“Wait, Is This a Date?” Podcast Episode 104: Sexting or Something Like It

What comes after DM slides? Sexting! Or if you’re me there are like six more steps. Nevertheless our main topic this week is sexting and we’re joined by one of my very favorite writers: Kayla Kumari Upadhyaya.

We start with a game of Sapho or Drew’s 2014 Journal before getting into all the ins and outs of sextual relationships. We’re talking tenses, we’re talking instigation, we’re talking pictures — including the vast possibilities of the Live Photo. This week our direct communication is even hotter than usual!


+ Unfortunately, you have to be Kayla’s girlfriend to see her writing skills via sext, but anyone can read her writing skills in fiction. Here’s one of my favorite stories by her: Field Games.

+ We’ve been asking for a lesbian Grindr as evidenced by this article from B Nichols circa 2011.

+ And by this podcast episode with Shelli from this year.

+ Apparently Scissr made the Guardian before its ill-fated launch.

+ I’ve actually interviewed Mae Martin twice. After season one and after season two.

+ Okay now I’m confused how The Huntsman: Winter’s War isn’t gay?? I mean, look at this photo:

Still from The Huntsman. Charlize Theron as the evil queen strokes Emily Blunt's chin.

Drew: Are you doing role plays out of a scenario of, “You’re touching me right now” or, “I wish you were touching me?” What tense are we in?

Kayla: Yeah, I was going to ask the same question actually, because that’s something that’s always interesting to me, especially just because we are all writers also.

Christina: I was going to say a group of writers. What tense are we working in, how are we feeling? Is this a close third? What’s happening here?

Drew: Hi, I’m Drew!

Christina: I’m Christina!

Drew: And welcome to Wait, Is This A Date?

Christina: Wait, Is This A Date is an Autostraddle podcast dedicated to the wild and crazy world of dating.

Drew: Queer dating.

Christina: You said something wild. I was going to introduce myself again but I’m glad you said queer dating, I think that actually is a better transition.

Drew: But please queer, introduce yourself.

Christina: As Drew mentioned, my name is Queer, I go by Christina, occasionally. I’m a writer at Autostraddle, a queer on the internet who is often deranged and today I have been eating a bag of M&Ms, just a Ziploc bag of M&Ms all day. I do feel lightly nauseous, but that’s the gamble I’ve decided to take.

Drew: I think it sounds worth it?

Christina: Yeah, I’m feeling good about it. There’s just M&Ms in here and Whiteclaw.

Drew: Cool.

Christina: Let’s journey on. Who are you?

Drew: Winning combination. I’m Drew Gregory, I am also a writer at Autostraddle where I do a lot of film coverage and also talk about dating, queer dating. I’m also a filmmaker and a trans lesbian.

Christina: Hot. Sick and hot.

Drew: Yeah. I also spent the weekend with my family for the first time since the pandemic. So, that’s where I’m entering this podcast episode from that headspace and good times.

Christina: Yes. That’s a really interesting energy to bring in, I’m glad that you have it. We have a game, as per usual, to play.

Drew: Yes. Yes, we do.

Christina: And then we’re going to have our main conversation with our special secret guest, who you don’t get to know who it is yet, listeners.

Drew: Yeah. And our topic this week is sexting.

Christina: Blah! That’s how I feel about sexting, we’ll get into it.

Drew: Right.

Christina: Let’s start. Let’s start this game!

Drew: Cool, you seem super comfortable. Okay. So, the last time that I came up with a game, it was to roast you, Christina.

Christina: Yes, that’s me.

Drew: So, I thought that this week I would bring in a game to roast myself.

Christina: Oh, interesting.

Drew: Yeah. So, the name of this game is the very creatively titled “Sappho or Drew’s 2014 Journal?” So, I’m going to be saying some quotes and you’re going to tell me if you think that the quote is by Sappho or by me in 2014. I can give some context if you want, or we can just jump right in.

Christina: Nope, I get it. Let’s roll.

Drew: Great. Okay. So, first quote is: “The fear of death is simply the fear of time.”

Christina: Fuck. This is going to be harder than I thought. I’m going to say, I’m going to say that’s you.

Drew: It is me. Good job. Okay. The next one: “Once again, love drives me on.”

Christina: Are any of these going to be both? That feels like it could be both.

Drew: No. That would be great but no, none of them are both.

Christina: Okay. So, then again, I simply must say that that is Drew.

Drew: No, that’s Sappho.

Christina: Damn, that’s Drew energy.

Drew: Yeah. There’s a lot of these that are, they are pretty much all Drew energy, and apparently all Sappho energy.

Christina: No. Yeah. I get the game, turns out.
Drew: Yes.

Christina: Okay.

Drew: Okay. “I don’t know what to do, my mind is divided.”

Christina: Sappho.

Drew: Yes.

Christina: Yes. I’m fist pumping.

Drew: Yeah, fist pump away.

Christina: Thank you.

Drew: “Her hair is as gold as the mirror she holds and it flows all the way down her back.”

Christina: Sappho.

Drew: No, that’s me.

Christina: Drew! Wow, all right.

Drew: “I’m not supposed to talk but I nod and respond to her touch.”

Christina: Drew.

Drew: Yes.

Christina: Yeah.

Drew: “I must suffer.”

Christina: Again, Sappho but I want it to be both.

Drew: It is Sappho.

Christina: Yeah.

Drew: “Life will only be so patient.”

Christina: Drew?

Drew: Uh-huh (affirmative), you’re doing really well at this. I want you to know that I tried this out on a few friends and they failed, like statistically did worse than they should have, so you’re killing it so far. Okay. “She slid her hands down my back and through my hair and I began doing the same to her, soon we were kissing.”

Christina: Sappho?

Drew: No, that’s me.

Christina: Hair is a motif for you, clocking that.

