me to not burn out—bringing on top producers, collaborating with other writers, hiring social media experts, marketing people—it was all part of learning how to actually lead a creative project."

Senii's hustle is a sign of a broader shift in the entertainment industry. Traditional barriers to entry still exist, especially for women and people of color, but social media and digital platforms have paved new pathways.

"If you're not born into the industry or connected, you have to create your own opportunities," she says. "You can literally create from the palm of your hand now. That's how I started—uploading to YouTube."

Still, despite the proliferation of platforms, authenticity remains the true currency. Senii's work—whether comedic or gut-wrenchingly real—sits at the intersection of truth, culture, and humor.

"So many of our stories as Black women, as creators of color, have historically been left out," she says. "It's important for me to be authentic and tell the stories that haven't been told."

On the corporate side of the industry, she's seen how a focus on numbers and profit can strip projects of their realness.

"Audiences today don't want smoke and mirrors. They want real," she explains. "That's why people are leaning more into creators."

With that focus on authenticity, Senii also values connecting to her audience, which led, in 2024, to the launch of the Situationships podcast on Revolt TV. Beyond expanding the universe around Situationships, Senii says, “The podcast allows us to reach audiences directly and consistently—talking about dating, relationships, culture, and bringing in amazing experts.”

With the Situationships TV series now in development it’s undeniable that Senii is on the path toward greatness. Senii's story is proof that success isn't just about talent or luck. It's about perseverance, community, and an unwavering commitment to authenticity. And as Situationships continues to evolve, one thing remains clear: this is just the beginning.

"There are so many more stories to tell," she says, smiling. "And trust me—we're about to tell them all."

To keep with all things Cylla follow her here @cyllasenii .