“Wait, Is This a Date?” Podcast Episode 105: Best Sex Ever

Our episode topic this week is Best Sex Ever so we are talking about… the best sex we’ve ever had! We’re joined by Autostraddle writer, poet, and journalist Dani Janae as we get into some steamy anecdotes followed by an in-depth discussion about what makes good sex good. And we spend a lot of time on my sexual hang ups that I may or may not have actually done a lot of work on this summer!

Come for the lesbian movie-themed game, stay for the coming.

SHOW NOTES

+ The 200 Best Lesbian+ Movies list that Christina pulled the game from.

+ If you haven’t read Dani’s Anatomy of a Mango series you really must.

+ This is the essay I wrote about the person I talk about on the episode. It’s only been two years but so much has changed!

+ The summer has passed and we still stan Olivia Rodrigo. Watch the “Brutal” music video.


Dani: The cat and the dog were in the room and there was cat and dog hair everywhere. And so, I was definitely having an allergic reaction while we were having sex. But the orgasm was like chef’s kiss. It was the perfect, perfect experience physically.

Christina: I wonder if it’s something about the hives that really added a little je ne sais quoi to that orgasmic experience.

Theme song plays

Drew: Welcome to Wait, Is This a Date?

Christina: Wait, Is This a Date? is an Autostraddle podcast all about, you guessed it, dating.

Drew: Yay! I love dating. I’m Drew Gregory. I’m a writer for Autostraddle, and a filmmaker, and just general trans gay person around the internet and… I was going to say world, but it’s really more like Los Angeles and New York.

Christina: I love this globe trotting gay personality you’re taking on right here in 2021.

Drew: I want that. Yeah, it’s for the future.

Christina: Yeah. I am your other host, Christina Tucker, also a writer for Autostraddle, deranged loud gay on the internet. Just kind of out here, writing, being gay, doing what we can every minute to try to work through this life that we’re living.

Drew: You’re really doing it. You’re really working through that life.

Christina: Frankly, it’s all I can do. That’s all I have, it’s the only option.

Drew: I really respect the attempt.

Christina: The attempt to live?

Drew: Yeah.

Christina: Yeah. Actually, really brave of me to even attempt it. You’re not wrong, you are not wrong. Would you be interested in playing a little game today, Drew?

Drew: Oh my God, I’m so excited. Can’t wait to see what you have for me.

Christina: I’m so glad you said that because you absolutely have to say yes, because that’s part of this deal that we’ve created here. So you might be familiar with the fact that on autostraddle.com, the website, we have a list of 200 lesbian movies.

Drew: I am aware of it. I may have written it.

Christina: You may have. What I have done is pull a selection of 10 of those films. I’ve kept them to the top 50. I’m going to give you the plot keywords as decided by users on IMDb and you are going to have to guess what movie it is.

Drew: Okay. I just want the listeners, wherever you are, to know that I am not going to pull up the list. I think that’s right, am I assuming that’s correct in how I should be respecting this game?

Christina: I think that’s very respectful and I think that’s fair. I also kind of trust that this is going be something that comes to mind pretty easy for you, I didn’t go too left.

Drew: I have a terrible memory, but yes, I’m going to try to set people up for low expectations.

Christina: Fair enough.

Drew: So if I do really well, it’s like kind of blow them away, and if I don’t do well, they’ll be like, “Well, she mentioned…” Anyways, continue. Let’s start this.

Christina: Let’s start. I will start with pretty general ones and I will get more specific as we go, because some of them are literally just what the movie is in two words. So we’re going to try to start with a wider experience here.

Drew: I love it.

Christina: Our first film: drugs is the first plot word. Manhattan, New York City is the second. Hate crime is the third.

Drew: Okay. It’s All Over Me.

Christina: Yes, it is! See, I knew you would be able to do this.

Drew: Great.

Christina: I absolutely knew you’d be able to do this.

Drew: Also, I just need to let people know that that is one of the most underrated lesbian movies, and you really need to see it. And Leisha Hailey in that movie has been my phone background for a couple years now. So just a fun little fact there for all of you.

Christina: We love that. All right, movie number two. “Unknown father,” organ donor, cemetery, death of son. Oh, she’s thinking.

Drew: I feel like I should definitely get this based on — wait, unknown father, death of son, organ donor. Oh, All About My Mother.

Christina: There it is, see.

Drew: Another one of my favorites.

Christina: It’s very thrilling to see the things that people decide are a plot keyword that they need to pull from these films. I’m also not reading any of the ones that are just lesbian because that seems kind of like a gimme.

Drew: That’s how I put together a lot of the list because if you look up lesbian movies, what you found was the old Autostraddle list or some lists that aren’t very thorough, so I would actually scroll through lists of the keywords of lesbian, lesbian kissing, these things like girls kissing, these things, in order to find movies where they’re maybe not thought of as a lesbian movie because they’re a little bit more interesting, or just a little bit less direct, and that’s how I found some of the movies that are now on the list, so full circle.

Christina: Listen, IMDb keywords coming in handy for everybody all the time. This one, people went wild on this one. So just going to read some random words to you. Hey, whistling, girl, black sports bra, river, stomping out a cigarette, on the job accident.

Drew: On the job accident? Oh, I thought I had it and then, well—

Christina: Cold, in parentheses, the temperature.

Drew: Because initially I was going to say Foxfire, but then the on the job accident switched me up. On the job accident.

Christina: Do you want some more?

Drew: Yeah.

Christina: Pickup truck crashes through a fence.

Drew: Is it Miseducation of Cameron Post?

Christina: It is not.

Drew: Because on the job accident would be a really awful way of describing that one of the gay because you’re trying to convert to not gayness, tries to mutilate themselves or does mutilate themselves. That’d be pretty intense, but I didn’t know with the IMDb thinkers. Okay, wait, this is tricking me up.

Christina: Do you want some more from me?

Drew: Truck through a fence. I’m sure it’s something that I’m just not… Yeah, keep going.

Christina: Reference to a school loan. These are so nuts.

Drew: Wait, have you seen this movie?

