Simon Rich, the showrunner for FXX’s hilarious new comedy Man Seeking Woman, recently turned 30 – but he’s already done more than some people twice his age. The youngest son of New York magazine writer-at-large Frank Rich and brother of Rolling Stone contributor Nathaniel Rich, he ran Harvard’s campus humor publication, the Lampoon, during college, then became one of the youngest writers in the history of Saturday Night Live. He went on to crank out two novels and four laugh-out-loud funny short story collections – one of which, 2013’s surreal, romantic The Last Girlfriend on Earth, is the basis for his new show. “They’re some of the weirdest stories I’ve ever written,” says Rich. “But they’re also, bizarrely, the most personal.”
Man Seeking Woman follows Josh Greenberg (a stand-in of sorts for Rich himself, played by the excellent Jay Baruchel) as he navigates a fantastical nightmare world of millennial dating. In one episode, his sister sets him up on a blind date with an actual troll; later, he meets his ex’s new boyfriend — a certain German dictator who started WWII.
Rich spoke to Rolling Stone about romantic comedies, Hitler and his respectful fear of Lorne Michaels.
Is the whole series going to be taken from The Last Girlfriend on Earth? The hope is that the show will go on so long that you’ll eventually run out of stories from that collection, right?
Right, yeah. I think we definitely burned through most of the winners in Season One [laughs]. I would say there are a lot of premises that are taken from the collection, and it’s very tonally similar to the book, but there’s a whole bunch of new stuff in these first 10 episodes that I’m really excited about.
So what does your involvement with each episode look like?
Well, I get to really supervise the whole thing, which was super exciting for me, because I’ve never gotten to do that. I wrote or co-wrote most of the episodes, and I had a really incredible writing staff that I worked with: Ian Maxtone-Graham, who’s one of my idols from The Simpsons; Rob Padnick, who’s an unbelievably hilarious writer who worked on The Office for years; and this great playwright called Sofia Alvarez, who I’ve been a fan of for years. Oh, and Dan Mirk from The Onion. So it was a really great staff and it was so much fun to write with them.
And Lorne Michaels is involved as well, right?
Yeah, Lorne’s one of the executive producers. It’s a really weird show, obviously, and I was almost afraid to tell him about it. I trust Lorne so much what works in TV and film; I was worried that I’d tell him about it and he would tell me it was insane, that it would be crazy to pursue it. But he was supportive from the get-go, and I’m really thankful to him and everybody else for taking a chance on such a crazy project.
Has the dynamic with him kind of shifted? Obviously when you were on SNL that’s his show, his sandbox. What was it like to have him in yours?
Well, if you’re asking if I’ve gotten any less afraid of him, that answer is no [laughs]. I’m still completely terrified of him. I’m still as terrified of Lorne Michaels as I was when I first met him in my early twenties – that fear hasn’t abated.
There have been a million scenes about a guy meeting his ex-girlfriend’s new boyfriend. But I don’t think it’s ever been Hitler!
Yeah, I’m sure.
I still stutter in his presence. But it’s thrilling, too. The coolest. Because, you know, in the last 10 years I’ve mostly written books, which is a really solitary job. You’re sort of alone in your office all day, just typing by yourself. So the most thrilling part of TV for me is that I get to collaborate with all these really incredibly talented people.
Much of the show – and the book as well – has this kind of surrealist version of scenarios that are painfully true. You write like somebody who’s been on a lot of bad dates.
Ha! Yeah…these stories are the most true to my own dating life. It was interesting. Like, I spent years trying to write stories about my own [actual] dating experiences, but they always turned out really boring and low-stakes. There’s nothing that’s been unusual or unique in my own romantic history – it’s the same as everybody else’s, you know? But for me, when you’re in the middle of dating someone, it feels like the fate of the world is resting on every text and every phone call. So I decided, instead of writing about things the way they happened, I would write about the way it felt. Because when you find out your ex is dating somebody new, it feels like she’s dating Adolph Hitler.
You take these stories to the edgiest conclusions – it almost gets super uncomfortable. Like in the pilot, I walked away from it thinking, “Wow, Josh is being really hard on Hitler. Adolf seemed like a pretty cool guy…”
Yes! Exactly. That was one of the main reasons it worked, because Bill Hader is such an unbelievable performer. Because the most torturous part of that scene is that nobody takes Josh’s side, which is – not to give anything away – definitely a recurring motif in Man Seeking Woman.
In other interviews, you’ve mentioned that you have a formula for whether or not something is funny. Do you have a similar guideline for how an episode is going to adapt to the screen? Like a Simon Rich version of “no hugging, no learning?”
I sort of do. A big rule of mine is we try not to do an scenes that could exist in another sitcom. The goal is always to do something original, and we write about very universal subjects. The show is about things like falling in love, or getting dumped, or breaking up with somebody – the kinds of subjects and themes that we write about are as generic as you could ever imagine. But we try to do old stories in a new way. There have been a million scenes on a million shows about a guy meeting his ex-girlfriend’s new boyfriend. But I don’t think it’s ever been Hitler!
Would you describe it as a romantic comedy then?
For sure. I think it’s a pretty traditional romantic comedy. Obviously there are very unusual aspects to our show, but at it’s core – even though it’s chock full of space aliens and decapitations and trolls and time travel – I still think it’s just a show about a guy trying to meet a girl.