As a longtime fan of improv comedy, being gay, and hot redheads, it was a matter of time before I became a huge fan of Catherine McCafferty. When I need a relaxing night in, I like to kick back with a hard cider and put on either a show from Dropout or a Smosh YouTube video. I’m quite smitten in particular with Vic Michaelis and Angela Giarratana, both of whom are featured on McCafferty’s show Pretty Gay, a talk show in the vein of Amelia Dimoldenberg’s Chicken Shop Date, in that it features hot people flirting with each other.

Voyeuristic? Perhaps.

Below, find my conversation (edited and condensed for clarity and length) with Catherine about how Pretty Gay came to be, what it’s like to flirt with comedians, and how to stop apologizing so much.

Gabrielle Grace Hogan: Tell me more about your background. Where are you from, how did you get started in comedy?

Catherine McCafferty: I have always been interested in performing ever since I was very young. I would be in the school plays. My mom had a video camera, and I always wanted it to be on me. I really focused on school and being a perfect student, which was not a requirement for my family. I just decided that that was going to be my personality. I actually ended up dropping out of high school to go to college a year early. But I ended up at a school that was primarily male and sports-dominated. And it reflected back to me how important the arts were, because I felt like I was just drowning in a world that I didn’t understand. And so then, when I transferred schools, I didn’t study theater. All the theater students thought that I was a theater major, but I was a biology major — but I always knew I wanted to pursue the arts.

I just wasn’t sure what the avenue was going to be, and then I got cast right out of college in a show for Hell In A Handbag Productions, a drag theater company in Chicago. They were doing a production of The Birds, and I got cast to be Tippi Hedren, aka Melanie Daniels. So I was on stage the whole time, and I was so in love with the entire process of theater and performing and being on stage. Once I got a taste of that in the professional world, I was like, “Okay, well, it’s gonna be this forever.”

I also loved writing. So one of my friends was like, “you should try standup.” And then I went to an open mic, and I was like, “oh, okay, well, I’m mentally ill because I love this.” I’ve always been somebody who goes in 100%. And so for the past 10 years, it’s been me just throwing a lot of stuff at the wall and running at 120 miles per hour. So it’s been a roller coaster, and I feel like, you know, we’re all waiting for a break or whatever, and it doesn’t necessarily ever look like you think it’s going to when you’re a little kid. And it’s been so magical to see people respond to Pretty Gay and have that be the thing.

That sounds so exciting. A drag production of The Birds is the craziest thing to be the first break into the business. I bet that feels a bit like being spoiled. Like, “Oh, of course it’s always going to feel this cool and queer and exciting.”

Yeah, yeah! And then it wasn’t for a really long time. I moved out here to Los Angeles, I lived in a hostel, I had 100 different jobs. I had an air mattress that my roommate stepped on and broke, and so then it kept deflating during the night. There’s so many bumps along the way where you’re just like, what am I doing.

And then I was trying to model, and it’s a wonder how I’m still alive. The journey definitely wasn’t linear, but I don’t think it ever is.

In another interview you did for On the Mic, you talked about Mike Birbiglia and Tig Notaro being huge influences on your standup. You talked about how you really admired that they made their shows storytelling events — how they start with a central story, and then go off on tangents, but always come back to tie it together at the end. You mentioned that being your goal for your standup as well — could you talk more about that? Obviously Pretty Gay is not standup, but that is your other passion. Can you talk about why standup, and this particular type of standup, is so appealing for you as a performer?

Well, I love standup, and it does actually really relate to Pretty Gay, because it’s about taking back performing for the performer, you know? I feel like there’s so many gatekeepers in trying to be a performer. You feel like you’re asking permission all the time, like, “oh, I want to audition. Can I please do this?” I really felt like standup gave me more autonomy in my art. You just can go, you can do an open mic, you can start a show, which is what I did when I moved out here. You can just start a standup show, and then you can meet other people who are grinding in a similar way that you are, which I don’t think you do in acting as much. There’s less of a community in acting, unless you’re in a class or something like that.

The same with Pretty Gay, we were looking at, like, “Okay, well, Catherine is a performer, and she’s trying to get recognition for all these different things that she does. How can we do that?” And my friends Sam Reich and Elaine Carroll are big Internet people, and they believe the Internet puts the power back into the creator’s hands. So they really wanted to help me do that.

And then the Mike Birbiglia of it all is that I grew up listening to NPR. So Mike and Tig Notaro were on NPR a lot. And I was like, “wow, the way that these people do comedy and tell stories is just so fascinating.”