Drew: Oh, yeah. Look at that. “I have not had one word from her. Frankly, I wish I were dead.”

Christina: Drew?

Drew: No, that’s Sappho.

Christina: Deleting my account. Sappho.

Drew: Yeah. “You came and I was longing for you.”

Christina: Ooh, Sappho.

Drew: Yeah. “I want to say something but shame prevents me.”

Christina: Drew.

Drew: No, that’s Sappho.

Christina: But points were made, I think by me.

Drew: Yeah.

Christina: Yeah.

Drew: Absolutely.

Christina: For sure.

Drew: I think that’s probably the most me of them, which is great because gay shame has just been going on for millennia.

Christina: Yeah. Untold millennia, it’s part of our community and culture. Hot.

Drew: “There is the painter and there is the woman examining herself, exterior, interior, who is she?”

Christina: That’s Drew.

Drew: It is.

Christina: Yeah. Is that 14-year-old Drew?

Drew: No, no, no. 2014 me. So, this is yeah. So, this is all from my journal. So, that was actually me journaling in a museum and I was just very struck by painting, because who doesn’t journle in museums?

Christina: Are you gay?

Drew: I might be gay.

Christina: You might be gay. If your children are journaling in museums they might be gay, just a note.

Drew: Everyone should know that I was not out of the closet at the time so, it was fully just, thought I was a straight guy.

Christina: Vibing.

Drew: Yes. Vibing indeed. Okay, a few more. “You will have memories because of what we did back then when we were new at this.”

Christina: Sappho.

Drew: Yes.

Christina: Yes. I’m so good.

Drew: You’re doing quite well. Okay. “We simply drift together and drift apart the remnants of the greatest passions lingering as the next great passion presents itself.”

Christina: Drew.

Drew: Yeah. I wasn’t keeping score but you’ve gotten most of these.

Christina: Yeah, I’m also now regretting not keeping score. I would have hated if we were keeping score and I was doing poorly, but now that I’m doing well, I’m like, what—

Drew: I’m going to say you’ve gotten nine right.

Christina: Okay. That sounds like a great number.

Drew: Yeah. Okay. This is the last one.

Christina: Okay.

Drew: It’s a really tricky one though. Okay?

Christina: I’ve got to get 10.

Drew: Yeah. Okay. Ready? “I woke up this morning with a big zit starting to form under the skin between my eyebrows a day before my date, of course.”

Christina: I’m going to say that’s Drew.

Drew: It is. Big surprise, big surprise.

Christina: Big surprise, big surprise. Sappho was not letting us into the zits of her life, unfortunately.

Drew: Well, thank you so much for playing.

Christina: Wow. That was so fun.

Drew: I hope you learned a lot about me, or learned nothing about me.

Christina: I think I learned, I personally learned that my knowledge of you is correct and that we are friends. And I think that’s a great thing for me to learn.

Drew: Yeah. I was going through a breakup during this time, it was rough.

Christina: Yeah, didn’t seem not rough, I’ll say that, didn’t seem gentle, perhaps we could say?

Drew: I survived, and so did Sappho, well eventually she died but, you know

Christina: Sure, sure, sure. Are you ready to talk about our main topic? Do you think we’re mentally there?

Drew: Oh, my God, I’m so ready.

Christina: I’m ready, again, to do a lot of learning, this is going to be a listen and learn space for me and I’m really glad that we have such a guest who is so brilliant and thoughtful and, I think, an expert in the realm of sexting.

Drew: Oh, I agree. Kayla, do you want to introduce yourself?

Kayla: Yes. I’m Kayla Kumari Upadhyaya, I am also a writer at Autostraddle and elsewhere on the internet, yeah.

Christina: Sexting expert, sextpert.

Kayla: And sexting expert. Yes.

Christina: Yes. I will be putting that in all of your materials going forward.

Kayla: It’s a very important part of my CV.

Christina: Yes. Yes. We love to respect a CV here.

Drew: I want the people at home, or wherever you’re listening to this, to know that, I don’t know, a month ago I texted Kayla to ask for advice on what it’s like to meet someone when you’ve been having an internet courtship, whatever, and Kayla, I was wanting all of this emotional assistance, et cetera, et cetera. And Kayla was like, Oh, we just sexted. I was like, got it, got it, got it. Okay, cool. Cool, cool.

Kayla: Yeah, it wasn’t that deep, I guess in the beginning.

Christina: I think that’s really a beautiful, just a nice way of framing things. Things we can always bring a Drew/perhaps Sappho perspective to things. It can always be quite deep, but sometimes it can start out not that deep and get deep, that’s really beautiful. I want everybody out there to remember that beautiful thing.

Drew: Yeah. So, what’s your relationship to sexting? Have you always liked it? Is it always been something that’s, has it developed over time your comfortability with it?

Kayla: Yeah. I mean, I think I did always like it, I wasn’t sexting up a storm in my, I don’t know, like in college or anything, I mean, to be fair, I was deeply closeted. And so, my dating and sexual history was all kind of a mess for a while but once I did come out, I would say yes, that sexting was something I was into pretty much right away and part of it, I think is just being a former Tumblr kid a little bit. I was just used to connecting with people in that way, online, over text or whatever. I’d done that for so long, that it just felt very natural to me, especially since I hadn’t had a lot of sex and stuff. So, it almost felt easier at first and then I just realized that I liked it, and it continued, and yeah. But then there was a long period of time where I didn’t really think about sexting that much, it was during my last relationship and then when that relationship ended in a pretty dramatic way, all of a sudden there was this period of time where I was sexting all the time, whoever, whenever, wherever.

Christina: Just “You up?” constantly.

Kayla: Exactly. It was a steady stream. Yeah. That’s my journey with sexting, I guess. It’s not a lot, a lot, not a lot again.

Christina: Peaks and valleys.

