‘Insecure’ star Issa Rae doles out dating tips and spills on the cast’s close bond

By Meaghan Wray

Issa Rae has come a long way from her YouTube days, where she gained a following with her debut web series Awkward Black Girl while studying as Stanford University, but rest assured that she’s just getting started. Now, she finds herself producing, writing and starring in HBO’s Insecure, a show that follows her character Issa Dee and her friends as they navigate life in Los Angeles. With so much on her plate, a solid work ethic and drive to keep making art are the foundation of what she does, on top of counting Donald Glover and Tina Fey as just two of her biggest inspirations. “If you work hard, you’ll get the fruits of your labour,” Issa told Hello! while in Toronto for the Live Life Experience with American Express. “I still have so much more work to do and so many more opportunities and so much more to say.”

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With two critically acclaimed series under her belt ­– on top of a roster of upcoming writing and production opportunities – the Los Angeles native, 33, was game to use her platform to help open an interactive pop-up art exhibit featuring local Toronto artists. Here, we discuss her recent Peabody Award win, top dating tips, the close bond she shares with her Insecure castmates and how she hopes her series is making an impact for the black community.

How did you react when you saw that you won a Peabody Award? I was in bed, scrolling. I wasn’t on Twitter or anything at the time or any social media, and [then] I saw the Peabodys come up. It was confusing because on their website they have so many names! So, I sent it to our writer group chat because we just have [one] where we just share stupid things. I sent them a screenshot and was like, “guys, did we win a Peabody because I can’t tell?” And they were like “oh sh-t, we won!” So, I was celebrating in bed. [ Laughs.]

Insecure does such a great job dissecting the monotony of dating. Do you have any tips for us? I wish I did. [Laughs.] Just be persistent because you never know, but don’t rely solely on [online dating]. I’m still big about the chemistry of meeting people in person but I always keep my options open. Don’t just date one person at a time; you got to date multiple people at a time because you just never know. So many dudes are doing that. I just feel like we should do the same thing.

Issa and Yvonne shared a laugh while on a panel in LA. Photo: © Jeff Kravitz/FilmMagic for HBO

It seems like you and your castmates have so much fun together. How do you guys unwind after filming? We hang out between takes. There’s love for each other. It’s so much fun! Yvonne [Orji, who plays Molly] specifically is such a cool, generous [person]. I’ve been following her career for a long time before we even casted her in Insecure. I always just wanted to be her friend, so to be able to be her friend on TV and be her friend off screen is such a treat. It feels like we’re all coming up together.

Insecure has been ground-breaking for its portrayal of black actors. What else does the show do to shape the way actors of colour are seen onscreen? I think we’re ground-breaking in terms of uplifting unknown artists in terms of music, actors, talent, directors and that’s something that actually drew me to participating in this event here – the support and using a platform to support local artists. We just had a contest the other day to have people submit their music to be featured on the show and the soundtrack. And that will put money in people’s pockets, drive initiatives that support up-and-coming writers who never have the chance to work in television or film. To be able to put them in the pipeline, because so many writers of colour don’t get that opportunity. I think Insecure is ground-breaking in that sense of just giving people opportunities that they wouldn’t normally have.

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