Welcome to UnF*ck Your Brain. I’m your host, Kara Loewentheil, Master Certified Coach and Founder of the School of New Feminist Thought. I’m here to help you turn down your anxiety, turn up your confidence and create a life on your own terms, one that you’re truly excited to live. Let’s go.

Hello my friends. I am so happy to share this bonus episode with you today because it is a conversation with one of my favorite people, a good friend of mine, Lily Womble, who is the founder and creator of Date Brazen. Which is a feminist dating coaching program and movement that I wish I’d had when I was dating. And her new book, Thank You, More Please comes out today. And I think you’re going to really enjoy this conversation.

And I want to encourage you to go order her book because we need to show the dating industries and all of the apps and all of the kind of heteronormative patriarchal conditioning and businesses out there that are contributing to that conditioning and making money off of it, that there is a market for smart, respectful, authentic feminist dating advice. And the truth is, dating isn’t something that comes super naturally to a lot of people, it can be hard and complicated.

And there is a way to kind of grow and evolve yourself without compromising your values or your principles, and find that partnership that you want. And Lily herself is such an embodiment of Thank You, More Please, just as an attitude and an energy. That she is just such a lovely breath of fresh air and joy and the best hype and wing-woman a person could ever have. And so, I’m just so thrilled for her, for her book coming out. Having just gone through this, I know what a process that is. And I really, really want her book to be a success as well.

So, if you are dating, you’re going to want to go order a copy of this book. It’s anywhere books are sold is where you can find it. And if you think you’re going to want it, order it this week, please, because the first week of sales are the most important for a new book. And if you are happily married or partnered, I honestly recommend reading it anyway. As you know from my work, romantic socialization shows up in your relationships also. And the same way you thought during dating is the same way you’ll think in your relationship.

Or you’ll have it on hand to give to a good friend when they are finally at their dating rock bottom and ready to accept some coaching help. So, I’m going to stop gushing now and let you all listen to this conversation that really digs into how we are socialized around dating and the power of that sort of positive, thank you, more please approach. This is actually one of the techniques that I used when I was changing my thoughts on dating, that sort of gratitude for what I’ve been shown and asking for more, and it was really helpful for me. So I can’t wait for you all to hear it.

Kara: Hello, my friends. I am here with one of my favorite people to commiserate and laugh with, especially because we both have books coming out around the same time. And so, we have just been like, “Someday, maybe we’ll do the unfiltered behind the scenes of having a book and having it come out.” That would have to be a ticket, private, no recording, only experience.

Lily: No phones, put them away.

Kara: No phones, put phones in those little Kevlar bags. I am here with Lily Womble, who is an amazing feminist dating coach. And I’m going to have her give her, you know, I like to make women brag about themselves. But I’ll say I met Lily at actually a book party for Farnoosh Torabi, my other friend and our mutual friend Hillary, who’s now my sales and marketing director, introduced us.

And Lily was wearing this fabulous off the shoulder pink dress. I don’t even know how to describe it. I just was like, “This whole thing, whatever’s happening here, this is great. I like you. Let’s be friends. I don’t know what’s going on here but I’m into this.” The only time I’ve ever felt like the quiet person in the group was hanging out with Lily and Hillary. That Lily, Hillary and me, is the only scenario in which I am the wallflower. So that’s just a fun experience for me in general. So, Lily, tell us who you are and what you do. Why are you here? Why are you on my podcast?

Lily: Why am I here? Because you liked my dress. That’s why I’m here.

Kara: Because I liked your dress, that’s right. That’s how [crosstalk].

Lily: It was very breast tit forward.

Kara: Yeah, it was a tit forward dress, which I appreciate as somebody who is essentially always tits forward despite my best efforts. I mean I’m always trying to not be but there’s no way to not be.

Lily: No way, why would I hide my light? You know what I’m saying?

Kara: That’s right. Don’t hide your light under a bushel or a bra.

Lily: Yeah, absolutely. So, I am here because as you mentioned, I’m a feminist dating coach. I’m Lily Womble. I am a professional feminist dating coach. I was a top matchmaker at one of the nation’s largest firms. I was the third most successful.

Kara: I didn’t know that about you.

