“Wait, Is This a Date?” Podcast Episode 106: You Should Probably Break Up

Dating isn’t all sexting and thirst traps. It’s also heartbreak. This week on Wait, Is This a Date? we’re joined by Autostraddle’s very own Sex and Dating Editor Ro White to discuss break ups. We’re talking break up strategy, when to break up, and the gay tradition of remaining friends afterward.

But first! We begin with my free association of break ups to cancel culture and play a game of “Is This a Real Queer Celebrity Scandal or Did Drew Just Make It Up?” Fun!


+ Speaking of cancel culture, listen to these very good cancel culture episodes of Bad with Money and You’re Wrong About.

+ I haven’t read it but here’s the Marlene Dietrich biography written by her daughter Maria Riva.

+ I was going to link to a You Need Help about break ups but honestly just scroll through the whole tag. It’s  what Riese sent me back in 2019.

+ The Janelle Monáe post Christina mentioned.

+ This is what I wrote about Princess Cyd for our 50 Best Lesbian+ Films of the Decade list:

The first time I watched Princess Cyd I watched it again a few hours later. My girlfriend at the time got home from work and I was bursting with a certain chaotic enthusiasm anyone who knows me knows too well. I insisted it would just be easier to show her than try and articulate why I’d fallen so deeply and completely in love with this movie. So we watched it! And she understood! How could she not? Because Princess Cyd is so, so good.

The mostly non-existent plot is Cyd decides to spend a summer with her novelist aunt Miranda. As she explores her casually pansexual desires – most significantly with hottie barista Katie – she also reflects on the memory of her mother and learns to respect Miranda’s less sexual approach to life. The experience of watching the movie is like being invited to one of Miranda’s living room readings. The experience of watching the movie is like being a part of one of Cyd’s trysts. The experience of watching the movie is like remembering the best summer of your life that you didn’t even realize was the best summer of your life until years later you think back on a small moment that shouldn’t mean much and realize it means everything. Every time I open Netflix I hover the cursor over Princess Cyd tempted to sink back into its world. After texting one friend about this movie for the millionth time she said: “I feel like instead of an eternal flame at your grave should just be a speaker of your voice wailing PRINCESS CYD IS SO GOOOOOD on repeat. Forever.” Add it to my will.

Ro: This thing happens in queer communities that I’m wondering if we could talk about, where I’ve noticed a lot of monogamous queer folks and monogamous relationships opening up their relationship rather than breaking up. And I think that is a huge mistake, and I know this because I have done it.

Christina: Okay, we love the wisdom of experience.

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 the fun, fabulous, exhausting, whatever kind of adjective you feel like using, world of dating.

Drew: All of the above. My name is Drew Gregory. I’m a writer and a filmmaker. I write for Autostraddle.com, the website, where I do a lot of film and TV stuff, and also dating stuff. I am a trans lesbian.

Christina: I am Christina Tucker. I’m also a writer at Autostraddle. I am a lesbian on the Internet who is also a very tired experience today in this moment that’s feeling really beautiful, feeling really special, but I think we’re going to get somewhere fun today.

Drew: Yeah, I think that you’re bringing tiredness to a good episode because our main topic today is knowing when to break up. Fun stuff.

Christina: I am rather bafflingly just giving Drew a hang ten, famously podcasts are an audio medium, but it feels — just like transparency for our listeners that I am just kind of doing a hang ten. So we’ll see what happens today, I think.

Drew: That’s really brave of you to share. Really brave of you. Okay. Before we get to our main topic though, I have a game for us.

Christina: I bet you do!

Drew: Because we’re talking about breakups, I was thinking about more social breakups, existential breakups, scandals you might say, getting canceled. I mean, getting canceled, I think, actually usually means like there’s a little bit of drama and then everything’s fine. So I think these reflect that appropriately. And so I’m going to describe a scandal with a queer, and I want you to tell me if it is a real scandal that happened, or if me, Drew Gregory, wrote that. Okay?

Christina: I love this, and not only because you kind of just free associated with the idea of breakups, loving this energy.

Drew: Great. Thank you.

Christina: All right. I’m ready.

Drew: Okay. On the set of classic film, Charlie’s Angels, known abuser, Bill Murray, said to famed lesbian erotica painter, Lucy Lu, “You can’t act.” She started throwing punches and they had to be pulled off one another. Many believe this is why Murray was replaced by Bernie Mac in the sequel.

Christina: I believe this is true.

Drew: It is true.

Christina: As true as gossip stories can be, I suppose.

Drew: Sure. Yes. Thank you for really maintaining the journalistic integrity here, that the true ones are true in the sense that they were reported.

Christina: I think what we can use is it feels emotionally true that that occurred.

Drew: Yeah. Honestly, I think all of them feel emotionally true, but we’ll get to that.

Christina: Of course, you do.

Drew: Yes. Okay. Next up, Kate McKinnon faced backlash in April of 2019 when she was asked about ex-girlfriend, Bari Weiss. “We were young,” McKinnon said, “But I wish only the best for Bari. I love seeing her name pop up on my newsfeed.” Some felt McKinnon should have been much harsher toward Weiss, while others related to not wanting to get on the bad side of your most toxic ex.

Christina: Unfortunately this is true.

Drew: It’s not true.

Christina: Which isn’t true?

Drew: Kate McKinnon has never commented on Bari Weiss being her ex-girlfriend, which I think is really wise. I think she probably should continue to not comment on it because I can’t imagine that that would go well for her.

Christina: No good will come of her commenting on that, but in my head she already has, and, poorly, so.

Drew: Yeah. Okay. On March 3rd, 2014, power couple, Cara Delevingne and Michelle Rodriguez, got in trouble with PETA after pictures surfaced of them at the Big Cat Encounters Ranch. In one of the photos, Delevingne is kissing a six-month-old tiger on the head, even though the USDA explicitly bands kissing a tiger at that age. The owner of the ranch lost his conditional permit to house tigers.