I’m glad that you mentioned Sam and Elaine, because I found Pretty Gay through being a huge Dropout fan, and being a huge Smosh fan. I think the way I found you specifically was your episode with Vic Michaelis, because I’m obsessed with Vic (because every gay person on the internet is obsessed with Vic). And I was like, “Oh, what’s this? What’s going on?” And I fell hard for all of it. I know you’re friends with Sam and Elaine, and they’re also the producers of your show. Knowing that, how did Pretty Gay happen? How did that project develop initially?

So I had moved back to Los Angeles on a trial run, to see if I wanted to fully move back from NYC, and I had known Sam and Elaine for five years by that point. They’re two of my dearest friends. And Sam is a big fan of the internet. He’s really interested in how it gives the power back to the creatives. And he helped Elaine build her social presence through doing sketches and characters. And he was like, “we want to help you build your social presence in a similar way.” So we had quite a few brainstorms to be like, “okay, so what does Catherine do?”

I don’t do a lot of characters. I don’t come from the sketch comedy world. I can certainly write a sketch, and I find them to be very fun. It’s just not what I’ve been working towards for years and years and years. So it was tough for me, because I was like, “Well, I felt like I knew how to be like, pretty on the internet, and I knew how to be funny in person.” And I was single, and it had been the first time that I was dating around again, and we were just throwing out all these different ideas. And we were like, well, what if it was kind of like a dating show, like a dating podcast?

Sam, coming from the Dropout universe, was like, “you know, I really like the model of an interview-based segment show. It’s what works for Dropout, and I think it would work for you if you want to just do an experiment, we could build a set.” And I was like, “Okay, sure. Like, let’s build it. Let’s have it be like a gay bar.” There’s not a lot of lesbian bars, but I really like the aesthetic of Honey’s at Star Love — they have a lot of teal and tile, and it just felt cool when I moved back here and went dancing there.

The first season had six episodes. We had no idea what we were doing. Chloe Badner, they’re a fantastic set designer, and they built the set on the bottom floor of Sam and Elaine’s house. So we weren’t even in a studio.

Oh, wow. I didn’t even know that. 

Season one, we had something like 150 subscribers on Patreon. We had to take a long pause between season one and season two. I had no idea if Sam and Elaine wanted to partner with me again on season two. We threw out all these different ideas with in order to make it less costly. We considered just having me shoot it on a GoPro, in a car. And then they had a little meeting without me, and they were like, “You know what? We want to invest even more money towards this and scale up and see if that is gonna bring subscribers, and see if that is gonna be what catches people’s eye.” Like, let’s make it even prettier and shinier. And then we moved into a studio. Sam and Elaine were able to talk to some Dropout people to have them as guests on it, and that’s really what made it take off.

What did that look like on your end of seeing the show progress in popularity and see more people interested in it?

I mean, it was so exciting! Because whenever you create anything, you’re like, “Well, I guess we’ll see if people like this,” and you’re sort of just throwing darts in the dark. I was so thrilled that people responded so positively and, and I think it’s the chemistry that I have with the guests. But then also these were seasoned comedians from different universes, people who had been Internet people so they knew how to be funny in this sort of format. And I really think that helped me grow as a host. Seeing more and more people subscribe has been just like such a dream. I text my mom about it.

With Vic’s episode, we saw a huge bump. They were the first episode of season two. And then we were like, “Oh, let’s see what happens,” and we started growing 100 subscribers a week or something like that, and that felt crazy. And then with the Angela Giarratana episode from Smosh, we got a big bump from that as well.

It’s really just been quite dreamy and terrifying at the same time being like, “Oh no. When is it all just gonna go away?”

So this is your first, or if not first, most significant foray into using the Internet for your comedy. How has that transition felt for you?

I’m just very lucky that I have the executive producers that I have, because they really held my hand through, especially the first half of season two in terms of choosing clips and things like that. And just telling me to just really pummel the Internet and post every day. And that felt crazy, because I’m literally from the Midwest, and I apologize for existing. I’m bumping into chairs and apologizing, and now I’m supposed to be so incredibly seen, and ask people to give me money? Yeah, it just felt nuts. But then it’s like, well, this is a product. I am selling a product, and I just blindly followed what I was told to do. And once it started to work, and nobody was yelling at me, I was like, oh, this doesn’t matter. It’s fine, as long as you don’t tie your self worth to the Internet, you’re gonna be okay.

I admire you and teach me, because I’m also from the Midwest and I love to apologize. It’s almost like my favorite hobby at this point.

