“Wait, Is This a Date?” Podcast Episode 109: Fucking Your Friends

Is it a date or are we just friends? Why not both! This week we’re talking about fucking your friends with Autostraddle community editor and fucking your friends expert Vanessa Friedman. We get into the difference between friends with benefits and one time encounters and the range from drug fueled nights to thoughtful discussions over tea. Is platonic sex a thing? Listen and find out!

And to start us off we have a good ol’ fashioned game of Would You Rather? — with a personalized twist.

SHOW NOTES

+ In case anyone was wondering, my middle name is Burnett. But I think I’m going to stick with just Drew Gregory for now.

+ Despite that hetero moment, this season of The Circle was pretty gay so we did a roundtable about it.

+ Vanessa’s “6 Easy Steps to Having Sex With Your Friends”

+ Here is Bernadette’s titty dress:

Bernadette Peters at the 2021 Tonys in a black Bob Mackie dress that's off the shoulder and covered in stars.

Photo by Arturo Holmes/Getty Images


Vanessa: I have a very, very dear friend who’s definitely chosen family who once said, “The arc of the universe bends towards you fucking your friends.” And so I do feel confident that at some point in time, over the course of our lives, we will probably fuck.

Christina: Wow.

Vanessa: And I thought that was so beautiful, because who knows when? And who knows if? And maybe not. And we’re both bottoms, so honestly what would happen? I don’t know.

Drew: Hi, I’m Drew.

Christina: And 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 age old question: wait, is this a date?

Drew: I’m very excited about the fact that I think as I’ve gotten older, I have also asked that question less.

Christina: I’m very excited about the fact that whenever you start a sentence, I’m like, “No idea where this is going to go. Could go anywhere. It could be anything.” It’s incredible and it makes me feel so alive with the spirit of podcasting and friendship.

Drew: I’m so glad. I’m Drew Gregory. I am a writer and a filmmaker and a trans woman and a queer person. I also am currently trying to figure out if I want to go by my first middle and last name or just my first and last name or drop my last name altogether. So, that’s today’s fun fact about myself is that I have been spiraling about that. Who are you?

Christina: I’m Christina Tucker, and when I first became a person who was like, “Oh, I’m doing stuff on the internet,” I always thought I was going to go by Christina Grace. That was always my plan because like, “Oh my God, she’s famous. Her name’s Christina Grace.”

Drew: Right.

Christina: And then I never did and forgot to do so.

Drew: Sure.

Christina: So, that’s another option that could happen for you.

Drew: Sure.

Christina: I’m also a lesbian writer at Autostraddle. It’s fun. We do gay stuff there and here on this very podcast where we are going to be doing gay conversation. Wow. That was so natural and cool.

Drew: That’s really exciting that we’re going to be doing gay conversation.

Christina: Yeah. It’s actually a huge change from our usual conversation, which is just deeply straight.

Drew: What had happened recently where I was like, “That was too heterosexual?” Oh, it was these two people flirting on the television program, The Circle, and I was like, “This is too straight for me. I can’t watch this anymore. I don’t like this.”

Christina: Fair enough. I can’t grok The Circle as a…

Drew: That’s not your thing. That’s fine.

Christina: Something doesn’t quite click with me. But what I can grok is a fun game for you because it’s my turn to game you, and I went for a classic. This is a Drew edition Would You Rather because these are the kinds of questions that tend to send you into a light spiral which I think is very fun for me, and also the listeners. I’m not sure about your brain, but you’re doing your best and that’s all we could ask.

Drew: I like spiraling.

Christina: Yeah. So, let’s start with an easy one.

Drew: Okay.

Christina: Well, maybe it’s easy. Would you rather have an orgasm every time you hear “All Star” by Smash Mouth, or every time you have an orgasm, “All Star” by Smash Mouth plays?

Drew: Do the other people around me hear it?

Christina: Yes. People hear it.

Drew: Where is it coming from?

Christina: This is not the point of Would You Rather.

Drew: Okay, okay.

Christina: Unfortunately you can’t have that much context.

Drew: Am I singing it?

Christina: I kind of wish.

Drew: I would say that every time it plays, I have an orgasm.

Christina: That’s bold. I feel like that song plays a lot for me.

Drew: I can do the sort of classic sex rom com thing of keep being, “Ah, I’m having an orgasm and I’m trying to keep it a secret as like…” Whatever. I can pull that off, I think.

Christina: Sure, sure, sure, sure. I love that energy. All right. Would you rather identify as sapphic or tender queer?

Drew: Sapphic, for sure.

Christina: Smart.

Drew: I mean, because even if it’s not a word that I use it is accurate, whereas I don’t think tender queer is accurate at all.

Christina: I think that’s very fair. Would you rather be trapped in a car with Ilene Chaiken or Quentin Tarantino?

Drew: Okay. So, if I was trapped in a car with Quentin Tarantino, I think he might kill me. If I was trapped in a car with Ilene Chaiken, I think I might kill her.

Christina: Right.

Drew: So, it’s a real tricky situation, but I do trust my own self control more than Quentin Tarantino’s, so I think I’m going to go with Ilene Chaiken. Also, I could ask her some questions. There’s no mystery with Quentin Tarantino. I know his deal.

Christina: You’re going to go from pissed off to exhausted to probably dead. That’s it.

Drew: But with Ilene Chaiken, I would love to just be like, “Why?”

Christina: Yeah, that’s always the question that we’re all asking, kind of specifically, to her.

Drew: Also, I want to clarify for the record that if I was ever in a space with Ilene Chaiken, I would not kill her. That was just a pithy joke thing.

Christina: Trapped in a car is a different context than in a general space.

Drew: Sure. But even if I was trapped in a car, I’m not going to murder anyone. I just want that to be known for anyone listening.

Christina: We love you, NSA. Would you rather be able to only consume media about straight people, but be in the perfect relationship or only consume gay media and be in a string of terrible relationships for the rest of your life?

Drew: What do you mean by terrible relationships?

Christina: Drew, I’m letting you define terrible however terrible is to you.

Drew: Can I still create queer media? I just can’t watch it.

Christina: Sure. Yeah. You just can’t watch it.

Drew: I feel like I can’t say the terrible relationships. That is where I’m leaning, but I can’t.