Christina: I have seen this movie.

Drew: Is it wild that I’m not getting it?

Christina: It’s a little wild. I can give you a year, if you want a year.

Drew: If you give me a year, I’ll definitely get it.

Christina: Okay. 2016 is your year.

Drew: 2016. Okay, tell me what it is.

Christina: It is the film, Certain Women, 2016.

Drew: Oh! Yeah.

Christina: I really thought pickup truck crashes through a fence would get you, but I also just love these people just pulling out nouns and just being like, “male.” Is that what you think?

Drew: Yeah.

Christina: Okay.

Drew: That’s a great movie. I need to see that again.

Christina: It is. It’s a great movie.

Drew: Yeah, it’s a really great movie.

Christina: All right, our next film. Kissing while having sex.

Drew: The best kind of both, maybe, you might say.

Christina: Seduction, dude ranch.

Drew: Is it Desert Hearts?

Christina: Yeah. So I was like, “Okay, you got to get that after that one.” The other one I was going to give you was — “nipples” was the really prominently featured. And I was like, “Sure, that is part of that film.”

Drew: God, Desert Hearts. You know how there’s all these annoying people out there trying to be Shane. Sorry, I mean, if you’re trying to be Shane, I accept you. But me, my annoying thing is that I’m trying to be Cay. Cay in that movie is like that is who I think of as the kind of lesbian that I want to be.

Christina: Yeah, that’s true, can confirm. All right, are we ready for our next one?

Drew: Yeah.

Christina: Year—

Drew: Wait, no, I have one more thing to say about Desert Hearts.

Christina: Sure.

Drew: After the last time I re-watched it over the summer, it sort of sent me into a slight spiral, and I texted this older semi-closeted person who I had sort of started tentatively wanting to date or date whatever, and who had disappeared for a month, and I had given up on because I don’t beg people to date me. But I just was like, “Okay.” I watched Desert Hearts and I was like, “I guess maybe sometimes people have their internalized whatever.” And I texted her and I said, “If we never meet, I think you’re going to regret it.” And we did meet, so that’s what Desert Hearts can do to you.

Christina: Wow, that’s a really powerful endorsement.

Drew: We probably shouldn’t have met. I probably should have just let it be. But anyways, moving on, next movie.

Christina: Our next film, metaphysics, scene during opening credits — what that means, it’s up to you — high school soccer, Chicago, Illinois.

Drew: Oh, Princess Cyd.

Christina: There you go.

Drew: That’s another great movie. I like that I keep being surprised by this list that I had a very strong hand in ranking. It’s not my ranking, but I did have a big say in the ranking and I love it.

Christina: Yeah. I just want to be clear to you and our listeners — again, I picked from the top 50, so these are really good ones. Of the good ones, these are good ones. I know Drew’s going to continually say this is a great movie after every one, but—

Drew: They’re really good movies, you guys should watch them.

Christina: All right. Short skirt with heels.

Drew: Love it.

Christina: Cock blocked, mini skirt with boots.

Drew: I mean, is it Blockers?

Christina: It is not. That would be too easy, I think, for Blockers.

Drew: I don’t remember any miniskirts, but—

Christina: Female rear nudity.

Drew: Okay. Wait a second. Okay, what a second. Okay, cock blocked, mini skirt, female rear nudity.

Christina: Mm-hmm (affirmative). Break dance.

Drew: Is it Bound?

Christina: It’s not.

Drew: No, I would love a break dancing scene.

Christina: I love a break dancing scene in Bound.

Drew: A break dancing scene.

Christina: I’m going to give you: English woman abroad.

Drew: English woman abroad? This is another one where I feel I definitely should get it.

Christina: I’m going to have to give you a pretty obvious one at some point, so that’s going to help.

Drew: Okay, give me an obvious one.

Christina: Undercover agent.

Drew: Is it D.E.B.S?

Christina: It is not D.E.B.S. It’s adjacent to D.E.B.S., type of film wise. Here’s another one, intrigue.

Drew: Okay, wait, there’s not that many genre movies.

Christina: There aren’t, that is true.

Drew: Undercover agent. Well, maybe they’re using the term, is it The Handmaiden?

Christina: It is not.

Drew: Okay, I didn’t think so. Undercover agent.

Christina: Do you want your year?

Drew: I thought that… Sure.

Christina: Your year is 2017.

Drew: Undercover agent.

Christina: I’m so sorry. You’re going to feel so dumb when I say the title of this one.

Drew: Oh no.

Christina: I’m really sorry about that, but that’s kind of just the way the cookie crumbles.

Drew: Oh, it’s Carol.

Christina: No, it’s not Carol.

Drew: No, it says 2015.

Christina: Yes, I know that. It’s not Carol.

Drew: But there’s an undercover — the guy, that’s where I was thinking. Okay, what is it? Why does it make me feel stupid?

Christina: It’s Atomic Blonde, you dummy.

Drew: Oh, that’s in the top 50?

Christina: It is. I know.

Drew: Oh, okay.

Christina: All right. We’ve got four more, you ready?

Drew: I don’t feel that stupid because that one I… I mean, I think Atomic Blonde is fun, but I don’t think it’s great. That would not be in my personal top 50. I do want the world to know that I know that Carol came out in 2015. My brain hurt. I just want the world to know that. Anyways, continue.

Christina: The world now knows that, the record has been reflected. All righty: restaurant, sense of smell, novelist, reference to a hamburger, reference to Larry King, based on memoir, alcoholic, theft, woman wears eyeglasses, living alone, destroying evidence.

Drew: The reference to Larry King is really—

Christina: It’s a really weird one.

Drew: Reference to Larry King, destroying evidence.

Christina: Cat.

Drew: Oh, is it Can You Ever Forgive Me?

Christina: It is.

Drew: I needed to redeem myself. I was really in a slump there.

Christina: You nailed it. I think you got there, I think you absolutely got there. All right, three more, our top three. I think these ones will be easy for you because I know you.

Drew: Great, okay, well…

Christina: I know, but I’m saying, are you ready?

