“I followed her, she followed me back, and then she tweeted a couple days later: ‘I’m looking for a mixed-looking girl to play my best friend on a web series.’ And I wrote back, and I said: ‘Hi, I’m not mixed, but this is what I look like. Let me know.’”
Everything about the process of what became Rae’s YouTube series “The Misadventures of Awkward Black Girl” was really scrappy. Day remembers that when Rae invited her to audition, the directions led to someone’s house. The audition took only a few minutes, and just hours later, Rae emailed her to tell her she got the job. A few weeks later, they shot the first episode.
“It was just me, Issa, [and] I believe her brother was working the video camera that was attached to the microphone, so no fancy equipment or anything. We did our own hair, makeup and came dressed in our own outfits,” Day said. “After we were done shooting, she thanked me, and then I left, and I was like, ‘What did I get myself into?!’ And then it blew up, and we were pretty shocked about the audience.”
In the 10 years since Rae uploaded the first episode of “Awkward Black Girl” to YouTube, she has built a TV empire, with the fifth and final season of her groundbreaking HBO show “Insecure” wrapping up and several new projects in the works. Many of her collaborators on “Awkward Black Girl” and “Insecure” have also gone on to have thriving creative careers — including Day, whose directorial debut feature film “Definition Please” has been screening at various film festivals around the country. Last fall, the Center for Asian American Media’s CAAMFest FORWARD named it the best narrative film at the festival, and earlier this year, it won the Los Angeles Asian Pacific Film Festival’s award for Fresh Narrative Voice.
Day’s path to directing, writing, producing and starring in her own award-winning movie runs through those early years of watching Rae create “Awkward Black Girl” and “Insecure.”
“Issa just inspired me to write more and write truer to my voice and my experiences,” Day said. “That’s really where the premise and the seed of ‘Definition Please’ came from. I’m gonna write about this girl who’s a former spelling bee champion and might not be the stereotype of what an Indian American character plays in the media. And I want to make it real and true for other people.”
Executive produced by Mindy Kaling, “Definition Please” stars Day as Monica, who won the National Spelling Bee as a kid. Since then, everyone in her hometown still remembers her for that one moment of fame. But her life hasn’t turned out as expected. She lives at home as a caretaker for her mom, makes money from tutoring other aspiring spelling bee winners, and hangs out with her best friend from high school, Krista (Lalaine), a bartender at the local bar.
In writing the movie, Day brought in a few elements of her upbringing. But more broadly, she wanted to see a story that reflected the specificities of people she grew up around: her friends, family and family friends in the South Asian community of her hometown.
Growing up in Greensburg, Pennsylvania, an hour east of Pittsburgh, Day was always very creative. She read and wrote voraciously, studied Indian classical dance and performed in musicals at her high school. In the meantime, she also excelled academically in her AP science classes, which led to “this internal confusion of, ‘Oh, I’m really good at this, and this is obviously a great career path to go down, in terms of science and technology,’” she said. “But I think my heart was really into writing and acting and performing.”
She tried to do both whenever she could. In college at Case Western Reserve University, she studied engineering, but also graduated a few credits shy of a minor in theater. While studying abroad for a year in Australia, “I did a lot of plays and made a lot of theater friends, and that’s where I kind of decided, ‘Oh, this is what I want to do for my career.’”
After graduation, she landed a job at the consulting firm Accenture. She got to choose where she wanted to work, so naturally, she picked Los Angeles. Because her work schedule was flexible, and the job paid well, “in the meantime, I was meeting with agents, doing auditions, going to acting class, writing, and then I got laid off from Accenture after a year, which was actually fantastic because I got severance and unemployment, and then about six to eight months later, I booked three national commercials, and that’s where my professional career started.”
It took more than a decade for Day to reach a point where she was working steadily, a reminder that “everything takes so much time,” she said, pointing out that Rae’s journey of making “Awkward Black Girl” a smash hit was also a story of “incremental success.”
“I feel like when Hollywood anoints someone an overnight success, that story is never the truth because that person has been toiling for years before that overnight success that people don’t know about,” she said. “Even with Issa, people don’t really know that she had two web series before ‘Awkward Black Girl.’ And even when we started doing ‘Awkward Black Girl,’ there was a very clear journey of ‘Awkward Black Girl’ getting better: better production quality, better stories.”
When Season 2 of “Awkward Black Girl” wrapped up in 2013, Rae got a deal at HBO to develop what became “Insecure.” When the show finally moved into production three years later, Rae asked Day if she wanted to be in the pilot. For Day, filming it brought back a flood of memories that reminded her of how far Rae had come.
