We chatted about what it’s like to write a humor column over these bleak past four years, how he balances short-term and long-term projects, and how he’s planning to spend the evening of November 3. It’s an extra-good one; enjoy!
Your column at ELLE was born out of a viral Facebook post you wrote in the summer of 2016. Cut to four chaotic years — a lifetime’s worth of news cycles — later: how has the work of writing the column changed for you?
That's something I think about a lot, particularly since my expectations for what the column is have been constantly changing over the course of this presidency.
To be honest, at the beginning I was just having fun writing a column that felt like sending nonsense to a group chat. I'm glad for that, because I think if I'd thought to ask permission to do something like that, I would have been tempted to dress it up or formalize it or something.
As the political landscape darkened, though, I began to work harder to suss out column topics that added something redeemable to our time. I knew that writing about Trump was going to be sometimes unavoidable, but I didn't want to be an accomplice to his megalomania. So the work of writing the column began, by necessity, to be more intentional.
I hope my sense of humor hasn't changed all that much, although there are definitely some joke constructions that I was using in 2016 and 2017 that just look bonkers to me now. It's like, babe you were just free-associating for the gawds back then. Truly wild west times.
For someone who’s very Twitter-native, I imagine you’re no stranger to this sort of arms race that happens during events like say, a presidential debate, where everyone’s racing to get the funniest meme or joke up immediately and be the one who goes viral.
Do you follow any of that — this like, Twitter joke cycle — when you’re planning what to write for your column?
One of my favorite things used to be live-commenting on award shows on Facebook, which felt at one time more communal and fun than Twitter. I've largely stopped doing that because it does feel like the conversation aspect of social media has moved over Twitter. There are still times that I feel a real rush to get to a joke first, but since everything happens at once on Twitter and none of it matters, I feel less compelled by that.
If anything, I use Twitter to gauge what joke has been played out by the time I get around to writing a column. It's really helpful to see what's the low-hanging fruit or what subject everyone got to first with a better take and then challenge myself to find a different angle. There are other times that I will just let myself live-tweet something and then, the next day when I'm writing a column, go back and say "Okay, which one of these wine tweets is getting a promotion?"
To build off that, I was really interested in what you said in this interview for Baltimore Magazine about how of course there’s a space for writing humor in this time, but also that “there’s also a space for making a community.” Have you noticed your relationship change with Twitter at all?
While I do sometimes test out material on Twitter, mostly I think I'm using it as a direct communication that stands on its own. So when I tweet I'm mostly working on impulse rather than testing comedic premises.
This is because I like to write longer and do more calling back, and so the tweet form just doesn't allow for me to use all the muscles I like to use most. But I do feel like I've gotten better at being funny on Twitter, which is something I purposefully tried to do about 7 years ago (and failed at for the next 4 years).
On Twitter, though — and this is where the community aspect comes in I think — I'm always thinking about audience. Although I have upwards of 40k followers, I am always sort of ambiently aware of the way that other people I find funny or insightful are playing with the form and I'm trying to be in conversation with them. Sometimes this doesn't work out so well, like the times I get a little too lost in NYC Gay Twitter even though I am not an NYC Gay and I start tweeting about Adele being at Pieces. Like, who am I trying to fool here?
How do you divide your time and like, general brain space between being the full-time writer of a daily column versus the longer-view work you do as an author, playwright, host of The Moth, and all that?
Ideally, I would have dedicated stretches for different projects but I haven't had the opportunity to really commit to that for a while, so I tend to take a piece-meal approach.
I'll work on the column during the day, which involves a lot of navigating the news cycle and online conversation, and do other work for ELLE. Then in the evenings I'll jump into a play or the novel I'm working on or other things.
Right now, I'm in the middle of four different creative projects and I will literally be switching browser windows at night writing a line here and a note there. Chaos. True chaos. Why am I like this? Deadlines, I guess. But also I need to always have something going on the back burners while I'm cooking on the front burner. Maybe. Who can say? Check in next year when I've taken three months off to write a pilot and I look like Tom Hanks in Cast Away.
Finally, what can you tell us about your plans for Election Night? Should we be staying up late for a column to drop while the results are coming in….or are you going the pop-a-sleeping-pill-see-you-at-9.a.m-route?
I really did plan to take a Benadryl at like 6:30 pm and Leave the World Behind (shoutout to Rumaan Alam!) but I have to work Election Night so... I don't know.
I've been thinking a lot about what kind of #content will be useful to have on hand, and what kind of pivot I can do for various happenings. From a dramatic standpoint, if I was a fictional character writing a comedy politics column during this presidency, the climax of my journey would be an election night that has no shortage of noteworthy events but was utterly bleak. Like, if I was a tragic figure, I'd be in front of my screen, illuminated by the glow, muttering "None of it is funny. Nothing is funny. It's all so bad." LOL what a mess!
I do feel like this moment (I'm writing this less than three weeks from Election Day) has really pushed us to our limits. It's not to say that nothing is funny, but the Trump show is so grotesque and deranged that one doesn't want to engage with it anymore. I've found real catharsis in the last few weeks working on fictional projects that brim with light, infused with hope in their DNA — a novel and a pilot specifically. That's the refuge for me.
So, I think I'll keep an eye on what's going on on Election Night and perhaps write about things we can do while we wait the six years for the results to come in (we're not going to know on the 3rd, for sure), but also give some of my attention to another, better world, coming to a screen or store near you... at some point?
Deez Links is a dailyish newsletter written by delia cai.