Christina: That’s what I thought you would say.

Drew: I can’t do it, though. Right? I can’t. Well, so what is media? Is it film and television or also music and books?

Christina: I mean, I was just kind of thinking about film and television. I mean, I used media to include a wide breadth, but…

Drew: Great. I’m going to have good relationships and pivot towards being a literary gay.

Christina: Incredible. I think that’s really healthy and really beautiful. I really was like, “The way she’s going to pick bad relationships and gay media.”

Drew: I really thought about it. I really, really thought about it.

Christina: I really thought about it mostly because I was like, “Well, then she’d also have stuff to write about. She would have content.”

Drew: Right, yeah. I don’t know.

Christina: I think you can make content kind of no matter what. That’s one of my favorite things about you.

Drew: I actually think that oftentimes my best experiences lead to my best work.

Christina: Not the worst ones.

Drew: Sometimes my most chaotic experiences, but they’re usually good chaos.

Christina: You like good chaos.

Drew: The bad chaos doesn’t usually lead to good stuff because I don’t usually write about it because I don’t really like to write about people negatively.

Christina: Yeah. I hear that.

Drew: So, I tend to avoid writing about my more negative experiences

Christina: And that’s really beautiful. Would you rather only use Lex as a dating app or only use Twitter as a dating app?

Drew: Oh, Twitter.

Christina: Yeah, I thought I’d toss you a light one.

Drew: That’s no question.

Christina: Yeah. That one’s easy. Would you rather have a mullet or an undercut? I know, this is tough. You have a very specific hair type that neither of these styles really lend themselves to being easy to deal with.

Drew: Yeah. I mean, I think probably with my hair type, a mullet would be the more go-to thing, but I think I’m going to go with undercut.

Christina: I think it would look hot.

Drew: Oh, thank you.

Christina: And I do think the growing out process would probably be a struggle bus, but I think that’s kind of—

Drew: But if I’m forced by this game to have an undercut, then maybe I have to have it forever. I mean, I don’t know the rules.

Christina: Yeah. No one really knows the rules of Would You Rather. That’s kind of the fun of it. Would you feel worse if no one showed up to your funeral or your wedding?

Drew: Wait, is the person I’m marrying showing up to my wedding or is it literally no one?

Christina: I think it’s the person you’re marrying, but nobody else. That’s how I’m interpreting it, anyway.

Drew: I see. I see.

Christina: Because then you’re not having a wedding if the person you’re marrying doesn’t show up. You’re just kind of standing somewhere.

Drew: I’ve done that already. I do that all the time. I stand places. I’m just trying to think of the context where no one would show up to either of those things. I sort of can’t fathom.

Christina: Oh, I’m with you. I’m absolutely with you.

Drew: I think I would rather no one show up for my wedding because the scenario that I’ve created in my head is that maybe I’m eloping. Maybe it’s a destination wedding and something happens or maybe it’s like… I don’t know. If my significant other is still there, then that’s all I really—

Christina: That’s really all that matters, yeah.

Drew: I don’t really want a big wedding anyways, and if no one shows up to my funeral, then it’s like, “What did I do? Who did I hurt?”

Christina: When I was a barista I used to ask my regulars if I died tragically if they would come to my funeral. And they were always like, “Christina, I just want a coffee. Why are you like this?” And I was like, “Well, you can’t have it until you answer the question. Ha ha ha.” Most of them said yes, but I was holding caffeine against them, so who can say?

Drew: If they said no, would you have given them the coffee?

Christina: Yeah, because I was at work.

Drew: Right, right, right. Sure.

Christina: Whatever.

Drew: Sure, sure, sure.

Christina: All right. We’ve got two more.

Drew: Okay.

Christina: Would you rather go without TV or would you rather go without musicals for the rest of your life?

Drew: I got to give up musicals, because it’s just more of a narrow thing, but that’s sad.

Christina: Isn’t it?

Drew: Can I still go to Marie’s Crisis or is it like—

Christina: Yeah, that’s definitionally not a musical. That’s just theater kids.

Drew: It’s just people singing. Yeah, I can still be around. Okay. I’m going to give up musicals.

Christina: Yeah. I think you have to. It’s sad, but…

Drew: What about TV musicals? Those also have to go?

Christina: I mean, if you want to watch Rent live for the rest of your life, absolutely go off. If you want to watch The Grinch live, go off.

Drew: I was thinking more like Crazy Ex-Girlfriend.

Christina: Sure. I mean that falls in the category of TV. That’s like definitionally TV. So, you would still have it and that’s something. All right. The last one.

Drew: Oh boy.

Christina: Would you rather accidentally send a nude to your mom or your sister?

Drew: I mean, I guess my sister. The obvious answer is my sister, right? But when I actually think about what this would look like, I got to go with send it to my sister.

Christina: That’s what I thought you would say, but I was also like, “This is a tough one,” because I feel like in both scenarios, the other one is going to know about it almost instantly. So it’s like—

Drew: Right. It’s a good point.

Christina: Just knowing how your family is.

Drew: If I send it to my mom, my sister won’t see it. If I send it to my sister, my mom might see it.

Christina: Right.

Drew: So…

Christina: That’s part of the journey. Well, I feel like I am very satisfied in how well I know you as a person.

Drew: Thank you.

Christina: And I think I would happily show up to your funeral.

Drew: Thank you so much. That is all I was waiting to hear, but would you show up to my wedding is the question?

Christina: Yeah. I’m going to be absolutely the best person at your wedding. I crush weddings. Are you kidding me?

Drew: I believe that. That’s really exciting. I’m not planning on getting married, but now I want to just so you can come to it and have a great time.

Christina: I can bring that energy if you need it at any other event. I’m happy to do that.

Drew: I want more people that I know to get married, though, because I want to go to some more gay weddings.

Christina: Same.

Drew: I mean, I guess it’s more likely that I would get married before you got married.

Christina: The way things are going, yeah.

Drew: But also life’s interesting. Twists happen. And so I’m just saying that if you got married, I would be so excited to attend that wedding.

Christina: Yes. If I get married, you’re coming to my wedding. Spoiler.

Drew: Great.

Christina: Okay.

Drew: Thrilling.

Christina: Great.