Drew: Okay, yeah.

Christina: Mental health, drug overdose.

Drew: Is it Foxfire?

Christina: No. Photographer.

Drew: Oh, Higher.

Christina: There we go. Tattoo, girl gang.

Drew: Is this Foxfire?

Christina: Yeah.

Drew: Oh, I know Foxfire.

Christina: I was like, “Oh, she’s going to just keep guessing Foxfire until I just give her Foxfire.”

Drew: The secret is that I love Foxfire and I keep wanting to think about Foxfire.

Christina: I mean, whomst among us?

Drew: Angelina Jolie, gosh.

Christina: All right. This one, one of them is—

Drew: This is the last one?

Christina:This is the last one. This is our last one. Church, denial, family relationships.

Drew: Is it Miseducation of Cameron Post?

Christina: It’s not.

Drew: Is it But I’m a Cheerleader?

Christina: It is, yes.

Drew: Yes. Comedic Miseducation of Cameron Post.

Christina: Jokes on jokes. So that was the game I’m calling, How Well Does Drew Know Lesbian Movies???

Drew: I love how good we are coming up with names for our games.

Christina: Yeah, it’s actually mortifying that I even wrote that in the title of a Google Doc, what was I thinking? That doesn’t even look good in my Google Docs.

Drew: I had a great time and I’m really glad that I got to tell all the listeners about all the movies that they should watch. And we’ll put the list in the show notes.

Christina: Absolutely.

Drew: I would say that the list is now at a place where I think you would get something out of watching all 200 movies. The first version of the list, there was some stuff on there that I was not too pleased with. There still is stuff that I think that I don’t personally but I think that as a whole, there’s a certain quality control after this most recent update that I feel very pleased with and I think they’re all worth seeing.

Christina: Our main topic today is about the best sex ever. And we had to bring in just an absolute fountain of knowledge on this front. We had to bring in the person we knew who would come in and say, “Listen up, I got tales to tell, I got stories, I got thoughts, I got opinions.” And that person is our dear friend, Dani. Would you like to introduce yourself to the listeners at home?

Dani: Hi, my name’s Dani Janae. I am a writer at Autostraddle. I’m a poet. I’m also a journalist now, which is a new title that I’ve added to my resume.

Christina: We love that.

Dani: Yeah, I’m a writer, that’s what I do.

Christina: And here we all are to talk about the best sex ever.

Dani: Yes.

Drew: Yeah. Maybe let’s start with that. Then, do you feel, as a writer, because I know that you write about sex, have written about sex, do you feel like you are more inclined to write about sex that is really, really good or sex that is maybe complicated and not as good?

Christina: That’s a good question.

Dani: That is a really good question. I think that I tend to write about sex that is really, really good.

Drew: We love that.

Dani: Yeah. I tend to write about sex that is stamped in my memory as like, “Oh, that was fucking awesome.” But also there are sex stories that I have written that are also complicated and have layers to them, you know? But I definitely lean toward trying to emphasize the positive sexual experiences.

Drew: Yeah. I mean, I guess also those things don’t have to be mutually exclusive. Thinking about some of my best sexual experiences, some of them were really good physically and complicated emotionally, or maybe vice versa, but I don’t know, maybe for all of us, I’m curious… Well, first of all, when someone says best sex ever, is there a person or an experience that you immediately think about?

Dani: Yeah, totally.

Christina: Oh, that rocks. See, I was like, I got there and I do think it is true, what I was thinking, but it didn’t come immediately to mind, it wasn’t like, “Oh yeah, I think about that specific sex I had all the time.” But when I was given this prompt by us creating this podcast and thus this episode of this podcast, I was like, “Oh no, that would be it.” I felt part of me was like, “Is it it? If it doesn’t hit that hard, can you really say that that is the best sex ever?” If it’s not immediate, can you just be out here calling any sex you find on the corner, the best sex ever? I don’t know, maybe you can.

Drew: I would love to know what you eventually came up with, but first, Dani, you obviously can get into as many or as few details as you feel comfortable sharing. But I would love for you to give us a little bit of info about that automatic, yes, this was the best sex ever.

Christina: Yes, automatic, impressive.

Dani: Yeah. Well, I have two experiences that I would say are tied for the best sex ever.

Christina: Okay. Brag, absolute, incredible.

Dani: Yeah, so the first one was, unfortunately, with my ex that I do not talk to anymore which is complicated, but I remember it so vividly, it was the second date. First date we had already hooked up and it was fine, but the second date was mind blowing. We had gone to this tea shop that she worked at as a tea specialist, and had tea, and all this sexual tension. And then we went back to her place and just had really intense, passionate sex that was really new for me because I always identifed as a hoe. So I had a lot of sexual partners that I was a top and I wasn’t really letting them touch me, and all that sort of stuff. So this was the first time that I was really being vulnerable in a sexual way with somebody, and letting them pleasure me, so it was just super intense.

Christina: Yeah, that tracks.

Dani: The second one was with the person that I hooked up with after I broke up with that woman. And this person was someone that I liked but I was definitely putting them on the back burner, waiting for somebody else to text me back. And they just totally rocked it out and changed my mind about this other person. And that was one of the sex stories that I tell a lot because it was so wild of like — I went over to their house to hang out and I wasn’t expecting anything, I was just expecting to have a chill time, so I had dressed kind of sloppily and was not really in the mood. And then a bunch of little things happened that were like, “Are we going to fuck now?” And then I finally asked like, “Did you invite me over here to have sex? Are we going to have sex?” And they were like, “Yeah, that’s what I wanted to happen.” And it was like, the cat and the dog were in the room, and there was cat and dog hair everywhere. And so, I was definitely having an allergic reaction while we were having sex, but the orgasm was like chef’s kiss. It was the perfect experience physically.

Christina: I wonder if it’s something about the hives that really added a little je ne sais quoi to that orgasm experience. Just like, “Ooh, I’m a little itchy also.” I wonder how much that factored in.

Dani: Yeah, exactly.