Kayla: Exactly.

Drew: When you are sexting, do you primarily, does that mean sending photos to you or does it mean dirty talk text texting sexting?

Kayla: Yeah…

Christina: That was a question I actually have for both of you, because I have trouble delineating on that front.

Kayla: Yeah, I think that, that’s something that varies person to person because for me I usually, it’s a multimedia experience. You have the texts, you have the photos, you have I guess that’s it, I know some people do audio message type stuff, I’m less into that, I think.

Christina: You’re not sending a VR lens or anything, there’s no Oculus happening?

Kayla: I want a 4D experience.

Christina: Yeah.

Kayla: No. It’s pretty much just texts and photos but I’m not necessarily expecting that in return, I guess, is what I would say is that, I like to use photos but I’m not like, “I need photos!’

Christina: Yeah, “Pics or it didn’t happen!”

Kayla: Exactly. I don’t know about you, Drew.

Drew: Yeah. I mean, I feel like I’ll do both but usually at different times. I feel like when I’m sending photos, I’m photo ready and that doesn’t just mean, I don’t know, the proper things are trimmed and shaved and et cetera, et cetera, but also just spiritually, I think it is a different energy that I need in order to text sext versus send pictures sext, and I don’t know. I also feel like a lot of times when it comes to sending pictures, I think I tend to do more of, this is for — not for everybody, but for like 20 people on my close friends or whatever, as opposed to sending it specifically to someone. That’s more for, if I’m in a relationship, I’ll send sexy photos but I don’t often send photos to someone who I’m newly dating or interested in, but I will more text. I also think I’m better at, I don’t know, just like I’m a writer better than I’m a photographer?

Christina: For sure, yeah. That’s true.

Drew: And so, I feel like I could confidently say that I’m pretty good at the texting side of sexting.

Christina: Yeah, I would believe that of you. That seems like something, a skill set you would have.

Drew: Yeah. But I pretty much only do that if I’ve had sex with someone before. I don’t—

Kayla: Really?

Drew: Yeah…

Christina: Okay. So, interesting, interesting.

Drew: Well, there’s two. Either, I will do it with someone who I’ve had sex with before or who I don’t think that I will ever have sex with.

Christina: Oh, okay. Sure. Okay.

Drew: For example, I have sexted with people who are, I don’t know, who slid into my DMS and live in, I don’t know, there was someone who lived in Paris who was talking to me during the pandemic and I was like, “It’s a pandemic. You live on a different continent, this is so not real—

Kayla: The stakes are low.

Drew: Yeah, like whatever. And if someday we met, great, but it didn’t feel — I wasn’t dating this person, but I have cut off when things started to move in that direction with the person who I’m virtually dating in Canada where it actually feels like, “Oh, someday I will have sex with this person, probably.” And so much of sexting to me in text is based on what I know the person is into, and what we’ve done together or what I think that they would want me to do, and I just feel like if I haven’t actually had sex with the person—

Christina: You need that baseline experience.

Drew: I think so.

Christina: And then you want to translate that into the texting space.

Drew: Yeah, I think so.

Christina: Interesting.

Kayla: Yeah, I mean, I’m the complete opposite. I’m trying to think of an instance where I didn’t do the exact inverse of that. I have almost always, if I was regularly sexting with someone, it was sexting happened for a while before we actually had sex, and I actually almost use it as an opportunity and figure out what they’re into.

Christina: Right, you’re bringing your study knowledge into the physical space at some point.

Kayla: Yes.

Christina: You’re bringing, I’ve done this reading, let me bring you the course book I’ve done.

Kayla: Exactly. It’s like research, it’s a little exploratory, which can be difficult at first, I think, because it’s, anytime that you’re having sex with somebody for the first time too, you are feeling out like, okay. In a perfect world of course we’d be able to have these clear cut conversations, “This is what I’m into,” but I think we all know that, that’s not really how it works a lot of the time, and so, it’s just like yeah, “doing research” a little bit, exploratory moment.

Christina: Putting together an exploratory committee.

Kayla: Yes. I have my binder and my notes… So, that’s what sexting has felt like for me. And I think for me too, especially when I was coming out and first starting to sext and stuff, it was a way for me to explore and research myself. It felt like a lower pressure, less vulnerable setting for maybe saying, “This is something I’m specifically into,” or research on myself.

Christina: I think that makes sense. Yeah, I don’t do a ton of sexting to the surprise of — checks notes — literally no one. But when I did, when I was youthful and had more vim/vigor, it was easier to do before a meetup scenario or in, we’re sliding into DMs, we’ve slid into texts scenario, even though it was less sliding into DMs, because again, I was youthful and I was on social media less. But it always felt like, “Okay, yeah, this is the first step and then we can move into the pressure of being in real life sex.” But this moment is a “we’re exploring, we’re figuring stuff out, we’re typing.”

Drew: That makes so much sense to me and yet in practice, I just am like, what do you, I guess you’d say something and if the person’s not into it, then I just, I think it’s connected to something that I need to let go of in sex in general which is, I want to be doing a good job. And I want to be, “Well, what if I say something and they’re not into that? In real life, I can pick up on body language or ask. But I feel like with sexting, it feels, yeah, it’s exploratory in a way that maybe this should be a challenge for myself, maybe I should try sext without — oof, yeah. Because it makes total sense of, what a great way to figure out what you’re into before the stakes are as high as you actually being there naked with another person or not naked, if what you’re into is not being naked.

Christina: Yeah. I mean, I do hear what you’re saying.

Kayla: I mean, I will say, it does run a risk some of the times because I have had experiences where it’s like the dynamic over sexting was not the dynamic in person. And I naturally would feel disappointed, or at least taken off guard, which isn’t fair because I do think that’s what makes sexting weird is, in some ways it can feel like the most authentic expression of desire in what you want because it is so low stakes, you’re not facing this person, you can just say whatever, but then that also introduces a fantasy element to it. So, sometimes I feel like people might present themselves in a certain way. I will say this has only ever been people asserting that they are tops and then they are not tops. I’ve never seen it in the other direction.

