“Wait, Is This a Date?” Podcast Episode 203: Dating Men

A fun fact about the queer community is most people have experience dating men. No, I’m not just talking about the cis gay boys — I’m talking about most of our listeners! (Though I do hope we have a large contingency of cis gay male listeners tbh.) Whether you’re a lesbian who dated men as a teen or a queer person who dates lots of genders, our community is far too mixed and gender is far too complicated to leave men — cis and trans — out of our discussions.

That’s why this week our topic is dating men and our very special guest is writer, director, podcaster, icon, and my best friend, Gaby Dunn! For those who don’t know them, Gaby has been dating men throughout their entire identity journey. They talk to us about dating men when they thought they were a cis woman and dating men now that they’re out as transmasculine. We also get into the awful cis men from Boston that Christina dated before coming out and wonder why I have a desire to fuck Jon Hamm.

But first! We play a game I call “Netflix & Shill” that asks such questions as: How gay is the Olsen Twin vehicle New York Minute?

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SHOW NOTES

+ If you want more of Gaby check out the episode of Bad with Money that Christina and I were on last year.

+ Since recording, Gaby got their two new Swayze tattoos!

+ And just a reminder: You should watch Road House.

+ Important footage of Jenifer Lewis at the 2019 GLAAD Awards:

+ Jaida Essence Hall. The hottest pig in town.

+ Watch Gaby’s short film, Grindr Baby.


EPISODE

Gaby: I think if I get top surgery, it’s going to change immensely. That’s my fear is that once I get top surgery, these guys are going to be like, “Wait a minute.”

Christina: “Hold on. You took the titties away.”

Gaby: Right. That’s what I think.

Christina: “What’s going on?”

Gaby: “Wait a minute. You have full facial hair and shh, but these titties are giving me an out” and then when I don’t have them, I’m curious what they’re going to think.

[theme song plays]

Drew: Hi, I’m Drew.

Christina: I’m Christina.

Drew: Welcome to, Wait, Is This a Date?

Christina: Wait, Is This a Date? is an Autostraddle podcast all about dating and figuring out if things are dates and other topics, as we decide, those topics will be, as we record more episodes of this podcast called, Wait, Is This a Date? That took a turn. Got to say, didn’t expect a single word to come out of my mouth in that order, but wow, here we are.

Drew: I realized that in our intro, I have given you the responsibility of saying something new every time. I say, “Welcome to Wait, Is This a Date?” Then I go, “Christina,” and you get to just ad lib and it’s always entertaining.

Christina: It’s always something. As they say, heavy is the head that wears the crown and my crown is, occasionally, these headphones and this podcast.

Drew: Incredible. My name is Drew Gregory. I am a writer for Autostraddle, a filmmaker. You said last time that I always paused before I say my identities. Once again, I’m a queer trans woman and general gay person.

Christina: That’s gorgeous. I’m Christina Tucker. I’m also a writer at Autostraddle and the internet abound, I am a gay cis woman. In that way, I think we’re a really beautiful team.

Drew: When I think of Christina, I think cis woman.

Christina: Yeah.

Drew: I don’t think big faggot.

Christina: Yeah. No. Thank you. That is, actually, also a large part of my identity is being a gigantic faggot.

Drew: Yeah.

Christina: I’ve heard a rumor that you have a game for me.

Drew: I sure do.

Christina: By I’ve heard a rumor, I mean, you texted me directly.

Drew: Yeah.

Christina: In many ways, what is a rumor? Who can say? It can be whatever you want it to be for the sake of a podcast.

Drew: I hope this is okay.

Christina: Oh boy.

Drew: I’m just going to talk for a little while and you don’t have to say anything because I don’t want you to incriminate yourself.

Christina: Okay.

Drew: You used to work for an account called, Most. It wasn’t owned by Netflix. I don’t really understand the inner workings, but basically, it was in charge of sharing the queer content on Netflix each month. Now, before Netflix decided to fire a bunch of their queer employees right before Pride, but before that, you were part of the team that was in charge of pitching what I would say is Netflix’s lackluster queer content. Every month, the Most account was tasked with releasing the queer content for the month. A lot of times, there wasn’t enough queer content or the queer content that was there, Netflix, for some reason, didn’t want to promote because it was maybe too edgy or was foreign or whatever.

A lot of the stuff that’s on these lists is to call it queer is generous, but because you no longer have that job, I thought you could do one last hurrah, a two weeks notice if you will that was not granted by this corporation. I have a game called, “Netflix and Shill” where I’m going to name titles that were on the monthly “this is what’s queer and coming to Netflix.” I haven’t seen all of them, but I do think that most of them are not… at least the queerness is subtle or minor or supporting character. What I’m going to need from you is for you to explain to me why this work of media is so deeply important to queer history and the queer community.

Christina: Okay. I think I can do this and not get sued.

Drew: Great.

Christina: I think that’s thrilling.

Drew: Great. Well, okay. Our first title is, a Netflix flagship series. We’re going to go with Bridgerton.

Christina: Bridgerton. Bridgerton is deeply important to the queer community due to two actors, the leads of, I guess, this last season are both queer. We celebrate queer actors even if they are both playing straight in that way.

Drew: That’s really beautiful.

Christina: Yeah.

Drew: Queer actors can play straight roles.

Christina: Yes, they can. Honestly, Jonathan Bailey did a pretty impressive job of being a straight man. Good for him.

Drew: I do love that. Okay. Next up, Is it Cake?

Christina: Is it Cake? Honestly, of Netflix reality shows that I watched during my tenure there, I had a ball watching Is it Cake? which is either a comment on how many terrible reality shows there are or how broken my brain was by this job. It’s tough to say. Is it Cake? had a bevy of queer contestants and also, many gay judges including Rebecca Black, which was very fun and thrilling.

Drew: Right. That’s nice.

Christina: Yeah.

Drew: Okay. The ’90s film, You’ve Got Mail.

Christina: Quick cameo from Sara Ramirez and Nora Ephron really knows how to write and gays like writing. I don’t know.

Drew: I think we do like writing. I can attest to that.

Christina: It is not my favorite of the Ephrons, but it’s there. It’s in the canon.

Drew: Sure.

Christina: But I do think it was that 10-second Sara Ramirez moment.

Drew: Okay. Wow. I was going to say I should rewatch it because I don’t remember them being in it, but maybe I shouldn’t rewatch it. Who’s to say. Next up is, I Know What You Did Last Summer.

Christina: I’m going to draw a big old blank on this one. Gays do love horror in a way that I don’t because I am not that kind of gay. Screaming is camp. I don’t know. Who can say?

Drew: You heard it here, folks, screaming is camp.

Christina: Who can say? I don’t even know if I’ve ever seen that movie, to be honest. I must have as like a child. I must have looked at it and then decided, no, horror is simply not for me.

Drew: Next up is one that you probably have seen. New York Minute.

Christina: That’s the Lindsay Lohan film, I believe.

Drew: I think it’s Mary-Kate and Ashley Olsen.

Christina: There’s a Lindsay one that’s also about New York, but that has something to do with luck or something. Again, Mary-Kate and Ashley are iconic and that they are swamp witches now and refuse to do anything normal except for like, make large beige clothing for The Row, which is somehow pretty gay of them, but actually, I don’t think I have seen that film.

Drew: Wow.

Christina: I do support the Olsens in their work.

Drew: I love that.

Christina: And/or their lack of work recently. I think that’s actually equally inspirational. They really put in their time as children.

Drew: The next one I have not seen and you probably have not seen it. I tried to Google how gay it was and I don’t think it’s gay. Maybe it is gay and I just… The Lincoln Lawyer. Is The Lincoln Lawyer gay?

Christina: What?

Drew: With Matthew McConaughey?

Christina: If it is, I am shocked to hear it. I’m trying to… No, I’ve never seen it. I know a little bit about Lincoln. He was tall.

Drew: He was also rumored to be like a little gay, which is why I’m like, “Was The Lincoln Lawyer about… was Matthew McConaughey playing a gay lawyer?” I don’t think so based on my quick Google, but listener, if you’ve seen The Lincoln Lawyer, please send us an email. How gay is it?

