Mining the Comedy from Uncomfortable Situations: An Interview with ‘Pen15’ Co-Creator Anna Konkle

Pen15 is an R-rated “traumedy” set in middle school as it really happened in the year 2000. Anna Konkle and Maya Erskine play versions of themselves as thirteen year old outcasts, surrounded by actual thirteen year olds. In this world, seventh grade never ends and the pains of growing up are inevitable.

If you were to point to a show that perfectly sums up the millennial experience as a teenager in the early aughts, Pen15 is that show. I'll even go on record saying that Pen15 is Gen Y's Freaks and Geeks [if only we could get a second season of Paul Feig's quintessential television masterpiece and a third season of Pen15 - crossover anyone?] The second season of this show does a deeper dive into the life and world of the two awkward teens that are Maya and Anna and how they traverse through these new chapters in their lives. The storylines are grounded and relatable and the humor stems from those dramatic and awkward encounters.

I had the grand opportunity to speak one-on-one with co-creator, co-showrunner, writer, director, and co-star Anna Konkle about tackling the second season, character development, and arcs, where and when nostalgia fit in, and how they were able to mine for comedy from the most uncomfortable situations.

This interview has been edited for content and clarity.

Sadie Dean: I’m curious, was it always known that the show was going to be only two seasons, or was this something that was prompted midway through? And what was the approach to breaking season two and developing those character arcs?

Anna Konkle: Yeah, even thinking back to the pitch of the show, it was pitched in three seasons, which, we think of the last eight episodes is sort of the final chapter. And so there's three story arcs in the series, and the first season being sort of loss of innocence and the sort of the more obvious firsts: your first kiss, not a fun obvious first, but first experience with racism or where you truly deal with it, the first time you masturbate, and the first time your family breaks apart. And then the second arc being emotional first, and the less obvious ones and we're always interested in the minutia, but I think it gets really into the minutiae of mother-daughter relationships and they're maturing a little bit, they're starting to lose a bit of innocence. Even Anna and her parents and seeing sort of the more brutal side of what that is like, or Maya and her relationship with her mother and herself, and that sort of breaking apart and getting brutal, and eventually finding themselves and their identities in a new way at the end of that arc.

The last arc was always meant to be sort of a mirror to the high school more so even though they're always in seventh grade, but there are those kids that, and I don't know what it's like now, but dabbled in drugs and alcohol at that time, and were more mature and talking about more sexual stuff, and I didn't happen to be on that end of the spectrum believe it or not [laughs] but we knew that if we got a third season, which is sort of our final season now, that's where we want it to go. In this final arc, we're dealing with more mature things; death, drugs, alcohol, more serious sexual experiences, and feeling a little violated as a girl for the first time. The goal was by the end of that season, that arc to go back home again. And that's what the final episode really is about, which I'm really proud of.

[Creating the Murder Mystery Comedy with 'Only Murders in the Building' Co-Creator and Showrunner John Hoffman]

Sadie: You really do tap into that idea and feeling of the loss of innocence and adolescence because it does feel grounded in reality with the dynamics of family relationships, and the realization as a child that your parental figure is not perfect, they’re broken too. There's also a lot of nostalgia in the show – were there specific references that you were using to develop certain storylines, like when you introduce Maya’s brother getting his first cellphone or the phenomenon that was AIM chat rooms?

Anna: The goal at the time was let's not lean on the nostalgia, because what if we miss deeper stories because of that? But whenever we could, and it was true to the reality of the experience and didn't distract from it, we brought it in. I think the exception is the AIM episode, which I was pretty annoyingly obsessive about, I think anyone can attest to, because I was really curious and we all were; this very alive story that we felt every time we signed on to AOL, or AIM, however you say it in your part of the country if we could mimic that experience, it could be so alive and have high stakes. It was just this feeling of anything's possible, and I could talk to anybody, and I can be anybody. And I'm growing up. And there's this world and this community online in such a simplified way than what we experience today also. It was sort of a challenge of, 'Can we live in that world and just be typing and messaging? And can we send people back to that story?' So that was a really exciting episode.

Sadie: For you and Maya, you both were tapping into your own personal stories and experiences, and bringing that into this world for this television series, and there’s that fine line between fact and fiction – did either of you ever have a moment where you had to step back because it was getting a little too extreme or was it whatever you had to do in order to service the story?

Anna: Yeah, we did. I mean, it was rare. I think most of the time, we tried to just kind of go for it and put it all on the table, which I think is really more evident in the last arc. The real challenge in the stories and we didn't have a lot I remember in the beginning of season one writer's room when we were learning and very scared, always, but especially that season, we were like, ‘Oh, we have to intricately share the stories of two main characters that are sharing their emotional experiences all the time, and they have their stories together, and then they're going to have their stories a part of their personal growth,’ that's a lot of real estate in a very short amount of time. So that, I think, has been one of the more limiting things in this series, actually. And it forced us to just use as much kind of creative storytelling as we could.