Lily You didn’t? There we go, yeah. So, I was matchmaking up a storm and I didn’t have any intention of being a matchmaker, it was eight years ago. But I saw a job posting, I needed another job as you do living in New York City. Did you know I was also at the same time as applying for this job, a balloon hat maker at Señor Frogs in Times Square?

Kara: No. I’m now realizing that we really didn’t do the deep dive on childhood that we needed to. I really missed a lot.

Lily: Childhood, this was my 20s.

Kara: I know but I only recently learned you were a child voiceover actress. Yeah, so this has been a lot going on here.

Lily: It’s a winding road. It’s a winding road. But no, I mean I needed a second job. I was trying to be in musical theater, who am I kidding? A fourth job. I got the job as a matchmaker. I realized my roots were in feminist advocacy and non-profit work. And so that’s what my first beat of my career was. So, I realized in starting to be a matchmaker that (a), I was really good at it, (b) it was a place where I could help women be well. When I helped people with their dating lives specifically, it helps them step into their agency.

It was a deeper portal to wellbeing I found. So, I got really passionate about the dating space, particularly because it also felt culturally, single women who were dating were sort of this left behind group of people who were treated as behind, treated as less than, treated as if they were idiots for not having found a relationship yet. And I got really passionate about being with them in the dating trenches and helping them thrive and helping them take up more space.

While I was matchmaking I was also in the worst romantic relationship that I could have imagined for myself. I was settling every single day. I was giving this advice professionally like, “You deserve more, let’s get you on some great dates.” And then I’d be crying on his bathroom floor 15 minutes later silently, very, very painful. He was somebody who met all of my checklist items. I thought that it was going to be this, somebody likes me, they really liked me. I had this deeper narrative that I’m too much.

My mother literally told me at age 12, “You’re too much and you will have a hard time finding a husband.” And so, this proof of you’re not too much was this person who wanted to date me, but it ended up being a fiery hellscape of a relationship. So, when I was done being out of alignment and when my therapist really helped me sort of understand the cognitive dissonance that I was living within and I realized that I was done taking his shit. I broke it off with him. But then I was like, “What do I do now? How do I never settle again?”

Because my therapist hasn’t dated in 30 years. My friends and family just tell me to get on another dating app and to play the numbers game. And matchmaking is a first date solution and I know I need something much deeper than a first date. So about six years ago I started building the solution that I needed for myself. I started learning about coaching. I started immersing myself. I was mentored by a few incredibly highly skilled coaches at the time.

I was then practicing these new coaching skills that I developed with my matchmaking clients, getting real time experience, helping people uncover their own internalized stories as I did the same for myself. And what I found with the tools of self-compassion and getting beneath the surface of my old dusty, crusty stories and neural pathways is that I created a plan both mindset wise and tactically, to thrive in my dating life, to have fun in my dating life, to start setting more boundaries in my dating life. And that led to more freedom.

That led to me feeling flirty and giving my number to cute strangers and going on fun dates and fucking around more and feeling confident at doing that. And that eventually led me to meeting the love of my life, Chris, who I’m not married to. Who is not somebody who I necessarily would have chosen had I not gotten beneath the surface of my old checklist. So, when I was coaching my matchmaking clients with these tools, they started to find better dates for themselves than I or anybody else could find for them.

And so, six years ago, seven years ago, I broke up with matchmaking and started Date Brazen to be the feminist badass coach that I had become and to start coaching people of becoming their own expert matchmaker.

Kara: I love that story because it’s so often we just want someone to give us a solution. So, with matchmaking, if you have the belief that somehow you can’t find the good people. So, you need to pay someone who somehow knows them, who can figure out for you. It’s such a way that I feel women and men probably go to matchmakers for very different reasons and with different thought patterns. So, I love that sort of, once you’re empowered.

I’m always saying to my clients, “I don’t know what you should do. You’re going to know once you clean up your thinking, then you’re going to know what to. You know your life much better than me.” Sorry, go ahead.

Lily: Outsourcing your agency is what it is. I mean, some people, matchmaking works, great, good for you. I’m talking about the people who have this feeling, I know I could be more powerful. I know I could be more confident. I know I could be, but something’s stopping me. So, really owning your agency and taking steps to create your own best solution is what I help my clients do every single day with a bunch of bossy tactical dating strategy as well rooted in feminist values.

