If you have a great life and dating just doesn’t feel like part of it — this one’s for you.

In episode 265, I’m coaching Christina live. She’s 36, has a great life, one long-term relationship under her belt, and is asking the question a lot of you are quietly asking: is it even worth it to try dating after so much disappointment?

She’s frustrated by the single tax — the emotional and financial cost of being the only single person in her circle, coordinating everything alone while everyone else has a built-in teammate.

She wants a partner more than she lets herself admit.

And she’s bi, but feels like an adolescent there compared to her experience dating men — and keeps wondering if it’s even worth exploring.

In this episode, we dive into ALL of this, and come up with a concrete plan to make dating a part of her amazing life– with permission, boundaries, and a plan to attract more.

Work with Lily:

Read Lily’s book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

---

Show transcript:

Lily @ Date Brazen (00:00)

Hey gorgeous friend, welcome to another episode of the Feminist Dating Show. I’m so excited for you to listen to this episode with Christina. It’s a coaching session that I know is going to resonate so hard with you. Here is what Christina shared when she applied to be coached on this podcast. She grew up religious, was taught to be more passive, to wait for men.

Her first relationship was at 28, now she’s 36 and wondering what next. She’s bi, she’s less experienced dating women and is unsure if she should start dating women, right? Like, is it worth it to try something new right now? She’s frustrated with the single tax, with the family vacations, the only one single in her circle. ⁓ Seemingly, it seems like nobody will drop everything to be with her, but she has those relationships where she plays that role for other people.

And Christina has a great life. It’s just that dating doesn’t feel like a part of that great life. And that’s what we’re here to change in this episode. She walked away with massive permission to own what she wants to start going after it with confidence. And I know that this episode is going to inspire you to, to ⁓ really acknowledge how your black and white thinking might be causing stress and strain and how to start really giving yourself permission to want everything that you want, even if it

feels like too much, or even if you feel like you’re too inexperienced, you aren’t. You can get more of what you want, and this episode gets to be your roadmap. So I want you to listen and ask yourself, how is this for me today? And really, I know that you’re gonna resonate so hardcore with Christina’s story and her shares, and I’m so grateful that she was game to come on and be coached, because I know that so many of you are struggling with the same questions that she was. So with that, let’s get into the episode.

Lily (02:30)

Christina, welcome. Hello. How are you feeling about this?

Christina (02:31)

Thank you. Hi.

I’m excited. I’m really psyched. I’m like a little bit nervous, but I’m mostly just excited because ⁓ I’ve been listening to you for a couple months. And yeah, I’m psyched to do this and dive into some stuff.

Lily (02:47)

I’m so excited to support you in this way and I loved your application. I wanted to dive right Okay, before I dive into what struck me about your application and what I wanna like.

what I see an opportunity for. I do wanna hear about your dating history and your love life history. So I’ve read about it a little bit, but can you share with me ⁓ what’s it been like? How many relationships have you been in? Tell me all about it.

Christina (03:14)

I had my first long-term relationship and relationship of any kind in my late 20s. So I think I was 28. Yeah, because it was like right after I turned 28, a year after I moved to New York City and I met this guy on Coffee Meets Bagel. He was the fourth person I went on a date with, so it didn’t take very long for me to meet him. And we just hit it off and we dated for a year and a half.

But prior to that, I didn’t have any relationships in high school, nothing in college, nothing at all.

And I largely attribute that to being raised really religious and being raised to believe that I should be very passive in the process of dating. And so I was taught that women should be submissive and wait, and the man should be the leader and we should wait for him to come. yeah, it was very bad. But that was what I was, and I was a very like…

Lily (04:02)

Yeah.

Christina (04:09)

good girl, like follow all the rules, that’s kind of my personality. So was like, yes, I’m gonna do this the right way. so I never, even when I had crushes on people, like I had a crush on somebody for years, I never did anything about it. Which now I’m like, ugh. anyways, but yeah, so yeah, sure.

Lily (04:12)

Mm-hmm. Mm-hmm.

Hmm.

Can we pause there? Because I do think that this,

especially for people who feel behind in dating or feel like they came late to the party, past, like a conservative religious past is something that I have in common with you. And I think a lot of people have in common ⁓ who are listening. So can you unpack like what it was like for you to start deconstructing some of those more passive ideas that

Christina (04:40)

Mmm.

Lily (04:55)

I mean, I’m using the word deconstructing. You can use whatever word I don’t mean to project onto you, but like, what was that like to start something new for yourself?

Christina (05:07)

Yeah, and I do call it deconstructing also, so that works for me. Yeah, I mean, the deconstruction process was a big, a huge upending thing, as I’m sure you’ll really, anybody who’s upended their.

deeply held religious beliefs will understand because it’s not just about like one thing It’s about your entire life being restructured, but I think in terms of dating ⁓ What change was that I started to realize like ⁓ well first of all I was like gender roles are bullshit That’s what I

That’s one of the things, like one of the realizations that I had in the deconstruction process and actually like the traditional gender roles, like I am much more of a man. Like that role fits my personality.

Lily (05:44)

Yeah.

Christina (05:54)

But I was trying to like, yeah, like the version of a man that I was taught existed as like, know, gender roles impact everyone, right? Not just women. Like I was taught that men should be like leaders and take initiative and, you know, go out and get the thing. And that’s how I am. But I thought I wasn’t supposed to be that way. There’s this like really absolutely horrible book called Captivating. Do you know this book?

Lily (05:55)

Tell me about that, what do you mean?

I haven’t read it myself. Tell me.

Christina (06:27)

It’s horrible. If you ever want to, I don’t know if you could even get through like a chapter, but that was like given like in college, I think it was, we were all reading that book. It’s a book about, there’s one called Wild at Heart. There’s like a companion series. It’s captivating for the women, wild at heart for the men. I think that’s what the men’s one is called.

Lily (06:35)

What is it?

Yes, yes.