Christina: I have no idea. I’m going to say that that did not happen.

Drew: It did happen.

Christina: Yeah, I should have known. I’ve been following Cara on Instagram for too long.

Drew: Yeah. I mean, I will say that I phrased it in a way, like — you cannot kiss a tiger at six months old, but it’s not only at six months. It is that after the age of three months, you cannot kiss a tiger, because after the age of three months they are very dangerous.

Christina: I’m going to take the kind of radical position that no human should be kissing tigers. Not to get political on our dating podcast, but that’s annoying. Yeah.

Drew: I think that’s really good. Yeah, it’s an important issue. Okay. Going back a little further in time. Upon moving to Hollywood, Marlene Dietrich made her husband, Rudolf Sieber… Are you mocking me? Are you laughing at me? Okay, live away from her on a ranch in the San Fernando Valley. When he got his girlfriend pregnant, Dietrich insisted the woman get an abortion to avoid any scandal, even though they were married in name only. She then had Sieber moved back into her home where he acted as her butler.

Christina: I want this to be true. And also full transparency, I was laughing because you had said, “Let’s go back a little further back in time,” and then said Marlene Dietrich, who was alive in, like, the thirties, so quite a bit further. I’m going to say that this is true because it feels, to me, emotionally true.

Drew: It is true.

Christina: Great. Yeah.

Drew: Or at least this is what Marlene Dietrich’s daughter said happened.

Christina: Iconic. Incredible.

Drew: In a memoir about how awful a mother Marlene Dietrich was. So I think there’s a bias here, which makes me wonder if Sunset Boulevard is based on the relationship between Norma Desmond and her butler, if that’s based on Marlene Dietrich. This is what I was thinking about today.

Christina: Loving your day, for you.

Drew: Thanks. Okay. Next up, on February 14th, 2000, Anne Heche and Ellen DeGeneres attempted to apply for a marriage license in the state of Vermont. When they were denied, Heche began screaming at the registrar and they were removed from the county clerk’s office. DeGeneres stated that she was not aware of Heche’s plan and had merely accompanied her girlfriend for a “Valentine’s day surprise.” They broke up soon after.

Christina: I don’t believe that’s true.

Drew: It’s not — it’s so hard not to laugh! It’s not true, but I just really enjoyed picturing it. That one, to me, does feel emotionally true. That feels like what their dynamic would be, and I just can see Ellen DeGeneres throwing her girlfriend under the bus in the midst of a scandal.

Christina: I can see parts of that happening I think, Anne Heche having some kind of Vermont-based yelling experience, I can absolutely see. But I can’t see Ellen talking to press about it.

Drew: That’s a really good point. She would’ve said nothing. Good catch, good catch. Okay. This is the last one. In November of 2013, a group of South Dakotan ranchers demanded Joan Jett be removed from South Dakota’s official float in the Macy’s Thanksgiving Day Parade due to Jett being vegan. The organizers of the South Dakota float complied and Jett did not participate. One rancher said, “I call this a win for South Dakota and for beef producers everywhere.”

Christina: Wow. So many words that were in that that I didn’t expect. South Dakota, frankly, really threw me. I’m going to have to go ahead and say that that is not true.

Drew: It is true!

Christina: Great, incredible. I am happy for… Actually I don’t know who I’m happiest for in that scenario.

Drew: Oh, God. I had so much fun putting this together. Thank you for playing with me. Okay, the other thing that I learned, but this felt a little intense and also it’s not really a scandal because it’s not Jodie Foster’s fault, but did you know that Jodie Foster had a second stalker after John Hinckley Jr?

Christina: I did know that.

Drew: Okay. I didn’t know this, but the detail that I love the most from her Wikipedia page that — when you go to the article, it’s phrased a little bit differently, but on Wikipedia it says that the second stalker went to Yale, where she was at school, to kill her, but then decided not to after watching her college play.

Christina: When you see talent, you have to respect it.

Drew: I just think it’s so funny, the idea of going to a college theater performance and being like, “Yeah, I’m not going to kill this person because of that.”

Christina: Yeah. I didn’t know it was possible for a college theater performance to make that much of a difference in a person’s life.

Drew: I mean, that’s really what I’m getting at here.

Christina: Yeah, it’s beautiful.

Drew: Okay. Well, I’m a real fun world in the queer celebrity gossip and also, I guess, almost attempted murders. Now, it’s time to move on to hopefully a brighter topic, or maybe not, which is — look, I think breakups are a brighter topic than murder! Do you disagree?

Christina: Yeah. I think no one’s going to argue with you on that categorization specifically, fair enough.

Drew: Thank you. So you’re ready? Let’s do this.

Christina: Let’s absolutely do this.

Drew: Today, we are joined by a very special guest. Very special guest, do you want to introduce yourself?

Ro: Sure! Hi, I am Ro White and I write for Autostraddle. I’m also the editor for our Slick series, which is our erotica series. And I teach sex ed, and I talk about dating a lot.

Christina: We love that. That’s the perfect experience and energy to bring right here to Wait, Is This a Date?

Ro: I am so thrilled to be here.

Christina: Talking about breakups? We’re going to have so much fun. The lightest topic of all, breakups.

Ro: Breakups are the best.

Christina: Yeah. They really can be, is the thing.

Drew: I want you to expand on that, because that feels genuine and I like that.

Ro: Yeah. I think we think of breakups as a terrible thing. And of course, they’re hard. But there is something really freeing about imagining your life a certain way and then moving in another direction. I think it’s similar to when someone quits a job. Sometimes there’s this feeling of relief and elation that goes along with just making a different choice for your life, especially when you find yourself going down a path that isn’t going to work for you. So I think whenever we either give ourselves the power to make that choice or whether that choice is just given to us by a partner, it can be a really beautiful life-changing thing.