Kara: Yeah, of course, there’s always some tactics, but I think that whole believing you have to change the circumstance. I need someone else to bring dates to me, or I need to move or I need to look different or be different. That there’s this gatekeeping happening. So, you have a new book coming out called Thank you, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love. And so obviously you’re just singing my song.

So, can you talk a little bit about how you see patriarchal traditions have conditioned people, especially women and femmes, to settle for what you call crumbs in their dating lives? How do you know if you’re settling for a crumb, and why does the way we’re socialized make us do that?

Lily: There are so many ways to answer that question. I was trying to think of the phrase, how could it not have impacted every single inch of our choices in every single way? However, just to focus on dating specifically, the way that I was just taking it personally, the way that I was raised in Birmingham, Alabama, to see that single women were literally treated as behind, childlike, leper-ish, how married women …

Kara: You’re a child leper and you’re also behind.

Lily: One of my clients put it so beautifully. She was in her mid-30s and she was like, “I was treated as if I were pathetic for wanting a relationship and also pathetic for not having one.” And so, this double bind of, if you want something, you’re desperate. If you don’t have something, you’re pathetic. I think that double bind is rooted in patriarchal expectations of women and femmes to be partnered to signal value in our society. And top level down, that makes a lot of sense. So historically that makes a lot of sense.

It wasn’t until, I mean, I know that you talk about this literally all the time, but it wasn’t until historically very recently that women didn’t have to settle in order to thrive or survive economically. So, I think that in terms of why people, specifically people in their 30s or 40s who might feel behind in their dating lives, why they might feel a little cuckoo or a little bit frantic.

Kara: Frantic is the word I like to use.

Lily: Frantic is because of the patriarchal expectation that you should have figured this out by now. And by the way, there’s something wrong with you for not having figured out how to catch a person already. And so really what I get to do is help people give themselves radical permission to own what they want. Because another way that the patriarchy has seeped into our dating lives is that most women and femmes are shrinking what they want in response to stimuli like somebody who is wrong for you.

They’re centering their exes in whether or not they believe what they want is possible. I think, again for people who date men, centering men who were wrong for you and whether or not you believe that what you want is possible. All of these things need and deserve to be untangled if you want to attract the best relationship of your life and feel amazing about yourself while doing it.

Kara: Yeah, that’s such an interesting point because people do this all the time with business or anything else. You’re defining what you think is possible based, I want something different, but also I don’t believe it’s possible because I haven’t had it yet.

Lily: Yeah, 100%.

Kara: You broke up with somebody because they weren’t what you wanted, but then you’re telling yourself what you left is already only what exists. The brain is so resistant to believing that something better is possible. And of course, society tells women, there’s a scarcity, especially if you’re heterosexual or, I guess, bisexual, but dating men. There aren’t enough good men. There’s a scarcity. You have to settle down. If you find someone who’s not a total deadbeat loser then just make do.

And maybe even if they are a total deadbeat loser, you should probably make do anyway, because all of that scarcely gets so ingrained. This is sort of a tangent, what your take is on dating apps? Because I’m seeing, people obviously have a lot of thoughts and feelings about dating apps. I’ve certainly experienced some of the terrible parts of them but I also met my fiancé on one.

And I’m seeing this sort of feminist backlash to dating apps where they’re sort of compared to diet culture kind of. These are companies that are profiting off of your desperation and your self-esteem issues and they are abusive. There’s just this new take that I think is kind of bubbling up. And I’m curious, what your thought, do you encourage your clients to use dating apps, to not use apps? What do you think about apps? What’s your take?

Lily Yeah, I have several chapters devoted to this in my book, Thank You, More Please.

Kara: You probably can’t write a dating book these days without addressing dating apps.

Lily: No. And they have fundamentally changed the landscape in the last 11 years. So of course, we have to talk about them as it relates to how we find love and connection. Especially because the perception is that they’re ubiquitous, that you can’t find love without one these days, that in-person dating is dead. All of these, I think, fallacies, that we’re under the impression that dating apps are the only answer because of these multimillion, potentially billion dollar marketing budgets that dating apps have utilized over the last 11 years.