Christina (06:45)

And you know, so the captivating is about how to be a captivating, godly woman. And it’s like absolutely horrendous. It’s like not that some of the things they’re talking about being are bad in and of themselves, but it’s all about like submission and just being meek and like you have to be this very particular kind of woman to be a godly woman. That does not fit me. That’s not who I am, but I thought I had to be that way. And actually, I think the role of man that I was taught.

Lily (07:03)

Right.

Right.

Christina (07:13)

was how I am. So once I realized that, first of all, gender roles aren’t a thing that I want in my life, I was like, oh, actually, I am somebody who could have more agency over my dating life. So was kind of, on the one hand, it’s a bummer, because I didn’t do anything for the first 10 years of adulthood. But also, then I was like, actually, I could do something. So that was the big.

Lily (07:15)

Hmm.

Mm-hmm.

Christina (07:41)

switcheroo is like I feel like the traditional gender roles has literally taught me to be the opposite of what I am and I think it can work like I think for people who tend to already be the way that the roles are defined it can be less damaging but I think for anybody men or women or anyone any gender who’s like taught you should be a certain way and you’re actually not that way naturally it’s like really bad so

Lily (07:47)

Hmm.

Mm-hmm.

Absolutely. Well, and

then we have the question of like nature versus nurture, which is like how much of the cultural upbringing has influenced how you perceive yourself to quote naturally be. And I think that that’s really tricky for people who are deconstructing.

Christina (08:08)

Right, right.

That’s true, yeah.

Yeah, like which one is it? Like is this actually how I am or was I just, you know, it was it? And that, I mean, I mentioned in my application that I’m bi and I feel like that’s the part we don’t necessarily have to get into that piece right now. But like, I sometimes wonder, is the reason that I feel like I’m a two on the Kinsey scale and not a four or three.

Lily (08:26)

Yeah.

Yeah.

Christina (08:40)

because, or even a five, because I spent most of my life repressing that side of myself or is that just because I am actually more attracted to men? Naturally. So I feel like that, yeah, that applies to a lot of things, but yeah.

Lily (08:48)

Mm-hmm. Mm-hmm.

Well,

I do wanna talk about that, because I think that that’s a great question to sit with, be with, interrogate. And I think that biphobia, homophobia, ⁓ the myriad types of oppression, especially if you were raised in a conservative environment where those types of questions were really unwelcome.

Christina (09:04)

Mm-hmm.

Yeah.

Lily (09:19)

Like in that environment, it’s dangerous to even question if like.

something religious specifically, nevermind your sexual identity or your gender identity, you know, and so I do wonder, ⁓ why I brought that up is that it can feel like a hot potato. This question of like, where am I on the kids scale and what do I actually want and who do I actually want to date? It can feel like a hot potato. I don’t know if you resonate with this, but when I was coming into realizing I was bi, I was like, I wanted to throw that question away. I wanted to like, I don’t know. I don’t need that. I’m OK. I’m OK.

Christina (09:40)

Mm-hmm.

Lily (09:56)

Like I am attracted to men, I know I’m attracted to men, I don’t need to explore, you know? And I think that having the, just like the time-space breadth to sit with the question and be okay with not exactly knowing for sure right now, but in like lovingly being curious about it can be really helpful. Does that resonate for you?

Christina (10:00)

Right.

Mm-hmm.

Yeah, yeah. I feel like I am kind of in that headspace. The issue I run into with that, at least that I’m running into currently, is more like how much because I feel like I’m in my adolescence with dating women.

and I’m more an adulthood with dating men. just, and I’m in my mid, getting into my late 30s. And you know, I’m wondering, like, is it even, quite frankly, like, is it even worth the time to have this adolescent phase when I’m almost middle-aged ⁓ with something, I’m 36.

Lily (10:48)

How old are you?

Christina (10:51)

yeah, like is it worth it to like if I if my main goal with dating is to find a partner more like sooner than later, you know, whatever that ends up meaning like

Lily (11:03)

Yeah.

Christina (11:05)

Not that I need to be like freaking out or frantic, but that like, don’t like if I’m gonna spend some time exploring the bisexual side, like is that going to hold up the process? Like if I already know I like men more and it’s easier for me to like find myself attracted to men than to women, like might as well just go with that because it works already and I know that it does and it might be easier to find someone. You know what I’m saying? Like it’s almost like an efficiency, an efficiency question.

Lily (11:30)

Got it.

Cool, yep, get it. So

efficiency for what though?

Christina (11:35)

Yeah.

Like if it like like efficiency from meeting somebody as soon as possible because I want to be in a relationship ideally sooner than later and like if I hmm

Lily (11:41)

Why?

Why?

Christina (11:53)

I mean, I want partnership and I think it would make my life easier and better if I could find that. And I recognize that there are things, well, I love my life right now, that there are also things that are like hard about being single. And if I know that I want this and it’s like a top priority, ⁓ you know, I wanna be sure that I’m pursuing it and like prioritizing it. I mean, maybe the…

maybe the explore- I don’t know, something about like dating women more seriously feels like it would take time away from getting to the goal even though maybe it wouldn’t. Like I think that maybe I’m just finding a- yeah. Finding a part. Yeah. Mm-hmm.

Lily (12:29)

Well, what’s your goal? Tell me about your goal regardless of gender. Yeah, I keep coming back to it because I hear urgency here and

I’m just like finding a partner because it would make your life easier. How?

Christina (12:44)

Like having somebody to share life with, share burdens, know, share like the emotional load, you know, all that stuff. That’s why people want partnership. Having somebody who prioritizes me, you know, having my number one, they’re my number one, you know.

Lily (12:46)

Yes!

Yes!

Yeah.

And I read, you you mentioned a couple times the single tax. Can you tell me more about how you are experiencing that in your life?

Christina (13:03)

Yes.

yeah, there’s literally this past weekend I had a big thing with that with my siblings who I love, both married and we’re trying to plan a trip together and it’s just been, I don’t need to get into the details, but just trying to figure out lodging that feels like it’s fairly divided and like I’m not getting penalized financially for not having a partner and.