Drew: I love the range of those experiences of one is like, “Oh, we were having tea and there was sexual tension that was building up.” And you’re like, “Yeah, that led to the best sex ever.” And then you have, “There was dog hair everywhere, I was having an allergic reaction, I wasn’t expecting it, and that also was the best sex ever.” I really love that range. Okay, Christina, your turn.

Christina: Yeah. So when I was thinking about it, I realized that it was the first woman who I ever went on a date with. We had gone on four dates, we had a good chemistry but nothing to talk about. Even on our first date, I was like, “Our chemistry is good, but what’s happening here? Don’t know, don’t necessarily care for it.” And then she was busy or had some emotional thing that she wasn’t done with. And I was like, “Fine, whatever.” This was in the summertime. And then it was months later, because it was between the week of Christmas and New Year when I worked in Academia and I would get that week off so I could do truly whatever I wanted. And I ended up at my favorite bar, bartenders’ pouring big old gulps of whiskey. And I was like, “What if I just shoot her a text?” And I just texted her and said, “I’m still mad we never had sex.” And she said, “What are you doing now?” And I said, “Nothing.” And I immediately dipped from my friend in the bar, hopped into an Uber that was in fact not an Uber. Well, I tried to get into a car that was not an Uber, just a woman at a stoplight. She was like, “Ma’am, please stop.”

Drew: “I need to have the best sex in my life!”

Christina: I went back to her apartment in some weird neighborhood in Boston that I had never been in, and was like, “Oh, this is incredible sex, this is incredible sex.” Also, I’m going to die because the next morning I was so hungover, I could not see, and I woke up in Charlestown or somewhere absolutely on the opposite side of the earth from where I lived. But the sex was incredible despite the fact that we still, even in the two seconds of pretense, chit chat conversation, I was like, “We have nothing to talk about, why are we doing this?” I was very clear in my text. “Why are we doing this?” Good sex though? Good for her, hope she’s well. Drew, it’s your turn.

Drew: No, I guess it would be my turn. Yeah. So I was thinking about this and I do think that I can’t answer it any other way, but this person who I met at this concert, and I was already pretty drunk, and it was just this whirlwind of she was from Brazil, and was there with a bunch of Brazilian friends, and they were all speaking Portuguese, and I was just very much like, “I have no idea what’s going on.” And then she was inviting me along with her friends and then said something to her friend… It’s so interesting to… Anyways, okay. I’m just going to tell the story, honestly. I mean, I think I already wrote about this.

Christina: I was going to say you’ve written about this experience.

Drew: I know. I don’t know why I’m feeling weird about it. I think because when I wrote about it, I’ve done a lot of work on myself since 2019 and I’m really proud of that work. So basically what happened was she misgendered me to her friend and I was like, “Oh God, I’m so stupid, this person who was complimenting me.” I thought it was that she was flirting with me, but really she saw me as a flamboyant, she’s like, “Ooh, fun, flamboyant, queer guy.” So I was like, “Oh God.” So I was like, “I’m a woman.” And she was like, “Oh.” And I was like, “I’m a gay woman.” And she was, “Oh, so you’re into girls.” And I was “Yeah.” And she was “Great.” And then she started making out with me.

Christina: Incredible turnaround time.

Drew: I think there was something about the like, “I don’t care.” And she then went on to respect my… she wasn’t misgendering me moving forward, but the idea of like, “I don’t care what gender you are, I just think you’re hot and I want you.” There is something about that that I’m into, and what’s interesting — so then we got into an Uber and I have — someone, on the essay that I wrote this, got mad at me for having sex in the back of an Uber, but I didn’t plan to. I’m not this person generally speaking, but we were just still making out. And her friends were next to us, and I was sitting on her lap because we were all squished into this Uber, and she… So I don’t really know the languages I would use. I would say that usually I’m a top and am very focused on… I’m not stone, I’m still figuring some things out.

Christina: We love that, everyone’s on a journey.

Drew: Yeah. I just usually focus on my partner’s pleasure more than my own. And this is really the only time that that was switched. And she touched my genitalia in a way that to me felt so gender euphoric. I felt I was being fingered and I don’t understand really what she was doing. She just unzipped my pants and whatever, however she was moving her hand, I just felt. I don’t know if it’s because we were in an Uber and I was so not expecting it. I think what can often happen is my dysphoria will be heightened by me thinking, being very conscious, and because I was so not expecting any of this, I just didn’t have a chance to have anything but it feel good. So anyways, I fully had an orgasm in the back of the Uber and then—

Christina: We love to see that, yes.

Drew: I don’t want people to feel bad. I hate the idea that someone would be like, “Oh, poor trans woman who can’t…” I like my sex life, I am trying to figure out how to make it better. But I have cum during sex, but oh, I’ll make myself cum while I’m having sex with someone else because it’s like I can tell they want me to cum. That’s the only time that someone has made me cum.

Christina: Taken the reins and done it.

Drew: And just done something that is — they made me cum. And yeah, it was in the back of Uber. But so we get to this West Hollywood gay bar, and are hooking up, and then we eventually go back to my place and have all sorts of sex. And I guess it’s just so interesting to think about top, bottom dynamics. I feel like the whole evening was so switchy, I still felt in control and then she would take control in these random moments. I don’t know. I let her fuck me, which I never… I’ve let my ex-girlfriend do that, I felt so free with her and we barely talked… And we hooked up one more time or two more times later in the summer. And one time was, again, in public, it was like in a bathroom stall at another West Hollywood gay bar. It was all so chaotic. And I think, I feel a little bit insecure about the fact that that was unequivocally the best sex of my life, all of that, all of the sex that I had with this person. I would love to be able to have sex that felt that good and I felt that comfortable when I also have the vulnerability of… I mean, the first time we had sex, I didn’t even have her social media, or her phone number, or anything, I knew nothing.

Christina: That’s kind of fun.