Drew: Yeah.

Christina: Yeah, no, yeah. I hear that.

Kayla: Yeah.

Drew: You see, that’s really interesting to me because I feel like I’m more dominant in person. I mean, I’m not sexting as a bottom, because I’m not — I’m not sexting before having sex but I feel like I feel in sexting a little bit timid about saying certain things or I don’t know, maybe something about it, like being written out, and maybe I should try voice memos, but it being written out and I’m putting it out into the world, it gives me—

Christina: Does it feel like it’s on the record for you?

Drew: Maybe.

Christina: You’re like, should this be on the record?

Drew: Maybe, yeah.

Christina: Like “I’ve said this, there’s no taking it back”?

Drew: But that’s also my own — again, not to make this about my own problems that I need to work through, but I mean, what is this podcast?

Christina: No. I think that’s why we decided to do this podcast.

Drew: Yeah. But, I think in person, I just again, I can pick up on whether someone’s into something and can work up to something. I mean, I guess you can work up to something message back and forth, I don’t know. I just think that in the heat of the moment, when — because when I’m sexting, I’m often not turned on. Often the other person is turned on and I’m like “Oh, cool. I’m going to get this person off,” which again is connected to the thing I was just saying before—

Christina: The performance thing and the doing well.

Drew: Yeah.

Christina: Yeah. So, you’re bringing a real “come into work” energy with this. You’re signing into the office, you’re punching that time card.

Drew: Not only is my sun in Capricorn but also my Mars is in Capricorn. So, but yeah, I just, maybe that’s something I should work on.

Christina: Could be good.

Drew: Also a lot of times when I’ve sexted, the people aren’t — a lot of people aren’t good at it.

Kayla: Well, that is true too.

Christina: Right. Well, I think that’s the elephant here in the room. I mean, people aren’t good at texting a lot of the time generally, finding your text rhythm with a person is always like “Oh, my God, we have it” or we simply don’t and that’s always a bummer, but sometimes you can have that text rhythm and then the sexting rhythm, you’re like, “Oh, no, where did it go? What happened?”

Drew: Yeah.

Christina: That’s not nice. And that’s a challenge that I usually would get. That for me is like, okay, I’m giving up. I’ve never been invested enough at that point to be, “Okay, I’m going to work on this, and figure out how we can sext better.” I’m like, “Oh, no. Well, there’s a butterfly or something I have to chase, I’m busy now.”

Drew: No, it’s just like anything inside, sometimes where you’re like, if you’re not good at this thing, we can do another thing. And some people are better at sending pictures than they are at the texting and knowing that and being cool.

Christina: Opening that mixed media approach, we love to see it.

Drew: Yeah. I’ve definitely had that where I would get someone off and then they would take a picture of themselves and be like, “I just came” and I’m like, cool. We both — and then maybe I could also come at some point because of that picture, as opposed to the back and forth. I’m also curious though, when you’re sexting via text, are you doing role-plays of a scenario of like, “You’re touching me right now” or “I wish you were touching me?” What tense are we in?

Kayla: Yeah, I was going to ask the same question, actually, because that’s something that’s always interesting to me, especially just because we are all writers also.

Christina: I was going to say, a group of writers, what tense are we working in, how are we feeling?

Kayla: What point of view?

Christina: Is this a close third, what’s happening here?

Kayla: Strictly second?

Christina: Challenge. Sext in strictly second person.

Kayla: I usually have done a mix, actually. It depends. And sometimes it’s meeting the other person and what they are doing but I would say more often than not, it was like, honestly I don’t sext as much as I used to, it’s, people stop sexting once they move in together, turns out, and pandemic.

Christina: I’m taking notes.

Kayla: Or the only people we talk to. So, but if I remember correctly I would go off of cues, because I feel like, yeah, I would definitely do both. And I don’t know if that was just like yeah, me responding to what they’re saying or just choosing something and going with it. But I know that I’ve done both and I’m comfortable with both. I feel like more often than not, it was the more prose style, this is what’s happening, let me set the scene.

Christina: Like a narrative candle, in some ways.

Kayla: Yeah, exactly. That has more of a contained fantasy. I think for me, at least it was easier to get off in a context like that versus, “Here’s what I wish you were doing to me right now,” or whatever.

Christina: Yeah. I’m trying to think because of history and time, I think also my gut says, because I probably am not ever going to be a person who initiates sexting, I was like, “Okay, whatever tenses, whatever vibe you’re bringing on, I’ll just match that energy. I’m just going to, that’s fine, I can do that.” I don’t know that I’ve ever really driven the conversation/tense discussion in that manner. Yeah. I don’t know. What about you, Drew?

Drew: I think I definitely skew towards, yeah, prose style, like this is a little fanfic starring the two of us.

Christina: Yeah.

Kayla: Yeah.

Christina: Quick one shot.

Drew: There’s just so many possibilities and that is a fun way I think, to explore certain things. Again, I’ve enjoyed using sexting as an exploratory tool with people who I’ve been having sex with, who have already, so, it’s interesting the idea of, yeah, you could do that beforehand. But because it’s not Oh, I would only sext by describing things that have already happened, I would delve out of that. So, yeah. But definitely keeping it in a narrative, I think was always something that, but I also with porn, I like narrative, I like a story, even if it’s a bad story, I like to have some sort of narrative.

Kayla: Same.

Christina: Genuinely, one of my favorite voice memos I ever got from Drew was like, “I just watched a porn and it was fine, but also it was a really lovely end to the narrative.”

Drew: Oh, because what I was happy about is that, usually the way porn works—

Christina: I’m listening.