Christina: Yeah. My guess would say that there’s some lightly gay subplot or there’s a gay actor in it.

Drew: Great.

Christina: That would be the two reasons it could make the list.

Drew: Okay. My Best Friend’s Wedding.

Christina: The most iconic gay friend, I think, of all time in Rupert Everett. Honestly, the only rom-com that has an ending that I’ve ever really identified with because girl, you will end up alone but you will have your best gay friend there at the wedding for you. That is gay culture.

Drew: That was an easy one, but it felt worth mentioning. This, also, might be an easy one for you specifically, the 1982, Annie.

Christina: Though I am a musical faggot, boy, do I hate Annie? Because boy, do I hate children singing more than almost anything in the world. I find them all incredibly annoying. I think, “The Sun Will Come Out Tomorrow” is one of the worst songs in musical theater history.

Drew: Bernadette Peters is in this one, right?

Christina: Bernadette is in that one. That is the one with Bernadette, which feels like enough would be enough for me. She’s famously a sticker on my water bottle, but I got nothing.

Drew: That’s not an expression. I want to clarify.

Christina: No.

Drew: That is literally… There’s a Bernadette Peters sticker on Christina’s water bottle. Yeah, staring at it right now. There you go.

Christina: She’s above Viola Davis.

Drew: That’s beautiful.

Christina: I love history. Herstory, I’m sorry.

Drew: I have three more. Oscar nominated film, Don’t Look Up.

Christina: Cate Blanchett gets to say whatever she wants because of Carol, I think. I think that’s it.

Drew: Okay.

Christina: Gay men love Ariana Grande.

Drew: Yeah. I definitely saw that movie though I like to pretend in my brain that I didn’t because it was so bad, but I didn’t remember there being any gay characters. Was Jennifer Lawrence bisexual in it?

Christina: She had a bisexual haircut in it.

Drew: Okay. That’s enough. Okay. Two more. My Little Pony: A New Generation.

Christina: I don’t know what happens with those ponies.

Drew: Are they gay?

Christina: They’re ponies. My gut says yes. There’s something gay about saying the phrase, “My little pony,” but what occurs on that program, that’s not my business.

Drew: Great. Well then, we have one more, which I don’t know if you had to see this one for work, but I’ve heard things. Diana: The Musical.

Christina: Oh boy did I watch Diana: The Musical. That was really hard to watch. I know there is a contingent of theater gays who are like, “No. Actually, we’re bravely coming out to say that Diana: The Musical is brilliant.” I would like to have a very long talk with those gays because I am perplexed by that. Well, it’s musical, so kind of just like, gays love a musical, but also, I think her valet or something is gay but not specifically gay, but has a big gay man dressing a pretty woman energy. Boy, that musical was awful.

Drew: Is there mention of AIDS in the musical?

Christina: Oh yeah, there is a whole, in fact, scene that I actually blocked due to trauma because it is a musical number about having HIV and AIDS and it’s bad, bad, bad lyrics.

Drew: Wow.

Christina: Lyrically a flop.

Drew: Wow. Well, this was a really beautiful time.

Christina: Yeah.

Drew: Thank you for playing this dangerous game with me. I’d just like to say that while I don’t support large corporations or comedians who are transphobic, I do love the show, Sex Education and I would take Netflix money to make my own show whenever they would like. Just putting that on the record.

Christina: I think that’s a great thing to be on the record.

Drew: Maybe after this I’ll pop some popcorn and watch The Lincoln Lawyer.

Christina: I love that. Of all the movies on the list, that’s the one where you’re like, “I’ve got some questions we got to untangle there.”

Drew: Well, let’s move on to our topic of the week, which is dating men. I often say, we have a very special guest because we don’t really do like not special guests because what’s the point of having a podcast for that.

Christina: Yeah.

Drew: But this person is my best friend. I will let them introduce themselves.

Gaby: Oh my God. Hi. I’m Gaby Dunn. I’m Drew’s best friend. I’m also a writer and a noted internet bisexual gay person. Yeah. I work in TV and film. Sometimes books, sometimes podcasts. I’m sure you’ll do the thing at the end, which is like, “promote whatever you want to promote or whatever.” I won’t bore you up top, but…

Christina: Please don’t.

Gaby: Yeah. Mostly, I am your friend. Hi.

Christina: Yeah.

Gaby: Yeah.

Christina: Yeah. That’s the best part, I think.

Drew: Have you ever dated a man?

Gaby: Oh my God. Oh boy. Okay. Here’s my journey.

Drew: Yeah.

Gaby: I was like the bisexual cis woman of the internet for a while. I, yeah, dated a lot of men. Now, I’m like a nonbinary transmasculine person. I’m still dating men, but it’s different. My partner is a transmasculine person. They’re on testosterone, then other people I’m seeing are a lot of trans men. There’s one cis man, but he is dead to me right now and then other people that… It’s gotten to be more of a T4T situation up in here, but yeah, I used to date a lot of… We’re roasting cis men. Is that what we’re doing?

Drew: No. No, I would never. No. I think what I’m interested in is, when we were first discussing the season and possible topics and guests, this was back in January, I was like, “Oh, well, by the time, we would have Gaby, I think they’ll be a man.” That’s also an interesting dynamic. I don’t know about that, but it definitely hasn’t not come true in certain ways. I’m interested in just mapping the trajectory of all the different ways. Obviously, gender is complicated. Every individual relationship is its own relationship, but I know Christina has experience dating cis men as a cis woman. You have experienced dating cis men as a “cis woman.”

Christina: Sure.

Drew: You have experience dating trans men as a “cis woman.”

Gaby: Yeah, air quotes. Air quotes around all of that.

Drew: Yeah. You can’t see the air quotes because—

Christina: Oh they could hear them. They were very audible to the audience.

Gaby: Yeah.

Drew: Now, you’re a transmasculine person still dating men, both cis and trans. I don’t know. I’m just interested in getting into the differences and certain patterns.

Gaby: Sure.

Drew: And what your relationship was to men as… Really, there’s a huge difference between being a closeted transmasculine person and a cis woman.

Gaby: Yeah.

Christina: Yeah.

Drew: You both offer those perspectives and wow.

Christina: Yeah.

Drew: How exciting for me.

Gaby: Okay. Here’s the thing. I’m two months on T, right now, as we speak. That is a very different journey. I came out as nonbinary a year ago, almost a year ago. I was still super femme at the time although, what does that mean? I had long hair, but I now have cut my hair. I’m on T. The T is starting to show. I have a little mustache. I still have boobs. I just don’t ever acknowledge them. Now, it’s a little interesting with the cis straight men that I see because I’m like, “Do I have to care about what you identify as? Does that matter to me? What are you? What are you seeing me as? What is this?”

One of them I was hooking up with before. No, two. Well, here’s the journey. I was hooking up with them before I went on T and cut my hair, right? They’re still around. One of them… Okay. I was a woman. I went out with this person. They were sort of, on their Hinge bio they were like a guy, but there was something about them that was very effeminate. I was like, “This is interesting.” Then we went out. It was like, “Why did you swipe on me?” I was like, “You have a really feminine energy.” I was like, let’s see what this person says. They were like, “Oh, I love that. Thank you.” We hooked up regular, like straight people or whatever and then—

Christina: Hooked up regular is my new favorite phrase.

Gaby: Yeah. I don’t know. Boring. Later, I saw this person again. We started to hook up and then they just broke down. This was, now, I look this way. So the last time they saw me, I was a lady. Now, I look this way. They came to see me again. They hit me up. Just FYI, they were like, “I can’t get enough.”

Drew: Returning customers.

Gaby: Always. They just broke down and were like, “I don’t know. I think I’m a woman. I don’t know.” I was like, “Yeah, babe.” They were saying all this stuff where they were like, “Maybe I’m not queer. I’m just jealous of all queer people. What if people think I’m faking being a trans woman? I’m not a trans woman, but I just wish I could be as confident as a trans woman.” All this stuff that was like, “Babe, you could just be a trans woman.” Then they were like, “I don’t know. Maybe I’m like not actually queer and I’m just pretending.” I started laughing. I was like, “I don’t mean to laugh at you, but this is gay.”