Drew: We’re just going to move on to our main topic of the week, which is fucking your friends and for that topic, of course our guest is…

Vanessa: Hi, I’m Vanessa Friedman. I love fucking my friends. I was honored to be asked to come talk about that. I’m the community editor at Autostraddle. I am also a freelance writer elsewhere and a teacher and I am working on my first novel, which is due to my agent on Friday. So, that’s fun. Yeah. That’s me. My Instagram bio says I’m hot and sad, which is true.

Christina: Incredible.

Drew: Those are both great things to be. So, in another sense, you’re queer.

Christina: Yes.

Vanessa: Yeah. So, I’m a dyke, I guess.

Christina: Yep, that’s what I heard when you said hot and sad. That’s exactly what I heard. When Drew and I were brainstorming topics for this here pod and I think genuinely one of the first things we were like, “Well, fucking your friends and we’ll have Vanessa on, of course.” That was just—

Vanessa: Thank you so much.

Christina: The brand is strong. You’re aligned with this topic. We’re calling in an expert here because I think this is a really fruitful convo. I feel like it’s a thing that happens a lot. I feel like it’s a thing that people want to happen, but don’t know how to make happen, and I think you’re the perfect person to join us for this discussion.

Drew: So, the first thing that I want to ask is when was the first time that you fucked a friend in the context not of “I fucked a friend and then we started dating,” but when was the first time that you fucked a friend and it was a friends with benefits situation or a one night thing or whatever, and you stayed friends? Or maybe you didn’t stay friends, but we’ll take that part out of the equation.

Vanessa: Okay. I feel like the question has multiple parts because I definitely think in high school, when I thought I was straight, L-O-L, I definitely… And even in early college, when I thought I was straight, I had friends with benefit situations, but basically what was happening was I was allowing myself to be taken advantage of by people who I had huge deep feelings for who were kind of like, “Yeah, you’ll do.” And I was like, “Great. Great. We are friends. I am deeply friends with this man and we are both benefiting, because feminism. Duh.” And I was very much trying to convince myself and I don’t even have negative feelings towards those men because I definitely was playing along. I don’t think at any point were they like, “I’m harming this girl and her self-esteem,” because I was just like, “No, no, no, no. It’s cool. I love this.” But I did not love it at all. I mean, for a lot of reasons, which later became clear when I was like, “Oh, I’m gay.” But emotionally it did not work for me, and I do think that a lot of queer people are still playing that game, just with other people and it will not work to fuck your friend—

Christina: Spoiler.

Vanessa: …if you secretly want to be dating that person, or if you secretly want anything that isn’t a like friend who you sometimes fuck, which I think is a very key point that people often get in the weeds about. And, I had no idea it was such a controversial topic until I wrote the article, “Six Easy Steps to Fuck Your Friends Without Fucking Up the Friendship.” And people on Instagram were like, mad. They were like, “Don’t do this! This is irresponsible.” And I was like, “Oh, okay. All right. Well, Instagram is a place for nuance and good, good deep discussions.” But to answer the second part of your question, Drew, I actually, because of my straight girl college and high school experiences, I was very against fucking my friends. When I came out as queer, I was like, “No, that’s not my jam.” And, I was in a lot of circles where people did kind of casually fuck their friends. And I was like, “That’s not for me. I like to fuck the people I’m dating, and I like to be friends with the people I’m friends with.” And then, I had a pretty serious breakup in 2018, and suddenly everything shifted. It was just kind of like, “Well, I am a slut. My friends are really hot. Most of us are pretty good at communicating. Oh…”

Christina: A little door opened.

Vanessa: And things sort of changed from there. Yeah. Mm-hmm (affirmative).

Drew: We’re just both nodding.

Christina: We’re just nodding. Yeah. I’m just taking it in.

Drew: It is interesting to think about the difference, because my longest friends with benefits situation was when I was a straight, and it actually was with the only person from my straight years who is still straight, she’s fully married to a man, that level of straight. Not that that inherently makes you straight, but she identifies as straight. He identifies as straight. They’re married together and they have a straight marriage and I love that for them.

Christina: Sometimes people are straight.

Drew: Sometimes people are straight. And, we both weren’t super sexually experienced, and I think because of her heterosexuality and my lack of, I don’t think we ever would’ve dated dated, but we just had a very long friends with benefits situation and it was really good, and it ended pretty okay. There was definitely a little bit, because I got into a relationship and then she texted me to be like, “Let’s have sex.” And I was like, “No, things are getting serious with this person and I’m more monogamous.” And then there was a little bit of hurt feelings, but they quickly, I would say a month later we were friends again. So, I would describe that as a pretty successful experience. And then, since being queer, I talk a lot about blurring the boundaries between friends and people who I have sex with, but I actually have really only had sex with two of, is this true, sex with two of my friends.

Christina: Real time fact track.

Drew: In the context of, we are friends, we have sex. Afterwards, we are still friends, and there is no drama, no one has more feelings. I mean feelings happen, but whatever, and with really only two people. So, it’s something that I’m very open to, but it’s also something I don’t do that often.

Christina: Yeah. I feel similarly in that my more successful friends with benefits was when I was dating cis men, and that’s obviously because I was like, “Well, I don’t like dating you, but I do like having sex.” So it’s very easy for me to be like, “No, I don’t want to spend more time with you, for the love of God, no.” But it has never, not has it never occurred to me to be like, “Oh, my friends are hot. All of my friends are hot. Hot people attract hot people.” It’s a beautiful… it’s what symbiosis is really all about. But the idea of having sex with any of my friends, I’m just like, “No. No thank you. No, I don’t want to do that.” It’s weird. And I think most of us feel the same way. One of my very good friends, Camille, when I was freshly post a breakup, was like, “Look, if you need to have an orgasm, I will close my eyes and I will give you a great orgasm,” but like, “Ew, we shouldn’t do that.” And I feel it is a lot of my close friendships do have kind of like, not necessarily a familial vibe, but it does kind of have that same sister-y feeling. It’s just like, “No, I don’t want, that’s like, no, I can’t fuck that person. That’s my sister friend. Like, no, absolutely not.” So I find it fascinating, this world wherein you can just sleep with a friend and not be like, “Hmm, no pass, pass away. Gross.”