Christina: Yeah. I super agree. I also think there’s a weird narrative that if we’ve broken up, that means everything about our relationship didn’t work and we have to look back on it with, okay, it was a terrible experience in my life, no matter how the actual relationship was. I don’t know that ending things necessarily means that the whole thing was bad. It just meant it wasn’t working anymore. And that’s okay. I have been seeing more willingness to talk like that and think of breakups like that, because I feel like for a while it was very just like, well, if you break up, then it’s over and that person was bad and your relationship was bad. That’s such a boring binary way to think about relationships and what we are to people.

Ro: Yeah. It feels like a very straight culture thing too, at least in my experience, I feel like my straight friends are the ones who are more likely to say, “Well, fuck that person, that person sucks if I end a relationship with someone.” Whereas queer people in my life are the ones who are more likely to maintain friendships with exes, or at least just see our exes in a holistic way.

Christina: Yeah. I suppose, I will say some of my straight friends I have been like, “Well, yeah. You got to say fuck that person and move on.”

Drew: Yeah. I guess, I think it’s so interesting. The idea that you meet someone, be it on a dating app or through a friend or whatever, and then you spend three years with them, share a life with them, share a space with them. That’s such a success to me. That is an incredible, remarkable thing that could happen. But I guess that’s because I’m not thinking about my life in a way where my end goal is — not that I don’t want to get married or I’m not open to getting married — but I don’t see my life in this linear sort of heteronormative, like getting married is this step of adulthood, or this thing that I’m looking for. And then once I’ve found it, I’m good to go. That’s not how I approach dating or am approaching my life. Whereas I guess if you are approaching your life for what you want is one partner for forever, then, yeah. I guess breakups feel like more of a failure.

Christina: I think that’s probably true for people, that if you’re on one linear path to marriage, then every breakup is not a success, because you didn’t end up getting married, unless you get married to every person and then break up with them, but that seems very chaotic to me.

Drew: I would love to be divorced. I shouldn’t say that because I’m sure for people who are actually divorced… I do feel like, I don’t know, maybe it’s a queer thing, but when I find out that people are divorced, I just feel like, “Oh, you’ve lived a whole life, haven’t you,” as opposed to, I think maybe in straight culture where it’s like, “Oh, well, you failed.” I’m like, “Oh, good for you. You had a relationship that mattered, theoretically.”

Christina: Yeah.

Ro: Yeah. I mean, you also made a choice to enter into a financial contract with a partner and then end it in a way that may have been really difficult and messy. So I think that’s the extra layer that marriage adds to relationships in addition to all of those social cultural pressures.

Drew: For sure.

Christina: Yeah. I mean, at the end of the day, kids, a marriage is a business proposal. So that’s what we have to say here at this podcast.

Drew: Yeah. I want to talk about knowing when to break up, because this is something that I think about a lot. I think maybe… I was trying to decide how personal to get, which is hilarious if you know what the previous episodes of the show have been. I guess, I think that my most recent serious relationship, like my ex, I know that she thinks that it was pretty sudden. I think that’s just so interesting because I believe in working on relationships and I believe in putting the time in it, that every relationship has problems, especially if you spend a lot of time with someone, like giving it a chance to work. But I also, because I can view a three-year long relationship that ends as a success, I don’t understand making it a four-year long relationship that wasn’t a success? I don’t understand the desire to elongate things past the point where it feels like they just aren’t working.

Christina: Yeah. I definitely feel the same way. I wonder if it’s that people are not necessarily great at knowing when it is beyond workable help. When that feeling feels like, okay, we could do some work here, but at the end of the day what would that really accomplish? Would it just be better to separate and go our separate ways, than try to do this and maybe poison the well of our friendship going forward or what our relationship meant before? I feel like that, people are more hesitant to let go. I think people are probably just scared of being alone in a big way.

Ro: Yeah. I think ending relationships feels like a bigger deal in some ways in the queer community, because for us, our partners are more likely to become our chosen family. Whereas for straight folks who might have closer connections to blood family, et cetera, that’s less of a thing. I mean, especially for queer women and trans folks who are less likely to have disposable income, a lot of us, we move in together. We make all of those choices where we fully integrate our lives financially and socially. And so then the idea of ending something like that, it doesn’t just mean ending a relationship. It means breaking up your whole social circle, it means finding a place to live when maybe you can’t afford to live on your own. It’s a mess and a disaster. I get why people don’t do it soon enough.

Christina: Yeah. It’s like, okay, so I’m going to break up with this person, but actually breaking up with this person means entirely reorienting my life. That’s a bigger swallow. I get that. I totally feel that.

Drew: I think that’s probably why my two major breakups have happened when we were in a phase of long distance. It was like, we sort of already started the shift in our lives being separate and not to say that… I think in both situations we wanted the relationship to work, but I do think in retrospect, and maybe this is something I will take responsibility for, but just in that, maybe I manifest that a little bit? Maybe there’s part of me that starts to create that separation, which I guess if any future people I’m dating are listening to this and they’re like, “Oh, Drew’s moving away for a job. So I guess our relationship’s over.” But it just like — look, I don’t have a huge sample size, but that is what my experience has been. It still was super difficult, but the difference of the difficulty of like, okay, we’re permanently moving away from each other, versus if we… because I was living with my former partner and if we had broken up while sharing that space, that would’ve been a much more challenging experience.

Christina: Yeah. My last serious breakup was right before my ex moved. And we knew she was moving — that was a thing, that’s part of the narrative. We kind of talked about how we weren’t particularly interested in doing long distance. So those last few months were kind of just like, “So we’re just going to call this at some point?” This is weird, just kind of living in this knowledge that this will end at some point. And then I decided that that point was Halloween. I can’t express to you enough how much of a bad idea it is to break up on Halloween, sitting on your stoop at 6:00 PM, because children will be trick-or-treating, and they will be confused that you have no candy to give them, but instead lesbian sadness. They will be very perplexed.