Christina: Whatever experience you’re having here, something’s gay about it, my friend.

Gaby: Yeah. They’re like, “I don’t know. Maybe I’m not queer.” I’m just sitting there, literally, a transmasculine person with this AMAB person being like, “Really, I don’t want to tell you what’s happening to you right now, but we are in a bed kissing and cuddling. I got to let you know that you are having gay sex actively right now.”

Christina: Yeah.

Gaby: This is gay right now.

Christina: Nothing straight is happening here in this conversation has ever happened betwixt us.

Gaby: They were like, “Oh,” and then, really, it just became like me sending them memes to try to get them to understand and then them being like, “Yeah, I’m probably trans feminine.” That was one of the last, “cis men” that had showed up in my life.

Drew: Right.

Gaby: I think even when I was very feminine, I had a lot of cis straight men that I dated who were unnerved. They liked me and they were into me, but there was some hump that they couldn’t get over there. There was some… And I didn’t know what they were reading on me at the time, but there was always this thing where they just couldn’t get a grasp on what I was and they were reading something that they liked a little bit because they got a proximity to queerness that they thought was interesting, but then it would start to get very queer and they were not into it. One partner that I had that was a long term boyfriend, just this is 2016 where I really thought I was a cis woman, I cut all my hair off and I started referring to myself as “ya boy.” I wore only men’s underwear. I wore men’s bathing suits.

At the time, this guy, this guy is the most cis straight, although now I suspect maybe something’s up with him, but anyway. When he was breaking up with me, he was like, “I feel like I’m not allowing you to be your true self.” I was like, “What an idiot.” I was like, “Why would he think that. That’s so fucking stupid. What a dumbass.” I actively had a coffee table book in my car that said genderqueer that was pictures of genderqueer people that I was going to put in my apartment as this was happening.

Christina: You were like, “Anyway, what a dummy. Ya boy out.”

Gaby: “What a fucking moron. Ya boy out.” Then I started dating a bi cis guy and that was very freeing. Now, in retrospect, I think being with him, let me feel like a gay guy. Because I had short hair, he was bi, everything we did was very faggoty. The last time I ran into him was at an Ariana Grande concert. I was like, “Oh, this person is my gender.” I don’t know. A lot of the men that I had dated in the past are now trans women.

Drew: I do know this about you.

Christina: That’s quite a pipeline. That’s—

Gaby: Yeah.

Christina: I do love that anybody who is like… There’s this group of cis dudes on apps who are like, “I’m working through something. I’m going to swipe on this and see what happens.”

Gaby: Well, yeah. Also, it’s different people. Once I change my pronouns to they/them it’s a totally different crowd.

Christina: Yeah.

Gaby: I always thought, even when I looked like a woman, right? My partner, Mal and I were in South Carolina and there was a group of frat guys in a car outside of a restaurant. We’re walking around the restaurant. I look like a woman, so they stop to check if I’m hot or whatever. I would say, out of the five of them, four of them are like, “That’s a weirdo.” One of the five does a second look. That’s happened my whole life. If I can get that fifth one, that’s the one I want and not anymore, but back when I was a woman. Because I’m like, “What’s up with you? You’re fucking weird.”

Christina: Yeah, something’s happening.

Gaby: You’re like bi or gay or you’re trans or something, because you took a second look at me and all your little frat bros didn’t. What’s your fucking deal?

Drew: Yeah.

Christina: Yeah, that’s going to be a sight that’s going to fester for that fifth one. That’s going to just be a recurring theme that they’re just going to keep running back to and being like, “What was that?”

Gaby: You’re different than your friends.

Christina: Yeah.

Drew: Yeah. One out of five dentists is super fucking gay.

Gaby: You’re going to try to get me to peg you or something and not tell your friends. I know. I can see you.

Drew: Yeah.

Christina: Listen, when you know, you know.

Drew: Well, now though, maybe this is a question for you in a year, but are you interacting with cis gay men now, in a new way? Do you feel like that world is starting to open up to you? Or is there just too much transphobia in the cis gay male world to quite get there yet?

Gaby: It depends. The big problem is, I still have boobs…

Drew: Right.

Gaby: …which I think gives the cis straight men that I date a little bit of an out, where they’re like, “Yeah, this is a person with facial hair and actively a man or a trans but titties are there, so plausible deniability.”

Drew: Right.

Gaby: Okay. Here’s what’s happening as I post more masculine thirst traps. The straight girls coming out of the woodwork.

Drew: Yeah.

Gaby: These are people that aren’t going to follow through, right? It’s the straight girls who are like, “Damn, thirst trapping.” And whatever. Those people are not going to follow through. The cis gay men who comment are also probably not going to follow through at this point.

Drew: Right.

Gaby: It is nice because they’ll write like, “Daddy” or whatever. I’m, literally, one of five tops in West Hollywood. Come on.

Christina: Well, well.

Gaby: There’s bottoms galore, but you need me. I don’t think they really have follow through. I don’t think they’re really going to try to ask me out or fuck me right now. You know what I mean? They’re like—

Drew: Right.

Christina: Yeah. They’re going to throw little heart eyes comment.

Gaby: Just to keep me on the line.

Christina: Yeah.

Drew: Right.

Gaby: Keep me spicy until I pass.

Christina: Just keeping an eye.

Gaby: Yeah, which is a strange thing to keep me on the line until I pass just to see.

Drew: I’m also interested in this idea of like, “Oh, if this person hooks up with me, then they’re gay.” Because I also think that there’s a level of, I don’t know, how is someone seeing you, right?

Gaby: Yeah.

Drew: I know in my experience, when I first moved to LA and my hair was luscious, but not quite so long, I was hit on a lot by cis gay men who were reading me as a little twink. The more… My boobs grew a little bit more and my hair got a little longer and then they disappeared.

Gaby: Yeah.

Drew: Which—

Christina: Fade into the tall grass.

Drew: Yeah. They’re not really there anymore. It’s like, do we read those cis gay men as more bisexual than they let themselves on?

Gaby: Yeah.

Drew: Or are they just transphobicly or ignorantly reading us differently. I think about that when it comes to the cis men, especially. I think with trans people and closeted trans people, we’re all on our own journeys. So it’s like what are you going to do?

Gaby: Yeah.

Drew: But with the cis men, I’m always interested in this idea of what can we, as a culture, be like everyone’s a lot gayer and transer then they are willing to admit.

Gaby: Right.

Drew: They need to deal with that. Versus being like they’re not respecting us and they’re seeing us wrong and how much do we want to put up with that and that sort of thing.

Gaby: I don’t know because I’m also like, as I’m hooking up with more other transmasculine people, which has been a delight, I am realizing that a lot of them have an opposite experience to me where they were seen as lesbians or butch lesbians, have almost no experience with men, and then have become more “passing” trans-masculine people, and then all of a sudden are hooking up with men. But I’m the opposite. I was a hot girl. I had no problem being a hot girl. I didn’t feel awkward about it. I was doing the utmost level of drag. I’m not joking, a hot girl, nightclub hot girl. I have a lot of experience with men. They’re largely boring. I have a lot of confidence. Even when I would date men, I would fuck around. I would touch the small of their back to lead them places. I would do things to try to make them feel the girl. I was like—

Christina: No reason anyway.

Gaby: I know because I was like, “It’s a bit.” I just was always so confident. With men, right now, I have no problem. Even looking like this, I’m like, “I could probably still get you.” Men are like a paint by numbers. They’re so easy to me, but then the opposite thing with me was women, which is a thing with bisexuals where it’s like, “Women are more difficult.” Now then once women started to become easier to me, I was like great and I was hooking up with more women. I had a long term partner. I was like, “We are girlfriends.” That person is a trans-masculine person also. I think I have a different experience where a lot of the trans men that I’m friends with are like, “Oh my God, boys. What do I do? Boys.” I’m like, “Who needs it? It’s boring shit.”

Drew: It’s inspiring.

Gaby: Yeah. I just never had that experience. When my partner and I first started dating and I was very feminine and they’re a transmasculine person, we would go to a coffee shop and the barista would be like, “What are you going to get?” Leave a smiley face on Mal’s receipt. For me, I’d be like, “They forgot my drink, fully.” You know what I mean?