So of course, your brain believes that dating apps are the only solution. I also think we’ve got to look at how they were, this thing that you’re describing as the new take, I have been talking about this shit for six years. Because dating apps have always been in the business of addicting their users because they were built like slot machines designed to keep people, I liken it to sitting in an Atlantic City casino with a big Slurpee with a gallon bag full of quarters, just putting quarters in the slot machine and trying to hit triple cherry, it’s an addictive thing, dating apps.

And that’s why I think that it’s important to take the power back from them, first with your thoughts and then obviously with your actions. Really unhooking from the belief that a match or a message means anything about you or your future potential in your love life. It’s just literally a tool. And I think it can be a really powerful fucking tool when you use it with boundaries, with intention, with self-knowledge.

I think that dating apps are good for two things. Meeting somebody outside of your social circle and getting to know your dating personality. What are your triggers? What is exciting to you? What turns you totally off? How are you being courageous in the questions you’re asking? How can you be more direct in your communication? This can be a playground for more courageous action and for attracting amazing people.

I have so many clients who meet their partner, spouses on dating apps. And because we focus, there’s another chapter of my book called Dating in Person with Main Character Energy, because I think that you’ve got to have both. If you’re going to have a fulfilling, joyful as fuck dating life, that is more likely to lead to the best relationship of your life. I really think you’ve got to create an in-person dating life so that your online dating life becomes more unbothered.

Kara: I think, definitely think of them as a tool. It’s like a hammer, you could kill someone with it or build a house. Your money or anything else is a tool like that. So, for me, for instance, as somebody who just loathes talking to strangers in public and hates bars and doesn’t really like socializing in groups. All of these, for me, they were just a very useful tool. I was like, “This is so much less energy expenditure for me to make initial connections this way.”

But I think of it as social media, you can use social media on your phone to numb out or beat yourself up about how you look on Instagram, all these things. Or you can use it to FaceTime your grandma who you would otherwise wouldn’t get to see before she passed away. It’s a powerful tool that can either, depending on how you’re thinking about it and how you’re using it. I don’t want anyone to give any particular tool or circumstance all of the power over their lives.

I mean, as somebody who worked in all women non-profits for my whole life I was like, “I’m not meeting anyone at work.” I’m in a world that’s very one [crosstalk].

Lily: Yeah. And I do think, I just contributed to this Washington Post article about how people are going to speed dating events instead of doing dating apps now. There is a renewed conversation, especially after the four years that we’ve all had on in-person dating. We’re coming back around to, we’ve got to renew our social skills. I think that a lot of social skills have been lost.

Kara: How do we interact again? [Crosstalk].

Lily: Well, how would I say hello to someone? And I do think it’s a both and with in-person dating and dating apps. I also say to my clients, they are optional when you have a really strong in-person plan and when you have the skills to confidently or awkwardly approach somebody and say hello.

Kara: When I started doing this work, I realized that probably I had actually been hit on quite a lot in the past. But I didn’t recognize it was happening because my thought was that I don’t get hit on in public or people don’t hit on me. So of course, I was not even recognizing when someone was hitting on me. So, I mean, there’s another reason why the mindset work is so crucial. You can go change your circumstances but if you haven’t done the mindset work, you can move to a new city and just not notice when anyone there hits on you either. That’s not going to solve your problem. You have to change the way you think.

Let’s talk about, how do you define dating as a feminist? Obviously, a lot of dating advice has been very anti-feminist in the past, I would say. And even now I see there’s dating coaches out there who are sort of like, “Get married in six months” or whatever. And I’ve always found in my own coaching women on dating, there is this balancing act of, yes, I want dating to be more enjoyable for you. Yes, I know you really want to find a partner. You’re really fixated on this specific outcome.

The outcome I want for you is that your relationship with yourself is changing. There’s this sort of, it’s both your relationship with yourself and then you are also trying to make a particular return, a result happen. So, I’m just curious, how you think of, what does dating as a feminist mean to you, and how do you try to bring that into your work?

Lily: Yeah, I think that being a feminist and striving to be intersectional in my feminism impacts every, hopefully impacts everything that I do as a coach and business owner. But I think it starts with not defining romantic relationship as the gold standard of human existence. As a dating coach that feels pretty radical.

Kara: But that’s the biggest part of it is you can’t not be frantic, if you believe this is the thing that defines my worth and value in the world and I don’t have it.