Drew: It’s a trick! Trick or treat, you know?

Christina: It was certainly a trick. Let me tell you what, we could have literally gone anywhere else, just not that one space would have been fine.

Drew: Yeah. Ro, do you have any bad breakup stories that you feel comfortable sharing?

Ro: I think overall, so right now my girlfriend and I say R and r when we’re talking about relationships. So when I’m saying R, I’m talking about the relationships that have been significant, sort of maybe long-term, but maybe just very important, like we were “a thing.” And then r is the casual kind of relationships. So of the Rs of mine that have ended, I absolutely believe that each of them could have and should have ended sooner. I think I fell into that trap that I was talking about earlier of, “Well, ending this means completely reorienting my life, and I don’t really feel prepared to do that right now.” I don’t think I had that thought consciously. This was the thing that I realized after the fact every single time.

Christina: Yeah. That’s one of those things that you’re like, loved if that learning had come in a little quicker.

Ro: Yeah. I mean, I get really invested in my relationships. I love caring for other people, whether those are partners or friends. And the idea of ending something like that has felt really scary for me. But the times when I have made the choice to end those relationships or when that choice was made for me, I have felt great about it every single time, which feels weird to say. Of course, I’ve been sad, but I’ve also had this part of me that has felt absolutely elated after every breakup of like, oh, I’m free to make this other choice with my life.

Christina: Yeah. I think that the weird thing about breakups, especially when you think about all the things that people can compromise in relationships and how you can have conversations, but it’s like, one person wants to break up, that’s the end of the relationship. There’s no halfway, there’s no like, oh, can we compromise? Can you meet me halfway on this one? It’s like, nope, that’s actually one thing a person gets to kind of unilaterally decide for your relationship if it’s over.

Drew: Yeah. And if your partner is the person who you go to and rely on when things are tough, it can be really challenging. I think this is a cliche, queer breakup of using the person who broke your heart as emotional support and how that does not really work. But I think it’s pretty natural when you have previously been relying on them, and it can be one of the challenges where you feel sad. And then you’re like, well, I want to call this person to talk about how I feel sad. And it’s like, that’s the exact person you should not call. That can be a little bit of a challenge. I’m very good at — again, this, I think, gets me into a little bit of trouble, that I’m very good at compartmentalizing. I’m not good at saying “compartmentalize,” but I’m going at doing it, in the sense that if I say to myself it is not healthy for me to check this person’s Instagram, I will meet them and I will not check their Instagram. I really can make myself do that. It doesn’t mean that I don’t have a lot of feelings about it. I think this is something that I’ve had a hard time communicating sometimes to people is like, I can feel a lot and I can feel really sad and I can feel a real loss and someone can mean a lot to me. But if I’ve made the decision in my brain that what we need is to not be together or if I’ve decided that we need a space or if I’ve decided, whatever, I can keep those commitments to myself and hold those boundaries pretty strictly.

Christina: That’s because you got a lot of earth sign up in that chart maybe. That’s what that is, because I am the exact same way. I’m like, “No, I’ve made the decision and now that’s over. We’re done with that. We are moving away from that space.”

Drew: Yeah. Ro, what’s your chart? I don’t remember.

Ro: I am an Aries Sun and a Sagittarius Moon and a Scorpio Rising.

Drew: Wow. That’s fun.

Christina: Wow. That is a chaotic chart. I really enjoy that. I like that a lot. That’s some fun energy.

Ro: It’s really like, if you look at my whole chart, it’s quite balanced. It’s kind of all over the place, which I really appreciate about myself, because I think there are definitely parts of me that are like big Aries vibes, but I have many friendships with other Aries people, and have had relationships with other Aries people, or I was like, “Oh, God, too much Aries.” So I’m glad that that’s not across the board my deal.

Christina: Yeah. That’s why we don’t do any sunshine shaming on this podcast because we love a full chart. We need to understand every facet of a person.

Ro: I’m a whole person. I’m not just an Aires.

Christina: We are here respecting and loving that person that you are.

Ro: Thank you very much.

Christina: Anytime.

Ro: Do you want to try to answer the question of when you know it’s time to break up? Because I feel like that’s a question that we get very often at Autostraddle in our advice box. I feel like I’m constantly telling people to break up, and I feel like such a downer when I do it, but I think it’s the right advice.

Drew: Yeah. Okay, there are things to consider. If you have spent 10 years with someone and you share a life and all those things we talked about, financially, et cetera, you’re entangled with them and you’re like, we’re having problems, should we break up? Maybe there are reasons not to if it’s a first thought that you’re having. But it’s wild to me, the amount of times we get questions where they’re like, “I love my girlfriends so much. We’ve been together for two months. They treat me like absolute shit, should we break up?” And it’s like, “Yes, you should break up!” I know that you love this person, but you don’t really know that. I mean, you do, but you know them in this very certain way. And also you could walk away so easily right now. All those other things we were talking about aren’t happening. I mean, I would even say to someone who’s been married for 10 years, if you’ve been questioning, should we break up for a good chunk of time, yeah. I just think that that’s one of those questions — it’s like, “Am I gay?” It’s like, not a lot of people who are straight are walking around being like, “Am I gay? Am I gay? Am I gay? Am I gay?” So I think similarly it’s like, “Should we break up? Should we break up? Should we break up? Should we break up?” Yes.

Yeah. I think that’s probably why we have such a high hit rate of saying, “Yes, you should break up,” because every time someone writes in asking should they break up, I’m like, “Well, you took the time to write this and ask somebody.” I’m like, “Yeah, you probably should if that’s where your head is at, then my gut says it’s probably time for you to break up, right now.”