Drew: Now you walk back into the coffee shop like the scene from Pretty Woman and are like—

Gaby: Big mistake!

Christina: Yeah.

Gaby: Huge!

Christina: Huge.

Drew: Christina, when you were in your straight era, what kind of men were drawn to you and what kind of men were you drawn to?

Christina: The worst kind. A lot of that, I will blame on living in Boston, Massachusetts.

Gaby: Hell yeah.

Christina: A thing that my friends love to joke about is like, “Well, thank God you’re a dyke now, because the men that you were dating were just the worst.” There is a straight version of me somewhere. She works in PR. Her boyfriend is some horrible capitalist, venture capitalist bro. Just like the doucheist finance lawyery types. Just like the…

Gaby: Oh my God.

Christina: …worst. I hated them because I was gay, but also, it was so easy to date them because I hated them. They were so into how uninterested I was in them that it made it very simple to just keep them around and then be like, “No, I’m done with this. I don’t like you. I don’t like being here.” Then three months later, I’d be like, “Let’s pick up another guy named John at a bar. Whatever.” It was just me negging men I could not stand due to being a dyke and then being like, “Yeah, I’m done. Done with this now.” It was a dark period.

Gaby: That is dark. I think I would pick not like that. I think I would pick effeminate guys and then I would be like, “We’re just both gay guys.” They would be like, “That’s not what’s happening.”

Christina: Yeah.

Drew: We’ve talked about this, but if we had met five years earlier, you would have ruined my life. I would’ve been obsessed with you.

Gaby: I would have been in love with you.

Drew: Yeah, but you also would’ve ruined my life.

Gaby: Absolutely. I’m a monster, but you—

Christina: Gorgeous transparency work right here. This is beautiful stuff. This is how communities stay together. This is nice.

Gaby: Drew as a boy was exactly who I would’ve gone after. Exactly. Which is like, then. she is a trans woman.

Drew: Yeah.

Christina: Yeah. The pattern continues.

Gaby: Yeah. I would’ve been like, “The little one who fucks.” That’s where I would’ve been like, “Hey.”

Christina: Hey.

Drew: I think I would’ve learned about bottoming a lot sooner.

Gaby: I was always trying to get those straight boys to let me at their butt holes. Sometimes they would do it and sometimes they would be like, “Why are you obsessed with this?”

Drew: I’ll tell you what, during that era, all I wanted was to not use my dick and to do exactly what my partner wanted—

Christina: Well…

Drew: Unfortunately, those things were in—

Christina: Constant conflict?

Gaby: Yeah.

Drew: It is interesting to me because I don’t have a lot of experience dating men. And by not a lot, I mean, basically zero. But I do have experienced dating people who, at the time, I thought were women or were nonbinary fems and have since transitioned or have since become more masculine. It’s definitely changed my relationship to my identity. As you will note, when I pause in the beginning of the intros, last year would end with me saying, lesbian. Look, I think the term lesbian, historically, encompasses a lot of genders and a lot of sexualities. I think I still could identify as a lesbian if anyone who I was dating wasn’t bothered by it, but I have just been like, “I don’t know.”

Gaby: Yeah.

Christina: Yeah.

Drew: I’m very open. I would love to have an experience… Love is maybe a strong word, but I do feel like, if, in my entire life, I never have sex with a cis man, that would be such a bummer. Just from a FOMO…

Christina: Wow.

Drew: …life experience sort of way.

Christina: Interesting.

Gaby: There’s some that you think are hot. You’ve said some are hot.

Drew: Yeah.

Christina: Yeah.

Drew: Usually, bisexual ones. Usually, queer. I love an effeminate queer man.

Gaby: Yeah.

Christina: Yeah.

Drew: I don’t feel any attachment to genders of people that I date.

Gaby: No. It seems weird to.

Christina: Yeah.

Drew: Also, a lot of the “women.” I don’t have to quote unquote, but women that I date. I don’t know. I will think of them more as, if we’re thinking of things in a binary way… Like I don’t generally date high femmes.

Christina: Right.

Drew: I generally date people who are tomboys. I’ve hooked up with a wide variety and have casually dated a wide variety, but most of the people I’ve had long term relationships with have a masculinity to them. Then it’s like, I don’t know. It just makes me feel like men be it like a binary trans guy or cis men are on the horizon at some point in my life. Why would you want to…? I just feel like… I don’t know. It also feels like I missed out on this really quintessential lesbian experience that Christina is describing where you date awful men for many years before you figure yourself out. I didn’t have that.

Christina:Yeah. You, too, could be miserable going on dates with men and slamming nips in the alleys before going to a date being like, “This is normal. This is what people who love dating men do. Just be like lightly blackout drunk when you arrive. It’s fine.”

Drew: To be fair. It does sound similar to what it was like dating straight girls, which I guess is another type of lesbian experience.

Christina: Well, sure. That is. That’s not one I’ve had, so in that way.

Drew: Oh.

Gaby: Christina, what’s your type?

Christina: See, and this is the other funny thing. Thinking about when we think about the genders that we are attracted to. When I was dating men, I was dating like, “That is a man. That is just like… That is a cis dude. That dude is big and like a giant. He had a big dumb head, just like a big idiot.” Every time I’m attracted to a woman, I’m like, “That is the most femme woman I’ve ever seen in my entire life.” I am extremely femme for femme even though my femme vibes have shifted to be more faggy. Truly, just Robin Williams in Birdcage femme.

Gaby: Yes.

Christina: I am always just like, it is very interesting that I went from extreme gender of man, extreme gender of woman, nothing in between. Like what is that about? What’s going on up here?

Drew: It’s interesting because so many people in the queer community are the opposite.

Christina: Yes.

Drew: Where they’re like, “I’m just attracted to androgyny.” Which I say in like a sarcastic voice, but I don’t mean it to be. If that’s what you’re into, that’s fine as long as you’re not being fetishy and weird. But it’s interesting that you’re the opposite.

Christina: Yeah.

Drew: I don’t know a lot of people that are the opposite who are like, “Be binary.”

Christina: I don’t either.

Gaby: Christina, I think, probably when you are closeted and you’re trying to find a man, you don’t have your own radar.

Christina: Yeah.

Gaby: You’re just like, “What has society told me? What have movies told me is a man.” I remember in middle school, I would just sit in the cafeteria and be like, “I got to choose a boy to have a crush on. Okay, who does everyone else like? Okay.”

Christina: Yeah.

Gaby: “I can’t do that. It’s too obvious. I’ll do his friend.”

Christina: Yeah, with a slightly different version of that. Yeah.

Gaby: Yeah. You’re picking from what other people are saying is hot.

Christina: Yeah. Except that I’ve always had those friends who are like you two. Like, “I love this tiny little sensitive emotion.” I’m like get that shit away from me. I don’t want to hear a man talk about a feeling. Not one time. Stop that. Never again. No man with a guitar. No man writing poetry. I don’t want to look at it. I don’t want to hear it. I’m not interested in that energy. I don’t know. Maybe I’m just like, “Feelings boys, away. Away from me.”

Gaby: Yeah.

Drew: Well, when you think of binary women who are very femme women, are they allowed to be super emotional?

Christina: Yeah. Women can do whatever they want.

Drew: Yeah, but like—

Christina: That’s science.

Drew: When I think of your crushes though, they are like ice queen mommi. Maybe that’s not in your actual dating life, it isn’t quite that, but in your crushes, that is what manifests and they are also not super emotional. There’s a masculinity… There is actually…

Christina: Yeah.

Drew: You can be so femme that you somehow gain a masculinity.

Gaby: Absolutely.

Christina: Right. That ice queen like emotionalist thing, I’m always like, “Is that a crush moment or is that a me feeling seen moment?” That’s always tough to say. Because like, “Is that just me? Am I just doing that?” That’s just what I do in the lack of feelings and vulnerability space that I’m constantly vibing in. Yeah. The women that I have tended to date, I’m always like, “Why am I dating another golden? Why is this golden retriever energy here? What is this peppy theater kid do-something-fun? What is this? Why am I here again?”

Gaby: Opposites attract.