Drew: I know. And I don’t think that there’s any shame in that or anything but I just… I mean, when I think of other good sex that I’ve had, so much of it is, like, I had this one night stand the last time I visited New York, that was so good. And I’m like, it was because I met — I mean, that, we actually spent the evening getting to know each other and that was like more of a little, I don’t know, link later-esque romantic evening, but I still didn’t really know that person. And the first time that I had really connected good sex with another trans woman, we matched on a dating app and I went that day and I went over. It was so immediate, I didn’t know her and it was really good as opposed to the first person, a trans woman who I had sex with, we were talking a little bit on a dating app and then we went out on a real date. I feel insecure about the fact that I have not had incredible sex with someone who I have an emotional connection with. I’ve developed emotional connections with people who I’ve had good sex with, but yeah, I don’t know, that’s something that I’m thinking about.

Christina: I was wondering that, because as your co-host, I know, and also as your friend, I know that you do like to have that emotional connection, and that emotional connection is very important to you. And listeners if you recall our episode about sexting, you were talking about how you don’t like sexting people that you haven’t actually had sex with in person.

Drew: None of it makes sense.

Christina: And what I see you doing is a little bit of like, “Wait, why did I like this thing that I say that I don’t like so much, but I really liked it in these moments?” I don’t know.

Drew: Yeah, I don’t have an answer.

Christina: You don’t have an answer. Sometimes we’re just weird, sometimes we just like the shit we like.

Drew: So I actually talked to my therapist about this fairly recently where I was talking about how I like fucking my friends and I like having like, “Oh, I’m at a bar, and I meet someone, and I wasn’t expecting to hook up with someone, and all of a sudden, I’m having this whirlwind sexual experience.” And what I feel deeply uncomfortable with is sexual experiences where it’s like, “Oh, we’ve been on a couple of dates and now it’s time that we’re going to have sex.” Or that sort of — there’s some intimacy established, but we don’t feel totally comfortable with each other. And what I realized is it’s because… Or even like, “Oh, I’ve hooked up with this person and it’s going to stay casual, but now we’re going to hook up again.” But we’re not really friends, we can hook up once in a while. And I think the thing is that then it becomes about sex. Whereas if you have a random hookup at a bar, or if you hook up with your friend, it is chaos. It’s about the chaos or with a friend it’s about the intimacy. It’s about like, “Oh, we have a friendship and I guess we’re going to cross this line.” And that’s interesting and fun, and there’s chaos there, but there’s also an intimacy and a trust there. And with someone out at a club, it’s like, “I never have to talk to you. I don’t even know you.” It’s so nothing and it’s so like what’s happening? And again, it pulls me out of my head as opposed to like, “Oh, I am meeting up with this person from this dating app where we are going to go on a date and then we might have sex tonight.” It’s so much about the sex and I get so in my head about it, and I think it makes it so I can’t enjoy myself, or I can enjoy myself, but I can only enjoy myself when I’m focusing on them. And then I’m enjoying making them feel good and making the date be… I’m focused on doing a good job. I’m focused on making them feel like, “Oh, it was good that I went out on this date, and this is a good date, and good success.”

Christina: This “absolute pleasure to have in class” ass comment over here.

Drew: Yeah, I know.

Christina: Dani, where do you see intimacy, chaos, are you like, “I see this pattern where maybe the sex I’ve had leads towards more chaotic experiences that I’m like oh, maybe that’s what I enjoy.” Or is it like, “Maybe there’s a more intimacy route.” Or you’re just kind of like, “Hey, maybe all sex can be good and all sex can be weird, and that’s kind of just the way the cookie crumbles?”

Dani: Yeah, I think that most of my sexual experiences have been with complete strangers that I met on dating apps. And maybe we’ve been talking for like 15 minutes, maybe we’ve been talking for like a couple of days, but usually in those experiences, I’m very toppy, and like Drew said, very focused on the other person’s pleasure. And I find those experiences fun, still. I still have a good time even if I’m not having an orgasm, I still think that they are valuable sexual experiences. The first time I ever had intimate sex with somebody that I was in a relationship with, it sort of just blew my mind in a way, because I was having a sustained emotional relationship with that person and I didn’t expect that sex would be better or different in that sort of environment, but it definitely was for me. Like I said, I was able to let my guard down and be pleasured, and let other people touch me for the first time. And that was a really big deal. But also, I think I just love sex in any form, which sounds like, duh. But yeah, I think I just prefer to be the person that’s giving the pleasure, and being the one that has this in-control sort of role in the sexual relationship. Yeah, for me it’s all about whatever feels good in my body.

Christina: Yeah. I think that can be really hard to predict what we’re going to think feels good on our body on any given day, that is something that can change. So of course, there are days the kinds of sex that I think are great change over time because of my relationship to my body, how I feel at any given moment also changes. So sometimes in retrospect I’m like, “Oh, that was really good.” While in the moment I felt like, “This was fine.” But maybe with the gift of hindsight, I’m like, “Oh, actually that was a little better than I gave it credit for.”

Dani: Totally.

Drew: Can I ask you a question as a bottom?

Christina: Oh, me? Yeah.

Drew: Yes.

Christina: Hello.

Drew: No, as Christina, resident—

Christina: Famous bottom, hello.

Dani: Famous bottom.

Drew: Yeah. The best sex that you’ve had, either one story you told or just good sex that you’ve had in general, do you feel part of that being good has been you feeling comfortable in communicating to the person what you wanted or was it that they were taking control and you truly were able to forget about figuring out what she wanted and that you just were able to sort of give yourself over to them?

Christina: I think it’s a little bit of both. I think in the story that I told, I had had sex with another woman before that, a couple of them before that, and it was fine, but this did feel very much like someone being like, “Can you just shut up and don’t talk? Can you just shut up and just… you’re going to be fine, I’m going to take care of this.” Which was great, love that energy, love to be taken care of. But I do think, especially in more relationship settings, I do think there is a place for having that ability to communicate and feeling comfortable in that communication, but I don’t know. I do think part of my gut reaction to be like, “Oh, the best sex I’ve had is the sex where I don’t have to do all of the work of communicating.” Because famously, I’m a bottom and I don’t like doing work. It’s just not my ministry, I don’t like doing that, it’s not for me, which is complicated because obviously communication is really important in sex, and as is all of the things that we love that come with communication, consent, all of those good things. Sometimes I’m just like, “I don’t know, I’ll just figure it out. I’m so tired.” The silence of two tops like… Mmm, that sounds interesting.

