When did you write Sillyboy?
I began in 2015.
I wasn’t even in the city. I was in middle school.
Cat’s out of the bag — Sillyboy wasn’t actually about you. I started in 2015, but the bulk of it was written from 2017 to 2021. Jon Lindsay, who started Cash4Gold and put the book out, and Nathan Dragon made some great refining edits. It’s incredible how much it takes to tell the story you want.
And what’s the story you wanted to tell?
When I began writing, there wasn’t that much content about how the phone influences relationships. So the overarching thesis was about social media and Instagram.
Boomers are going to love this book.
I’m willing it into existence. The boomers will love this book. Actually, Harris, one of the editors at Cash4Gold, told me he sent it to his 75-year-old father, who loved it for some reason. So the boomers do love this book.
Now we’ve got work about social media, but at the time it was uncharted territory. And I still think there’s not enough. For as much as we’re on our phones, there isn’t as much media dedicated to portraying that reality as there should be.
People are making memes about how much your phone messes you up, but no one’s writing novels.
Memes exist because they’re native to the phone. But in literature and cinema, there aren’t that many voices being honest about how phones mess you up. So I was motivated by that in the beginning. I’d even joke that I wanted my book to mention Instagram more than any other book.
So much of what we consider culture is happening on the internet now. We had places like Max’s and CBGB as sites of cultural happenings. But now, lots of “culturally significant” interactions happen on the phone. Journalism nowadays is just people talking about what we’re seeing on the internet. The phone is such a cultural location now.
The book portrays a time when everything was a lot more 1.0. I’m writing with a real vintage Instagram in mind, partly because of how long it took me to write. But now, all of our innocence around social media has been lost. I still think it’s surprising how we don’t have much media about that reality — partially because it’s so hard to capture.
Because what are you going to do? Make a film about people angrily typing in bed?
This is the reality I try to portray in rachelormont. It’s really difficult to represent, but we have to. Or else all we’ll have is the phone. You won’t have any other cultural artifacts that reference reality. We won’t have any way of documenting it.
Even if it was fucked up that all we did was sit on our phones.
Honestly, documentation shouldn’t be about whether something is fucked up or not. Art just needs to reflect reality so we have some way of dealing with it. So many people are making things that are overly referential to the past to the point where we miss the present. I just want the book to be entertaining. It’s not even that deep.
You didn’t mean for it to be deep. It was only deep to me because I have a similarly fucked up love life.
All the depth comes from the reader.
That’s a better way of putting it.
But Chloe and Sillyboy do have that kind of relationship that’s kept together by, like…
How much they love to hate each other?
How much they love to hate each other. It’s compulsive. You’re actually seeing really deeply into the book. One thing I wanted to get at is how you can end up in a fully committed relationship with someone you’re not necessarily right for. Some relationships just have a volatile quality and it’s what makes them valuable. For Chloe and Sillyboy, it’s part of the way they show love — dumping each other constantly. That can become a compulsion in and of itself. Have you ever had anything like that?
No. I’ve been in like, three relationships.
It can be a thing that adds to the romance.
I mean, hate sex is a thing, so I think I get it.
Exactly. Constantly reinvigorating the hate sex — that’s the goal. They’re trying to hate each other more so that they can have better hate sex.
Cheers to that.
Fuck it. I will cheers to that. I do think these characters grow to really love each other, but it’s a romance predicated on lust. They met on OKCupid — the most unserious hookup style. There’s nothing substantial about the way they come together. It’s the opposite. It’s deeply surface-level.
It’s also very archetypal. A Scott Pilgrim relationship.
Explain.
Younger Asian chick and an older white dude with quesitonable morals who don’t have a reason to be together. That’s just the first thing I noticed. I felt a little read, honestly.
Because?
I’ve had a lot of Sillyboy-Chloe-style entanglements. I was texting you about all the parallels the whole time I was reading. Like, “Dude, an Asian girl tattoo artist who went to NYU reminiscing with the guys she used to skate with? That’s so freaky.”
It’s crazy that I wrote the book about you. [Laughs]