I know, it’s so fun to apologize, but it’s like a tic, and then you realize that you’re making the other person do more work to make you feel better if you’re constantly apologizing. And if the point of apologizing is because you feel like you don’t want other people to be bothered, if you somehow switch it in your brain and you’re like, “actually, I’m bothering them more,” you stop apologizing.

Use your own anxiety to combat your own anxiety, whatever works honestly. All right. Well, enough of our therapy session. You talked a little bit about how Pretty Gay got started, and it reminds me a lot of Ziwe or Chicken Shop Date, where viewers really enjoy watching people goof off and flirt with each other. And we can get into the psychology of that another time, maybe. But I was curious: Pretty Gay has a, well, pretty gay spin on that particular interview format. Other than the Grant O’Brien episode, I’m pretty sure you exclusively interview other queer women or queer non-men. Obviously part of that queer twist is because you yourself are queer, so it’s just sort of a given. But I was curious, too, if you felt that focusing so explicitly on this queer experience felt like a niche you were trying to fill?

It was really important to me that it was primarily going to be queer women and non-binary people. I really wanted to be able to see a lot of people being funny and laughing. It was really important to me to see queer people laugh on the Internet. It’s so important to keep up on all the different things that are happening in the world, the different legislations, and the ways in which the world needs to be better for us. But I also think it’s really nice to just see queer people just joke around. Do you know what I mean? Like “Yeah, I’m here. I’m making content. I’m sitting across from somebody who is, like, gorgeous, who’s also thriving.” That’s cool to see.

It was also really important in my personal journey of dating and being able to accept my queerness. I’m very femme-presenting. When I first came out, I felt I had to dim that, be less somehow, because I’m a woman who’s queer. Obviously you see gay men wearing sparkles and shouting from their rooftops, but I wasn’t seeing that as much for women. Obviously the media favors gay white men, but I wanted to be something else. I wanted to bring a seat to the table for everyone who looked like me, or looked different than me, but was definitely in this space of queer women, queer non-men. Decentering men in the show was very important.

Every single day, I wake up I say, ‘oh my goodness, I’m so happy I’m gay.’

Did you feel it was important, as a queer comedian, as a queer woman, to make sure that it was giving that voice to other queer comedians and queer women? Like you said, when the mainstream media thinks gay, they’re like, “We want like a white gay man, a white cis gay man. We don’t really want the lesbians. We don’t want the bisexuals. We don’t want the butch women.” Have you seen that in the response from people, of being really excited about a show like this?

Yeah, I think so. People have commented and they’ve been like, “we want to see a trans femme woman as a guest.” We were like, “Yeah, we’re listening.” We have Persephone this season. We’re trying to have a wide representation, specifically, on our show, because that’s all I can control. I can’t control what shows get picked up on TV, but being in the queer space and listening to my friends talk, so many of my friends are masc-presenting, and they’re not seeing themselves on TV, or the way in which they’re presented is so stereotypical. So when we look at our guests for the seasons, we’re obviously looking at our friends who are funny and talented and all of that. But we’re also looking at the people who are masc-presenting, who are trans, who might not have a show on TV, and so, like, “Come do my show!” Geez Louise, I like these people, these guests that I have. They’re so talented. The world at large doesn’t see as much representation, as many people like that. And so it matters if you have any kind of platform to use it. And it really matters to platform people who you’re not seeing in your community. Platforming others is my job, and I take my job pretty seriously.

The show is not just queer and flirtatious, it’s pretty explicit in some parts. I’m thinking of the segment “Wink for Kink” in particular. There are definitely some segments that are coy and subtle, but there’s a lot that are just straight up, “let’s talk about strap-ons.” Do you feel that the show is trying to make a statement with that?

I think it’s a little bit of that. But when we were crafting the different segments, we were just thinking of what sounds fun, and that felt fun, and it became more explicit, as we found our guests’ willingness to talk about these things. It was really exciting for me, because I came out later in life, and the minute I came out, I got into my first queer relationship. We got engaged, and then I was in that monogamous relationship for five years. So when I got into that relationship initially, I felt very much like, “Well, who do I turn to? Who do I ask? Am I doing this right?” I was so nervous, and then even more so after getting out of that relationship and then dating and discovering my sexuality even more.

When you’re brought up and you’re cultured female, you get a lot of shame around sex. You’re not supposed to talk about it, but you’re supposed to be good at it, and you’re not supposed to want it, but somehow you’re supposed to pleasure other people without thinking of your own pleasure. But that’s not how it is in the queer community. It very much is more open. So being able to talk and get other people’s experiences who might have dated more than I have, or who are bolder than me, I get to feel some of their confidence.

How was the process for creating the segments? What are the ones that you enjoy doing the most?

