When Drew Gregory told me she made a movie in quarantine, my first thought was, “Well, of course you did.” And my second thought was “Give it to me!” Drew is Autostraddle’s resident queer film expert. She recently watched and ranked TWO HUNDRED lesbian, bisexual, and queer films. She knows her stuff. She’s also never not creating, never not pushing the conversation forward around queer and trans rep on the big and small screen, never not looking for ways to share her story as a connection point for other people to find themselves in narratives that have been lacking — or outright nonexistent — in the TV and film canon. So, well, of course she wasn’t just going to sit still and do nothing during a pandemic.

The First Time is everything I’ve come to love about her writing over the last several years: smart and wise (two separate things), hilarious, powerful, and deeply generous.

You can watch it right now, and then read our interview about it below.

The First Time from Drew Gregory on Vimeo.

Heather: When I first met you, and you know this because I’ve told you many times, I knew that you were going to go on to make great movies and TV — and this film just reaffirms that to me. We watch so much queer content, and two things: 1) It is so rare to ever see anything that feels fresh and new, and 2) It is so rare to see a short film that makes you want more more more. This did both of those things! Thank you for letting me watch it and thank you for letting me interview you about it!

Drew: Heather!! Thank YOU. When I was a teenager I was very obsessed with the French New Wave — I know, insufferable, sorry — and I loved how this group of filmmakers who started as critics went on to write back and forward to the films they loved and didn’t. I feel that way about the work I do at Autostraddle. I’ve learned so much about my own craft being immersed in queer cinema past and present, so thank you!

Can you talk a little bit about why you decided to make a quarantine movie about quarantine, and what your creative process was like?

So this is actually the first narrative film I’ve made since coming out 3.5 years ago. From 15 to 22 I was making at least a couple shorts each year and then I came out and just stopped. All of a sudden I had more to write about than ever before, but even the simplest short required time and resources that were all going to my transition — and my rent. I also think those early years of transition are so filled with change that any project I wrote felt outdated a month later. The one I came closest to making was my short about Gordo from Lizzie McGuire coming out as trans. But when faced with the time and resources it would’ve taken to do it right, I just couldn’t commit that to a coming out story I felt I was maturing beyond.

This is all to say that at the start of this year I was committed to making something. It had been over a year since I moved to LA, over a year since my last theatre directing job, and I just missed directing. I wrote a short that could be made in my house for a few thousand dollars with a small crew and was starting to think about who I’d want to collaborate with when the pandemic happened. When it became clear this wasn’t just going to be a few weeks, I knew this other short wasn’t going to happen. But I was still committed to doing something creative within the limitations.

And it was, honestly, great! I loved having such a low-key first post-transition filmmaking experience. I loved being able to work with Kerry even though she lives in New York. I loved how things that felt like hurdles turned into opportunities.

The film is almost shockingly narratively tight! It’s a complete story arc in 15 minutes that you really don’t know which way it’s going to go until the very end! It also, in 15 minutes, is so very specifically lesbian and so very specifically trans. What experiences did you know going in you wanted to represent here? Which ones have you never seen done well?

Thank you! It’s a bizarre experience to make a movie with a budget of $20 largely shot on Zoom and to have this be the first time I’ve ever seen my story on-screen. It’s a lot of pressure! I think I’m always, always thinking about other trans people, other queer people, and with that my desire is to just represent our lived experiences with as much nuance as possible. So I have some very broad goals, but I try to not stop there and to go even deeper. There simply is not work — at least work I’ve seen — about trans lesbians in their 20s dating and being messy. That alone feels new to me in a way it frankly shouldn’t. But that novelty isn’t a novelty for me — it’s my everyday life. It’s certainly something I’m committed to representing, but to hold my own interest I need another layer and with this film it’s specifically exploring this pattern I’ve experienced where queer people who have never been with women before are drawn to me.

For better or worse, my instinct when I feel hurt or uncomfortable is to try and understand where the person causing me to feel that way is coming from. And as I was dating in the pandemic and this pattern was showing up even more frequently than before I felt this desire to understand. I know that my experience of queerness and transness is only my experience. Look, I’ve only had sex with one person who identifies as a lesbian and the sex did not involve my genitalia — and I feel complicated about that! But whatever validation I am or am not receiving has nothing to do with a cis bisexual woman whose compulsory heterosexuality caused her to come out later in life. It has nothing to do with with a trans woman bisexual who has spent her life in cis gay male spaces because that’s what people assumed her to be. I think as a community we could all extend a lot more kindness to each other and how different all of our experiences are. It’s something I’m trying to be better about. And that isn’t to say I’ve never felt fetishized or like an experiment. But I think that needs to be taken on a case by case basis rather than making the kinds of generalizations my insecurities push me to instinctually make.