Drew: But no, but I get it. It’s just so interesting because I don’t know—

Christina: And in fairness, I know Drew has a complicated relationship with her top identity, so I just want to put that on the record. I want that in there.

Drew: Thank you.

Christina: I know that.

Drew: Thanks. Yeah, the listener can’t tell that.

Christina: Yeah, I know.

Drew: Well, I’ve had friends be like, “You’re not a top, you’re a bottom who just hasn’t figured their shit out yet.” And so, there was a period of time in 2019, especially after this experience with this one person, where I was like… I mean, I’ve read about this in this essay I wrote about her, where I talk about how after that experience, I was like, “I’m going to be a bottom now, I’m going to find someone who is a very vocal top and have sex with that person.” And I did and it didn’t go well. And I actually feel pretty badly about just… I mean, I don’t think I did anything wrong per se, I just think that it was probably pretty exhausting for them. And probably, as far as like, “Oh, I did a good job, it was worth going out with me.” I don’t think that person left our two encounters feeling that way. I think they left feeling like, “This kid needs to figure her shit out.” I was like, “Why am I forcing that?” Dani, I agree with you where I’ve had some sexual experiences where like yeah, I didn’t cum, it wasn’t focused on me, but I really enjoyed being intimate with that person. And I don’t know, I don’t think that’s inherently worse, I don’t think there’s anything worse about that. I do think there are people who would maybe have had the experiences I’ve had and feel totally satisfied. The reason why I’m dissatisfied is simply because I am dissatisfied, because I have had these hints at these other experiences where I’m like “Oh, I would also like to have that sometimes.” I would also like to have that be a part of what sex looks like to me, but I don’t know. Some of my best sexual experiences haven’t even really been sex, or at least not sex in the way that most people would define it. I don’t know, my 21st birthday hooking up with my… I’m probably not supposed to talk about this. Hooking up with this person who we just made out all night, and teased towards other things but then… No one’s going to listen to this podcast. It was a friend of my sisters and I swore that I would never repeat it, but now it has been so many years that I think — I’m a new gender, I think we’re all fine. But it just was such a sweet, intimate… I don’t know, before I came out, sex to me when I had penetrative sex, I was disassociating. And so, that night I wasn’t because my genitalia wasn’t involved for reasons other than transness. And so, when I think about the best sex I had before transitioning, that was it. But it wasn’t sex, we just felt like making out and had our shirts off, but it was sexual, and it was intimate, and nice, and I don’t know. So I don’t know, I feel complicated about that, because when I said before, that was the only time that I’ve ever had an or someone had given me an orgasm. I mean, for years, I was trying to be a guy, and was having penetrative sex, and I was having orgasms, but I wasn’t enjoying them. And it was more of a biological need/doing what I was to do/it does feel good, but it just is really complicated. So yeah, I think it was really hard for me with my ex once I transitioned to also to transition our sex life. I think it was something we both struggled with, but I definitely would take responsibility for that, of trusting the experimentation or the switching things up that she wanted to do it, rather than she had to do it. I think I was really insecure about that. I mean, it’s so interesting to think about. I mean, I’ve been out of the closet for over four years now, but I really didn’t start exploring the truth of my sexuality until spring of 2019. And then a year plus of that has been in a pandemic where the only people I fucked were my roommates, which was its own exploration and got to try some things with people I feel really comfortable with. But for the most part, I don’t know, that made me feel more confident that I was a top, hooking up with my roommates. Because that was also the first time that I got to top using a strap-on, and that felt great. And I was like, “This is what I want to do.” That felt very good to me. And I was like, “I’m into this.” And so, I don’t know, I mean, now that things are opening up and the world is whatever, who knows where I’ll end up? Anyways, yeah.

Christina: Yeah. Drew, I was wondering what is figuring out if you’re a top or bottom going to really do for you in the end?

Drew: Oh, nothing. I mean, that’s the thing, is for a while there, I let it go. I was really sort of comfortable letting go. But I think for me owning that identity at a certain point was me accepting that if I didn’t want to be penetrated or if I didn’t want someone to touch my genitalia, that that didn’t negate the sexual experience. I could sort of be like, “No, I was topping.” Not that people can’t top and have… Obviously, all these words are very fluid and, I mean, I think labels are as good as what they serve. Being a top is not something that I cling to, it is something that I’m very… I would still probably identify as a top-leaning switch and, I mean, it’s not something that I care that much about. I just think that it probably is an accurate descriptor and helpful in the sense of just me… As I work towards feeling more pleasure and experience — I just think the sexual experiences can provide different things. And maybe I only feel comfortable having certain experiences with certain people, and with other people I want to have a different thing. So maybe if I meet up with someone from a dating app who I’ve been chatting for a little bit, the first times we have sex, I do just want to top them in a way where my genitalia isn’t involved, whatever. And that is okay and that still can be like, I don’t have to be frustrated with myself. I think for a while there I was feeling very much like, “I need to solve this. I need to fix this. How do I fix my broken self?” And getting to a place of being like, “No.” It’s like, “Did you enjoy that experience? Did you enjoy being…” And usually, it’ll be like, “Yeah.” And the sexual experiences that I didn’t enjoy was when I pushed myself, was when I was having sex with someone, wasn’t into them — not wasn’t into them, but wasn’t into doing a certain — or maybe wasn’t into them — or wasn’t into doing whatever act that I felt like I needed to do, and that is actually what was leading to the experiences that were making me feel bad. And that I needed to be easier on myself as far as… There are places where I feel safe to experiment and there are places where it’s like, “No, we’re just going to fall back on old tricks.” I’m like, “That’s okay because you’re just hooking up with this random person and that’s fine.”

Christina: Yeah.

Dani: But where does kink and all that stuff come in for you for sex? Do you remember your first times exploring those parameters with another person?