Drew: But it’s also, I think the one thing that complicates it for me is that I know that I have never been in a relationship where I’ve talked about breaking up with the person throughout the… But I’ve witnessed that in friends who have good relationships where it’s just the way that they function more is a little bit more volatile and has a little bit more conflict. I’m really hesitant to get in a relationship, and maybe it’s an earth sign thing, but I’m very cautious about entangling my life in that way. And not just financially, but even in the sense of associating with someone. And then the way of introducing someone to my friends, and being like, this is someone who I care about and I want to bring them into your life. I just can be pretty hesitant about that. And so if I’m with someone, usually we’re compatible in a way where… I also don’t want a lot of conflict in my relationship, because then I just would be single. And so I want conflict in my flirtations. That’s really fun. But if I want to share a space with someone, I’m like, I don’t want — if we get into fight, it should not go to, so are we going to break up? Anytime that I’ve gotten into a fight with a partner, the assumption is we’re going to talk through it, we’re going to work through it. My definition of a fight in these circumstances is I think some people’s definition of a discussion. I don’t really like fight with my partners. And so I’m not the kind of person who would be in this head space of, “Should we break up? Should we not break up?” Because when I get in that head space, I do it. Yeah. I mean, if I have a passing thought, not necessarily if it’s like, oh, I am sort of annoyed at this person, maybe we were not good together. I’ve had those thoughts obviously, and then stayed in relationships. But even then, usually six months later or something, those passing thoughts are starting to come back more and I realized that that was sort of a sign of things to come. I don’t think you have to walk away the second you have a doubt, but I don’t know.

Christina: It’s a little file for later, put it on the record, the record of your mind, some might say.

Ro: Yeah. I think a lot of us have those record scratch moments where you identify a difference in values with your partner, whether it’s a difference in values that has always existed, or suddenly your partner has changed their values or desires. I think those moments can be pretty like make-or-break depending on how important that value is to you. I think those are really important to pay attention to when you’re trying to figure out, do I want to stay with this person or do I not? I mean, I’ve even told people before and have myself made a list of all of my values. I’ve made a list of the things that are important to a person I’m dating to determine, is there compatibility here? Or is this just never going to work down the line for whatever reason?

Christina: Yeah. I think there’s the values aspect of it and then there’s that moment where you’re having a conversation or you’re having a fight and you’re like, we are talking about two wildly different experiences and I don’t know that we’re ever actually going to be able to get on the same page with how you see me in this space or how you think that I react to things, or what you think my emotional shortcomings are, or too much — those kinds of moments where you’re like, “Oh, maybe this person actually doesn’t see or understand who I am.” That can be very troubling. It’s something that I think that people are better at talking themselves out of, that mattering, as opposed to being like, oh, well, this person’s values don’t line up with mine. So we simply won’t be dating anymore. It’s like, if someone can’t understand you emotionally, despite you being very clear about it. That’s also really going to matter down the line.

Drew: Yeah. I also think circumstance and timing is huge. I think it’s going to be really interesting as things open up post-pandemic or this fluid in-between space of pandemic and post-pandemic, where I think that it’s perfectly lovely if you met someone during the pandemic and are dating them. I mean, I sort of am. So it’s like, that’s fine, but I do think that it’s going to be interesting and we’re all going to have to adjust to this idea of now that what our day-to-day lives look like is different, some relationships will work better and some I think will not work at all. We’re just going to have to be prepared for that and be ready to adjust to that. I mean, I know that for me in my last relationship, I like to be sort of self-deprecating and take responsibility in the way that it’s important to take responsibility. But I also think in this joking about like, oh, it was because we were long distance and I was running away and whatever. And it’s like, yeah. But also what it was is that our circumstances just changed. When I was working a job that took up all my time, our relationship didn’t really work, as opposed to when I was soon-to-be college grad, post-college grad, sort of floaty space where I was very available and we were very sort of intertwined, our relationship really worked. That was great. Because that’s where I was at in that period of time, and that was lovely. But because I know myself and I know that I’m an ambitious person and that more of my life is going to be spent very busy with work stuff and very consumed with all these other things than it is going to be in that sort of floaty, in-between, post-college space. I was like, “Oh, this relationship isn’t going to work moving forward.” That is no judgment on the way that it worked when circumstances were different, but just am making the call that like, yeah. If I’m looking at this and my choices are this relationship works when I’m behaving this way, when I’m leading this kind of life and I’m looking at my next year, or my next 10 years, the rest of my life, and it’s looking a lot more like this other circumstance that doesn’t seem to work, then it just sort of became clear and becomes clear to me that it was just time.

Christina: Yeah. I think that’s true. I totally function similarly thought wise, but I do think that is circumstance breakups. People have a really hard time conceptualizing that your relationship could, for the most part, still be fine. What you feel about that person could not change, but something as dumb as a circumstance could just really get in your way. That’s not great, but it is a very valid reason for a breakup. I just find my friends who have gone through breakups like that, those are the ones that they are so resistant to breaking up, because they’re like, “No, this one thing shouldn’t be the thing that takes us down.” I get that. I get wanting to feel that way, but unfortch, circumstances are kind of the whole thing.

Drew: Yeah. I think it would be helpful if people realized that oftentimes circumstance breakups aren’t circumstance breakups, they’re priority breakups, people are making decisions about what — I don’t think you should not take a job in order to stay closer to your partner or whatever, but some people would make that decision. And also some relationships could do perfectly fine long distance, and they wouldn’t need to break up because of that circumstances change. And if the circumstance is more connected to like, oh, I don’t know. It’s hard sometimes to be in a relationship when a lot of tragedy has happened or other challenges. It’s like, okay, but that again isn’t a circumstance, that’s revealing that this relationship wasn’t meant to continue through this aspect of life that is going to happen and is going to be part of life.