Drew: That’s interesting, because I feel I have some friends who I feel that, where I feel they’re sort of familial to me. And then I have friends who I don’t feel that and would, but it’s not a matter of closeness. Vanessa, do you have, obviously you don’t want, well maybe I shouldn’t assume this, but do you have, I was going to be like, obviously you have some friends you want to fuck and some friends you don’t want to fuck. Maybe that’s not true. Maybe you want to fuck all of them. But do you have that delineation between certain friends where you’re like, and I’m not talking about friends who you don’t want to fuck because you’ve made the conscious choice for the health of your relationship or whatever. I’m talking more like, are there friends you have who you feel that sort of familial like, oh, we’re really close, but it’s not the sexually charged type?

Vanessa: No.

Drew: Yeah.

Christina: Iconic.

Vanessa: And I got to say one of my favorite things about Christina on this podcast is that you’re often kind of in this anthropological seat where you’re like, Drew and the guest are saying this thing and I am just—

Christina: I love to learn.

Vanessa: Huh.

Christina: Yeah.

Vanessa: Okay.

Christina: Yeah. I come from a higher ed background, so it’s really important to me to do scholarly research, and that’s what I’ve signed up for on this here pod, to be the Jane Goodall. That’s me.

Vanessa: This is famously my favorite podcast, which is a huge deal because, as Drew knows, I hate podcasts. So, the fact that I love this one is big, but I really love listening because sometimes I feel I’m in Drew’s seat where I’m like, “Yeah, yeah, yeah. I would participate in this convo.” And sometimes I feel I’m in Christina’s seat where I’m like, “This is fascinating. You don’t say? Whoa.”

Christina: Yeah. I love being a “you don’t say” guy.

Vanessa: I guess I haven’t thought about it from an anthropological way before. But a lot of my very, very close friends who are clearly familial, they are chosen family, forever people, are people who I would totally fuck. And, I guess I think of them as my chosen family, but that doesn’t make me feel like they’re my sister friend in that way.

Drew: Right.

Christina: Mm-hmm.

Drew: I have a very, very dear friend who’s definitely chosen family who once said, “The arc of the universe bends towards you fucking your friends.” And so, I do feel confident that at some point in time over the course of our lives, we will probably fuck. And I thought that was so beautiful, because who knows when? And who knows if? And maybe not. And we’re both bottoms. So honestly, what would happen? I don’t know. Maybe it’d be a group scenario. But just the idea that our friendship exists. I don’t think this person is going anywhere in my life. I see myself growing old with this person, and maybe sometime before we all die, we’ll fuck. And that’s how I feel about most of my friends.

Christina: I think that’s so beautiful.

Vanessa: Over the arc of our life. I guess to me, over the course of growing up, sex has become an activity as opposed to something that has to be deeply emotionally charged. And that doesn’t mean that I’m always capable of having it in a casual way, and there are people in my life who I couldn’t have casual sex with. And those people, I would probably not try to engage in casual sex with, or if I did, it would be a failure. It wouldn’t work. But most of my friends, when I think about fucking my friends and I think about the way that I specifically, as a control freak Capricorn, like to structure the art of fucking my friends, it just feels something that could happen with any friend.

Drew: Yeah. It’s interesting because when I think about life, it’s real long, theoretically.

Christina: Okay, huge take.

Drew: And so, I really only have one friend, because when you’re talking about chosen family and not thinking about them as family in that way, I am the same way. That isn’t the line for me. There are people who I’m like, “Oh, this person’s my chosen family. And also, I have or I would have sex with them.” So, I don’t know. I guess I’m not closed off there. I guess there are people who actively, not actively, there are people who I’m more like, oh yes, that is a friend who, if they said right now, “Let’s fuck,” I would be like, “Yeah, absolutely. Let’s do it.” And then there are people who I’m like, I don’t know if I would say yes right now, but yeah. Even my one friend, my really close friend Hirosch, who’s my friend from, we met in elementary school. That’s the only person who I’m a little bit like, “I don’t know.” But if you said you never will, will you never? I’m like, “I don’t know. Life’s really long.” And the two friends of mine who I have had sex with recently, they’re my chosen family, and I think for me though, like what you’re saying about it being an activity in that way, I don’t know if I have that capacity. What I have is the emotions attached to it can range so vastly. And so, having sex with the two of them wasn’t like, “Oh, I want to join their relationship.” But it was an extension of my feelings, it was still emotionally charged, if that makes sense.

Christina: I think anybody certainly who knows you and anybody who listened to the podcast will think it makes sense for you to find some emotional charge.

Drew: Yeah. Christina did get a voice memo at, what was it, 8:00 AM, that was like, “I am still on cocaine and I cannot sleep, and I had sex with Gaby and Mal and I don’t know what to do.” Oh, it was on Christmas morning, as well.

Christina: It was Christmas morning. Merry Christmas to me. Yes. It was one of the more beautiful gifts.

Drew: Yeah. But, I think also, communication is such an important thing, and being able to be comfortable enough with people to be like, “Well, let’s actually talk this out instead of, once I was sober, quietly spiraling. Let’s actually talk out how we feel. Let’s work through, et cetera, et cetera, et cetera.” So, I think most sexual things, communication is a real important part of it.

Christina: Yeah.

Vanessa: I think, as you’re speaking, I’m understanding something that I didn’t understand before—

Christina: Yes!

Vanessa: Which is that I think a lot of people, when they hear the idea of fucking your friends, they are assuming that I mean as an ongoing friends with benefit situation. I actually rarely mean that and I often mean making the very intentional choice to have a fun time with a friend, and then kind of immediately re solidify the friendship boundary. I also had a threesome with two friends who are together at one point, and beforehand, I went over. We were all clothed. It was the afternoon. We were not on cocaine. We had some tea. No shame of being on cocaine. I’m just trying to set the scene. We were deeply not on drugs. We were drinking tea on a sofa and kind of discussed what all three of us would want to get out of the scenario. And then we fucked. It was great. It was several hours. We had a very nice time. And then afterwards, we all put our clothes on again, and they were very much still a couple, and I was very much still not part of their couple. We all went for dinner. We had a very nice meal. And then they dropped me at home and I hugged both of them goodbye, pretty intentionally because I was like, we are not leaving this window open. It’s not like, “Oh my God. Are you all looking for a third?” No, these were two of my extreMaly close friends. We had so much fun. A lot of our kinks overlap, a lot of stuff was really fun and good. Would I do it again? For sure. But would I do it again frequently? No. Because I am self aware enough to know that I can’t fuck the same person too many times with too much frequency who lives in the same city as me without getting feelings. And that’s not what I want from these people who are deeply my chosen family. So, I’m very much making that choice. Do I now understand that some people who are hearing me say fuck your friends think I just mean then keep fucking that couple every weekend for the next six months, and then be like, “Damn it! Why do I have these deeply hurt feelings that they’re still a couple and I’m still…” But, I would never do that because I just don’t trust myself to not get confused.