Christina: Yes. A large part of it is that I am aware of who I am as a person and that I can be a stubborn and not fun. I do need someone to be like, “Shut the fuck up. We’re going outside today.”

Gaby: Yeah.

Christina: Which is, yeah. I think that’s life sometimes, but yeah.

Gaby: Here’s another thing. Here’s a problem that I have had. Now, I’m unpacking it the opposite way. I had a thing where I was like oh, you don’t actually want to date these guys. You want to be them or you think that they are cool. Versus like… So I would be like oh, I want to be this person or I want to be like this person, so I’m going to get proximity to them. Or I see myself in them or I see something that I want to be or I want to take away in them, mostly from men. There’s two things, two lyrics that I like. There’s a Neko Case lyric where she is like, “I fucked every man that I wanted to be.” Then there’s a Lil Nas X lyric where he says, “I only fuck the ones I envy.”

Christina: Wow. The two genders, really, right?

Gaby: I know.

Christina: That’s where it is.

Gaby: The two genders. I was like, “Wow,” but then I thought that was bad. I was like, “Okay, you can’t do that anymore. That’s bad. You have to parse out. That’s not attraction. That’s not whatever.” Now, I’m back and I’m like, “Who cares? Why is that bad? People fuck for all kinds of reasons.”

Drew: Yeah.

Gaby: If I envy someone and I want to fuck them because I envy them, why am I pathologizing myself?

Drew: Yeah.

Christina: Yeah. I think, at some point, I do think it is good to be aware of the things that shape your desires and wants and et cetera, but I do think, at some point, pathologizing all of your interests, be it sexual, be it like… you’re going to run into trouble. It’s not going to be successful after a while.

Gaby: Yeah.

Christina: You’re just going to end up tangled into a moral quandary where you’re like, “Can I do anything ever? Have I ever made a choice?” That doesn’t seem like a fun way to live.

Gaby: Yeah.

Drew: Yeah. I think it’s definitely good to… I agree with that. Be aware, but then also, at the end of the day…

Christina: You gotta get out of your head sometimes.

Drew: I do wonder what the experience would be like for me to like fuck Jon Hamm. One of those guys—

Gaby: Like a GUY.

Drew: A guy who… Like I wonder—

Gaby: Would you bottom for them?

Drew: Well, yeah.

Christina: Yeah.

Gaby: That would be fun.

Christina: That does sound fun.

Drew: It’s also funny because I think of my five-foot-four cis woman girlfriend that way.

Gaby: Yeah. Well, she is.

Christina: Yeah. Well, she is.

Drew: You know what I mean?

Christina: Exactly.

Gaby: Yeah.

Drew: So then it’s like, what is—

Christina: You could pop her right in Top Gun: Maverick and she’d be fine.

Drew: Wow. She’ll love to hear that.

Gaby: She’s so funny towards you where she’s just like a high school jock grabbing at your tits and you’re like, “Ahh,” but you like it.

Christina: Yeah, exactly that energy, in fact.

Drew: Yeah. It’s like why fuck Jon Hamm? What’s the need to do that? I don’t think Jon Hamm would be as good at sex.

Gaby: Right.

Drew: There is still a part of my brain that wants the bad experience or wants to try it out.

Gaby: Yeah.

Christina: Yeah.

Drew: I do think, ultimately, if I were to have sex with a cis man, it would be a little twink. It probably would be a case where I was topping them, but I could do all of it.

Christina: I love the idea of being like this cis man, a little twink.

Gaby: Also like, what? The two of you would just, what, blow away in the wind? You need like a…

Drew: Yeah.

Christina: Just something to weigh you down.

Gaby: Yeah. I think you need a bigger guy.

Drew: It’d be interesting. What I’m saying… It’s funny though because I say this and then the majority of the people who hit on me and look, fellas, don’t stop. I love the praise. I love the validation, but it’s largely transmasculine people or queer cis men. That’s my demo. Those people are the most attracted to me of anyone. When I was single and actively dating a lot, I wasn’t usually into those individuals. So then it makes me go like, “Well, how much of it is just theoretical?”

Gaby: What if it was a cis straight guy was like, came to you and was like, into you?

Drew: Well, that’s what’s interesting, right? Is that like… I just think I maybe passed the place of finding validation in that.

Gaby: Yeah.

Christina: Yeah.

Drew: Maybe I’m not as evolved as I think and maybe there would be something validating about it, but then at the end of the day, when you… I think it depends on how that experience went.

Gaby: Yeah.

Drew: I don’t know. I guess, you and Mal are the only… You were figuring… Were you out as… No, you were starting to talk about it, but you weren’t fully—

Gaby: No, I wasn’t out.

Drew: You weren’t out.

Gaby: No, I wasn’t out.

Drew: You were starting to like… We were having gender conversations.

Gaby: Yeah, yeah, yeah.

Drew: Mal was obviously out. I feel like the two of you are probably the most… Well, I can think of a couple other people, but those weren’t really good experiences.

Gaby: Right.

Drew: Of experiences that were generally positive, and it did feel different for sure.

Gaby: Yeah.

Drew: It’s interesting, actually, what it allowed me was to be toppier.

Gaby: Yeah.

Drew: Not with you because no one can top Gaby Dunn.

Gaby: No one can top me, obviously, but—

Drew: With Mal, it was interesting to be like, “Oh, because this person is a boy…” I’m being binary, but yeah.

Gaby: Yeah, yeah, yeah.

Drew: I feel less. I think my relationship to being a top with partners who wanted that and were cis women, I was really following their lead. I wasn’t really owning it.

Gaby: Yeah.

Drew: I was a little bit timid, which is not what you want from a top, but I could get into… I could do it. I could be like oh, they want me to do this thing, so I’ll do it and I’ll do it well. I can get into it and whatever. But I felt something very different when with someone who was masculine and able to be, I don’t know. I’m being very binary and very stereotypical.

Gaby: Yeah.

Drew: Being like oh, masculinity isn’t as fragile and I don’t owe this person as much.

Gaby: Exactly.

Christina: Yeah.

Drew: Or I’m not worried about being creepy to this person or I don’t even know. I can just let myself loose. There was something fun about that.

Christina: Well, yeah.

Drew: Maybe I’ll, maybe I’ll top Jon Hamm. Maybe that’s what I’ll do.

Gaby: Thank you.

Christina: Well, that would be hot.

Gaby: Yeah.

Christina: That would rock. That’s what we’re all trying to see in this one nation.

Drew: Yeah. Yeah.

Gaby: Christina, who was your last straw? Like you dated a guy and you were like I’m done.

Christina: Oh God. That’s really taking me back. I’m trying to remember. I guarantee you, he had the name like Chris or something. I do think there was one hookup that I had met in a bar and I was like I am done. I just have such a feeling of waking up the next morning being like okay. No, thank you.

Gaby: Why?

Christina: I don’t remember. I was quite drunk. He definitely left in the middle of the night because he was like, “I’m really allergic to cats.” I was like, “Okay, whatever.” Then he came over and he was like, “No, but I’m really allergic to cats.” I was like, “I’m so uninterested in this narrative.” Like, “Are we having sex or not?” We did and then he did leave because he was sneezing quite a bit. Hope he’s well.

Drew: He died.

Christina: Then he died. His name was Matt, I think. I just remember being like okay. I think no more of that. I think I am making myself miserable in a way that I could probably not do and maybe I could have some more fun in this scenario.

Drew: Yeah.

Christina: Be less cranky and upset all the time because I’m just forcing myself to go on these horrible dates with men that I hate. It seems that I don’t have to do that.

Gaby: Why was it horrible? What were they doing? What were they doing?

Christina: Nothing. They were just being men talking to me and I was like, “I hate this. I hate everything about this.” Sure. They were all douchey in the way of, they were all, mostly, white guys from Boston.

Gaby: God. I’ve dated a lot of white guys from Boston too.

Christina: Can’t recommend it, but they weren’t horrible to me. I just hated the experience of speaking to them.

Gaby: Yeah.

Christina: I was like, “Perhaps not everybody feels this way when they speak to men. Maybe I don’t have to feel like this.” My friends were like, “Fuckin, finally. Jesus Christ.” Yeah. I was doing my really iconic. “Oh, I’m just an ally for so long.” All of my friends were like, “Sure, sure. Okay. All right.”