There’s other stuff too, but there’s that, just like, then Partners Uniting Against Me for preferences and things and like, and that’s just like, that’s for vacation, that should be fun and I’m like stressed about it. But like, and it’ll be, it’ll be good I think, but like.

Lily (13:39)

Mm-hmm.

Christina (13:42)

And then there’s just the, I mean, there’s literally like a cost to being single. Like lot of things are more expensive for single people. So there’s that. But honestly, I feel like the emotional tax is bigger for me. Like I’m living in New York City, I have a roommate, like I am sharing expenses. So I feel like a lot of the cost sharing, able to, like I do share the cost of a lot of things like couples already, but like I’m not getting my own space.

Lily (13:49)

Mm-hmm.

Mm-hmm.

Mm-hmm.

Christina (14:10)

you know, like if I wanted my own space, I would have to spend double of what a couple yeah, it’s kind of like that having the united front thing. And I feel like in a lot of social situations, like the more that.

Lily (14:15)

Mm-hmm.

Christina (14:22)

my closest circle’s partner. I’m one of the only single people in my close circle. And it’s fine. Like I’m not jealous of people’s relationships, but I am jealous of the like teamness of it. Always having a person to like, you know, keep the company at a wedding or, know, somebody you can text about something, somebody who’s going to like take you to doctor’s appointments. You know, I have to coordinate everything for myself, which I’m able to do. And I’m glad I can do do that independently as a woman.

Lily (14:29)

Mm-hmm.

Hmm.

Mm-hmm. Mm-hmm.

Christina (14:52)

But like, yeah, it’s just like, would be nice to share those things and yeah.

Lily (14:53)

Mm-hmm.

Yeah, of course.

Of course, that makes total sense to me. That you, how do you feel in your body as you’re talking about this?

Christina (15:02)

Mm-hmm.

Like part of me is like I don’t want to be a complainer. You know, I like if there’s any time little self-judgment. Yeah, definitely Look, I judge myself. I’m like, it’s such a good time like of all the times to be a woman This is probably like one of the best times ever cuz like we have increasingly. I mean, you know

Lily (15:12)

So self judgment, you’ve got judgment of, yep, okay. Keep going.

Christina (15:25)

Obviously there’s stuff going on right now politically that you could argue we’re getting less freedoms, but like, generally speaking in the arc of history, I can get a credit card out in my name. In my parents’ lifetime, probably in yours, like that wasn’t possible for women if they weren’t married, or at all. know, and like voting is only in the past hundred or so years. You know, like there’s a lot of rights and freedoms that I have now.

Lily (15:34)

Mm-hmm.

Mm-hmm. Mm-hmm. Mm-hmm.

Christina (15:47)

And I’m glad that I’m alive, but sometimes I am like, what do I have to complain about? Like, you know, I have such a good life. I’m, you know, doing what I want to do with my career and I have my cat and like, you know, whatever. But, but yeah, I would say like, so I do judge myself for complaining about the single tax sometimes. But also I’m like, sometimes I’m like also compassionate towards myself. Like it kind of goes back and forth between like, yeah, no, this is a real thing. And

Lily (16:07)

you

Christina (16:14)

And I have one good friend. I have one friend who is in the same boat. So at least we have each other to talk to about stuff and like she can relate. ⁓ So that’s nice. ⁓ Yeah, but sometimes I just feel like I am kind of like out here doing my thing by myself and floating and like, you know, just with like family dynamics, especially and friend dynamics and I don’t know. I know I’m not

Lily (16:21)

Mm-hmm. Mm-hmm.

Mm-hmm. Mm-hmm.

Christina (16:43)

number one on anybody’s list, which is fine. Like maybe on my mom’s list, like, equal with my brothers. But like, I’m like, everybody else with a partner in theory has, you know, a person, like the person they can call, the person who will drop everything to go be with them in a crisis, you know. And I just want that. So sometimes I do feel kind of sad and like sometimes lonely, even though I have a full life, but I wouldn’t say loneliness is like the pervading

Lily (16:49)

Mm-hmm.

Mm-hmm.

Yeah.

Christina (17:11)

Feeling for me. It’s more just kind of like low aloneness in things maybe

Lily (17:15)

I

want to pitch that I hear anger.

Do you feel angry?

Christina (17:26)

I don’t I don’t know if anger is definitely frustration. Maybe that is a form of anger Yeah

Lily (17:28)

or frustration.

I’m just curious about it. I’m saying this with zero judgment and all of the curiosity and empathy. Because especially for those raised in conservative environments, especially those who are socialized as women, anger is a really dangerous emotion that does not fit with the good woman, quote, identity.

Christina (17:39)

Mm-hmm.

Hmm.

Lily (18:00)

You shouldn’t be angry. That’s not pleasant. That’s not helpful. That’s not right. And when you’re talking, I hear real frustration. And then I hear you sort of doing this like seesaw brain thing, which is very normal, which is like trying to logic your way out of the frustration by saying like, I’m not really in a bad way. I’m not really in a bad way because I have all these privileges or I have all of these. I do have good things in my life. Why am I complaining?

Christina (18:02)

Right, that’s true. Yeah.

Yeah, definitely.

Lily (18:29)

It’s like either or, but then that’s cognitive dissonance. You have on the one end of the seesaw, God, I really want a partner. I really want to live life with a partner and it really fucking sucks that in our society, coupled women are treated as a head of single women and that they get, potentially if they’re with a supportive partner, they get somebody who is, right, because that’s not a given, unfortunately.

Christina (18:33)

Hmm.

Right.

Yeah.

Lily (18:58)

They get somebody who is their number one, and vice versa. They get this opportunity to plan vacations in a way that is like a team with people that might have differing opinions and you have somebody to team with. Like all of these things are super valid. That’s on one end of the seesaw for you. On the other end of the seesaw, Christina, what I’m hearing is, I should just be grateful though. It’s not that bad.

Christina (19:20)

Yeah.