I laughed out loud several times, and I especially cackled like a cartoon witch when you said, “If anything, you’re a Molly.” There’s also elements of that dark humor you tend to love from like British TV series where it starts off kind of awkward and ends in a breakdown about death. How did you approach the humor for this film?

I think the reason I respond to shows like The Bisexual and Fleabag and I May Destroy You — why are so many British? I don’t know! — isn’t because they’re dark persay, but because the humor is coming from reality. So I don’t think when writing I’m ever trying to be funny. I’m just trying to write dialogue that feels authentic and inevitably the humor follows.

I also think casting is incredibly important when it comes to humor. I wrote this part for Kerry knowing her comic timing and knowing that her humor is different than my own. That’s one reason I love her as a friend and a collaborator. I think our brains work very differently. Maybe it’s a Capricorn vs. Sag thing. I know that she’ll take a line I write and do something with it I never expected and I love that. And while only one moment was improvised — when she asks if she should put on Fiona Apple — that’s now the end of the movie! So it’s about reflecting our reality that has humor and trauma all in one and it’s about knowing who to work with.

I feel like it’s often impossible for screenwriters to capture that very distinct banter that happens around queer dating, and you nailed it. The dialogue had me, like, shipping these characters! Can you talk about capturing that experience?

I think banter is one of the most important things to me when it comes to dating. It’s like okay base level your politics don’t suck and then right after that is banter. Because banter is everything! It’s chemistry and humor and intelligence. I have things I’m theoretically looking for in people when dating, but if I have good banter with someone a lot of those things no longer matter. I’ve met a few people during the pandemic I have good banter with, but when I wrote this back in April I think I was creating a sort of wish fulfillment of oh I wish I could match with someone on Tinder who I had this kind of banter with. When I’m writing dialogue I basically just let the characters have a conversation in my head and I transcribe it. And here I was creating the kind of conversation I wish I could always have on a first date, but condensed and more dramatic.

And of course it’s sexy! I was thinking when I was watching it a second time about Christina Tesoro’s Here’s Your Roadmap to Finding Your Authentic Sexual Self that we published this week, actually: “often we’re taught to relate to ourselves as objects rather than subjects; things to be acted on rather than protagonists with agency at the center of our own narratives; performers for others’ pleasure rather than people capable of experiencing and pursuing immense pleasure of our own.” You quite literally made yourself the protagonist! Did you find that empowering? Or a vulnerable experience? Or both or neither?

The movie opens with a shot that includes adrienne marie brown’s Pleasure Activism. I read that book during the first months of the pandemic and — while I know it’s incredibly basic of me as a queer person to say this — it really ignited something in me. I really relate to the quote from Christina you just said, and in these six months of quarantine celibacy — not counting FaceTime sex — I’ve had time to really reflect on my relationship to my own pleasure. It’s weird because in the film I’m the experienced character, but the fact is I’m actually quite new. My ex and I broke up February 2019 so pre-pandemic I dated as a queer person and a woman for the first time for only a year. And it’s been challenging and really important to reflect on a lot of those experiences and realize that sometimes I said yes when I didn’t want to say yes or did things because I felt they were expected of me even though I didn’t want to do them.

I love that connection between protagonism and pleasure. Because, of course, they’re connected. I’ve joked that people in the queer community don’t know what to do with me because they’ve never seen someone like me as a romantic lead on screen. But I think it’s true! Even other trans women don’t have a road map beyond what we’ve experienced and what people we know have experienced and the fucked up representation we’ve seen on screen. I mean, last summer all these cis women started flirting with me by telling me Hunter Schafer was their celebrity crush. Hunter and I look nothing alike! But to me what that said is for the first time they were watching a television show that told them a trans girl was someone they should be into.

It’s absolutely something I’m thinking about. And not to over explain too much, but it’s what the ending is about. In the script, we cut to black and hear the vibrators click on. But when filming and in the editing I just felt like no I’m not going to let cis audience members decide my sexuality in that way. I want them to watch me masturbate even only for a few moments. I want them to see that me — just me, not all trans women, just me — that’s how I masturbate. This is my relationship to my tits, this is my relationship to my penis, this is the kind of sex toy I use most frequently. And then I look into the camera because I also want to remind any cis people watching that I’m watching them too. This time it’s my narrative, I’m in control, and they are seeing what I want them to see. You can get turned on, but for once it’s going to be on my terms.

