Michelle Obama And Brother Craig Robinson Discuss Friendship With Issa Rae In First Podcast Episode

Michelle Obama and her older brother Craig Robinson have introduced the first guest on their IMO (In My Opinion) podcast: the incomparable actress, writer, and producer Issa Rae. In this episode, Issa joined the siblings to talk about the expansive topic of friendship, specifically about how to maintain them and the complexities of them.

Diving deeper into Issa’s opinions on the topic, the co-hosts asked the Insecure creator about her personal support system, opinions on high and low-maintenance friendships, and other aspects. When asked about the kind of friend she believes she is, Issa admitted that she’s questioned if she’s a “bad friend.”

“I think about you, but I might not text you to be like, ‘Hey I just want to make sure you’re okay,’” Issa admitted. “But you should know that I would hope you would call me if you weren’t okay and know that I would show up for you and be there for you.” She added, “I’m not a considerate friend in the way that i would like to be. It’s like one of my biggest flaws.” She also explained that because she is “so work focused” she doesn’t reach out to her friends as much, although she’s always thinking of them.

Elsewhere in the convo, the co-hosts asked about the right time to “end a friendship,” to which Issa shared a story about her most “painful” friendship breakup.

“I had a friend who I thought I was going to be friends with forever,” she began. “But she went through two major milestones — kind of traumatic milestones really young — she got married when we were in college and divorced when none of my other friends had experienced those things. And as a friend I didn’t know how to handle that. That was actually strike two, on my part, for her. I couldn’t be there for her like she needed me to.”

Issa’s openness on friendship comes almost a year after her former co-star and friend, Amanda Seales, claimed that Issa wasn’t “empowering” her during their time on set for Insecure. In a 2024 viral interview with Shannon Sharpe, the comedian and actress alleged that Issa “didn’t feel like I deserved to be protected. But that was my experience. And nonetheless, I have still always protected her because I felt like it was my responsibility to do so. But it is not.”

To counter that, Issa joined The Breakfast Club last September where she said admitted that she’s never going to work with “anyone who goes on a podcast and talks sh*t” about her again. Although she didn’t mention any names, it was assumed that she was speaking about Seales.

Take a look at Issa Rae speaking with Michelle Obama and Craig Robinson above about friendships and revisit her spill about Amanda Seales below.