My family storyline specifically, like the autobiographical part of it, we kind of skimmed the surface of that. And that was intentional in the sense that we talked about going further, but it felt sort of beside the point, we kind of went where we needed to go for Anna's character development, and to go farther, felt like it needed its own show or something [laughs] that no one would watch. In terms of feeling violated as a girl, we went there a little bit, but I think that was where it felt like if we're going to do this fully, this is a full season; this is a very dark, sad, full season and mining the comedy out of that, as well, it just wasn't enough time to really go into those things. So, I like to think that there's very few places that we wouldn't go, but there has to be ample real estate in the season to do it in a way that it deserves.

[Telling Your Truth on the Page with 'Ted Lasso' Writer Jane Becker]

Sadie: Both of you wear many creative hats from writing, directing, and obviously staring in the show, when it came down to getting pre-teen and teenager mannerisms and attitudes both for writing and on the acting side of it, how much were you able to tap into your awkward teenage self? And also, were there times you were either conferring with your teen cast mates or maybe just observing them, like at a zoo?

Anna: For sure. I would have moments right before a scene, sort of closing my eyes and picturing myself at 13, what I probably looked like to other people, and just kind of trying to assume the stance of not being as tall as I was. And one of my biggest insecurities was my stomach. And so, I'd always be trying to hide that, which I thought was effective, just covering it with my arm, but I'm sure it wasn't. But those are the funny-sad things that interest me. As adults, we get better at effectively hiding the insecurity. And it's very funny to me that you're not good at it at that age [laughs] and you think you are. On set I would watch, that influenced me. I was always correcting hairs, ‘If I just get this right here, I’ll feel pretty today,’ it's barely a difference. But seeing kids, especially where they would just pull up at the same side of their jeans over and over like it was changing the world [laughs] and that was very interesting and funny to me. Yeah, I totally would steal that.

Sadie: When putting your writer’s room together, what kind of voices were you looking for tonally to fill out that room?

Anna: I think one of the things just in samples that first popped off the page was a script that had a lot of jokes, just wasn't our kind of sensibility and looking for this show in particular, not to say that they can't do that, but you're only going off the sample for the most part. So, we sort of gravitated towards scripts that created just full and visceral environments, and the characters felt full and interesting. And the humor came from the situation or the character, instead of sort of a punch line. I think that was the leading thing and then getting to meet the people behind the samples. It was just about how much we all connected and got along. And I also think their willingness to find humor or importance in like a deep candidness about your past and that it's not just for the sake of being cringe or being how crazy can we be are something that the purpose under it is to expose our own shame so that the more we expose our secrets or things that feel like they're unique to us, we keep hearing that they're unique to other people, too. And then it's not so unique, and that can feel really healing. That's sort of the point of the stories. So, if they could buy into that with us, that was important. And again, we were lucky for it.

Sadie: For the second season, what was the most complicated to creatively tackle or maybe the most creatively fulfilling?

Anna: That's a good question. I definitely think the whole series was really fulfilling and challenging and scary. Anna's breaking up with her first love and, Maya's just had this sort of blurry experience with her first blow job and kind of retribution to that person that maybe there wasn't enough clear consent and the sort of original family of Pen; Sam, Gabe, Jafeer and Shuji and going all together to take down Derek's house and in like a symbolic way more than anything, and then coming back home to Anna's house, and fantasizing about what a future in their life could be like together and knowing as the writer that that's not what it looks like, you're not going to live in clouds and next to each other, and go to every doctor's appointment with each other and always be there when something goes wrong - you might try, but for most of us, were not so lucky. And so just sculpting the trajectory, and Vera did an amazing job on that episode, sculpting the trajectory of that one in particular. The blow job makes me cry, cringe and laugh all at the same time. [laughs] Very little, believe it or not, on the show makes me look away and cringe, I don't get it, ‘Cringe comedy, where?’ But that episode does and so the fact that we're pushing the line is exciting. I also think the Yuki episode that Maya directed brilliantly and wrote, just in the outlining phase and all of that of going in a different tonal direction and just a swing of a different kind of storytelling that we weren't doing a lot that was interesting. And she just eviscerated every expectation that I had with the direction and the performances.

There was an episode that I wrote and directed about death and cancer and being confronted by death for the first time and the episode before that is based on the relationship I have with my grandmother and she dies in the episode, but we don't really understand death. And then the next episode is trying to process the abstractness of it. So that was very intimidating. But I learned a lot from it.

Sadie: Yeah, with your directing both the animated episode and that episode you just referenced – you’ve lived in this world and show for so long as both a writer and actor - what was it like for you to dive in as a director?