Drew: Is that there might be a narrative but then once they have sex, they have sex, sometimes they even drop the dynamic while they’re having sex, that always really annoys me where I’m like, “Wait, it’s that person’s first time with a woman and she’s like, well, how is she? Keep the story going, come on.” But in this, it had a little epilogue at the end where there was more story, just a two minute little epilogue, I really appreciated it. And I did, I think I recorded it and sent it to Christina.

Christina: It was a very charming, listen to this little button. How cute is that? I woke up, like me at 7:00 AM, like, okay, vibes. But I do understand that because I am the same way, not necessarily in porn, but I’ve never been a person who understands how do you masturbate and have just a fantasy? Because how did you get to that place even in a fantasy, I’m like, well, how did I get here? What do I have with me? What am I doing later? What was I doing before this? Where am I going? What am I like, all of those details, I need to have nailed down or else I’m just too distracted. So, I think in the sexting form, having a space to be like this is this, here’s the scene, I’m setting it.

Kayla: Here’s the scene. I need bare minimum, a dynamic to be established.

Christina: Here’s an energy.

Kayla: Yeah.

Drew: Yeah. I had an ex once who was trying to create a little whatever scenario and the scenario was that we were having sex in a bookstore and I was like, “Wait, what kind of bookstore?” And she was like, “What?” And I was like, “How big is the bookstore?” “Does that matter?” I’m like—

Christina: Yes!

Drew: Yes, it matters. The difference between The Strand and—

Christina: Am I in a Borders?

Drew: An East Village Books, like Barnes & Noble, those are all very different energies.

Christina: Where’s the Starbucks? Is it built in? Yeah, talk about that, absolutely matters.

Drew: I need to know these things. Yeah. She did not understand but, that’s why we’re not together. That’s not why we’re not together, but.

Kayla: It all came down to the bookstore, the imaginary bookstore.

Drew: Yeah.

Christina: I don’t know. I feel the vibe in this chat right now is we would all say, yeah, of course. That’s why you’re not together, that totally makes sense.

Drew: Is it a fair assumption that people who are good writers are good at texting sexting? Which is now why I’m calling sexting when it’s with sex?

Christina: Texting sexting.

Kayla: Textual sexting.

Christina: Textual sexting.

Kayla: I don’t think it’s necessarily a given because it is its own specific type of writing, I feel like, so, I don’t know.

Christina: Yeah. Now, I’m just thinking and I’m trying to think of every person that I text and I just feel like, I think it probably helps more than it — less than it would hurt. I think it’s more helpful in — but I don’t know that it’s necessary. But then again, I don’t know that I’ve actually really texted long-term with someone who isn’t in some way a writer of some kind.

Drew: Isn’t everyone a writer?

Christina: Yeah, I was generally just going through my contacts, well, no, I don’t think, I think everybody turns out that way. That’s a brain teaser.

Drew: Okay. Well, moving on to pictures and that type of sexting.

Kayla: Yeah.

Drew: I don’t have anything—

Christina: Oh, okay.

Drew: Oh, sorry—

Christina: I was really just listening. I was just like—

Drew: Actually wait, I do have a fun thing that I have — who did I tell this to? I don’t know. I’ve definitely preached this before and either people are like, yeah, obviously, or people are very surprised by this. And that is the potential of the live photo. I think people in their sexting lives aren’t utilizing the live photo to the extent that they could because it’s such a fun little, I think if you send a video to someone, that’s a choice in a way, which is a great choice, but it is a choice in a way that a live photo it feels like a little tease or it’s a sexy photo but then I don’t know, you like — move your, depending on where the photo is of, but your hand along your thigh or lick your lips, or just something where it’s a little and I don’t know, it’s a fun little thing that I think people should do more.

Kayla: Yeah. I would’ve never thought of that.

Christina: Yeah. I think the idea of bringing a live photo into intentional space instead of “Oh, whoops, that’s a live photo,” which is usually what happens to me when I’m taking photos of I don’t know, a baked good, that’s usually where I’m like, “Oh, damn it, that’s a live photo.” But bringing them into an intentional space, I think that has potential. It’s like you’re making a GIF, is what you’re doing.

Drew: Yes, exactly. I mean, and this started as an, I discovered this because someone sent me and then was like, “Oh my God, did I accidentally send a live photo?” I was like, “Yeah, it’s really hot.” And it’s like, “Oh, my God, your peanut butter is in my chocolate, Reese’s are born.” It was very exciting. And since then it has been a little go-to.

Christina: Yeah. I’m going to meditate on that, that’s a hot tip. Also, I am straight up a person who almost never photo sexts, I’m trying to think if I have actually genuinely done it.

Drew: Yeah. When was the last time you sent, and how naked, if you don’t mind sharing?

Christina: I’m going to have to be thinking of that for a minute. I honestly might have never done it. That doesn’t seem right, but it might be right.

Drew: That’s fine.

Christina: Yeah, no, I mean the memory banks coming up empty there. Yikes.

Drew: That’s not yikes. You don’t have to send naked photos to anyone you don’t want to.

Christina: Oh, certainly. But I’m just very vain and I always have a full face of makeup on, so it’s what the hell are you doing, really? But yeah.

Drew: It’s something you want to bring into your life?

Christina: It’s something I could probably move into.

Drew: Okay.

Christina: But again, there’s never a natural space for me to reach into a photo space. I’m always like, “Well, I could just write that down instead, I could write words instead.” Yeah.

Drew: Okay. So, how do you both — well, especially Kayla, and Christina, weigh in if you have memories that you want to bring up.

Christina: Sure.

