Tampa native Ashley Wooten is adding a dash of flavor to the digital film industry with the upcoming release of the second season of her series My Beautiful Pain.
Inspired by Between Women, the first lesbian YouTube series, and the ever-popular lesbian cult series, The L-Word, Wooten’s series delves into toxic relationships involving lesbians of color. The title of the series stemmed from a toxic relationship between Wooten and an ex-girlfriend whom Wooten once referred to as “a beautiful pain.”
“I found myself in a dark place,” she said. “I started writing. Once I began to re-read what I wrote, I started thinking that it might be something I should put out there. I wanted the title to represent any bad situation that feels good but you can’t get out of.”
Although her college career began in the culinary arts and ended with a degree in business, she dreamed of going into the entertainment industry as a music producer or manager. After graduation, Wooten worked her way through the financial services field as a fraud investigator. At the same time, she developed her own side business as a photographer.
While snapping photos for clients, she realized that her high-end camera had some fairly high-end video features. She spent hours on YouTube studying video techniques and soaking in as much as she could until she knew enough to begin her own company, LeJoi Media, in 2015.
Wooten has been a lover of film as long as she can remember. Unlike her peers, who enjoyed Sunday morning cartoons in their youth and comedies in their teenage years, Wooten was captivated by old classics. She was very aware that people of color, especially women, were not represented in film. She asked herself at the time, “what if I did this?”
Wooten admitted that her first script was terrible. “I went back to figure out what I could do to spice it up more. I focused on character development and story lines,” she said. “The script got better.”
With a limited budget, Wooten put a cast together for Season 1 through Facebook. “There were definitely learning curves. I was so focused on creating a story, not acting skills.”
The lessons she learned are helping Wooten with Season 2. “My prior actors go to class now and the new cast includes professional actors and actresses. I also sought assistance from two outside writers this season, Ebony De Priest and Tonnecqua Davis.”
While Season 1 of My Beautiful Pain focused on the lives of a few characters in toxic situations who are building a business network together, Season 2 taps further into the personal lives and pain of the three main characters — Mo, Tori and Casey.
Casey’s character is played by a new actor in Season 2, Nakia Freshie, star of the YouTube series Breath. To effectively utilize Freshie’s acting skills, Wooten further developed Casey’s character. In Season 1, Casey was featured as a player who couldn’t love or be loved. In Season 2, Casey goes on a quest to find her birth parents and figure out why she was never adopted by her long-term foster parents after years of being in the system.
Wooten, raised by family members in St Petersburg while her parents battled drug addiction in the ‘80s, thinks of herself as fortunate.
“I was lucky,” she said. “I went back to my mom around the age of three and never had to navigate the foster system. My mom has been clean for 30 years now and became a substance abuse counselor 20 years ago. Others aren’t so lucky. This show is around adults dealing with their past, which is why Casey is such an important character to me this year.”
Funded 80% by her own finances, 20% via donations and 100% by love and support from her longtime girlfriend, Jessica, Wooten has utilized her money and time this year to meet with industry professionals throughout the country in order to build her network. And she’s creating lots of hype over Season 2 of My Beautiful Pain. In fact, the series, which aired solely on YouTube last year, will also be featured on Amazon Prime when it is released later this year.
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This article appears in Jun 20-27, 2019.