The segments came from a combination of improv games. A lot of them are queer-specific, to somebody who’s not dating in the straight realm. I have great writers like Kaylin Mahoney, Elaine Carroll, and Margaret Kaminsky. They all are just very funny, talented writers who come from different worlds. So Elaine’s bringing her improv experience, and then Margaret came out later in life, and she was dating and struggling with certain things. So then she’s able to provide those questions. And Kaylin comes from the standup world, and she’s writing fun little one-liners that I can throw out during those segments. So it’s definitely a group effort.

I love “Friend or Flirt.” That’s one of my favorite segments. That’s a great one. The kissing segment, “First Kiss,” I really love, and I also love “Break Up With Me,” because I think that a lot of people are really bad at breaking up. That’s always fun, because I also get to see my guests sort of squirm because I try to make it really hard for them.

What does the production of an episode look like? What does it look like taking one from start to finish?

Each season, we’ve scaled up more. So I’m so excited for season three, because we had more hands on deck. We do a ton of prep work. We do all the writing, and then we research all the guests, and we make lists of things that might be fun for the guest. If we’re getting the energy that this is going to be more of a talking episode, we might do less games. We shoot for an hour and a half with each guest, and that includes stopping and me checking in. I shoot with four different guests in a day.

That’s a lot of flirting to get through in one day.

I know, what a lucky lady I am!

I’m bad at flirting, too. I would be terrified to go on my show. Does that make sense? My friends have seen me flirt, and they’ve been like, “This is why you had to create a show for this. People are making concessions for your personality because you’re pretty, damn.”

That’s surprising to hear, you seem extremely confident and flirtatious, but maybe that’s the confidence of being the host, and being in charge.

I think part of it is that and also knowing what’s coming. What’s so tough about flirting is not always knowing what the game is, but as the host, I always know what the game is. But when you’re out in the real world, somebody could buy you a drink and then stand near their friends, and you’re like, “Okay, well, okay, so am I supposed to then go up to them and then what do I say?”

I think this is a cool format to have for the show too, because of the stereotype that lesbians and queer women don’t know how to flirt.

Every single day, I wake up I say, “oh my goodness, I’m so happy I’m gay,” but I was existing in the world for so long as an object of the male gaze. It was extremely uncomfortable all the time to be out and to have somebody enter your consciousness without permission and tell you to smile or whatever. All of it feels gross. And so I think then when lesbians and queer women come out, we’re sensitive to that experience — whether or not you’ve had it, you’ve heard of it, you’ve heard your friends have it. And so it’s like, I don’t want to bother this woman. She’s perfect.

I’m already in love with her so I’ll leave her alone.

Exactly. I think it’s just harder to navigate. You know, it’s not impossible, it’s just harder.

Which guests are you most excited to have on season three?

This next season, we have Cameron Esposito on and, I mean, I watched their comedy, and I was so enamored. A big part of me coming out was listening to the podcast that they used to do, and then watching their first special was very important to my healing journey. So then being able to have them come on to my show and pick me up. I mean, literally, she picks me up. She picked me up.

We had Liv Hewson on, and they’re a literal star. They’re so nice, they’re so funny, and they were so responsive even afterwards. Being reminded that I’m a part of this absolutely fantastic community of queer people, it’s been so wonderful, especially with where we are right now in the world. It’s been nice to be able to be like, “Oh, we’re still holding each other, at any level.”

Who would be a dream guest to have on the show? You can name multiple people if you have more than one answer.

Oh my gosh. Of course I have more than one answer! Wow, this is tough because I do want to name people that I just want to date.

So Doechii — she commented on one of the videos I did with Jiavani, and I immediately burst into tears. I mean, this was before she won a Grammy.

I’m really trying to get Margaret Cho, because I’ve always loved her comedy, but I also think she’s been a fantastic queer person to follow — the way she talks about her sexuality has made me more comfortable in talking about the nuances in my sexuality. I really want to get Holland Taylor and Sophia Bush in there as well.

That’s all for the questions I had to ask, but do you have any parting words?

Oh no, I’m just so thrilled. I really love Autostraddle as well. So you reaching out— I can’t express my gratitude enough. I love them. This show, it’s my literal dream. And I know that I wouldn’t have it without people like you, people who reach out.. I just want to give a shout out to the fans and the people who are watching, because people don’t know how much it means. I think they’re surprised even in real life, that it can turn around my entire day.

Season three of Pretty Gay premieres May 7 on Patreon. Some notable guests will include: Cameron Esposito, Liv Hewson, Shannon Beveridge, Angela Giarratana, Persephone Valentine, and more!

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!