Drew: That makes a lot of sense, and also what you just described is way healthier than what I described. No shame, I guess, towards myself.

Vanessa: No shame to anyone.

Drew: But, I do think after that happened, one of the things in us talking about it was that I felt complicated about the fact that that line had been crossed when we were all really fucked up. And when we talked about doing it again, I was like, “I want to be sober.” And so, that did happen, and we had another threesome sober and, well, I was sober. I don’t remember exactly how, but no one was on cocaine. If there was a little bit of pot or alcohol, I don’t know. But I was very pointedly like, “This is going to be sober for me.” And it was nice. And it was sort of a month long thing of the bookends, and after it was over, I was like, “I live here. These are two of my best friends.” This month was a little bit messy as it was just always up in the air of, “We’ve said we want this to happen again. When’s it going to happen?” And I was just like, “Oh, this can’t stay an open thing.” Now, do I think in my entire life, will I never not have sex with either of them again? No, I think probably it will happen at some point, but it is what you’re saying, like it is closed. I hang out with the two, I continued to live with them for another whatever, long period of time, and it was funny how quickly it went back to, isn’t it weird how a month ago, there was tension in the house because we all were waiting to have sex again? And it’s like now we are so back to being platonic. But also, sometimes I’m like, can you fuck people platonically? I know that is the opposite of the word, but sometimes it does feel, I would be open to it with most of my friends because even if it would mean something emotionally to me, it wouldn’t mean something emotionally in the sense that, it doesn’t mean something romantic.

Christina: It would be romance, yeah.

Drew: Yeah. And I think the reason it usually doesn’t happen is because I don’t always know if people have that same relationship to sex. I mean, and that was something about Gaby and Mal where I talked to them about polyamory all the time and I’m very much aware of how both of them feel about polyamory and about sex and about… But I don’t know. So, I mean, I talk enough about sort of the blurred lines of friendship and whatever that I guess I also sort of just assume that any of my friends know that that’s a topic they could broach with me if they ever wanted to have sex. And I’m just sort of like, yeah, I mean, it’s casual and it’s there and it’s like… I’m not, I don’t know… It’s like, again, life is long. Who knows when certain things can happen.

Christina: Yeah. I feel like, well, two points. I do have “Blurred Lines” stuck in my head, so that’s something I just want to contend with.

Drew: Sorry about that.

Christina: You know what? It’s fine. It’s frankly a bop. I think we should all stop pretending it’s not. And two, I think it’s interesting that people would assume… As a person who does not fuck my friends, when I read that piece, I was like, obviously what Vanessa is talking about is a very specific, kind of one and done scenario. Because even to me, I was like, well, obviously if you continue this, just open this kind of place, this borderless place, where people are just fucking whenever, because it’s, I don’t know, Tuesday night and we thought a show was on and now it’s not and now we’re having sex again, obviously that is going to bamboozle some minds, and some hearts even, minds and hearts.

Drew: Wow.

Christina: Could you even imagine? So that is very interesting to me that people would assume that what you mean is a long-term friends with benefits thing. Because I find that is such a different negotiation with your relationship with somebody than fucking a friend as like a one-off or a once every couple of years off is, to me anyway. Again, famously a person who does not do this, has not done this.

Vanessa: Yeah. And I think there are people I’m friends with who live in Portland who I occasionally sleep with and it’s kind of a thing that’s on the table. But again, as an activity. We do not do that every time we hang out. I find that often if a person is poly and partnered, that’s useful. I mean, depending on how you practice polyamory. But a lot of people who are polyamorous and have one or two partners aren’t necessarily able to fit more partner time into their lives. I also do think it’s the group of people you’re hanging out with. If you are friends with a bunch of dykes who all want to get married and maybe live in singular houses with their spouse and maybe have a kid or two, and they’re all monogamous and they’re not talking about blurring any boundaries, that’s the kind of life that they want, which is just a choice, that’s fine, then you’re probably not so much going to be looking to fuck your friends after a certain point in time. Unless you’re living that kind of life and suddenly a couple of different people are like, “Hey, we actually love being married and we love being mostly monogamous and we love our kids. But hey, our pals are so hot, do you want to maybe have a foursome together? Do you want to maybe do some kind of swap situation?” Do know what I mean?

Christina: Yeah.

Drew: Mm-hmm (affirmative).

Vanessa: It’s kind of like the boundaries of where you live. Like I live in Portland, Oregon. Most people here are either actually polyamorous or they think they’re polyamorous. I’m friends with a lot of people who say things like relationship anarchy, unironically and just kind of like as part of their lives.

Christina: So brave.

Vanessa: And I’m friends with a lot of people who don’t want to get married. I’m friends with a lot of people who don’t have kids yet. And so there’s kind of like this space to almost play, I think, which has been fun for me. I maybe want to have a kid. I don’t know if I have a kid if I’m going to have that much time to be thinking about fucking my friends, but I hope I still do because I hope I’m still myself, even if I’m a mom.

Christina: Moms can fuck too is a really large part of my political platform, so.

Vanessa: I love that for you, and I love that for those moms. You know? And I love that for me one day if I decide to have a kid. So I don’t know, I think I’m a little bit getting in the weeds, but I’m kind of saying I don’t care if people don’t want to fuck their friends. That was what was so funny to me. People were deeply angry that I was like, “Hey, you can fuck your friends.” And here’s my bossy, Capricorn, control freak way of kind of trying to give you a framework to do that without confusing yourself, without confusing your friends. And hopefully to have just like a fun, sexy experience that doesn’t blur the lines or blurs them in a positive way and then you can go back to unblurring them or whatever. And people were really like, “You are telling me that I have to do this thing that I know doesn’t work. And it is an unhealthy choice.” And I was like, sounds like you’re making some unhealthy choices. I’m just trying to help you.