Lily: Yes. And I’m a married person. I got married last year. And my husband is the most incredible person. I love him so much. Both, and if we were to get divorced at any point, we have discussed this openly, I would trust myself. And I think that that’s also what I want my clients to have is that they also, when they meet somebody, there’s this franticness of, well, what if this isn’t the right person? What if this doesn’t work out?

And my own thing is, how can we zero in on your self-trust so hard, how can you have your back so hard that no matter what happens in your love life, you’re going to be fine?

Kara: Because they’re thinking of it as if there’s a break up, if there’s a divorce, if there’s a whatever, then I made the wrong choice. It doesn’t matter.

Lily: I made the wrong choice. I’m a failure, yeah.

Kara: I’ve been married for 30 years and then I made the wrong choice. I did it wrong.

Lily: And I also think dating as a feminist means having the skills to own what you want and to be able to fundamentally verbalize what you want without apology. I think that that’s also in a dating space that teaches women and people socialized as women to shrink, to want less, to stop being so much, to stop having so many needs or so inconvenient that you are so emotional, whatever.

To boldly in the face of those ex patriarchal expectations to coach people on how to really revolutionize how they take up space in this world and how they ask for what they want. Directly leads to them finding the best fucking relationships of their lives. I do think fundamentally this is about a relationship with self first. I think that that comes with any, I think, aligned coaching practice that I’ve found.

I want to work on what I can control, which is my relationship with myself, both and when you create a relationship with yourself or you’re constantly giving yourself permission to want what you want. And give yourself permission to ask for it, even when you feel awkward, even when it doesn’t please somebody, to release that people pleasing or as you call people deceiving. Really speeds up your trajectory towards the best relationship.

Instead of doing what you’ve been doing for the last 15 years, settling, being in relationships that you know aren’t working, being in situationships or hiding from your desire and not dating at all.

Kara: Doing the work to uncover why you want what you want because I think sometimes people hear, have a list of what you want and don’t be afraid to say that. And they’re like, “Great, needs to be a doctor and 6 feet tall.” And those things have nothing to do with whether or not you’re in a good relationship.

So, I struggle sometimes with talking, not talking about it, but just with settling discourse. Because it feels like this term that is sometimes used really appropriately in my view, which is, you’re in a relationship where the person doesn’t treat you the way you’d want a person to treat you. You’ve done your own work and the person is not respectful or kind or doesn’t seem to care about you or whatever.

So, there’s certainly a lot of scarcity messaging leads to women believing it’s better. Sort of settling to me is being in a relationship because your thought is, it’s better to be in any relationship than no relationship or I can’t find what I really want or whatever. I’m not good enough, so that is settling. Then at the same time, I think sometimes, I see this especially in some of my younger clients or students or family members, whoever, who I feel like came up more in the Instagram era.

There’s certain expectations of what a relationship should look like or of, if your partner is really good at asking you about your day and caring about your family and doing the little things but they don’t do grand romantic gestures. And you’re like, “Well, my list is that somebody will take me on a hot air balloon ride over Turkey and propose in the air. I saw that on Instagram. That’s really romantic.” That’s not selling.

I mean, you and I both, I think, it’s not, what’s the right word? It’s not a coincidence that you and I both have done a lot of work in this area, teach about this and both ended up with people, having done that work, ended up with people who were not what the original checklist would have been.

Lily I find that that’s more often the case than not, that the person you end up with is not on paper who you would have thought you ended up with.

Kara: Because when you haven’t done the work, your paper is the person who you think would allow you to think, I’m good enough, look what I got. We understand, I think feminists are very aware that men are taught to objectify women and to value them only for how they look and to believe that being with a woman who looks a certain way makes them a manly enough man or a high status man or whatever. We’re very tuned into that dynamic.

But I don’t know that we are always taking as much responsibility for the flip dynamic of my status as a woman is not only being partnered, but being partnered with a man who meets certain socially conventional criteria of how he looks, what his size is, what his height is, what his job is. Is he the earner? Is he the provider?

The number of women like me who are high-powered, making a lot of money, doing all the things women who I coach, who are considering breaking up with some great guy who loves them, who they love because he’s not ambitious enough or shouldn’t he also be making enough money or whatever. And there’s nothing wrong with wanting, if that’s what you want, great. If you want to marry another captain of industry and have you both fly around the globe all the time, that’s fine.