I was thinking also, as I was watching, of your Portrait of a Lady on Fire review, and the lesbian gaze, which is happening on multiple levels here because you’re watching you watch someone on Zoom, and vice versa. Can you talk a little about that?

I love that you’re seeing what my character is seeing and what Kerry’s character is seeing and for most of the movie that’s it. This was something I thought about a lot when editing — when is it like a Zoom call where the person speaking is on-screen and when do we get to see the other person watching. It’s strange how this current moment has so explicitly emphasized how we all appear on screen. But I also think there’s a limit to the webcam image. There’s a difference between a flat Zoom image and something more dynamic. I think that’s why the beginning and ending were important to me. Those brief images are more my gaze of myself. They’re still limited by being on an iPhone and being set up without help, but I have more tools to utilize. I do find it interesting though how we attempt to frame ourselves on a Zoom or a FaceTime call — the clothes we wear, what we choose to sit in front of, the angles we decide upon.

You recently watched 200 lesbian, bi, and queer movies and ranked them and wrote about all of them. Did that experience change the way you approach your own film-making?

As I said at the beginning, the impact that writing criticism has had on my own work is enormous. We could do a whole other interview where I talked about what I learned from each film — even Girltrash: All Night Long. But to speak generally I think what I was given most was a commitment to my larger goals. When the list was first posted on Instagram a lot of people were upset with how white it was and my reaction was GOOD. Sure, this updated list was less white and less cis and less US/Eurocentric than the previous one, but it is still so limited by what exists and what’s available. I love the majority of the films on that list but most of them do not love me back. And I want all of us to keep asking for more and when we don’t get more to make it ourselves.

Is there a specific thing you hope people come away feeling after watching your film?

That! I want queer and trans people with all sorts of experiences we haven’t seen on-screen to see that I made a movie on Zoom with a $20 budget and to know that they can do that too. I have a deep love for the vast possibilities of cinema and I have so many images in my head that require resources I don’t currently have. But if I have to make a movie for no money with limited technology I’ll do it. And other people should too. And not because it can lead to something else. I feel like that happened post-Broad City. There was a wave of people making web series to get noticed. No. This is the thing. This is my movie. Obviously I want to do bigger projects someday and I hope work like this shows that people like me can be the protagonist. But I want to get over the voice in my head that says this is just a little movie I made for fun or as a step. No. This is a work of art that I made that reflects an experience I’ve never seen on-screen. Engage with it like you would any big-budget movie about cis lesbians.

We can all do that with whatever resources we have. Some of the most talented people with the stories we most need to see are also the most insecure and hesitant to create. I want those people to push through our culture that tells them they don’t know enough to make movies. It would thrill me if another trans person saw this and thought oh I could make something better than that and then went and did it.

What’s your dream project to create after quarantine?

I have so many! I have a couple pilots that I’d love to make — one that’s basically The L Word but starring a trans woman. I’m working on a trans horror feature and have a horror short that’s ready to go when I have a hospital set I can shoot on. I’m really interested in how trans women can reclaim the horror genre. I’m also writing an explicitly trans body swap movie I’m really excited about. The feature I’d most like to make is my trans coming of age movie that I wrote an essay about but that requires me to shoot in Italy and a budget that doesn’t feel within my grasp in the super near future. But that’s the one I’m always thinking about and always returning to.

And then I have like Dream Projects that feel totally disconnected from reality. I want to make a super queer anti-cop CW-style detective show based on this YA series I loved as a kid called the Sammy Keyes Mysteries. I started writing that a couple years ago and then was like I do not have the rights to this why am I spending so much time on it. But I still return to it for fun now and again. I also foolishly started writing an adaptation of Rubyfruit Jungle. My take on it is just so clear in my head I couldn’t help myself. And then, of course, adapting Andrea Lawlor’s Paul Takes the Form of a Mortal Girl. I don’t know why I said of course. Maybe because it just feels like such an of course thing in my brain. If no one beats me to it I’ll be adapting that book someday.

I have so many more — either finished scripts or vague ideas. And these are only the ones I’d personally want to write and direct. My ultimate dream project is being in a position where I could spend half my time on my own projects and half my time developing and producing projects for other queer and trans creators. There are so many of us with so many scripts and so many pitch decks just sitting on a hard drive somewhere ready to be made.

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