Christina: I just — that never even crossed my mind that that would be a reaction of yours. I did not think we were going to hop into this little recording and you were going to be like, “Well, Christina, you boring yawn of a bitch.” I did not think at all. Very interesting, the emotional baggage people bring to the things you write online for the internet.

Drew: Yeah. Wild, isn’t it?

Christina: Isn’t it wild?

Drew: Something I think about sometimes is that there are friends who I actively would want to have sex with, but who I am like it is not a smart choice based on these handful of things. And theoretically, I’m very open to having sex with most of my friends, but I, with sex in general, I think can usually come up with reasons why it shouldn’t happen, which some of those are valid and some of them I think are a little bit shame-based or something. But yeah, and what you’re saying, Vanessa, about it really working when it’s with a couple, I do think that I’m like, okay, well, if I had had sex with Gaby or Mal separate, as individuals, if they weren’t in that relationship, and we continued to have sex, what if I developed feelings in a way? I don’t know, I think — or would it have gotten messier or whatever? I’m not sure and I think sometimes that’s why I make the choices I make. The other thing is that it did happen in this very chaotic way. And I do sort of think that oftentimes… I don’t know, I’m trying to figure out, I guess this sort of goes into some of the stuff we talked about on our Best Sex Ever episode, but about the difference between like a chaotic sexual encounter versus a what you’re describing of, like, we sat down and we had tea and we talked about the pros and cons of us doing this. And “it’s my birthday and we’re all dressed up and doing cocaine and then have sex” is a more appealing narrative to me than “we drank tea and talked about our boundaries,” but obviously drinking tea and talking about your boundaries is so much better. And so I’m like, I mean, again, no judgment, but it is. It is better. And I think it’s interesting because as I sort of start to explore having romantic sex that is very discussed and boundaried and it’s incredible, I would love to bring that into my casual sex as well. Right? And to be like, oh, okay, so I used to be like, well, I don’t know if I can have these in-depth discussions about what I’m into, what my partner is into and it still feel exciting and have that energy. And I, since recording the Best Sex Ever episode, have learned that in fact it is possible and it’s even better and it’s great and everything people said about communication was real. So similarly, I do wonder about being like, oh, well maybe I would be able to get to a place of having tea with a friend and then having sex and it being really great.

Vanessa: I think the thing for me with sex with friends is it honestly feels really safe and good to me. Kind of what you were talking about with sitting down and talking about boundaries. When you say it that way, it sounds so dorky, but no shame to anyone for doing how they do anything. That’s how I like to do things. If I’m having sex with a friend, it’s usually, like we’ve talked a lot about like where our kinks overlap. And a lot of times there’s really fun specific stuff that I actually might not feel comfortable asking a stranger, a one night stand who I bring back from the bar, but I’m deeply close with this person and it doesn’t feel weird to be like, oh, you know I’m into this thing because you tease me about it all the time because we’re friends.

Drew: Right.

Christina: Yeah.

Drew: And so actually is that a place where you would like to try that? I slept with friends who are kind of getting their feet with topping and I’m a very encouraging bottom and have had great feedback from that. So it’s kind of like there’s space to play. I do feel like a lot of what I’ve been laughing about in this episode is people being mad about the concept of it. But something that I actually do want to highlight is if you’re shy about sex, if you want to try something that does feel really scary to do with a stranger, but is something that maybe could feel safer to do with a friend. If you have a new toy you want to try out. I don’t know, to me, one of the… And I’m always interested in figuring out what is friendship and what is the expansive definition of it? And where are all the places it can go and what can it do? And to me, something I’ve learned is if a friend is open to it, and not all my friends want to fuck. I famously have two deeply close friends who have been dating for eight years. And literally since the night I met them, I was like, “I’m down to fuck if you are.” And they were very sweet about it at first when we barely knew each other and they were like, “Oh, well, maybe.” And then as we got closer, they were like, “No.” And like, it’s just a thing. It’s not like I’m sexually harassing them by being like, “Do you want to sleep together?” But occasionally, like on my birthday, I was like, “Still available if you ever are.” And they were just like, “Babe, no, it’s never going to happen.” And then kind of sweetly kissed me on the lips and were like okay. And this was a birthday pre-COVID. But you know, so would I sleep with those friends? Yeah. A hundred percent. But do I understand that they’re not down and that’s not something they want to do? Yeah. And is that fine? Does it affect our friendship? No.

Christina: No, right.

Drew: Not even a little bit. Like not a once. It’s something they tease me about sometimes. Like if I’m in a particularly hot outfit, they’re like, “Oh, I see what you’re trying to do there.” And I’m like, “Well?” And they’re like, “Nope. Still, no. You’re very hot. Still no.” But I don’t know. So that to me is kind of beautiful, that even in a friendship… If someone rejects you on a dating app or rejects you at a bar, you’re kind of like, okay, that person is off to the wind. But you’re not losing your friendship because someone’s like, “Oh no, I’m not interested in that.” It’s just, I don’t know, to me, friendship is a very safe, sacred space and it’s nice to be able to fuck sometimes in that space, if both people are or all people want to.

Drew: Yeah. That makes total sense to me.

Christina: Yeah, that’s really lovely.

Vanessa: That’s my sentimental pitch for fucking your friends.

Drew: No. I think it really is true though that it can be a really safe space to explore. I think that is a real good pitch for the concept itself.

Vanessa: Thank you.

Drew: And I think sometimes you just also are so close with someone and it feels like you want to… It’s just like another way of expressing closeness and intimacy. And not that it has to manifest in every connection, obviously, but I think there is something that’s nice about, I don’t know… I do wish that even if I don’t necessarily want to have sex with all of my friends, I am like, oh, I wish I could make out with all of them. And I think a lot of people feel that more. Or like, well I make out with my friends. But yeah, it’s just interesting to think about where our lines are when it comes to physical intimacy with people who we have intense, emotional intimacy with. And it’s definitely something I think about. I don’t have anything wise to say. It’s just something that I think I’m always navigating of what are my actual desires in those relationships, et cetera, et cetera.