Lily (19:23)

Like it’s fine, I shouldn’t over index on this because you know, I really, I am fine. You you mentioned in your application, I’m gonna read it. You said, sometimes I’m totally content being single and thinking if I meet someone great, awesome, but if not, I’ll be okay. Other times though, I feel the effects of the single tax pretty heavily. I’m a strong independent woman and a good friend. Ultimately, many of my friends, good friends faded away after getting partnered and having kids despite me trying to show up for them for some time.

Christina (19:40)

Yeah.

Lily (19:52)

Society isn’t set up very well for single people and I sometimes have spells of loneliness and I wish I had my person to share the load of life with.

Christina (20:00)

Mm-hmm, mm-hmm.

Lily (20:02)

So this either or mentality is actually not serving you.

Christina (20:06)

Hmm. Yeah.

Lily (20:08)

in

any way, I hear it with your conversation about exploring dating women. I hear it in the conversation about, you know, a couple different things. And so I really wanna just like unpack together what it might be like to honor this feeling of frustration, potentially anger, and like allow it without making it mean that anything is like wrong with you.

Christina (20:17)

Hmm.

No, you’re definitely right.

Lily (20:45)

Tell me what, what’s this emotion? Tell me about it.

Christina (20:49)

it’s validation, like, that it’s okay to say it’s hard and not have to, like, hedge, you know, and, like, try to put on a front that it’s… that it’s not hard. I mean, and I do feel like sometimes I’m almost, like, relieved. Like, I mean, I’m not, but, like, I’ll hear about horrible situations in relationships where there’s not a supportive partner. I’m, I’m so glad that I’m single.

Lily (20:57)

Yeah.

Christina (21:17)

But then I’m like, but if I could have a great relationship, would be so much easier. I don’t know. I feel like there’s a lot of societal judgment and self-judgment and, you know, just. and I do relate to what you said about like, and I think a lot of women are socialized, not just religiously, but like just as women to be agreeable, to be, you know.

Lily (21:27)

Mm-hmm. Mm-hmm.

Mm-hmm. Mm-hmm.

Christina (21:43)

⁓ What’s the word? Not affirming. Yeah, yeah, pleasant, ⁓ not assimilating. What’s the word I’m looking for? It’s like, with an A. I can’t think of it. Like, ⁓ easy, you know, not making waves. Agreeable, thank you. Yeah.

Lily (21:45)

Pleasant.

Mm-hmm, agreeable.

Christina (22:07)

And I will say like in the past couple years I’ve been working on assertiveness and like trying to be more confident and like own what I want, not with dating specifically just in general and I’m starting to have like fights with my family that I’ve never had and you know, I do want to talk about that in therapy, you know, we don’t have to talk about that here but I think it’s part of the same thing. It’s like trying to own…

Lily (22:14)

Mm-hmm.

Mm-hmm.

Christina (22:38)

what I want and how it feels to not have it, while also just trying to own it and not like nothing else, just like this is what it is and not judge it.

Lily (22:49)

Yeah. Yeah.

So either or is stressful for anyone, everyone, right? Either I’m ahead or I’m behind. Either I’m angry or I’m okay, right? Either I’m, right, you are frustrated and you’re okay.

Christina (22:57)

Mm-hmm.

Right.

Lily (23:10)

Either you’re frustrated or you’re happy. It’s like, no, you contain multitudes. It’s okay to be frustrated and for the single tax to be real and to fucking suck. And it does not have to mean everything.

Christina (23:16)

Hmm

Right, that’s true. Yeah.

Lily (23:29)

Right? Right? Like it’s

a factor and it can be a factor amongst several factors in your love life as you pursue like getting what you want.

Christina (23:45)

Yeah, that’s true. No, I’ve never heard anybody, yeah, I’ve never heard anybody talk about the either or thing like you did and it’s so true. I definitely do that and I didn’t think about that. I think that this like black and white thinking is definitely for me anyways, it’s a vestige of being in a fundamentalist religion. Whereas I’ll like, it’s either right or wrong. It’s either heaven or hell. There’s no in between. There’s no purgatory. it’s Jesus or Satan.

Lily (23:47)

Does this make sense?

Yep.

It’s either Jesus or nothing else. It’s

Jesus or literal hell, yeah, for sure. What a fun environment to grow up in. Think about your cognitive development at that time, that your brain was knitting itself together and your logic was forming and you were being offered this idea of either or as the only way. let’s, you

Christina (24:15)

It’s like…

Super fun. Yeah.

Mm-hmm.

Lily (24:37)

let’s give props to either or. Having an organizational principle by which to organize your life and morals and whatever can be a more easy pill to swallow than, wow, this is really complicated, right? Because I don’t think at a fundamental level, education is getting, you know, a little bit, you know, we’re going beyond dating, but our educational system is not set up to teach people critical thinking skills effectively.

Christina (24:48)

Mm-hmm

Right.

Lily (25:06)

And so either or is an effective tool to use in lieu of having critical thinking skills.

Christina (25:14)

Right. Oh yeah. No, I definitely see why it’s like easy to jump to it and you see it all the time and like discourse and arguments about things and like I understand it but I never thought about it in relation to how I was like thinking about my dating life. So yeah, I’m gonna definitely, I’m gonna toy around with that some more on my own.

Lily (25:35)

Yeah, so I think that the visual that I give people here, and I wrote about this in my book, thank you more the either or, I love visuals. So the either or is like you’re living in a cramped studio apartment in New York City where the windows are outside on the windows. It’s perpetually dirty, so the sunlight can’t really get in. Imagine it’s in the middle of Midtown where there’s not much sunlight to begin with. It’s loud, it’s cramped in this apartment.

It kind of stinks. It’s a hoarder nest because you have all of these newspapers that have all of this evidence to prove that like it’s impossible. It’s not gonna happen. What are you doing? Why are you working toward this? All of this evidence is sort of piled up around you and you have this little snake path to the bathroom and maybe to your bed. That’s what either or feels like. It’s like the walls are closing in on you. It’s like, that’s where the urgency comes from. I’ve got to figure it out because I’ve got to get, I’ve got to.

Christina (26:04)

Yeah

Yeah.