Ro: Yeah. I don’t know — what made me think of this was when you were talking about people being resistant to a circumstance breakup, it’s making me think about all of these long drawn out breakups that I’ve encountered, either in my own life or that I’ve seen in friends lives or that I’ve seen in the Autostraddle advice box. This thing happens in queer communities that I wonder if we could talk about, where I’ve noticed a lot of monogamous queer folks in monogamous relationships, opening up their relationship rather than breaking up. I think that is a huge mistake. I know this because I have done it.

Christina: Okay. We love the wisdom of experience.

Ro: I mean, I certainly don’t think it’s always a bad thing to open up a monogamous relationship. I think that’s awesome when both partners are on board, but I’m seeing it happen a lot of times when really there are other issues that need to get addressed and the assumption, because we’re queer and we’re sexually free is, “Well, let’s just fuck some other people and it’s going to be great,” and no, it’s not going to be great. It’s really not, unless your relationship is super solid.

Christina: Yeah. I definitely see a lot of that. People who have really never identified as being interested in being open or being poly are like, “Yeah, no, what’s going to happen is we’re going to be open and it’s going to be awesome.” Usually in my experience, there has been one partner who is very interested in this idea and another who is totally resistant, and I’m always like, that is a terrible combination of feelings and ways to go into this. And yeah, it never works, because even in an open relationship, that’s always when I’m like, “How did that person manage to cheat on you in an open relationship?” You had all of these rules and all of these things and this person still decided to not do that, to not follow those rules and managed to cheat in an open relationship? Which says to me, should have just broken up from the jump, probably.

Ro: Yep. I have been on the other end of that of being “cheated on” in an open relationship. It’s brutal when you’ve laid all of that groundwork. Unlike in a monogamous situation, unless you are a very good communicator, usually queer person who talks about what monogamy means to you, usually cheating is pretty like cut and dry. But when you’re in an open situation, you’ve established exactly what the boundaries are. And then when those get violated, it just cuts extra deep.

Drew: Yeah. I love to talk about approaches to the breakup itself. So far we’ve covered don’t do it on Halloween, sitting on the stoop at 6:00 PM.

Christina: Just do it inside if you want to do it on Halloween. You could just go right inside your little home, perfect place.

Drew: But you’re still probably going to get some doorbells. So I would maybe make a blanket. I mean, if you have to do it on Halloween. I mean, I would say holidays in general maybe, but also what I think is so terrible though is the like, oh, I’ll wait to do it after the holiday. No, do it beforehand. It’s better that… Also, holidays are… Well, obviously every circumstance is different, but in my head I’m like, even if my birthday is next week, break up with me beforehand because do you know what will ruin my birthday? Is my partner being there miserable, and it’s clear that we’re having problems. Do you know what could be a slightly more fun birthday? Out partying with my friends a week after a breakup feeling chaotic. So please just… I really am a firm believer of, as we’ve already said a million times, break up when you want to. Don’t be like, well, I have to wait till dah, dah, dah. There are exceptions, but that’s my proverbial.

Christina: It’s a slippery slope to start doing that, “Well, not today because —” then it’s suddenly like, no, you can’t be doing that.

Drew: Yeah. But I also bring this up because — I could still continue to use my own life and failures — I do think that something that I did wrong in my last serious relationship was, I didn’t want to break up, but I wasn’t honest about… It was one of those things where I was like, “Oh, we’re going to be open.” I think I could probably tell that I was more enthusiastic about that than my partner, and obviously if she had said, “No, I don’t want to.” I wouldn’t have. But I knew her well enough at that point to understand that what I was wanting and what she was wanting were probably a little bit different. I also understood that I just wasn’t being as good of a girlfriend as I had throughout. It’s funny because I never even hooked up with anyone else while we were together, but even just the way we were talking about it and whatever. I also think on the flip side of that, she was treating me differently in a way that was pretty negative. I think I was in denial about those things, and also that the relationship was coming to a close. So I just was like, well, I feel trapped and I feel like I’m being treated poorly. So I’m just going to pull away, which there’s the difference between, I can say, oh, well, every time I know that I want to break up, I do it. And it’s like, yeah. But I’m very good at lying to myself. I’m not good at lying to other people, but I’m very good at lying to myself. Part of that is that extended period of time where I just was pulling away and that’s not — I wasn’t checking in. I think that’s an important thing to do. And so I think part of the breakup maybe feeling sudden was that it was, even though it wasn’t sudden emotionally, that it was sudden in the sense that the minute that that was suggested as a possibility, I was like, “Oh, yeah. This is what we should do.”

Christina: That’s the one I want. I pick that one.

Drew: And then she was like, “Wait, no, that wasn’t…” I was like, “No, no, no, babe, that’s the one.” I heard the words out loud. I thought about it as a reality and I’m sobbing right now, but also that is absolutely the only option. I probably should have figured that out outside of that conversation on my own with some self-reflection earlier.

Christina: And then bring that to the table in a…

Drew: Yeah. I mean, look, relationships are so hard and breakups are so hard, and we’re all going to make mistakes and can not communicate perfectly 100% of the time and not know how we feel or not know how our partners feel all the time. But I do think for myself, I’m constantly trying to work towards a space of realizing that for me, the challenge of good communication is, on a large part communication with myself, that I think I’m pretty good at communicating with others, except for the fact that if I’m not communicating with myself I can’t communicate well with others, and acknowledging that is a real hindrance than something that I’m working on.

Christina: Ro, what’s your recipe for a perfect breakup? What do you need? What do you put into that little stew to create that?

Ro: I think when one is initiating a breakup, it is very important to say the actual words, “I want to break up” or “I want to end this relationship,” or something super clear. Because I think sometimes when we’re trying to be kind and considerate, we’re a little loosey-goosey with our language. And then the person we’re trying to break up with ends up having no idea what’s happened, they think you’re still together. Just say the words, it’s going to suck, but I think that clarity is super important, and being honest about your reasons as to why the relationship needs to end. I think that’s another area where we’re trying to be kind, we’re not honest about what those reasons are, and then the other person is left feeling really confused. I mean, obviously I think if someone is threatening your safety, you don’t owe them any reasons, you don’t know them any explanation, just get the hell out of there, but with someone that you do feel safe with but the relationship isn’t working anymore, a clear “we’re breaking up” and a clear reason or list of reasons is super important.