Gaby: I guess what I’m getting at is, what is different? Because I’m imagining, literally, a split screen where a guy is like, “Yeah and then I got into venture capital” or whatever and then it’s like a high femme woman who’s like, “And then I got into venture capital,” and you’re like, “That is fascinating.”

Christina: Quite literally, that could be true. I don’t think I’ve dated any venture capitalist women, but I do think that, yeah, that would be, if my life were a sitcom, that would be the little split screen right there. If I had some HBO max series dedicated to my life, that would be the split screen.

Drew: Not to have a Bad with Money detour, but what’s a venture capitalist?

Gaby: It’s just like someone who invests money. It’s stupid.

Christina: They just have money to give other people money and there’s cocaine involved. I don’t know.

Gaby: Yeah. If you have a business, you go to them and you’re like, “Here’s a presentation. Do you want to invest in my business?” And they’re like, “Okay,” but that’s their whole thing.

Christina: Then they ruin it and then they shut it down three weeks later.

Gaby: Then they go, “Yeah, I have a bunch of ideas,” and you go, “I wish I was not involved with you,” and then—

Drew: Like Shark Tank?

Gaby: Yeah, like Shark Tank.

Christina: It’s Shark Tank. Yeah, it’s like Shark Tank.

Gaby: Yeah. Yeah, like Shark Tank.

Christina: Yeah. It’s like Shark Tank and then they say, “Should we pivot to video,” and then they shut it down.

Gaby: Yeah.

Drew: I see.

Gaby: A real Succession.

Christina: Basically what happens. It’s what’s happened to media, basically.

Drew: Right. Cool. Cool.

Christina: It’s cool. It’s a cool thing to do. Yeah. I genuinely just… I was just like, “I don’t enjoy the experience of speaking to, specifically in that scenario, cis men.” I was like, “This is not fun for me.”

Gaby: I was going to say, were most of them white?

Christina: Majority. Actually, I do think the last guy I dated was Black and I was like, “This could work,” And then I was like, “No.”

Gaby: That’s why I’m wondering.

Christina: “No, this is not going to work either. I’m sorry.”

Gaby: Yeah. Yeah.

Drew: Now that you’re in a very gender diverse queer community, and I would imagine most of the men who you interact with are queer, are trans. Is it connected to being more attracted to more binary genders that’s preventing you? For Christina, like—

Gaby: Yeah.

Christina: For dating men, dating nonbinary folks.

Drew: Yeah.

Gaby: Yeah.

Drew: Yeah. Is it something that you’re open to?

Christina: It’s definitely something I’m open to. I am… Living in my femme for femme life is always a struggle because it is a hard thing to do because a lot of the other femmes I know are interested in dating—

Gaby: Yeah.

Christina: Either masc of center, masc folks, which I get and respect, but it has not happened to me. I have not had the great moment of some masc of center romance moment. Most of my friends who are some nonbinary, but even more like femme presenting, I’m always like, “Well, that is where my attraction would lie.”

Gaby: Right.

Christina: Yeah, it’s always just like that. I don’t know. I like a tiny little woman who’s going to yell at me. That’s really all I want. Just like a woman who is five-three to be mad at me.

Drew: Wow.

Gaby: Wow.

Drew: We should be able to find you that. I just can’t imagine that we couldn’t. You would have to date and that is something you’re reluctant to do, but—

Christina: Then it always comes back to that, doesn’t it?

Drew: They’re out there.

Gaby: Do you not want to date as much because you care more now?

Christina: Interesting. My gut says no, but maybe.

Gaby: Welcome to therapy, bitch.

Christina: Every time we hop on one of these goddamn podcast recording sessions, it’s a ding dang therapy session every single time. No, I think my lack of interest in dating is definitely tied to my lack of ability to be vulnerable, is definitely my fear of getting intimate with people that are not— in a romantic specific sense. I’m very good at being intimate with my friends. I do just find it more panic inducing for some reason in a romantic context. And it is a reason some have said that I should go to therapy, but–

Gaby: Well, okay, because I’m saying with men, you’re like, “I can have all these boyfriends. I don’t care. I don’t have to be vulnerable with them, whatever.” Whereas, once you start dating someone where you’re like, “Ah, fuck.”

Christina: Yeah.

Gaby: “I actually want to be vulnerable with this person and there’s actual stakes here.” You’re like, “Well, fuck me.”

Christina: Yeah. Quite literally, yes.

Gaby: I didn’t even care. I cared about men, but I think I… Okay, so here we go. When I was a cis woman, which is what I’m calling my memoir.

Christina: Gorgeous.

Drew: That’ll sell quick, let me tell you.

Gaby: I know.

Christina: It really will.

Drew: That’s what they want from you.

Gaby: I know. When I was a cis woman, I was like, “Pfft.” I was one of those 2014 feminists who was like, “Men don’t have feelings. Kill all men.” I literally, had—

Christina: Get a bed frame.

Gaby: Girl, I had a male tears mug. When I started dating Mal, I would make them pose with it for pictures. They were like, “This is upsetting to me.” I’d be like, “No, it’s ironic now, you see.”

Christina: It’s feminism now.

Gaby: No, but they were like, “You used to be one of those.” I was like, “Absolutely.” Which, now, I have so much of a more expansive idea of what male is that I’m like, “That’s so dismissive and shitty and not great and not feminism and not funny.” Mal was like, when I showed them that mug, they thought I was like for real and they were like, “Oh my God, another femme who’s going to be mean to me just for being masc,” but then I was like, “No, no, it’s a bit you see.” Cut to three years later, I’m a man. Now, being on testosterone and stuff, I have this weird, now, like I’m getting more empathy for men, where something in my brain is being like, “This might be a little bit how they think.” I always thought that way, but I just was like, “It’s acceptable because I’m a woman, you see?”

It’s interesting. It’s going to be interesting for me to navigate being so confident and so forward. A friend of ours who won’t care, but a friend of ours posted a picture of her ass on close friends. I just immediately was like, “What that ass do,” right?

Christina: Yeah.

Gaby: This is my friend, so it’s fine, but that’s going to be a little bit different in the world when I look different, I think.

Christina: Yeah.

Gaby: Now, I’m like, “Oh, I see. Men have those thoughts, but they can’t say them,” but I—

Drew: When will men finally get to talk?

Christina: When will they get to say that a woman’s ass looks good? God.

Gaby: You know what I mean? It’s different. Now, I’m second guessing it or I’m like, “Well,” but I’m still at the place where it is flattering to some people or definitely to cis gay men, I’ll be like thirsty towards them and they’ll be like, “Mm-hmm.” They like it now, but I don’t know.

Drew: Yeah.

Gaby: It’s interesting.

Drew: No, it’s real. That’s definitely played a big part… I think I still have leftover stuff from like… and it all intersects with trans feelings and shame around all that.

Gaby: Yeah.

Christina: Yeah.

Drew: When I was like… I thought it was a guy, I was so timid because I didn’t want to be a creepy guy.

Gaby: Right.

Drew: I didn’t want to be like that kind of guy. Something we talk about on this podcast so much is encouraging people to be forward and to talk. Literally, the title of the podcast. That’s something that we’re doing because it’s something that I still struggle with.

Christina: Yeah.

Drew: It’s not because like oh, I’m an expert. And we’ve talked about this before, but I had to make the decision of like, “Oh, I’m never going to date anyone. I’m never going to have anything I want. I’m never going to be with anyone I want if I don’t get over myself and take some risks and get less rejection sensitive and get less…” It wasn’t even about the rejection itself, but about the idea of being a creepy trans woman.

Gaby: Yeah.

Drew: Or previously, a creepy man, but it is so interesting. I get why it’s gendered in the sense that cis men cause a lot of the harm…

Gaby: Right.

Drew: …and sexual violence and et cetera, et cetera, but it also is this thing where like I don’t think the solution is for a level of shame. It’s more about like consent.

Gaby: No.

Christina: Yeah.

