We’re With Her: Issa Rae on Lousy Bosses, Writing Scripts at 11, and Learning Not to Give a Damn

Photograph by Elton Anderson

The Emmy-nominated creator of HBO’s Insecure, now starring in the new film Little, on lousy bosses and learning to not give a damn.

In Little (out April 12), you play an assistant to an abusive boss. Have you ever had a terrible boss in real life?
I had a terrible coworker who acted like my boss, which is unacceptable. I had a shitty boss once—but I was also a shitty intern at the time, so I can’t be mad.

How, exactly, were you a shitty intern?
It’s embarrassing to think about now, but I had just graduated from college and I was used to running my own production. It was stupid, entitled shit. I didn’t want to get coffee. She was like, “Girl, calm down. We’ve been doing this for years. Just pay your dues.”

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Well to be fair, I remember from your memoir The Misadventures of Awkward Black Girl, which you’ve been writing for TV since you were really young.
I started writing scripts when I was 11 because of watching the formulas from ’90s television. And obviously mine were terrible, but it was just like, “Oh, I could do this.” It was before Google, so I was Yahooing the addresses and names of studio heads and just sending my scripts out with a cover letter.

Precocious! What kinds of shows were you writing?
An original script I submitted was called Ronnie, about a young black boy in high school in L.A. trying not to get caught up in gang life. It was corny, I’m sure. I also wrote a spec script for Cosby about Bill Cosby’s character flipping out over his daughter getting a tongue ring. That was the most scandalous thing my 11-year-old mind could come up with.

Can you watch Cosby reruns and enjoy them, or not anymore?
Since those allegations came out, I can’t watch them. Same thing with R. Kelly. Anytime I hear something that yucky, I can’t really revisit the work without thinking about it. My brother and I were just talking about that.

Speaking of your brother, does your family watch Insecure? You have some very graphic sex scenes.
I have three brothers. They watch the show, but they do not watch the sex scenes. I don’t blame them. I wouldn’t want to watch their sex scenes either.

What did growing up with all those boys teach you about guys?
Nothing! I wish it had taught me more. I’ve always thought about that: I grew up with brothers, but I’ve always still been awkward around guys. They taught me literally nothing. They never helped in any way.

It’s interesting that you continue to describe yourself as awkward. I mean, you’re a beautiful spokeswoman for CoverGirl. You’ve been nominated for an Emmy.
It just stays, no matter what comes from the outside. In addition to that, you have a magnifying glass on your behavior, so it kind of makes you even more scrutinous of yourself. That’s something I’m trying to get over. I’m trying to get into more of the I-don’t-give-a-fuck-ness of how I started, where I didn’t have an audience, so I didn’t really care. Now I care a bit more—I’m trying to shed some of that.

How do you relax in your limited downtime?
This past winter break was the first time I had no obligations in three or four years. I took every minute to just say no to everything and chill. I feel so fresh.

Are you normally a yes-person?
I stopped being a yes-person a couple years ago because I had no time to create. I’ve become more of a calculated-yes-person.

So much of Insecure is about relationships between men and women. What’s your dating life like?
I’m never really looking. I’m not out there like, “Oh, I’m going to meet my Prince Charming.” Dating in L.A. sucks. We’re always in our cars, and the neighborhoods are really spread out. I imagine dating is better in the South. I have this idea in my mind that there’re a bunch of southern gentlemen who are just out there living and dating and courting women.

What do you look for in a guy?
A sense of humor and intellect. And teeth. That’s a big thing.

I’m going to be kissing you, or we’re going to be talking, and your breath stinks. All of that really goes hand in hand for me.

Makes sense. What about clothes? How important are they to you?
I’m a jeans-and-sweater person—I’m not into guys wearing athleisure. You’re not at the gym—it’s like, are you even trying? I just like a guy to look like he tried. My standards are really low there. I like fitted clothes on men, and I love men in suits. Male fashion is so much easier, so that’s why I’m kind of disgusted when men wear these baggy T-shirts or baggy polos. You have so many options to look good. Put in some effort! And put on some cologne.

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