Lily (26:30)

prove all these stories wrong, that it’s impossible for me to get what I want. So here’s what we’re gonna do. We’re gonna call a moving van. Moving van’s gonna come. Gonna pile all the shit from the studio apartment into that moving van. You’re gonna move into a gorgeous gleaming white giant airplane hanger where the door is open. I imagine the airplane hanger in Crazy Rich Asians where they’re going to that bachelor and bachelorette party. The door’s open, it’s huge.

Christina (26:31)

Yeah.

Yeah.

Lily (26:59)

suddenly in this airplane hanger, your stuff is unloaded and it only takes up one little teeny bit of this giant space. Because there’s so, yeah, those moments of like hardship and not getting what you want, like they exist, they’re in the room with you, but there’s so much more space in this both and land. It’s like in this space of both and you can have the Muppets and that evidence and Gilmore Girls and a peanut butter jelly sandwich and like.

All of like new evidence can be gathered and new ideas can be born and you can decide new things about yourself and what you want and you have room to explore and play. Right? So like tactically, whenever you catch, I want you to start catching yourself in your black and white thinking and either or thinking with dating. I want you to recognize it and imagine that you’re on a seesaw. Maybe even name the two pieces. ⁓ I’m thinking either this or that. Can you give me an example?

Christina (27:33)

Mm-hmm.

Okay.

Like right now. Or like just for dating.

Either, I mean there’s so many things it could be, like either he’s gonna be, okay, so since egalitarianism is a big thing for me if I’m dating a man, like either he’s gonna be super egalitarian and awesome or he’s gonna suck.

Lily (28:15)

Okay, yeah, yeah, yeah, okay. So either he’s gonna be amazing or sucky and, you know, ⁓ and I would say to get off that seesaw.

Christina (28:17)

Yeah.

Lily (28:28)

I would say self-compassion. Self-compassion, self-compassion, self-compassion says, of course, self-compassion says three things. Of course I’m struggling with this because, insert your context here, give it to me, Christina, like, of course I’m having this either or because.

Christina (28:30)

Mm-hmm.

Mm-hmm.

because a lot of relationships, heteroreal relationships, are egalitarian and I’ve seen it and I’ve seen how damaging it is and I don’t want that.

Lily (28:51)

are not egalitarian, yeah, you don’t want that, of course. And you grew up in an environment where egalitarianism was not a given. In fact, that was something that maybe was not discouraged. So of course my brain is bouncing between these two extremes, of course. That’s kindness offering to yourself. Like it makes total sense to me, instead of being like you’re abnormal. Okay, so of course is what self-compassion says. Self-compassion also says I’m not alone.

Christina (28:53)

Yeah.

Yeah. It was discouraged. It was discouraged. Yeah.

Mm-hmm.

Yeah.

Hmm.

Lily (29:21)

A

lot of people struggle with this, especially those that want to date men. This is tough, right? We can’t escape the gender socialization and how patriarchy has messed us all up, like of course, and I’m not alone in struggling with this. Finally, thoughts, not facts. This is mindfulness over over-identification. These are the three guideposts of self-compassion adapted from the work of Dr. Kristin Neff.

Christina (29:26)

Right.

Yeah.

Mm-hmm.

Lily (29:47)

So the third and final is like, ⁓ shit, I’m having an assumption. My brain is offering an assumption that says it’s either or, and it’s already assuming that I’m gonna lose.

Christina (30:00)

Hmm.

Lily (30:00)

And

so like, wow, my brain is serving up a really hard human thought that is not a fact.

What else might be true? Now we’re gonna do a both and sentence. What else might be true, Christina? It might be true that both.

Christina (30:17)

We’re all socialized in various ways, but also there are still people out there, including men, who are dedicated to not being in that kind of relationship. So it’s not a given that I would need to be in one like that.

Lily (30:31)

I’m allowed to want what I want and accept nothing less.

Christina (30:41)

Mm-hmm.

Lily (30:43)

and I just haven’t met that person yet.

Christina (30:47)

Right, yeah. That I feel like I do believe. It’s funny, because it’s like I definitely have these thought patterns that aren’t helping me, but at the end of the day, I do believe that I understand intellectually that there are people out there like that. You know what I mean? I get it, I’m here. Obviously, I’m not the only one. But yeah, think to just get caught up in the weeds of the…

Lily (30:49)

Right?

Yeah, yeah.

Yeah.

Christina (31:16)

of the day-to-day like, it hasn’t happened yet, my age, like where I live, all these things that like might make it harder to find somebody as quickly or ever, you know, and then I start to like catastrophize like maybe it will never happen, you know, like maybe it will never happen but like the likelihood, I think the likelihood of that is probably lower than I, it sometimes feels.

Lily (31:31)

Yeah!

you are over-exaggerating the likelihood of not getting what you want in order to protect yourself and try to beat the universe to the punch of not getting what you want because wanting something that’s not here yet is incredibly vulnerable.

Christina (31:41)

Mm-hmm. Yeah. Yes. Yes. ⁓

Yes. Yeah, that resonates.

Lily (31:52)

But I’m

here to tell you like more than likely, if you own what you want, advocate for it, and keep showing up and care for your nervous system when you need to, you will find the love of your life. You will.

Christina (32:09)

Yeah.

Lily (32:11)

And I also think that, you know, I’m gonna read this sentence that you said, this relates to the either or that you were feeling stuck in. I’m scared of turning into all the women who slowly but surely give up things that are important to them in order to center their husbands’ desires and goals.

Christina (32:30)

Mm-hmm.

Lily (32:32)

It’s so interesting to me that that is such a prevalent fear. I mean, it makes sense, but it’s interesting.