Drew: Being like, “Okay, how well do I know this person I’m talking to?” It’s all just judgment calls and it’s all just people having to like, I don’t know, use some critical thinking and actually go case by case and try to be like, “Okay, would this person I know be okay with me being a little bit lewd? Yes or no or I don’t know.” If I don’t know, maybe it’s… Tone it down a little.

Gaby: No. Here’s the thing is that I’m infantilized right now. I’m two months on T. This is what I’m saying, is I’m two months on T, so I can be so forward to a cis gay guy and they’re like, “Oh, cutie.”

Christina: Yeah.

Gaby: Or the queer women in my life are like, “Ahahah.” Or even the straight women. The straight women are like “Ahahah,” but it’s like, they think of me as like, I’m like a little brother.

Drew: Right.

Gaby: I’m like Roger from Tia and Tamera. They’re like, “Aw,” but also like, “Go home.”

Christina: “Isn’t it past your bad time now?”

Gaby: “Yeah, go home, Roger!” That’s my energy right now. I don’t know. When you’re talking about rejection sensitivity, I also throw things at the wall. I also maybe have no concept of looking transmasculine now. I, still, if I meet a cis guy or I have like a cis guy I used to hook up with, I’ll be like, “Hey, is that still on the table?” I’m very much like, “Is this a date?”

Christina: Yeah.

Gaby: I’m thinking now about how I wasn’t like, “Hey, are you queer now with these guys?” I’m just like, “Do you want to still fuck?”

Christina: Yeah.

Drew: Yeah.

Gaby: I don’t ask like, “What’s your identity? Do you have any problems here?”

Drew: Yeah.

Gaby: Nothing like that.

Drew: Yeah.

Christina: Yeah. Sometimes that’s the question you want to ask. It’s not like, “Let’s talk about your identity.” It’s like, “Do you still want to smash?”

Gaby: Yeah. I don’t have time. It’s not occurring to me to be like, “What’s your”… The cis guy, that is dead to me now, is…

Christina: May he rest.

Gaby: Yeah, may he rest. It was not anything to do with… He was like, “I’m attracted to you regardless of gender. I don’t know what I am. I don’t care.” I think that’s true, but the reason that… I thought this is going to end because I’m on T, but what happened is, he had a polyamory freak out. I was like, “Oh, this isn’t even about…” The reason this ends isn’t because I went on testosterone and now I look like a guy. The reason this is ending is because you, all of a sudden, have decided polyamory is immoral. Fascinating.

Drew: Well, as a gender nonconforming trans person, I also know that sort of how someone identifies, you feel it more than you can hear it, right? I’ve had sex with people who don’t really know how they identify and maybe, don’t even know what gender they’re reading upon me, but just in our sexual interactions, I feel very affirmed and I feel very good with them.

Gaby: Yeah. Yeah.

Drew: It feels like they’re seeing me and seeing me as a person and seeing me as my gender. I’ve had sex with people who are proudly bisexual in the queer community.

Gaby: Right.

Drew: Love all genders and are very open about that and then treat me like a guy and it feels awful.

Christina: Yeah.

Drew: It doesn’t matter, necessarily…

Christina: Matter.

Drew: …how. It’s like what someone… Not that it doesn’t matter what someone is saying, but I think you feel it and that’s more important.

Christina: Yeah.

Drew: I think it would bother me if someone was like, “I would never be with a woman” and then is hooking up with me. That would feel weird.

Christina: Right.

Drew: But if someone is just like, “I don’t know,” then I’m like, “Okay, well, I know how it feels.”

Gaby: Yeah.

Christina: Yeah.

Gaby: Or it’s not my business. If you are still interested in fucking me, I’m not going to sit there and do a checklist and be like, “Are you queer?”

Drew: Right.

Gaby: Whatever.

Christina: Yeah.

Gaby: You are in my mind, but sure. Live your life.

Christina: Yeah. I’m perceiving you in a way that works for me. You’re perceiving whatever you’re doing in your way. That, sometimes, is enough.

Gaby: I think if I get top surgery, it’s going to change immensely. That’s my fear. Is that once I get top surgery, these guys are going to be like, “Wait a minute.”

Christina: “Hold on. You took the titties away.”

Gaby: Right. That’s what I think.

Christina: “What’s going on?”

Gaby: “Wait a minute, you have full facial hair and shh, but these are giving me an out.” When I don’t have them, I’m curious what they’re going to think.

Drew: Yeah.

Christina: Yeah.

Gaby: Doesn’t matter. I’ll probably still just be doing T4T anyway.

Drew: Well, we are going to have to have you back.

Christina: We’ll just have continual check-ins.

Gaby: Wait, Is This a Date: “Post-Titties.”

Christina: Yeah. Post-Titties edition.

Drew: Okay. Let’s move to our last segment, which I realized I didn’t prepare you for, but I think you should be able to. We always have a crush corner…

Gaby: Yeah.

Drew: … which is like a person in pop culture that we’re crushing on and that is an excuse to talk about something or you can just to talk about a person. It can also be an actual person we know, but if you can think of someone while we say our crushes, then we’ll double back to you.

Gaby: Yeah, yeah, yeah.

Drew: Okay. Because this is our dating men episode and because Gaby is here, I have two male crushes because I just saw Road House for the first time and my crushes are Patrick Swayze and Jane Campion hater himself, Sam Elliot.

Christina: Sam Elliot.

Drew: Who was so hot back in the day. I had no idea. That movie is incredible. It’s like—

Gaby: I have a Road House tattoo. I have a Road—

Drew: Yeah.

Gaby: Where is it? I have a Road House tattoo.

Drew: It’s on there. Yeah. What kind of fucking friend am I that I didn’t see that. I was just like, “Yeah, I’ll see it.” I just was dismissive of it and then it’s an incredible movie. I won’t do my—

Gaby: I was trying to tell you.

Drew: I won’t give my whole essay about why it’s really a great movie.

Gaby: It’s about class. It’s about masculinity.

Drew: It’s about how violence is… Physical violence is okay when faced with social violence.

Gaby: Yes.

Drew: Which so few movies, especially big budget movies are about that.

Christina: Yeah.

Drew: It’s brilliant. It’s bonkers and a really good time. Patrick Swayze does rip a throat out, but it’s great. I’m big fan. Patrick Swayze…

Gaby: Swayze.

Drew: …Sam Elliott, hot, hot, hot. Love both of them. Yeah.

Christina: Iconic.

Gaby: Swayze is my boy. I have a Swayze sleeve that I’m working on.

Christina: Swayze.

Drew: What would be your third one, if you got to—

Gaby: Okay. I’m thinking of watermelon for Dirty Dancing because, “I carry the watermelon.”

Christina: Gorgeous.

Gaby: Then I’m thinking, okay, then like a surfboard for Point Break.

Christina: Sure.

Gaby: I’m thinking maybe a strawberry for To Wong Foo because it’s a strawberry festival, but I don’t know. I’m still up in the air about the To Wong Foo one if anyone’s interested. Maybe a hat, because it’s to say something hat day. I’m not sure, but right now, I just have “pain don’t hurt” and a ghost. I got to get the rest.

Christina: Got to get the rest. That’s a gorgeous sleeve.

Gaby: Thank you. Then I’m going to try to do the other side, Kurt Russell. I’m a cis woman.

Christina: Yeah. Okay. Just going to—

Gaby: My two boys.

Christina: No comment on that one. Much like Drew, I was thinking that I should, in honor of the episode, have a dating men appropriate crush, but then I was like the other week said your crush was Jerry Orbach on a totally unrelated episode.

Drew: That’s true.

Christina: On this episode, I would like to say that my crush this week is Jenifer Lewis. We have been watching I Love That for You, which is a show that is pretty good. I feel like it’s 6% away from being truly great. I don’t really know what’s missing, but there is something missing. Boy, what it’s not missing is Jenifer Lewis being literally the most perfect woman on earth to be alive. She is so mean. She drinks so many martinis. She has so much sex with men at just like a drop of a hat and then has her butler give them a goodbye gift bag. I think it’s gorgeous. She sang “Feeling Good” in the last episode. I was like, “Yeah, of course. Why not sing “Feeling Good” if you’re Jenifer Lewis and you’re on a television show. You should go to a piano bar exclusively to do that.” I accept this as a plot. Thank you so much. She truly is the mother of Black Hollywood and I have never loved a woman more.