Christina: That is an excellent question. No, I don’t think kink has come into my life a ton, not because I am not interested, but I think because as the resident non-dater of this dating podcast, I don’t put myself in a position to have those experiences very often. But it is definitely, I think, coming out of this Paul Blart, Mall Cop, it’s on the docket of things, it’s like on the docket of experiences that I’m like, “All right, we’re going to have to enter a new world, we’re going to enter the world again, everybody’s going to get jabbed and do some weird shit, let’s be a little more open to new experiences” than perhaps I have been in the past, because my other reaction usually is like, “No, I’m all set. Actually, I’m going home. I don’t want to have any conversations that I’m not ready for. I wasn’t actually prepared for this. I have to go. I got to go right now.” So I’m trying to do less reactionary “no” and actually allow myself a second to, like — but maybe you would actually enjoy something different than what you assume that you would enjoy. So I think TBD on kink for me.

Drew: I’m excited to see where that goes for you.

Christina: It could go crazy, who can say?

Drew: For me, I think it’s — unsurprising, based on everything I’ve said — I think a lot of it’s been based on what my partner is into and I’m pretty open, but I think for the most part it’s been guided by what my partner is interested in and then I’m like, “Yeah, I can totally do that.” What about you, Dani?

Christina: Yeah, what’s your origin story there?

Dani: Yeah, I think that I’m very similar to Drew in that way of like… The first time that I had ever started having sex that I would describe as kinky was with this woman that I met while I was doing AmeriCorps.

Christina: Love that.

Dani: We were doing that together and she would just ask me to do things to her. And I was like, “Well, I want you to have a good time and I want you to feel like this sexual experience has been fulfilling for you, even if this is something that I’ve never done before, I’ll do it if it makes you feel good.” So yeah, that was my first foray into it and then I was very into it after that. And I would explore it with other partners a little bit. I can definitely be down with kinky sex, but sometimes I just want to be vanilla and just have normal, average sex, yeah.

Christina: Yes. Yeah, I think I just want to have boring sex, that’s like we have a house with a picket fence and 2.5 kids, let’s be boring as shit about this.

Dani: Yeah.

Drew: Yeah. I think there’s a middle ground for me that is usually where I’d like to live. I love when something can be intense enough for me to just get out of my head.

Christina: That does seem to be the thing that—

Drew: It’s such a big thing for me in sex.

Christina: … Is recurring, yeah.

Drew: It’s just like how do I get my brain to… It’s not even turn off, because I want to be present. I can turn my brain off, that’s what I don’t want to do. It’s like I want to be present in a way that is well, present and not… Yeah, I don’t know.

Christina: Yeah, because your brain too “on” is another form of dissociating. It’s too thinky, overthinking that. It’s just another form of deciding to take yourself out of that moment.

Drew: But it depends because it depends if we’re talking about sex that’s kinkier sex or kink that is very organized and thought through, I’m not in a kink community. I’m not one to talk about it in that sense. And I don’t have experience with that. And so, that is very thoughtful and I don’t want to say that’s not thoughtful, but I think what I’m saying… I guess I’m not really talking about kinky sex, I guess I’m more talking about aggressive sex.

Christina: Sure.

Drew: But aggressive sex can be better for me as far as not thinking, whereas if it’s… But then also, more vanilla sex, it can be really lovely and nice. And I think I just maybe have to be more into the person and maybe it’s just been a while since I’ve been really into a person, I don’t know. Dani, when you say that you sometimes really like vanilla sex, is that with any person or is that with someone who you actually might want to have a house in 2.5 kids with?

Dani: Yeah, I think that it is. With my ex that I talked about, even though we’d only gone on a couple of dates, I was definitely on the verge of having feelings for her and being a total dyke about it. And so, I was able to have that very intimate, sensual sex with her in a way that was devoid of any kinkiness. I think because, I don’t know, it just felt like that was a kind of sex that I was supposed to be having with her. I don’t think she would’ve ever asked me to do anything very kinky with her, which is why I sort of explore that side of myself more with very casual hookups, I guess? I’ve had this person that I hook up with on and for a year or more, and that’s a person that I feel safe exploring that side with, and they are very down to do whatever, and demand whatever from me, and I’m totally cool with that. But yeah, I think that it’s very different with different people. But for me, personally, when I have feelings of emotional connection with, it’s a little bit less likely for me to have kinky sex with them.

Christina: Yeah, that’s interesting. As our ending moment in this conversation, should we think about some sex energy we want for the year 2021? What are we hoping for? Apparently, I’m out here exploring kink, I guess.

Drew: Love it.

Christina: Something I said on a podcast, now it’s true. So Dani, what are you hoping to get in your year of 2021? What do you want your sex to look like?

Dani: I definitely want to explore more of the things that I have been dreaming of during my quarantine year in lockdown. So there are things that I was like, “I would never do that.” And then I’m like, “Maybe I would actually.” So getting into those things. But also, I famously have been looking for a tourist wife for a long time.

Christina: We’d make excellent wives, of course, you are.

Dani: So I think that there’s a part of me that wants that stability, but also the ability to be free-roaming, and have sex with other people on the side, and have relationships with other people. So I’m looking forward to exploring that more. I’ve been dating and it’s fine for the most part. And I don’t know where things are going to go with different people, but I guess the big thing that I’m looking forward to is just having sex for the first time in a year.

Christina: Yes, I agree with you there. That seems like it’ll be good when that happens.

Dani: Yeah.

Christina: Drew, what do you got?

Drew: Yeah, so since my ex and I broke up, I have not had sex with anyone more than two times, everyone who I’ve had sex with, we’ve either had sex once or twice. Some of those I would’ve had sex with them more times, but it just didn’t work out. And some of them, not so much. And I think, though, a lot of it is somewhat of a defense mechanism. You don’t really have to explore certain things or really get into certain things… Well, I was doing that on my own, but you don’t have to do it with another person when you’re only having sex casually in that way. So I think probably I would like to have sex with someone like, I don’t know, three times, four times, who knows, or even more? Look, I think you can explore on your own, absolutely, I have been, and I really have. If I sound fucked up right now, you should have seen me in 2019, I’ve really made so much progress. And I think that exploration on my own was really important to me, but now I feel like I’m at a place where bringing a partner in or partners in who get to know me a little bit more intimately and having to confront that vulnerability is probably what would really serve me.