“I showed up to set, and it was incredible to have remembered the first episode of shooting ‘Awkward Black Girl,’ to being on an HBO set, surrounded by women of color that were in charge, and being in my trailer and getting my hair and makeup done and having wardrobe,” Day said. “It showed such growth and perseverance.”
In the first three seasons, Day played Sarah, a co-worker of protagonist Issa (played by Rae) at We Got Y’All, a dysfunctional education nonprofit. Day remembers having another one of those full-circle moments later in Season 1, when the We Got Y’All staff takes a group of students to the beach. It was one of the first big location shoots for the show.
“Tears started falling down my cheeks. And one of the little girls looked up at me and was like, ‘Are you crying?’ I was like, ‘No, no, it’s the beach, the wind! The air is, like, hitting my contacts.’ I just lied,” she said. “I’m looking around, and there’s a crane, and there’s the cinematographers, and there’s video village, all the producers are there, Issa, the whole We Got Y’all family, and it just hit me. I remember filming in Issa’s dad’s doctor’s office in Inglewood with, like, two other people — and now, this is the actual show.”
Throughout her career, Day had been writing in various forms, from short stories to scripts. But watching Rae build “Awkward Black Girl” and “Insecure” from scratch and tell stories that reflected herself “supercharged” Day into trying to achieve something similar.
The idea for what became “Definition Please” first came to her in 2015, when she was taking improv classes and performing regularly at the famed Upright Citizens Brigade theater. One of her classes was on sketch writing, so she thought back to her childhood memories of competing in spelling bees. In fourth grade, Day won her class spelling bee, but lost in the first round of regionals, misspelling the word “radish.” (“I spelled it with two d’s instead of one, and it was devastating,” she remembers.)
“We had to pump out sketches every week, and one of my sketches was based on that experience,” she said. “It was called: ‘Where Are They Now?: Spelling Bee Winners.’ So generally, if you look up spelling bee winners, they’re working at NASA, or designing robots, or winning the World Poker Tour, doing really great, amazing things. So where my interest lay was with the spelling bee winner who maybe did not live up to his or her potential.”
A series of events inspired her to turn the sketch into a feature film. In 2016, she was selected for the Sundance Screenwriting Lab, and in 2017, her friend, director Justin Chon, premiered his first movie, “Gook,” at the festival. She then started writing the script for “Definition Please” and shot it in the summer of 2019.
Like the early days of “Awkward Black Girl,” filming “Definition Please” was a scrappy, DIY effort. Day partially self-financed the movie, putting it on her own credit cards. Her production designer and head of wardrobe went to high school with her. The house where much of the movie was shot and takes place is the home of Day’s parents. And Esha Chundru, who plays young Monica in the movie, is a family friend.
Woven into “Definition Please” are topics that are relatable to many Asian Americans, such as the stigma against talking about mental health, the pressures of the model minority trope and the ways Asian Americans are often reduced to just that. It shouldn’t be notable that the movie is a slice-of-life comedy and drama where Asian American characters get to exist as themselves. But unfortunately, it is, since those roles aren’t exactly in abundance quite yet.
“I think that’s what drew a lot of my actors to the script,” Day said. For example, Anna Khaja, who plays Jaya, Monica’s mom, “immediately said yes” because the character was so unlike many of the mostly one-dimensional characters she has played over the years.
“She plays a lot of South Asian moms on television — like, she has played Priyanka Chopra’s mom on ‘Quantico.’ She has played Jameela Jamil’s mom on ‘The Good Place.’ She was getting a lot of scripts, and the South Asian mom characters were very strict and controlling and wanted their kids to do certain things,” Day said. “She told me that her character was such a breath of fresh air for her to read, and she has such a fun arc in our movie that she couldn’t turn it down.”
Right now, Day is trying to get “Definition Please” out to a wider audience, looking for a distributor. She has more projects on the horizon, including a television series based on a short film she wrote and directed in 2016: “Cowboy and Indian.” She also somehow managed to be very productive during the pandemic, writing scripts for a couple more feature films she hopes to develop in the near future. As she keeps trying to tell more Asian American stories, Day looks back fondly on those early years of “Awkward Black Girl.”
“I think it inspired all of us ― the cast, the crew, everybody ― to just get out there, make your own content, no matter what, even if people reject you or pass on the idea,” she said. “Don’t worry about those passes, and just go out there and do it.”