Samantha Irby Started Writing To Impress A Boy

The acclaimed essayist can trace her entire career — including her latest book, Quietly Hostile — back to some flirtatious messages on MySpace.

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It all started with a crush. Back in late aughts, Samantha Irby was messaging with a “cool” seeming guy on MySpace when he revealed that he was “really attracted to writers.” Obviously, Irby would do what was necessary to impress him — but rather than just pretend to be a writer, Irby set out to become one. “I decided to go on my MySpace blog and start writing these off-the-cuff little things I was thinking about. Then I was like, ‘You like writers, huh? Here's my blog,’” the Quietly Hostile author tells Bustle. “I don't even know that he read it, but I did it for his benefit. Then we dated and it was f*cking terrible. Then it ended. But I kept doing this — I turned it into a whole thing.”

In the years after her breakup, Irby went on to publish New York Times bestselling essay collections like We Are Never Meeting in Real Life and Wow, No Thank You. And though she was now writing to make a living, not to impress some guy, the desire to please others with her work never waned. “It feels so pathetic to say, but I think there is still a part of me in my writing that's like, ‘You like me, right? Am I making you happy? Did I make you laugh?’” Irby says. Usually, the answer is an emphatic yes, so she found herself in uncharted territory when she took a job in the writer’s room for the Sex and the City reboot, And Just Like That... For all the people who were elated to see Carrie, Miranda, and Charlotte reunite, there were just as many who had thoughts. “I was really surprised [by the reaction]. Some lady on Instagram called me a murderer [after Big died]! I'm like, ‘Do you really [I] make all of the decisions for this beloved television program?’ There's no way to tell people that, though. So you just have to shut the f*ck up and wait for it to go away.”

While she waited it out, Irby went back to the medium she knows best: humor essays. And as she worked on Quietly Hostile — her latest collection, which offers musings on everything from QVC to pandemic puppies — Irby sought to find the positive in her people-pleasing tendencies, reframing her perceived fault as a rejection of writerly pretension. “I'm not one of those writers who's like, ‘You're going to get what I'm giving you and you're going to love it,’” she says. “I think about, ‘Is this useful? Will people like this?’” She almost had herself convinced — but she couldn’t hide from the truth forever. “I’m always tap-dancing for approval,” Irby jokes.

Below, Irby reflects on her love of jelly beans, horror novels, and The National.

On loving books that “f*cking terrify” her:

I read a lot of horror and I just finished Grady Hendrix's How to Sell a Haunted House. I’m a huge Grady Hendrix person; he’s genius to me. This book is about this woman who’s a tech person living in San Francisco. Her parents die in a car accident and she has to go back to South Carolina to her childhood home that she left when she was 16 to try to sell the house. But the house is inhabited by some things and it’s f*cking terrifying. Like, the hair on the back of my neck was standing up in some parts.

On her taste for the worst flavors:

I need to have a stream of small things to chew when I’m writing. [I’ll eat] Jelly Belly Jelly Beans. I like to get the individual flavors because it's too hard to think about combinations when you get the big bags. So I buy cantaloupe and kiwi — the flavors you get and you're like, “Who's this for?” Well, it's for me.

On her fear of the computer screen:

I have to think the sentences over in my mind before I type them. This is nuts, but it feels bad to me to type and then go back and fix it. Even though it's just a secret between me and the screen, it feels like a failure if I type a thing and I'm like, “Ugh, that's bad.” I do not recommend beating up on yourself so much that you take 10 hours to write a thing because you're too afraid to type it. It’s real sicko sh*t.

On creating a wall of noise:

The trick I swear by is listening to series of songs, one at a time, on repeat. I like the noise in my headphones — it feels safe, and makes me feel in my zone. But because I like songs with lyrics — and I need to not be paying attention to the lyrics — I listen to the same song until it blends into a wall of noise. A big one, that’s been with me through lots of books is “About Today” by The National. It can up your end-of-the-year Spotify [Wrapped], but honestly, it's worth it.

On sneaking episodes of Succession:

[I procrastinate by watching] sh*t on the iPad, movies, TV. There’s a little cutout in my office where my desk is, and from the door you can’t see what I’m doing. The iPad's kind of tucked in there, so no one has any idea if I'm writing or if I'm watching Succession. You can connect your AirPods to it and no one will even hear that you're watching something else. Not like anyone ever is checking what I'm doing — but just in case!

This interview has been edited and condensed.

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