Drew: How do you initiate with people if you haven’t sexted with a person before, does it just naturally get there because things are getting flirty? Because there’s that in-between where it’s not sexting but you are talking about sex or it’s like in the area or you send a picture and it’s “Oh, my God, look, I’m cooking dinner!” And it’s like, um, you’re topless. You know what I mean? Not like topless topless, that would be a choice. But like a teaser, the point of that photo is not that you’re cooking. But like how do you get there, to sext actually?

Christina: Yeah. I think I’ve only ever gotten there from the, “we’re flirting and then we’ve led into it naturally” zone, I don’t think I’ve ever sent out just a, “Hey, you up, let’s sext” vibe. I don’t think I’ve done that one.

Kayla: Yeah. I think I too have always done kind of, like, where, it’s somewhere between awkward and natural dance of escalating the flirtation. Yeah. Because I will say also, when I was first on dating apps and stuff and that was two relationships ago now. So, dating apps were also just becoming a thing but in that space, I always found it actually really hard to get to that point. And I don’t know if that was also just when I was on dating apps because they were somewhat new, like Tinder was very new. And so, I don’t know if people just didn’t have practice or what but I remember that being a struggle where it’s just like, okay, we’ve been so flirty and it feels very, like we’re stuck in a place now. But after that, it’s always worked out better for me when somebody has slid into my DMs, I mean, that’s literally how I’m in a relationship now, is she slid into my DMs. But she and I, we also did a little bit of a dance leading up to before we actually started sexting. And if I remember correctly, I actually made the first move on that but I think she just didn’t want to, because of our age difference.

Christina: Age gap discourses has entered the chat. Considering that Kayla and I are both on this call, it took a shockingly long time for time for that.

Kayla: Shocking. Shocking, finally got there.

Christina: Finally got there. Incredible work.

Kayla: But then every time too, once it does hit that point, it’s just okay, we’re fine now. We don’t have to do the dance again, once you start, it’s okay, that door is open now.

Drew: Totally.

Kayla: Yeah.

Drew: Did it start with text or pictures, when that line was first crossed?

Kayla: Text, I think. Yeah, text. Yeah.

Christina: Yeah, I feel like text is easier.

Kayla: And I feel that’s usually the case for me. Yeah.

Drew: Yeah.

Kayla: I really like photos a lot, I really do, but I feel like for starting out, it’s usually texts and then, yeah, that’s phase one of the exploration, next is some photos, and you know.

Drew: Yeah.

Christina: Yeah. I think that’s interesting because I wonder if, what the difference in-between, sliding into a DM versus if you’re on a dating app and you meet somebody? I do feel there is a difference there and the ease in which you can move to a sexting space, but I’m not sure why that difference exists at the same time.

Kayla: I think part of it is just, I don’t know, if somebody, I mean, obviously in theory, if you’re on a dating app, you are looking for either sex or to date or something like that, but that’s not always totally the case. Whereas, if you slide into somebody’s DMs, it seems like a very active, I am hitting on you, even more so than the dating apps do.

Christina: I’ve seen this content from you and I’m like, I’m into it.

Kayla: Yeah.

Christina: Hello, I’d like to be more involved in your life in some way.

Drew: It should be the opposite, theoretically.

Kayla: It should be!

Christina: Absolutely! That’s why I’m confused.

Drew: Theoretically, if you’re on a dating app, but I actually, when I think about it, I’m like, “Oh yeah, I’ve made friends on dating apps,” but it’s annoying but it’s also because of, I think specifically queer women and non-binary people in this lesbian community on dating apps, we don’t have a Grindr and people don’t really use Tinder that way. And so, I think part of it is that people are pretty timid on dating apps and I think maybe feel a little bolder in a social media space because it feels like you maybe know the person more, or there’s a little bit more of a… yeah.

Kayla: Because usually if the slide into the DMs comes after another little awkward dance of, okay, we’ve been following each other, we’ve been each other’s content, there’s something that’s established here and now I am going, it does feel like making a move. But you just made me think of something. I don’t know if either of you know about — this is a tangent for a second, but there was briefly a lesbian version of Grindr that only existed in Chicago and it was called Scissr.

Christina: Good.

Drew: Wow.

Christina: Great. Tempting. More notes.

Kayla: But like S-C-I-S-R, or something—

Christina: It simply didn’t need a single vowel. Absolutely not, Consonants only.

Kayla: It did not last very long, but it existed when I lived in Chicago so I was one of the beta users of Scissr, the application Scissr.

Christina: So, what was that like? Was it successful? Did you succeed ever?

Kayla: I hooked up with one person out of it, but it felt like a very drawn out and dramatic thing that I was just like, “Ok, I don’t think this is…” Yeah. And that was the girl who every time I went back to her apartment, she had an additional ferret.

Drew: Oh, my God. Ferret girl!

Kayla: Ferret girl.

Drew: Wow.

Christina: How many ferrets?

Kayla: We only got up to two.

Drew: Christina’s face is the face of someone who has never heard about ferret girl.

Christina: I’m not, and we’ll be following up off mic about that one, my friend. But the phrase “additional ferret” made me immediately jump to six ferrets, I got very worried about ferrets because they are gross. Wow. Okay.

Kayla: Yeah. That was Scissr. The funniest part about Scissr too, was that I read some interview with the dykes who created it and they did this whole interview about how they wanted it to be classier than Grindr and how it could actually be used for professional networking, and I was like—

Drew: No!

Kayla: I was like, you called it Scissr, first of all!

Drew: That’s exactly what we don’t need.

Kayla: That’s the opposite.

Christina: We need less places to professionally network as lesbians, I’d say. We need less of that, we’re good.

Kayla: We are maxed out on networking.

Drew: Yeah.

Christina: No more. No more of that I say.

Drew: But then you fuck your coworkers because there’s no lesbian Grindr and then boundaries are problems. And this is why all of the problems could just be solved by Scissr.