I’m not saying there’s any way a relationship should be. I think sometimes feminists skip the step where you have to decondition all your beliefs about masculinity and about that version of value and status that society has taught you. It’s not feminist coaching. If you’re like, “I know my value, so here’s my conventionally specified list of what a man needs to be, and I should get that kind of man. That’s me knowing my value.”

Lily: Absolutely. And also, with this deconstruction comes deconstruction of sexuality. That deconstruction is how I finally realized that I was bi. And how I finally was like, “Oh, these things make sense, why I was attracted to women at a certain age. I make more sense.” People are going to make so much more sense to themselves when they start that deconstruction of the expectations that were placed on you, that you inherited from your mom, from your brother, from your co-worker.

Whatever it is, that chapter of my book that I think is my favorite is about essence based preferences, which is my answer to this problem. Because people do come in with either an over-functioning list, over-functioning, meaning rigid checklist, you shall not pass energy or an under-functioning blob of nothing, somebody nice with a job.

Kara: Right. Or not that nice or maybe only sometimes.

Lily: Right. Has some money sometimes. Yeah, we go out to dinner sometimes. No, but how to come in the middle of those two things, not over-function, not under-function is to come to, how do you want to feel in the right relationship? And getting really granular with your language to describe how you want to feel in the right relationship.

In my view, there are two categories of preferences. There’s logistics, the resumé stuff, age range, height, whatever. And there’s the personality traits and values. And so, with an essence based preferences lens, this is me putting on my glasses with an EBP lens with height range for example. When somebody comes in, they’re like, “I want somebody 6 feet or taller and I won’t date anybody under 6 feet tall.” I say, “Okay, cool. You get to want what you want, both and, how do you want somebody who is 6 feet or taller to make you feel? How does that feel and to be in their presence?”

And they generally say, “I feel attracted. I feel enveloped.” I feel, now here’s the kicker, “I feel smaller than them.”

Kara: Of course, always, yes. I mean, there’s a whole thing about dating tall men in that baked in …

Lily: Body, and the body stuff. And then I’m like, “Okay, so here’s the work we’re going to do.” Also, another reason I’m a feminist dating coach, we’ve got to unpack, we’ve got to be thoughtful about this stuff so that you can feel freer in your dating life and in your life in general. So, then we get to the essence of, once we unpack and separate out what is patriarchal bullshit of you thinking that you’re too big versus how you want to feel with the right person.

And then I ask, inevitably, “Have you ever felt attracted to or have you ever felt enveloped and warmth by someone who is less than 6 feet tall?” And inevitably they say, “Yes, I have.” And so, then I say, “Cool. You get to want what you want both with this essence based approach of knowing how you want to feel, you can be open to being surprised by the right person because you’re going to tune in after the date with how did I feel? Did I feel the way I want to feel?” And you can use the same tool for personality traits and values as well.

Kara: Yeah, I think some of you listening may be like, “Wait a minute, Kara’s always telling us we create our feelings.” So, we partially may just have different approaches. But for me, I think we can think about feelings in a slightly broader sense here, which is, if you feel attractive because of a man’s certain height is because your thought is, I feel small next to him. And then you feel a certain way. I don’t believe he’s causing it, although of course you have your own framework.

But I think about my relationship with my partner, I think part of what would have fucked me up, part of what would have kept me from being in this relationship previously is that women are sold this belief that when you just find the right guy, you’re going to feel amazing. And for a lot of us, that’s not true because a lot of shit comes up. If you have been emotionally unavailable and you have started doing this work on yourself. And it’s not like I had finished the work and then I met him. It was ongoing.

Lily: No. Shannon Silver says, “A relationship isn’t a prize for healing.” I love that, yeah.

Kara: Totally. So, I think there is this, for me it wasn’t even, how do I feel moment to moment sort of because moment to moment I am confused, angry, scared. I’m having all of these feelings along with the good ones. That wouldn’t have worked as a guide for me. But for me it was, what are my values in dating? Which is a version of kind of how do I want to feel? It’s not about what status do they confer on me. Or it’s not about kind of, I met the right person and now I magically feel good about myself all the time or I’m magically, blissfully happy all the time.