Gaby: I love her.

Christina: Jenifer Lewis.

Gaby: I love her.

Christina: She’s a perfect person.

Gaby: I love her.

Christina: Simply perfect. Yeah.

Gaby: Saw her at the GLAAD awards once. I think she touched my hand. I don’t know. I blacked out.

Christina: Yeah. I would die.

Gaby: Yeah, it was crazy. She was acting like she ran that place. I was like, “You do.”

Christina: You do. If she could run at any place and I’d be like, “Absolutely. She’s Jennifer Lewis.”

Gaby: She walked in and was like, “This is the Jenifer Lewis awards.”

Christina: Yeah.

Gaby: I was like, “I believe you.”

Christina: True. That’s gay culture.

Gaby: Yeah. I was like, “Gay what? Who cares? Give her all the awards.”

Christina: Who cares. Give it to her.

Gaby: Yeah. Oh my gosh. Okay. I’ll give you two.

Christina: Great. Gorgeous.

Gaby: Right now, I’m watching All Stars 7 Drag Race. Jaida Essence Hall, so fucking gorgeous.

Christina: Yeah.

Gaby: There was a challenge where she is dressed as a pig, a literal pig.

Drew: Oh my God.

Christina: Oh my God.

Drew: The hottest pig.

Gaby: She looks stunning. I would—

Christina: Truly like, “Do I have a pig fetish?”

Gaby: I would fuck that pig.

Christina: Like, “What’s happening?”

Drew: Yeah.

Christina: Yeah.

Gaby: She’s so—

Drew: Her and Jinkx—

Gaby: Beautiful.

Drew: And Monet. Hottest pigs.

Gaby: Well, Jinkx is also very hot to me, but she is just stunning.

Christina: Yeah.

Gaby: I would love to look at her. I would love to fuck her as a pig. I could not believe and just her face… That’s her face? That’s her face.

Drew: Yeah, yeah. That’s her face.

Gaby: Good fucking Lord. She got the short end of the stick in terms of winning during the pandemic. Honestly, I don’t want her to win All Stars 7, because that’ll be Jinkx’s game, but I do. Wow. She’s really beautiful.

Drew: Yeah. Top four for sure.

Christina: Yeah.

Gaby: Top four.

Christina: Yeah, no doubt.

Gaby: I love Raja too. I’m very sexually attracted to Raja, but…

Drew: All of them.

Gaby: …extremely. I don’t care. Lip sync, standing still. I don’t give a fuck, but yeah, I would say my crush is Jaida as a pig.

Christina: Okay.

Drew: Great.

Christina: I think that’s gorgeous.

Gaby: Yeah.

Drew: Thank you so much.

Gaby: You’re welcome.

Drew: Well, now is the time.

Christina: Yeah.

Drew: Do you want to tell the people where they can find you and your work and what you’re working on and the million things you’re working on?

Gaby: Oh Lord.

Christina: Promote yourself.

Gaby: I’m @gabyroad on Instagram. I have a podcast called, Just Between Us. I have a podcast called, Bad With Money. Just Between Us is, we just had Monet X Change on, speaking of, and she and I fell in love, no big deal. Then I have a million. I have a Bad With Money book. I have a graphic novel called, Bury the Lede. I have a million things going on. I have eBook out called, Stimulus Wrecks. I do a show on AMP at 8:00 AM on Wednesday mornings called, This Week in Gay, where I talk about gay stuff and spin gay tunes. I don’t know. I feel like I don’t do anything, but here we are.

Drew: That’s absurd that you feel that way because it also like—

Christina: I was literally just going to say, I forgot how truly booked and busy your ass is.

Gaby: Yeah.

Christina: My good Lord.

Drew: There’s also 14 different things that you’re not allowed to talk about because they’re in development.

Gaby: Yeah, and then some development stuff that’s very nice. A lot of it is gay. Well, I would say, it’s all gay.

Drew: Yeah.

Christina: It’s all gay.

Gaby: I don’t know when this comes out, but if you want to see my short Grindr Baby, it’ll be on YouTube, but it’s also at Frameline festival and you can watch it on-

Drew: I think Frameline will have already.

Gaby: Okay.

Drew: Right. Right.

Gaby: Frameline passed, but you can see it on YouTube. It’s called, Grindr Baby.

Drew: Right. Thank you so much for listening to Wait, Is This a Date? You can find us on Twitter and Instagram at Wait Is This a Date? You can email us at waitisthisadate@gmail.com.

Christina: Our theme was written by Lauren Klein. Our logo is by Manya Dahr. This podcast was produced, edited and mixed by Lauren Klein.

Drew: You can find me on Twitter, Instagram, and TikTok, at draw_gregory.

Christina: You can find me on Twitter at C_GraceT and on Instagram at christina_gracet. You can find Autostraddle, of course, at Autostraddle.

Drew: You can find Autostraddle at autostraddle.com, the reason we’re all here today. Thank you so much and see you next week. Christina, what is the difference between a date and a podcast?

Christina: Actually, that’s really interesting that you asked that because scientists are, at this very moment, hurriedly trying to figure this out. We have some of our best scholars on this. On the case here, we don’t have an answer, but I think every day we journey closer to understanding.

Drew: I wish them and us the greatest luck.

Drew (voice memo): There have definitely been points in my life where if a reasonably attractive straight couple pulled like, “We saw you from across the bar and we really liked your vibe,” I would’ve done it just for the validation and experience. I don’t think I’m there anymore. They’d have to be actually attractive now. I think that’s growth.


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Drew Gregory

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 288 articles for us.

11 Comments

  1. Thanks for the conversation. I have been ‘following’ Gaby for quite some time, very similar gender/identity evolution which has been interesting to see unfold on parallel timelines. Drawn to people for a reason even before knowing it I guess.
    Always impressed by how out and thriving they are. And living a bit vicariously through their journey.
    I am a (closeted) transman, currently semi-out as nonbinary, living in the suburbs after Eastern Europe, and a bit older (38). I fear I won’t reach every being out, but hope so. Pray so even. Not a very productive comment, but I am thankful for Gaby being so public. Lifesaving at times. Thanks again. :)

  2. Super interesting to read this and hear your different experiences! As a lesbian who has never had a totally consensual sexual experience with a man, part of me is always just surprised to be reminded that yes sometimes people who are not cis men can have positive and consensual experiences with dudes.

    Also I think this gave me more insight to the whole thing where bisexual women talk a lot about how much harder it is to date women. (Which always confused me since everything I’ve heard from straight and bi friends makes it sound like dating men is really hard?) it’s not necessarily that dating men is easy – it’s that it’s simple and there is more of a clear script to follow so even if that script leaves you miserable, at least it’s a script.

    • Yeah, the script thing really is the key of it. I’m not a bi woman, but I am a trans lesbian, and one of the ways I coped in the dating scene before coming out to myself was that I developed almost a *literal* script of what I was supposed to do as an ostensible straight dude on a date with a straight* woman (since, left to my own devices, I was objectively terrible at being a straight dude). Now, dating women is a lot more complicated, even if I feel like I can be infinitely more free and spontaneous.

      *Well, in retrospect, only one of the women I seriously dated as an adult was straight–the others were all bi or later came out as lesbian. Funny how that works out, isn’t it?

  3. Hi Drew and team-
    I just want to say how I appreciate you guys so much for tackling these cross over/somewhere at the boundary of queer themes *heart*
    Homosexual transsexuals ( = who used to live a cis straight life) Yeah :D !! Always seeing these cracks and crevices.

  4. Yo this was amazing! This is the dating men content that is relatable and interesting and thought provoking! No offence to the “I’m bi and married to a cis straight dude” crowd but like …we done heard that story. This was all so fresh and interesting!!! Loved it.

    • i mean, i’d be pretty surprised if this was *the only* relatable dating-men content to everyone seeing this ;) maybe we done heard that story, but there’ve been a lot of times when we also done forgot it or dismissed it. we can enjoy gaby’s perspective without telling other bi people to be quiet. but i agree that this was delightful! :)

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