Christina: Yeah. I think for me, it’s also a part of thinking about, when I say friends, what do I mean? Do I mean an acquaintance? Do I mean like all of my super close best friends? How do I delineate along the line of friendship? And how does that change how I feel about sleeping with a super close friend v. a casual friend that I’ve known for a few months? That feels less gross to me than sleeping with, I don’t know, Shoshana. That would be horrid. We made out one time when we were 19 and it was disgusting. But yeah, a casual pal who I’ve known for a couple of months, there’s more space, I think, probably because that relationship is less defined for me. And also as a Taurus, I’m like, you have been put into a place in my brain and that’s where you go. So there’ll be no changing of that.

Drew: I think I’m with Vanessa in the sense that that feels more vulnerable to me. I think part of it with Gaby is that we’re so close that it did feel safe and it did feel fine. And I never had any… There was no world where, regardless of what happened, regardless of anything, that Gaby and I wouldn’t have been friends after that. And so I think with someone who I’ve known for a few months, or even people who I’ve known for longer who I’m close with, but I’m not that close with, I think I have more of a like, I don’t know how you’d react. I don’t know how I’d react. I don’t know what would happen there. And so if I’m potentially wanting something more then I’m like, yeah, sure. Why not? Let’s see what this relationship could be. And I know that I have the capacity very much where if it didn’t work out that I could like be like, okay, let’s get back to building that friendship of ours. But I wouldn’t have the same trust that they would have that. And so it’s so interesting because I have… So many of my close friends started as people who I wanted to hook up with. And a lot of them I didn’t hook up with though, but it did just turn into a friendship. And it’s like, I don’t think the attraction ever really went away, but I think it gets to a place where it’s like, well, this is either they’re just not interested at all or I’m no longer interested because that’s not what we’re doing. But then I think it can get to that next level where it’s like… I mean, even like with my friend Hirosch. We could have sex and I don’t think it would change our relationship at all. I think it would be fine. It’s just I don’t think of them that way, in the way that I think I always feel a little bit of they’re the only person who I think of a little bit differently. But I wouldn’t have any fears with that. So, there’s this little margin of intense closeness, but not the person I’ve known since elementary school, that is like, oh, I feel like that could really work out.

Christina: That’s the sweet spot for you.

Drew: Yeah.

Christina: That makes sense. Vanessa, you look like you have a closing thought, which is your right.

Vanessa: I think my closing thought is that humans are fascinating because—

Christina: That could be the subtitle of this podcast.

Vanessa: Yeah. Christina, everything you said about slotting people into places in your brain, that is so true for me too. And I think my nightmare in life is being wrong about where I’m slotted in someone’s brain. And to me that’s why fucking my friends feels so nice and easy because I’m like, great, you are my friend.

Christina: Fascinating.

Vanessa: What Drew was saying.

Drew: Ooh.

Christina: Ooh, interesting.

Vanessa: There’s no world in which you as a person are not going to be my depart friend until we die. We will probably be knitting sparkly sweaters together at the old age home when we’re 90. So if we fuck or if we don’t fuck, that’s still who we are.

Christina: Mm-hmm (affirmative).

Vanessa: Versus if I’m dating someone, if I’m having a confusing situationship, et cetera, et cetera, that’s really hard for my brain. But if you’re my friend and we happen to fuck, amazing. I also just think I’m a deeply horny person and maybe that can be my closing statement.

Drew: Okay, I have one last thing, which is just that’s so impressive to me because… Not you being horny. I mean, yes it is, but I also feel like I’m also very horny. But it’s the—

Christina: Horny pod.

Drew: If I fuck a friend, I have faith that we will still be friends, but I do not have faith that we won’t be something else in addition to friends. Fully in the middle of the Gaby and Mal stuff, I was like, “I’m bisexual, and I’m in love with both of you.” I did get to that headspace. It passed, and we went back to being friends. And I always had faith that it would pass and we would go back to being friends. But I am very anxious about not slotting people in the right place, so I like to have a little test. And I think that is part of what it is for me, being like, well I’d love to date all my friends for a few months sometime in our lives just to see if maybe that’s what it’s supposed to be. So I think what we’ve learned from this episode is that Vanessa is more clear-headed than I am.

Christina: All I keep hearing every time Drew talks is just Venus in Sag, Venus in Sag, Venus in Sag.

Vanessa: My Venus is in Sag too!

Christina: Fascinating!

Drew: Yeah. Yeah.

Christina: That is fascinating.

Drew: We’re both Capricorns with Venus’s in Sag. Vanessa’s just more evolved than me, and you have a few years on me though. And I’m getting more evolved, even just throughout this podcast.

Vanessa: Yeah. Wait, Drew, how old are you? Not to be a bitch, but how old are you?

Drew: I am 27.

Vanessa: Totally. So I’m 32.

Christina: Same.

Vanessa: And I do feel like what we’re seeing is a Caps on Venus in Sag at 27.

Drew: Great.

Vanessa: And a Caps on Venus in Sag at 32. And I think that’s beautiful.

Drew: That is really beautiful.

Christina: That really is beautiful. Speaking of things that are beautiful, crushes. You know what are beautiful? Having a crush on, sometimes, people in pop culture that is platonic or maybe is just a vibe that you’re digging. And I think we’re going to celebrate that right now. Vanessa, who are you digging on?

Vanessa: I’m so glad you asked. I texted Drew in advance of this telling her I was very nervous about the crush aspect and I put a lot of thought into it and I thought about the theme and I realized, duh, I have a crush on my friends, Christina and Drew.

Christina: Wow.

Drew: Wow.

Christina: This is actually brilliant because it’s also kind of getting ahead of our actual final question, which I’m loving.

Drew: Wow. That’s great.

Christina: That’s really beautiful.

Drew: That is really exciting.

Christina: I feel a little giggly. I feel a little toasty suddenly. I don’t know.

Vanessa: Oh my God.

Christina: Should I crack a window? What’s happening? I’m loving that. Okay, Drew. While I collect myself, who is your crush on?

Drew: Okay. So I’m doing a classic crush.

Christina: Mm-hmm (affirmative).

Drew: I’m doing an all-time crush. Someone who I think about all the time. Wait, did I do this crush already?