Christina (32:38)

Yeah, well and I think part of it is because I And they don’t know this podcast or listen to it because they’re married. ⁓ so I don’t think they’re ever gonna see those But i’ll say at least i’ll say it to you like one of my brothers is ⁓ and I love him we get along but like So he and his wife Super in love. They’ve been together for seven years married for two But I can already see how like as you know, I love my brother and he is very socialized

Like he’s much more of a trad kind of mindset about marriage and his wife isn’t. But, and they do have a lot of wonderful aspects of the relationship, but just one example I’ve seen very recently is she was like, when I first, we first started dating, I told him I’m not changing my last name. And he was like, aw, but okay. And then seven years, then, and then after they got married, she still wasn’t gonna do it. And then.

this Christmas, she was like, did you notice that on our Christmas cards we called ourselves the, you know, the family?

by the family name, and I was like, oh, I didn’t notice that. She’s like, yeah, I’ve decided I’m gonna change my name. I was like, oh, okay, how do you feel about that? Because I don’t judge, know, look, if somebody wants to do it, go for it. She was like, well, you know, I’ll get used to it, but I want our kids to have the same last name. She did not sound excited about it. And my brother was standing right there, just kinda like, yay, she’s finally doing it. And I’m like, oh my god.

Lily (33:47)

Mm-hmm.

Yeah, yeah.

Yeah.

Yeah… Yeah.

Christina (34:08)

⁓ And she’s so like she’s so sweet and so accommodating and like he is so persistent and so persuasive and he’s also like he loves her but like he wants what he wants and he centers himself like and she centers around him and she’s like, we never fight I’m like, well Interesting, but like yeah, but like I mean, obviously no relationship is perfect

Lily (34:21)

Mm-hmm.

Yeah, yeah.

Christina (34:33)

and think they’re gonna be fine, but I just see that kind of thing and I’m like, I don’t want that and they’re so in love. And like, I don’t think that necessarily means that their relationship is like the wrong one for them. But I feel like it’s so complicated where it’s not just like, you just find an egalitarian person and then it’s fine. It’s like.

I feel like she probably didn’t think she was ever gonna change her last name, but like now seven years later, she’s in it and she just wants to keep the peace and make her husband happy and have the same last name with her kids. Like all of them have the same name and he’s not willing to compromise. And he’s used to getting what he wants in this regard because that’s how life has treated him. And she’s used to accommodating because that’s what she’s been taught to do. And I just feel like it can happen more easily than one thinks. So sometimes I’m like, ⁓

and I was trained to be accommodating, I’m like, well, maybe despite my best efforts, I’ll still do it anyways. You know, or I’ll like get too far into something and then I’ll, not too far, but like I’ll get into something enough, you know. And then I think I get like hypervigilant in the beginning where I’m like, I want to avoid any signs of anything and then I get like a little bit too rigid.

Lily (35:35)

Mmm.

Yeah. Yeah. Uh-huh.

I think at the base of this for you, because honestly, like, we could wax on that relationship for a long time. And honestly, that’s a hard story. And unfortunately, I think pretty common. And also, we don’t know what choices and conversations were happening behind closed doors for them. And also, I do think that this is about, if you do choose to be with a man,

Christina (36:04)

I know, yeah, I know.

Lily (36:10)

that being, choosing a man who is always curious about what you think and who is always like, who when it comes to issues of your body, when it comes to issues of your name, when it comes to, he is allowed to, ⁓ you know, like be a human who has thoughts and feelings, but ultimately he needs to be someone who’s about what you think and want. And being curious about.

Christina (36:16)

Hmm.

Mm-hmm.

Yeah.

Lily (36:39)

how you feel, this is how you gauge it early on. Curious about how you feel, curious about where you wanna go, curious about what’s maybe convenient for you on this date, right? These are all ways, and you can by the way co-create with them as well in this regard, but I get that the way you were raised was accommodate 100 % and I take zero, and so you’re maybe wanting to make sure that you’re abandoning yourself.

Christina (36:42)

Hmm.

Mm-hmm.

Right. Yeah. Yeah.

Lily (37:10)

And I don’t want that for you either,

but I do think that you need to acknowledge that like, you are going to be with a different kind of partner than your brother is.

Christina (37:18)

Yeah, yeah.

Lily (37:20)

and that there might be times where, okay, for example, I was raised to fawn. Like I loved this book, Are You Mad At Me? ⁓ which I recently read about the fawn response, which is one of the responses they recently added it just for anybody that doesn’t know, fight, flight, freeze, fawn. Fawn is like fight, it’s like fight the lion coming at you, freeze, maybe they’ll think I’m a tree.

flee, run away, fawn. Let me make you my best friend and you’re gonna love me forever and I’m gonna be accommodating for you because you could literally kill me and I wanna be safe, okay? There are times in my marriage where I have realized, ⁓ shit, I’m fawning because of how I was raised. Not because my husband is asking me to, but because I am, sometimes I still,

Christina (37:59)

Right.

Yeah.

Lily (38:15)

Core wounds are gonna core wound, man. And I still have moments of like, I was not stating exactly what I wanted there because this is why I say this work that I get to do is life work. Whether or not you’re in a relationship, you will have to face, how do I allow myself to get curious when I’m fawning, when I’m shrinking, so that I can make a different decision? And in the right partnership, you will be able to change your mind about shit.

In the right partnership, you will be able to come back and say, you know what, I realized like yesterday, I kind of shrunk when you asked me what I wanted to do. And I just want to say, I would like to go to this place, to this restaurant. I actually may not feel in that restaurant. You’ll be able to change your mind. When you think about a name change, there are so many inflection points legally, logistically, that they had to move through. She had to move through before that decision was made. Most decisions will not take that. Like most decisions are reversible.

Christina (38:56)

Mm-hmm.

Mm-hmm. Yeah. Yeah.

Lily (39:14)

Period. Marriage is, it’s like, it’s okay

to trust that maybe sometimes you will fall back into old patterns and that your partner will be curious about what you want and that you, this is what’s most important, you will be curious about what you want. And that’s what either or robs people of is curiosity. Thinking about a faith example, either or, either it’s this or that, either it’s like,

Christina (39:38)

Mmm.

Lily (39:44)

heaven or hell and there’s one choice that gets you into the heaven and one choice that gets you into the hell. That either or robs people of curiosity and questions.