Christina: I feel like when personals transitioned from personals to the Lex App, I feel there was an idea that that could have been a space where in we were doing, “Want to have sex tonight, come find me tonight at X time.” And that just didn’t work out because of all the reasons we enumerated. Yeah. It became, “Do witch magic with me under the moonlight.”

Drew: I logged on to Lex, I redownloaded it to be like, “Okay, we’re all starting to get vaccinated, maybe Lex is going to return to that. And the first two things I saw — one was, “Just because we’re all vaccinated doesn’t mean I’m not traumatized, I’m still not meeting up with people.” I was like, cool, thanks for sharing that thought. And then the next one was like, it was I don’t know, it was something similar, I just was like, I guess we’re not, I guess, okay.

Christina: I can’t imagine the energy it would take to log onto a dating app, create an ad that is, “Just so you know, I have trauma and I’m not doing this.” Okay. So, you could have just not done that, I guess.

Kayla: Write it in your diary, I don’t know.

Christina: Simply write it in the journal.

Drew: Wait, wait, wait, Lex isn’t your diary?

Christina: I’ve heard. I’ve been locked out of my diary for a long time because I don’t remember my password and I can’t get back in and I don’t care.

Drew: Should I just start posting quotes from my 2014 journal as Lex ads?

Kayla: Yes.

Christina: Yes.

Kayla: Absolutely.

Christina: You will have 18 relationships by summer’s begin. No doubt. Great. By Memorial Day you will have two girlfriends, no doubt.

Drew: I mean, fear of death is simply the fear of time, so.

Christina: Is there any final sexting thoughts we want to hit before we wrap? I want to make sure we’ve got all of our sexting feelings out there. What is one sexting piece of advice that you would give to people who are either thinking about it or wanting to try it anew perhaps? And I’m not talking about myself, certainly, not at all.

Kayla: I mean, I do think that, because I write advice semi-regularly for Autostraddle, and I feel like I do bring up sexting from time to time because I do feel like a lot of people really struggled to articulate their desires and stuff, which is understandable. I mean, sometimes we don’t even have that stuff really figured out, but I do think that sexting can be a really useful tool for figuring out what you’re into, also potentially figuring out what somebody else is into, exploring things, seeing if you’re open to it and just in a lower stakes environment than figuring out when you’re sweating in a room with someone.

Drew: Yeah. I think that’s really good advice that I’m going to really ruminate on and potentially bring into my own life and maybe report back on how that goes.

Christina: I can’t wait for that report back. I want it desperately.

Kayla: I guess that’s something that I could have mentioned when we were talking about tense and stuff, but I also do tend to ask questions — and not, there’s a way where that can be a cop out. I’ve definitely sexted with people who were either not good at sexting or just weren’t willing to be as vulnerable or whatever and so, their version of it is just only asking questions. They’re like, “What do you want me to do? What do you like?” And it’s just, okay, you’re not going to contribute to this at all? Where’s the improv 101, we are doing this together.

Christina: “Yes, and” energy please.

Kayla: Exactly. So, I think that can sometimes be a cop out, but I think that if there’s a mixture of yeah, me saying this, but then maybe I do break it and say, “Do you have something that you like to be called?” Or whatever, and then letting it be more of a madlibs situation where they can fill in some of the blanks.

Christina: “Workshop this with me” energy. Yeah. Drew, you look so thoughtful right now.

Drew: No, I’m just absorbing it all. I’m here to learn as well, so.

Christina: I love that. I love that for you.

Drew: Thanks.

Christina: Yeah. I feel like I don’t have any tips because I haven’t really used that muscle in a while, read the room, read the vibe, I feel like is always my go-to tip in most situations. Yeah. But I think, I don’t know, maybe Drew and I will bring some of this energy to our summer escapades and we’ll see what happens.

Drew: Yeah. I love it. I mean, I also think specificity is — this is just honestly, this is just like a tip for writers, where it’s just like, oh, it makes sense that I think in sexting, sometimes people who have been not as good with sexting with me, they’re just jumping too quickly to the next stage of this whatever imagined sexual encounter, and it’s for me, what’s going to work is if I can really imagine it. So you know, you gotta have a little digital language. Yeah. Come on. A little poetry here.

Christina: A little poetry here is great. Let’s have a crush! Yo Drew, do you have a crush?

Drew: I always have a crush.

Christina: I know you do. Who’s your crush this week?

Drew: Okay. So, this is actually a really landmark moment for me, because it is a celebrity crush but it’s a friend celebrity crush. So, it is a crush that is, for me, not sexual but for a lot of other people in my life, it is sexual, but I have done some mental work and realized that I just want to be this person or be friends with this person.

Christina: So, is this a crush or is this a humble brag? Just wanted to check.

Drew: What? No, no. This person is — no, no, it’s not a humble brag because this person is not my friend. I am just saying.

Kayla: Oh, it’s a friend crush?

Drew: Yeah. No. Well, first friend crush can mean, “This person is my friend and I have a crush on them” or, can mean all sorts of things. In this case, it’s a celebrity crush but it’s just someone who I really like a lot as a person, but it’s not really sexual for me. Okay.

Christina: Okay.

Drew: So, the second and final season of Feel Good is out and I think it’s great and I just love Mae Martin so much. Humble brag is that I have gotten to interview them.

Christina: Well, there it is.

Drew: But I just think that I love Feel Good and I think it’s that I love how messy the show is and how messy they’re willing to be in this fictional/autobiographical space. And I relate to them a lot, in a lot of gender ways and painful, romantic ways. So, they’re my crush of the week.

Christina: Yeah. It is a really, really, really good season. So, thrilled by that. I guess I’ll go. Oh, yeah. I watched Snow White and the Huntsman and Snow White and the Huntsman 2 last night. Couple of things. Both aren’t great. Second one, may be better. Tough to say. And while Charlize, incredible energy, she brings a performance, it’s really just like ma’am, you didn’t have to commit this hard. Emily Blunt in the second film, I said, well, okay, she’s giving you ice goddess, she’s giving you angry but sad mommy, and I said, I respect that, thank you Emily Blunt, I love your work, great. She’s my crush corner this week, Emily Blunt. Yay.