Christina: Maybe.

Drew: I don’t think I did.

Christina: You haven’t said it.

Drew: I don’t think I did. Did I?

Christina: Really no way to know.

Drew: If I did, you have to correct me.

Christina: You got to say it first.

Drew: My crush of the week is Katharine Hepburn.

Christina: Nope. You haven’t done that.

Drew: Okay. I guess I just was like, I must have already, we’re so many episodes in. Katharine Hepburn is just definitely one of my, “I don’t know if I want be you or be with you” people.

Christina: For sure.

Drew: It’s funny to say this because I’m always in a movie place, but I’ve been really in a movie place lately where I just feel like I’m getting into movies again, which again is a very silly thing for me to say. But, I don’t know. Last month I re-watched Bringing Up Baby with the person I’m dating. And Bringing Up Baby is just like one of my all-time favorites. And I just love Katharine Hepburn, she’s like chaotic energy, and her confidence, and the way she wears pants. And I love Katharine Hepburn, and she’s my crush of the week and my crush of my life.

Christina: That’s incredible. She wears pants really well. I’m going to give you that one. In honor of the Tony’s last night, one, Bernadette Peters showed up with her titties just sitting so high in a vintage ’80s dress. When I first saw the ethnic Cinderella, AKA the Brandy Cinderella, AKA the only Cinderella I recognize, I was struck by a lot of things in that film. But Bernadette Peters as the mean stepmother, I said, something’s happening within me at that. And it was something that I didn’t necessarily understand until much later.

Drew: Sure, sure.

Christina: But it was a very early evil mommy root for me.

Drew: Mm-hmm (affirmative).

Christina: And I’m just so glad that she is still doing all that she does. I’m so glad that she can barely move any part of her face except for her mouth. I find that actually inspirational.

Drew: Mm-hmm (affirmative).

Christina: And I just hope she’s well, every day going forward until the end of time.

Drew: Wow. That’s beautiful.

Christina: Thanks. So is Bernadette.

Drew: Yeah.

Christina: Vanessa, you want to tell our listeners where they can find you and all of your incredible work?

Vanessa: Thank you. Yeah, you can find my work on autostraddle.com. You can also find me on Twitter @vanessapamela. You can find me on Instagram @vanessatakesphotos. And you can find me at my really needs a renovation website, vanessapamela.com

Christina: We love it.

Drew: Okay. So the last thing, which, because this is your favorite podcast you know this is coming, and also now I feel a little bit flushed because we were your crushes, but was this a date?

Christina: Were we on a date?

Vanessa: I mean, how do you guys feel? Do you want it to be a date?

Drew: Oh wow. That’s such a good response.

Christina: No one ever throws it back on us, which is funny because we do throw this question at people whether they’re prepared or not for it. I think if we are going by the history of this podcast, I would be like, “No, this is not a date.” And Drew would be like, “Maybe this is a date.”

Drew: Yeah. Boom.

Christina: I’m going to be classic. But—

Drew: You got to stay on brand.

Christina: But maybe it was a date. I don’t know. You really threw me off with that crush moment.

Drew: My policy is that if something is a maybe date, then it is a date because a date isn’t a promise, it’s just an opportunity. So it’s like, if you are trying to figure it out… I’m going to say yes. I’m going to say that if the two of you went on a date it’d be very silly because you’re the two most bottomiest people I know.

Christina: Thank you.

Vanessa: I feel like if we were all in the same room and we were sitting on a couch and drinking some tea, I would be like, “If you agree that this is a date, I feel comfortable calling this a date.”

Drew: Oh.

Vanessa: But if you don’t want it to be, and you just want it to be a friend hang, that’s cool with me too. And we could go from there.

Drew: That’s really beautiful.

Vanessa: That’s because that’s how I like to communicate.

Christina: So beautiful.

Drew: Oh, you’re so good at communicating.

Christina: I think that’s really beautiful.

Vanessa: Thank you.

Christina: I just like to reflexively say no to things. So I think I’m trying to learn something from both of your energies today.

Drew: Great.

Christina: Maybe getting a little bit more comfortable in the in-between spaces. Trying.

Drew: I’m so glad. I really enjoyed this date that we went on.

Christina: Me too.

Vanessa: Me too.

Christina: I had a really lovely time. What a way to start the week.

Drew: I love it. Well, thanks so much for joining us.

Christina: Truly an honor.

Vanessa: Thank you for having me. Bye.

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 waitisthisadate@gmail.com.

Christina: Our theme is 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 @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 that’s the reason we’re all here today.

Drew: Thank you all so much and see you next week.

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

Drew: Yeah, and 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, you probably should take that as sort of 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, not really respecting someone’s boundaries. And 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: Before I came out, I dated so many straight girls who had fucked all of their friends and were like, “No, I’m straight. It’s just sometimes you get really close with people and there’s nowhere else to go, closeness-wise, except to have sex. But it was just a casual thing.” None of those people identify straight anymore. And you know what? Good for them.


Before you go! It takes funding to keep this publication by and for queer women and trans people of all genders running every day. And A+ members keep the majority of our site free for everyone. Still, 99.9% of our readers are not members. A+ membership starts at just $4/month. If you're able to, will you join A+ and keep Autostraddle here and working for everyone?

Join A+

drewgregory1224

Drew is an LA-based writer, filmmaker, and theatremaker. Her writing can be found at Bright Wall/Dark Room, Cosmopolitan UK, Refinery29, I Heart Female Directors, and, of course, Autostraddle. She is currently working on a million film and TV projects mostly about trans lesbians. Find her on Twitter and Instagram @draw_gregory.

Drew has written 206 articles for us.

3 Comments

    • i am SO sorry this took so many weeks to respond to, i literally didn’t remember what brand it was and kept making a mental note to get it out my closet and look at the tag but then obviously kept forgetting, ANYWAY it’s the Panache Envy bra! i love it, 11/10 would recommend. so glad you loved the episode also, thank you for listening and for complimenting my bra! <3

Contribute to the conversation...

Yay! You've decided to leave a comment. That's fantastic. Please keep in mind that comments are moderated by the guidelines laid out in our comment policy. Let's have a personal and meaningful conversation and thanks for stopping by!