Christina: Yeah. The clear “we’re breaking up” really has got to be said. That is definitely a thing I have seen happen. Just like, oh, wait, oh, no, no, no. That’s a break up. Got to say those words out loud.

Ro: And then just setting up your expectations for what your relationship to each other will be like, post breakup is really important. Whether that happens in the context of the actual breakup conversation, or maybe that happens later. But I think that’s really important to establish too, because — and this is another queer community thing. We love to try to be friends with our exes, and sometimes that’s totally possible and beautiful and great. Sometimes that doesn’t work for us. And so I think we need to be really honest with ourselves and with each other about what friendship with exes looks like, and whether or not that’s something that serves us.

Christina: Yeah. I do think there’s such a difference. I have this conversation with a lot of my queer friends about, oh, we’re still friends. Okay, are you just not actively mad at one another? You’re not friends. There’s a difference between I’ve burned this bridge, leaving this relationship or this bridge has just kind of got old and doesn’t really work that well, but it’s still open if you need to use it. We don’t have to be the best of friends maybe, but we can still be in community. We can still be in contact. I think there is a little bit more space within those kinds of friends with exes spaces than many people tend to think that there are.

Drew: Yeah. Also, I think it’s tricky in establishing that sometimes, of being like … Or maybe I think what’s important is to communicate the trickiness in the sense that if you don’t know, I think it is okay to say I maybe someday want to be friends, but I just in this space right now don’t know if that’s what I want. Communicating that, I think, is okay because I think sometimes when emotions are high, you don’t really have an answer. Similarly, Ro, I’m curious if you have any thoughts on, I agree that it can be really helpful to give concrete reasons and to be really clear and to not do the thing where you’re trying to be nice. So you lie or you say whatever.

Drew: But obviously there is a balance, there is some tact involved or there is some… So I’m just curious in your experience or just generally what you suggest as far as trying to be clear while also, I don’t know, if you’re not going to be dating the person, your problems aren’t as important as if you were continuing to date the person. So, rehashing them more or making someone feel bad. I don’t know. I think I really struggle with this because I think I have a bit of a people-pleaser streak in me. And so I think it’s sometimes hard for me to communicate those reasons.

Ro: Yeah. I think it’s important to include with your “these are the reasons why we’re breaking up” list. These are the things that helped me grow that I appreciated about our relationship. I think that’s important to acknowledge, but I think actually, I don’t even know if I’m answering your question. Your question is how to be clear about those reasons?

Drew: More like how do you find the balance between when should something be said versus when is it like… I just think about in break up mode, especially when you’re the one breaking up with someone and if they’re still in love with you and to list off the things that are wrong about them, the idea of being like, oh, well, I want to break up because I feel like you’re this. I mean, maybe it’s like an I-statement situation, or it’s better to be like “I feel this” instead of being like, “You are this way, so fuck you.”

Christina: Yeah. I think it should be less of like an airing of grievances, more of like “here are the reasons in which this does not work for me,” and kind of focus it that way instead of “the way you chew burritos makes me want to jump off a bridge.” I think there’s less of that energy.

Ro: Yeah, absolutely. I-statements are the key. And you are right, it should be the things that are not working for you. Specifically, I think acknowledging patterns is really important and acknowledging them from an I-statement place. So instead of saying, “You always forget to text me back and that’s why we’re breaking up,” you can say, “I have noticed a pattern where you don’t text me back. Communication is really important to me. I’ve talked to you about it several times. And so this is not going to work.” That’s a terrible reason to break up with someone, just “you don’t text back on time.”

Drew: No, but communication styles being different is a reasonable thing. I mean, I do think that’s a good example in the sense that something that could totally work for someone else doesn’t work for you. I mean, that’s how I felt. Every R relationship that I’ve been in, I feel really positively about all those people and I really only wish them the best regardless of how close or not close we are in each other’s lives or whatever, I really feel like they are great people and there are people out there who are super well-suited for them and it just wasn’t me. And so when I think about the problems in those relationships, so much of it’s about compatibility. So much of it’s like, oh, well, we just weren’t working together. It’s not. And not to say that again, there are obviously relationships where someone is particularly treating the other person poorly or whatever, but I think a lot of times it’s just we are not working. We are bringing out the worst in each other and we could find other people who we’d have really great relationships with. And so it doesn’t have to be like a judgment of your desirability or of your ability to be in a relationship. It’s just that for those individual people, they are not a compatible couple or group.

Christina: Yeah. I think that tracks. I think it’s like finding the thing that feels like the petty grievance and kind of tracing it back to its source of like, what is it — the not-texting is actually about our communication style, or the way that you don’t listen is also about how I feel valued, those kinds of things. I think that’s the important… chase that back to the source so you can come up with a good I-statement of feeling.

Drew: Yeah.

Christina: Did we just crush breakups?

Drew: I think we just solved breakups. So you’re all ready to go break up, have fun!

Christina: Okay. Let’s go break up.

Drew: Okay. Well, then we’re going to move to our next segment, which is Crush Corner, where we say who we’re crushing on this week. Ro, do you want to go first?

Ro: Yes. I have a controversial crush.

Drew: Ohhh!

Christina: Oh, we love that.

Ro: I’m crushing on Demi Lovato right now.

Drew: I approve.

Christina: What’s the controversy?

Ro: The controversy, did you read about that frozen yogurt stuff that happened?

Christina: Yeah. That’s just because celebrities shouldn’t speak out loud a lot of the time, is the problem with that. She has a lot of feelings and not necessarily the knowledge to know how to communicate those feelings out to the world. I’ve been there.