Christina (39:55)

yeah, I mean

absolutely yeah, that’s why it took me so long to deconstruct because I was so afraid of going to hell I was like I’m just not even gonna like I was afraid to take my questions to their Inevitable ending points because if that took me away from heaven Then I would get tortured forever, which sounds like so ridiculous, but Yeah, it’s in community yeah

Lily (40:11)

Well, and it also takes, but it takes you away from family, right? It takes you away from structures that can community. takes you away from so

much. So it’s a serious thing. I wanna go back to you exploring dating women.

Because I do think that either or is robbing you of curiosity.

Christina (40:28)

Yeah, I think that’s true now that we’ve talked. I definitely… Yeah. Yeah, that’s true.

Lily (40:34)

And I’m not, I don’t love the dynamic of like.

I know that some women who date women are sensitive to being with somebody who’s new to the community, who’s not sure if they wanna be with a woman, right? But I do think that there’s, and those people will filter themselves out, because they know what they want and they’ll ask for it, like I believe. And I think all you have to do is be honest about like, yeah, I haven’t dated many women, I’m excited to meet up with you, I’m really curious to get to know you more.

Christina (40:49)

Yeah.

Yeah.

Lily (41:08)

Like you can be, you don’t have to say, I’ve never been in a serious, you can say that, but because you can’t say the wrong thing to the right person, but you could just be like, I haven’t dated many women and I am bi and I’m excited to meet you.

Christina (41:21)

Yeah. Yeah, that’ll give them enough information. I think some of it’s, I mean, I’m not trying to offload responsibility for focusing more on men. And I have gone on a couple dates with women. I have noticed that on the apps, I have a harder time matching with women because a lot of… ⁓

I know if this is why, but a lot of the women I’m liking when I do like women are, like they say, they’re lesbian. And I have heard, I don’t know how common this is, that sometimes in the lesbian community they would rather just date other lesbians, which is fine. But I do sometimes have a hard time getting matches with women, and that also makes it feel like it’s less achievable.

Lily (41:52)

Sure.

How often are you, well, and I don’t think that the, I don’t, I’m not saying that like dating women is the answer to everything. I’m just saying like the, said at the very beginning of our conversation, what’s the point if I want to get in a relationship as soon as possible and I ⁓ am still an adolescent when it comes to dating women. I think that the story that you’re telling yourself that you’re an adolescent probably isn’t serving you.

Christina (42:08)

Right.

Right.

Yeah, I’m not an adolescent. I’m a full grown adult with lots of relationship experience with not just romantic partners. I know that’s like so that no one use when I say it that way. I’m like, no, it’s fine. I actually why do we like why do we think that that the only relevant experience to dating is dating experience like relationships are relationships? Yeah, no, that’s

Lily (42:31)

I think

There you go.

amazing point and I do think that

you can say like I’ve never had sex with a woman or I’ve never had penetrative sex with a man like whatever your sexual experience is you can own it and it not be a problem you know what I’m saying it’s like you’re this is about being honest with what you want being honest with the people that you’re meeting up with to the degree that feels appropriate not

Christina (43:00)

Mm-hmm.

Right. Yeah.

Yeah.

Lily (43:16)

not vulnerability dumping out of the fear of being judged, but really just saying like, here I am, here’s what I’m about, here’s what I’m looking for. I’m looking for the right partnership. And I’m going on dates with people that give me glimmers of the right partnership to see if we like each other, period. So I think that it would serve you and your ultimate goal of being in the right relationship so much more to only go on dates with people that you are genuinely curious about.

Christina (43:19)

Right, yeah.

glimmers. Yeah.

Lily (43:45)

That’s actually going to speed up your progress. And I think that you might find that you’re genuinely curious about some women, you’re genuinely curious about some men and their behavior, their ability to co-create a date increases or decreases curiosity based on their co-creation skills and their emotional maturity.

Christina (44:04)

Yeah, that makes sense. I think that’s like much simpler than I think I was like doing a lot of mental gymnastics to try to like, don’t know, justify fears or just like unknowns. Like, cause yeah, like I’m less experienced dating women. I, it’s not that I have none, but I, when it comes to dating, I have much less. I’ve only been in a long-term relationship with a man.

And actually you would have one

Lily (44:27)

And you’ve had one long-term relationship,

Christina (44:29)

long term in my 20s and then since then I’ve had like two shorter term like just a couple months each. But that’s it, you know, so with men,

Lily (44:37)

have you shared with your family that you’re, bye.

Christina (44:39)

I’ve told every

so my parents don’t know unless they figured it out somehow and just haven’t said anything which is totally possible because I think they would avoid it I haven’t told them and I my brothers know and they seem supportive or at least neutral One of them is very supportive. The other one is like supportive neutral And yeah, my aunt’s like actually my mom’s sisters know yeah, it’s just most of my parents because they’re not super like you know affirming they’re very still very conservative

Lily (45:04)

Yeah.

Christina (45:06)

We- Yeah. Yeah.

Lily (45:05)

Yeah, not a problem. was just curious about that. I mean, that is a problem in that you deserve to be affirmed, you know, but I also it’s not their opinion is not necessary. I just wondered their opinion doesn’t matter. It’s a bad opinion.

Christina (45:12)

Well yeah, no no no, I understand what you were saying. Yeah.

No,

no, it is, it’s wrong. But like, also, understand because that’s how I was raised. I like understand, and also because they, my mom at least makes plenty of, plenty of comments, not about me, because she doesn’t know, but like just about, you know, LGBTQ stuff in general when I’m home. And every time I’m like, well, maybe I’ll say it this time, then she says something. And I’m like, maybe not, unless I have to. But like, yeah.

Lily (45:44)

I think that protecting

your emotional safety in that relationship is something that you can handle. And when and if you want to have that conversation, I do think that you can, because you can trust yourself. But I think right now we need to laser focus in on you and your desire for the right partner. Because you could date, you could meet a woman.

Christina (45:58)

Mm-hmm.

Lily (46:10)

or a person who’s non-binary or a man fall in love very quickly and suddenly be in the right relationship. I think that the way that you set yourself up for that effectively is by centering your desire instead of trying to do the calculus of what is going to help me. Dating men is the fastest path, I think.