Drew: Okay.

Kayla: I saw both of those movies in the theater, so.

Christina: I saw the first one in the theater for sure, the second one, I don’t know that I knew it existed and I’m still a little perplexed as to how it exists but it does and there it is. Emily Blunt.

Drew: I’ve seen neither. I want to know, what’s the second one called?

Christina: Snow White and the Huntsman 2, or Huntsman’s Corner? I don’t know, something—

Drew: Wait, really? So, wait, wait. So there’s still the Huntsman?

Kayla: Yeah.

Christina: He’s still in it.

Drew: The Huntsman is still there. I just assumed that—

Christina: The only person who’s not in it is Kristen Stewart.

Kayla: Yeah.

Drew: Wait, Kristen Stewart isn’t in the second one?

Kayla: No.

Christina: Correct.

Drew: Wait, I’m sorry. This is not important, but—

Christina: That’s why I don’t know how it got made, I don’t know how it got made. She’s not in it.

Drew: Fascinating. Well, I love learning. Okay. Kayla, who’s your crush?

Christina: It’s The Huntsman: Winter’s War.

Drew: Wow.

Kayla: I was like, it has something to do with a battle or a war or something because it’s basically just Charlize Theron and Emily Blunt, fighting.

Drew: That sounds good.

Kayla: Which, you know, hot, so.

Christina: Right. So, right.

Kayla: Okay. I’m not done with it yet, but I’ve been watching Girls5eva, and so, I’m going to say Renee Elise Goldsberry is my crush.

Christina: Sick. Perfect.

Kayla: Which just feels like a circular moment for me from back when she was on The Good Wife, and was very underused on The Good Wife, but was great.

Christina: True.

Kayla: And yeah, I don’t know, her character is incredible, she’s just a self-obsessed bimbo, who knows she has the best voice in the room, and so she’ll just bust it out at any point. Yeah. It’s been a joy to watch. She’s definitely been the best part.

Drew: I love it.

Christina: That’s incredible.

Drew: Well Kayla, will you tell us where people can find you and your work?

Kayla: Yeah. So, I am @KaylaKumari on every single social media, I consolidated that at one point, so, very easy to find.

Christina: Nice job branding.

Kayla: Yeah. I mean I’m on Autostraddle almost every day, it seems I have something go up there, it’s an easy way to find me. And just at my website also kaylakumariupadhyaya.com that’s where you can find more of my fiction work and stuff.

Christina: Yay! Go find, we love, we respect. We do have a question and it’s: So, Kayla, was this a date? Are we on a date right now?

Kayla: Is this a date?

Christina: I don’t know.

Kayla: Is this a date? I feel like the true lesbian thing is always to not ask or answer that question but just let it sit there in the universe and then maybe ask everyone you know after the fact, like, “Do you think I was on a date or not?”

Christina: Cool. So, we’ll just send out a poll to the listeners after this episode airs and just let them decide if we were on a date or not.

Kayla: Yes. Need someone to make that decision for me.

Christina: Yeah. Okay. That tracks, great.

Drew: Great. Cool.

Christina: I think that’s amazing.

Drew: Thanks, Kayla.

Kayla: Yeah. Thank you guys. This was amazing. It’s great.

Christina: This is fun. I love fun.

Drew: Thank you so much for listening to Wait, Is This a Date? You can find us on Twitter and Instagram @waitisthisadate. And you can also email us at [email protected].

Christina: Our theme was written by Lauren Klein. Our logo is by Maanya Dhar. And this podcast was edited, produced, and mixed by Lauren Klein. You can find me online @c_gracet on twitter.com, the website. And you can find me on Instagram at @christina_gracet.

Drew: And you can find me on Twitter, Instagram, and TikTok @draw_gregory. And you can find Autostraddle on all social medias @autostraddle.

Christina: And go visit autostraddle.com, because it’s the reason we’re all here today.

Drew: Thank you all so much. And, you know, see you next week!

Christina: Yeah. We’ll absolutely see you next week. And we can’t wait.

Drew: Yeah. And you know, maybe next week, maybe next week will be a date.

Christina: Hey, maybe it will be! Wilder things have happened.

Drew: Except you know what? I also think it’s important to clarify to the listener that if you ask someone if something’s a date or not, we probably should take that as sort of like a moving forward — I don’t think every time you see someone you should… That’s not really direct communication as much as it is like not really respecting someone’s boundaries. And you know, we do like boundaries here at Wait, Is This a Date?

Christina: The gayest thing about this podcast is that the outro is a boundary.

Drew, in a voice memo: You now how in the old days in the Victorian era or whatever, people would lust after ankles because they weren’t seeing them. That’s how I’ve been feeling lately when it comes to sexting where I’m like the mildest sexual text, or picture, or video from someone who I’m flirting with, I’m just like, “Oh, my God, this is so hot.” And I’m like, “Is it? Or has it just been a really long time?” You know what I mean? Oh, this pandemic just keeps on going, doesn’t it?

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Drew Burnett Gregory

Drew is a Brooklyn-based writer, filmmaker, and theatremaker. She is a Senior Editor at Autostraddle with a focus in film and television, sex and dating, and politics. Her writing can also be found at Bright Wall/Dark Room, Cosmopolitan UK, Refinery29, Into, them, and Knock LA. She was a 2022 Outfest Screenwriting Lab Notable Writer and a 2023 Lambda Literary Screenwriting Fellow. She is currently working on a million film and TV projects mostly about queer trans women. Find her on Twitter and Instagram.

Drew Burnett has written 566 articles for us.