Ro: Yeah. I mean, I understand as someone who is also in eating disorder recovery like Demi Lovato, I understand where those feelings came from. They were really not well executed. So this is why they’re my controversial crush. I mean, I’m crushing on Demi Lovato, mostly because of the suits, they’ve been rocking these amazing suits. They have an incredible haircut. I’ve always been a fan and I’m just stoked on Demi.

Drew: I love that.

Christina: I have been a person who has, since “Cool for the Summer” came out, said that “Cool for the Summer” was the song of the summer every single year. So they have given me genuinely the summer anthem of my late twenties into my early thirties. I thank them for that.

Ro: Beautiful.

Drew: And I thank them for Glee. So we all have our—

Christina: Wow. To pull a late season Glee, wow.

Drew: Yeah. The only good thing about… I mean, really just—

Christina: That’s really true. Oh, you don’t think it was Sarah Jessica Parker, “Let’s Have a Kiki?”

Drew: Oh, God, the fact that that’s not even — we don’t need to get into it. It’s only season four. There’s two more. It’s a nightmare. Anyways, Christina, who’s your crush for the week?

Christina: I’m going with Janelle Monáe, because Janelle Monáe, whenever she decides to post on Instagram, it literally just gives me a heart attack and stops me from functioning throughout the rest of the day. It’s not consistent, it’s just whenever she feels like it. Today there was just like a very sexual post with like a, put this on your mood board. I was like, “Okay. That’s not my life, but I want it. I will. Thank you, Janelle. And talk about a person who rocks suits, like, go the hell off. So Janelle Monáe is hot. Hot take.

Drew: Did you see her live, like, where the cigar was from? Like that, did you see it?

Christina: Yes, I did. It really rocked kind of my reality perceptions.

Drew: Okay. Just wanted to make sure. Cool.

Christina: Who are you crushing on this week?

Drew: Okay. So we have our first in a Wait, Is This A Date history, because my crush this week is Ro, because I rewatched Princess Cyd this week, and I want to talk about Princess Cyd because I love it so much, which Ro knows that I love it so much. I rewatched it with the person who I’m virtually dating, and the whole time just was freaking out and just was like, it’s that thing where watching a movie with someone and being like, this is the best, isn’t this amazing? Isn’t this a good scene? Just constantly turning to the person. That was my energy. I feel like that movie is like if you took the two halves of myself and made them like aunt and niece and then had them gently argue for 90 minutes. So I really love the movie, and Ro’s great in it and it’s… I think most people have seen it, but if you haven’t seen it, you should see it.

Christina: I fully co-sign.

Drew: Yeah. It’s very, very good.

Christina: I really love this late-stage chaos that Drew decided to bring in here at this moment. I think that was good, because you know what there is in Drews’ chart? Sagittarius.

Drew: Yes. There is. Sag Venus!

Ro: I believe that. I mean, it’s appropriate that you have brought it up because I broke up with acting somewhat recently, which was a great choice for me, but I loved making Princess Cyd. I’m so proud of it. I love that it’s in the world, and I love that you love it, Drew.

Drew: Thank you. Thanks for being a part of it and making it exist and making it so good. Okay. So, do you want to let people know where they can find you?

Ro: Oh sure. You can find me at Autostraddle by searching for Ro White, you can find my articles there. And you can find me on Twitter @munrowhite, that’s M-U-N-R-O White. And then I don’t know if you feel like popping on over to Instagram, you can find me at @internationalmisterpleather. Mr. is all spelled out.

Drew: Perfect.

Christina: Incredible.

Drew: And so then the last thing that we do like because we really value clarity here, we really like to be just up front and—

Christina: Open and honest.

Drew: Yeah, and change the culture among queer people. And so we like to ask at the end of every session, just a little check-in, was this a date?

Christina: Right now, were we just on a date? I mean, we could have been, we just wanted to ask.

Ro: Are you asking me?

Christina: Mm-hmm (affirmative).

Ro: I mean, I’m not really dressed for a date.

Christina: Okay. That’s a really beautiful answer.

Drew: That’s my favorite answer so far.

Christina: That one’s really good actually.

Ro: Yeah. I am not appropriately dressed. Also, my air conditioning unit has been off for this recording, so I’m extremely sweaty. But I guess a date can be really sweaty. So, I honestly don’t know.

Drew: Sometimes you don’t, but I love that answer.

Christina: A lot of the times we’re learning we don’t know. Look, I believe we’re going to get there one day.

Drew: I think what’s great is that we’ve decided to end each of our podcast episodes by making our guests uncomfortable. I think it’s a really beautiful—

Christina: I think it’s so brave.

Drew: Yeah, I think so. Well, thank you so much for being here with us and thank you everyone for listening. Now, go break up with your person. And if you said, “No, I don’t want to.” Great, then you shouldn’t. That’s the trick.

Christina: Yeah. Perfect.

Drew: If you said, “I don’t know, maybe I should.” Then—

Christina: You should. Unfortunately you should.

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

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

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

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

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

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

Drew: Yeah, and maybe next week will be a date.

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

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

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

Drew, in a voice memo: I’m ready to have a new ex. I mean, I’m also ready to have a new partner, and I don’t need that to end right away. But I am also ready for the future, however long it is in the future, when I’m like, “Oh, my ex,” and I’m talking about a different person. I just get so bored when I have the same ex. I do sort of feel like after a certain point, you do only have sort of one ex, everyone else is just like someone you once dated. At least for me, I only have room for one person to occupy the role of “my ex,” you know?

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Drew Burnett Gregory

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

Drew Burnett has written 553 articles for us.


  1. I haven’t listened to this yet, but it showed up in my podcast feed and when I glanced at it, I thought the title was “You Should Probably Break up Today”

    And then I realized that Today referred to when the episode came out and not when one should break up. LOL.

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