Christina (46:13)

Right.

Mm-hmm.

Lily (46:38)

dating the people that you’re interested in is the fastest path to meeting the right partner.

Christina (46:38)

Right.

Yeah, I like that reframe.

Yeah, makes sense. ⁓

Lily (46:45)

So I think this whole session has been about

like acknowledging the stories that you’re telling yourself that I shouldn’t be so frustrated with the single tax. No, it’s okay. Stop judging yourself for having an emotion, a human experience with something that is present. Number one. Number two, stop limiting yourself with the idea of like, I know exactly how I’m gonna meet the right person because that means doing it.

Focus on finding the people that you’re curious about and ruthlessly saying no to the rest. You mentioned in your application, we didn’t have time to get to this, that it was difficult and frustrating to find something that worked and there were flaky people and like you’re traveling long distances for a different borough and what have you. Set standards for yourself for how long you will travel, on which days, what your limits are, right?

Christina (47:17)

Mm-hmm.

Mm-hmm.

Mm-hmm.

Lily (47:42)

know for yourself, center yourself in your dating life. ⁓ What borough do you live in?

Christina (47:44)

Mm-hmm.

Lily (47:50)

Okay, so maybe you say like, I’m game to meet in the middle in like the Lower East Side is like the longest I will travel or I will go to Astoria, but not Brooklyn. We can meet in the middle of there in Brooklyn. We can meet in Queen, whatever it is, like, like set your own, set your own standards so that you don’t continue to resent your dating experience.

Christina (48:10)

Oh yeah, yeah, yeah, yeah, absolutely. Yeah.

Lily (48:20)

insofar as you’re in control of.

Christina (48:22)

and I mean logistically I do do that in beginning and then I think it’s it can start to get harder like once you if you connect with somebody like in Brooklyn and you first you’re meeting in the middle But at some point you’re gonna be going to each other’s places now You’re looking at an hour and a half one way, you know So sometimes I wonder if maybe I should even be limiting like where the person lives. So I’m not worrying about that You know, I don’t know

Lily (48:31)

Yeah.

Yeah.

Yeah.

why don’t

we do a high quality experiment of that? I think that you’re getting ahead of yourself there, because for the right person, are going to be so fucking excited to hang out with them, and you will be able to figure it out, right? If it’s meeting up once a week for a sleepover instead of three or four times a week, maybe it’s like, you would be able to figure it out for the right person. And so that’s what we need to refocus on.

Christina (48:47)

Maybe, yeah.

Yeah. Okay. Yeah.

Right.

Yeah.

Okay. Yeah. Yeah. Yeah. I think, I think those are the kinds of things that I sometimes I’m like, ⁓ like, let me think for like, till like six months down the line or 10 years down the line. And that’s not necessarily helpful.

Lily (49:10)

Does that resonate?

It’s not helpful and it’s not factual. You actually can’t know what’s coming accept that you will have your own back through the process. That’s what the experience of self-trust can do is like, I don’t know what’s coming next month in this new relationship, but I trust that I will be able to figure it out no matter what. Instead of.

Christina (49:29)

Hmm.

Yeah.

Lily (49:50)

Let me future trip on if I’m dating somebody in Brooklyn, what will that be like? if they da da da da da da, you mentioned in your application that it was difficult when somebody says, definitely wanna leave New York or I definitely wanna live in the suburbs or I definitely wanna, and you’re not sure.

Christina (50:04)

Mm-hmm.

Lily (50:05)

I do think some of those people might be disqualified based on their answers, but some of them it just might be like, okay, cool. Let’s keep getting to know each other. We don’t know yet. We don’t know yet what’s coming. So I just want you to be firm in like, I’m centering what I want and I’m gonna get really curious about you and what you want. And I’m gonna get curious about how I feel in your presence. How do I want the right relationship to feel and tuning in with those essence based preferences, which you said.

Christina (50:14)

Right.

Hmm.

Lily (50:33)

you had done in the application, which I love, tune in with those every step of the way.

Christina (50:39)

Yeah, curiosity is one of the main values on my list actually, so yeah.

Lily (50:43)

Well then take that spotlight that you want

to like shine on somebody else of curiosity, put it on yourself here, right? Like what might I be curious about today about my desires? I wanna find the right partner and I’m whole and amazing as I am right now. I wanna find the right partner and sometimes that single tax feels so fucking unfair and I get to be angry about it and I am not going to make decisions that mean I abandoned myself.

Christina (50:49)

Mm-hmm.

Mm-hmm.

Lily (51:12)

even if it means not going on this family trip, even if it means, right? Like that is what I want you to do is center yourself to ensure that you are settle proof and that you find the right partner.

Christina (51:15)

Yeah.

Yeah, sometimes myself, I’m gonna like put that on a sign on my mirror.

Lily (51:30)

There you go. That’s it. What do you think you’re

taking away from this session, Christina?

Christina (51:35)

I think the seesaw thing you said earlier is ⁓ something I’m gonna be thinking about for a while just trying to catch myself in the black and white thinking I think trying yeah the curiosity just trying to be like in the moment I think rather than

trying to foresee all the stuff that might go wrong and just try to look for signs. Like initially, do I want, does this person, like am I excited to keep getting to know this person and do they seem curious about me as well?

Lily (51:52)

future tripping.

Christina (52:06)

I think that’s a really good place to go from. And I’m already using qualifying, disqualifying questions in my early, which has been really helpful to kind of cut down on the kind of flaky or going nowhere conversations. But yeah, just the curiosity thing, I think I’m going to keep that at the center as well. Yeah.

Lily (52:12)

Good.

Amazing. Christina, it’s been

so great coaching you and talking to you. And this is just the beginning. Thank you. Absolutely. Please keep me updated. All right. Bye.

Christina (52:31)

Thank you. Yeah, thank you so much. This has been awesome.

well.

Lily @ Date Brazen (52:39)

Thank you so much, Christina, for coming on the podcast. I’m so grateful that you allowed yourself to be seen and supported in this way. And let’s get into your follow-up.