Anna: To be honest, there was a lot of it that felt natural, just in the sense that the showrunning component, because I’m coming into it very green, is that every showrunner does it differently, but we're super involved in editing and really collaborative with all the amazing directors, and constant communication about the creative result. There was a part of finally directing these episodes that we had written and had been picturing forever, that sort of reduced the telephone game that inevitably happens and it was kind of a relief to just communicate directly and move forward with that, whatever the result. Also, I think, it's just so hard. I try and I know, Maya does too, to step out of whatever creative expectations you have when you're acting, but I'm not very good at it. And I ended up rewriting during the scene or right before. So yeah, being really creatively present as we're acting and making changes was sort of natural, but it was really intimidating. And especially the subject matter was just intimidating. Like, ‘Is the abstractness of the story coming through?’ And honestly, editing - Amelia is our editor and she was amazing, and is amazing - but was one of the more intimidating parts to us, ‘I don't know if the abstractness is going to come through here, and we'll just do our best.’

Sadie: What inspired you to become an actress and then a writer and eventually creatively connecting with Maya?

Anna: I didn't grow up watching a lot of comedy, except for what was on TV. I watched The Simpsons all the time and Seinfeld, Frasier, and Golden Girls, whatever comedy was on TV, but that wasn't really my trajectory. I found it, which I'm very grateful for. My parents were like characters, and both have really unique senses of humor. My dad, very dark sense of humor, [laughs] hit or miss with how those around him experienced him. I thought he was very funny. He was a human resource manager who got fired many times, I'm sure partly for his humor. [laughs]

Sadie: [laughs] That's a great story in itself, I'm sure.

Anna: Yeah, exactly. And then my mom is the funniest human being on the planet without trying and gets offended if you laugh at her, so that's like a hard dynamic. [laughs] Honestly just growing up around them was very funny, and so many stories and so much of my work, as much as I still talk about my family in therapy, and complain [laughs] so much of my work and my art is because of them. When I started reading memoirs, is when I started to feel less alone, and like the dysfunction in my home could be funny, you know, David Sedaris being an example, he's incredible. And it was so fucking funny and so sad, and I felt less alone. And so, in my mind, I wanted to be in the Squid and the Whale and be an actor from that. I didn't know that I wanted to write. I knew that I love storytelling, but my experience with that was seeing people on TV and so I was like, ‘OK, I want to play these characters that are in David Sedaris’ book.’

I did experimental theater in school, and that's sort of funny and serious in itself, and you're encouraged to think out of the box. And so, I think in a lot of ways comedy for me came from performance art, because just naturally my different way of thinking was funny and doing weird characters and stuff. And I think the same for Maya. And she was very much my muse for comedy of being like, ‘I want to write this character for you, this is the funniest thing in the world to see you do this. We're gonna make a web series just to see you do this.’ So, we eventually made a web series together, and they were all different characters. And that was our first real commitment to approaching comedy. And then Pen15 came after, ‘What's the most awkward stories we can tell and haven't been told?’ And that was 10 years ago, and now they're being told.

Sadie: And seeing how you two can play awkward 13-year-old teenagers as adults.

Anna: It's the dream. I remember when we were first pitching the idea, executives being like, ‘That's not going to work.’ And every actor we talked to was like, ‘This is my dream role.’ Again, experimental theater, I'd be like, ‘I'm playing a baby today in a scene.’ [laughs] ‘Never gonna get to do that professionally. Good luck.’ But the fact that we got to make something like this, that is a piece of experimental theater in a lot of ways. And it became a little bit mainstream like that. I didn't think that was possible.

Sadie: Well, you two did it and did it well. Any advice for writers who are also tapping into something that's very personal, like what you two did, and how to find the comedy within that?

Anna: I've been thinking about this a lot after Pen and being like, ‘What the hell do I want to do? What can I do?’ And I think, what keeps occurring to me is the scarier it is to write about, there's more to write about, because it's probably not been written a lot about. And the things that you think you're alone in feeling and it's too embarrassing or too telling, I'm just reminded over and over that nothing is unique to you. And someone is waiting to hear your story, or your thing that you feel you're the only one in and there's more power in that than anything, I think.

In terms of the comedy, for me, it's all about the characters that you could take the most serious content, and again, back to my parents, [laughs] and have a juxtaposition within a human being that makes them very, very funny and put it in this serious situation - and there's innately comedy. I mean, the best dramas are very funny also. I think about American Beauty all the time and Annette Bening in that and she's just a genius and it's hilarious. I mean, even the dark Todd Solondz movies that we think back on as inspiration for Pen, there's so many funny characters moments to me. 

Watch the second season of Pen15 only on Hulu.