Most recently, she opened up about a disastrous encounter she had with Rihanna at this year's Met Gala.
During an appearance on The Late Show with Stephen Colbert, Issa recounted the exact moment she "ruined" the opportunity to be friends with the beloved badgal.
"I just saw her sitting at the table and I had had a few drinks," she said. "So I was like 'RIhanna's over there, let me go say hi, she knows me, we homegirls.' And I went up to her and I was like, you know, tapped her."
Stunned by Rihanna's demeanor, Issa added, "And she was so friendly and nice, I wasn't expecting that, and she was like 'Hey girl, good to see you!' And I was like 'Uh...oh...we're, uh...' and just excused myself and waked away. So any chance that we had to be best friends, i ruined it with my drunken nervousness, starstruck-ness."
While their friendship might have been put on hold at this year's Met Gala, there might be some hope for a potential bond to form between Issa Rae and Rihanna. Rae is reportedly penning the script for a Twitter-inspired heist movie that's set to star Lupita Nyong'o, Rihanna and the Insecure star.
Take a look at Issa Rae's hilarious explanation below:
(Photo by FilmMagic/FilmMagic for HBO)