Christina: So I think it feels like everyone has kind of a ho shit but maybe allows some feelings to creep in. Everyone’s like, “Ho shit for sure, but also feelings? Not opposed.” Cool, I think that’s great. I think it’s a great place to be here in 2021. Does that mean it’s time for our second to last segment, called crush corner where we talk about things we have crushes on? Things, people, usually people. I don’t think any of us has picked a random thing.

Drew: I think, but that’s a good challenge for the future.

Christina: That could be fun. That could be fun.

Drew: Dani, do you have a crush for us today?

Dani: Yeah. I am very consistent, so I have had the same crush for a long ass time.

Drew: We love it.

Dani: And that is none other than Queen Latifah. I think about her all the time.

Christina: Yeah. God, that’s beautiful, yeah.

Dani: Yeah. I remember being a kid and watching her romantic comedies and being like, “Wow, she’s fucking beautiful.” And seeing her as a romantic lead, as a woman who was not petite, and who was Black, and all those things, it was really revolutionary for me as a little fat kid. Yeah, so I have a major crush on her. I took that Autostraddle quiz that we did a while ago that was your dream celebrity date or whatever, and I got her, and I was like, “That makes sense.” Yeah.

Christina: Absolutely. Yeah, she is really quite a formative moment that—

Dani: Oh yeah.

Christina: … Chicago really did.
Dani: Oh, yeah.

Christina: It’s a lot to take in for a young CT. Drew, who are you crushing on this week?

Drew: Well, okay, so we had a conversation earlier today where we decided… We were both gushing about the same person, and then we were both like, “Can we not sexually say that this person is our crush because of just our pop culture enthusiasm for her, even though it is not sexual because she is a child?” And that person is Olivia Rodrigo.

Christina: Yeah. So that damn album came out today.

Drew: Yeah, we recorded these early, so that’s a little context.

Christina: So listeners, you’re going to say, “Oh, that album that I have memorized by this point, the thing I’ve been listening to for months on repeat?” And I will say, no matter when this episode comes out, I will say, “Same, I am also listening to it, still probably.” I texted Drew this morning and said, “Could we just transition into having a Sour podcast? It’s just only about this album.” She is a phenomenal talent. I think I am so thrilled to see her teenage rage, and joy, and anger and insecurity all in one album. It feels incredible to bang and when I finally deign to visit my parents, I will turn that shit all the way up, and drive down the streets I used to live on, and just cruise with my feelings, and it’ll feel so good. So thank you, Olivia. And again, I can’t express how non-sexual this is, you are so young. God bless you, girl. Go off, but my gosh, oh God.

Drew: Yeah. I was really a skeptic at first when “Driver’s License” came out. I was like, “I’m not going to listen to a song written by a 17-year-old. I’m getting too old for that, I’m sorry, whatever.” And then I listened and then I was like, “Oh, okay.” I mean, look, as we established at the beginning of this episode, I love coming of age movies and I think there’s something about adolescence that… I mean, I think for a lot of queer people, it feels really palpable because we didn’t necessarily have the adolescence we wanted, or maybe we feel like we’re having a second adolescence, or whatever. It’s not an excuse for bad behavior, but I do think it is a pretty common pattern. And I think there is something about art focusing on teenagers, made by teenagers that can just feel… there’s just like an emotion to it that just, I don’t know, it just really speaks to me and feels I can channel some lowercase ‘t’ trauma, maybe a little bit of uppercase ‘t’ trauma. I certainly did not have an experience like Olivia’s that inspired this album. There’s something about the emotion of it that it just feels so resonant and brings me back. And I was just dancing around the house listening to it.

Christina: It’s good as hell. Well, we have one last question for our guest before we leave and that was, Dani, was this a date? Was us recording this podcast right now a date? Are we all three of us on a date? It’s possible.

Dani: I hope so.

Christina: See, love that, love that energy. Drew always says, “Yes, it’s a date.” And I’m like, “Is it though?”

Drew: I don’t think every podcast recording is a date. I do think every time I go on a date with someone, it’s a date, which you don’t.

Christina: And that’s beautiful.

Drew: And sometimes they don’t… Look, being queer is a wild journey for all of us.

Dani: Yes.

Christina: We’re all just trying to learn something.

Drew: Dani, where can people find you and your work?

Dani: You can find me on Autostraddle, just search Dani Janae and you’ll find me. You can find me on Instagram @bell.biv.dahoe, that’s my Instagram handle. And then I’m also on Twitter @figwidow, that’s F-I-G-W-I-D-O-W. Yeah, that’s where you can find me.

Drew: Great. Thank you so much for being with us today!

Dani: Thank you for having me, this was fun!

Christina: Yeah, thanks for kicking it!

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, that I don’t think every time you see someone… 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 the boundary.

Drew, in a voice memo: It’s so weird that our best sex ever episode comes out this week because we recorded at the beginning of the summer, and then I spent the summer having the best sex of my life. And not that everything in the episode is inaccurate, it’s like a time capsule. And I love that. It’s like a little inspirational moment for people, of like, “If you are having the problems Drew was having, give it a few months. Everything might be… not everything, let’s take it easy, but you might have some good sex in your future.” Love that for our listeners and for me.

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?

Drew is an LA-based writer, filmmaker, and theatremaker. Her writing can be found at Bright Wall/Dark Room, Cosmopolitan UK, Thrillist, 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 191 articles for us.

3 Comments

  1. Drew yes I am always here for the Desert Hearts content. Cay Rivers is one of my roots and absolutely the lesbian icon I aspire to be.

    Also this episode was so good! Dani Janae is my AS crush and has been since her poetry series and anatomy of a mango series and she has an incredible voice and I’m so glad to hear more of her here!

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