For me, that’s maybe the right way to say this is, what I teach people as that middle way is, maybe I talk about it differently as these values but it’s the same thing. Rather than it being under inclusive of, well, I hate myself and you’re willing to date me and I don’t think anyone else would, so I’m in. Or over inclusive of, yeah, but you’re 5’ 8 so forget it. Rather than this over checklist or this under checklist. If you are not doing this based on what society’s taught you, how do you navigate? What are your values?

So, for me it was my dating values were curiosity, fun, and I think, openness or growth, which fun is sort of a feeling. These are sort of qualities of this connection. So maybe that’s the way to talk about it. It’s how you feel with the person or what are the qualities of the connection? Are you both in this kind of space? I never want anyone listening to me or anyone else talk about dating to think that you feel amazing and that’s how you know they’re the right one because you always feel good. Because that was just not my experience at all.

And it doesn’t get talked about enough. I feel a lot of what we leave out in coaching, not you at all, just in the coaching world in general, in all of our, we can coach you to help you create this result you want which is really true and powerful. If that’s been your kind of most fucked up issue your whole life, getting it will actually probably feel terrible.

Lily: I agree.

Kara: I have seen this happen with people who make a million in their business the first time where money was their most fucked up issue. That’s how I felt finding the perfect partner for me. It’s sometimes not going to feel good, but I think that’s so powerful because so much of the time we’re dating to feel better about ourselves. And so, if you’re not going to feel amazing, is it still worth doing and why? And that I think helps you make much better choices.

Lily: Absolutely. And that’s why I am very passionate about working with my clients now, on how they care for their nervous system now, how they work on their thoughts now, how they create self-trust now. Because I tell them, “One of the most activating things that you will experience is finding the best relationship of your life. It’s going to bring up all of your shit.” And so, it’s important to, I use the phrase, “Have your own back now so that you can trust yourself in that relationship even when you feel anxious or even when you feel really caring for yourself through that.”

And I would say that our approaches are more similar than dissimilar. The personality traits and values piece of the essence based preferences framework. Are about identifying the root words to describe how that person shows up in the world, compassionately curious or joyfully nerdy. These are things that a lot of my clients come to, and then they have a succinct, clear language to describe what they’re looking for in their terms, instead of just saying kind, funny, smart, which is very vague and unhelpful.

Kara: Right. Or tall and successful.

Lily: 100%. And when I say, how do you feel in their presence? I think back to my first date with Chris and how his energy and how he’s showing up, how he showed up as a human triggered something subconsciously for me that I felt safe in his presence. And I felt that he would be a soft place to land. And that was very new for me. And so, when I say, that’s what I mean by that.

Kara: And everybody has, there’s something pheromonal or energetic that’s part of this, obviously. I mean, I definitely felt with my partner that there was just an ease to the conversation and there was a certain, of course, energy there. So, I think I’m more just I’m always kind of, I guess, scanning for and trying to correct how I think other people in the midst of this journey are thinking which is often, well, once it happens, I’m going to feel so good. And you are talking about exactly this. People think that they can hate the dating process, hate the process into a happy relationship.

Lily: Yes. Like the get out of jail free card. I’m going to be in prison until.

Kara: Well, I’m just going to [crosstalk] myself through this until but the destination is going to feel like the journey. And so, I love that, what you’re saying about you teach that sort of, that journey is going to be activating. And once you get there you just have to learn a whole new thing which is how to be in an adult intimate partnership which is not the same as the dating skills. If you’re thinking about this as then I get there and I’m done, no, man, that’s just the next.

Lily: No. Then they say something, your new partner says something and you’re like, “Whoa, you’re a human being who has thoughts and feelings and work of your own to do. You’re complicated and we have to figure out how to talk about money.” There’s another life chapter to do then. And then in terms of people who are super highly successful, around money is a really interesting piece, especially for highly successful feminist humans who are like, “I want them to bring the same amount to the table.” Or, “I want them to bring the same kind of ambition to the table.”

I would be curious for those people how they want someone to mirror their own success, to believe their own success.

Kara: Why do you want that? I think women have really been taught that that’s what makes, I mean, we are socialized to see dating so much as an indication and reflector of social status. And so, what women are socialized to see as social status in men is that they are ambitious and successful and make money. And so, my teacher and friend Brooke Castillo, we talk about this on the podcast. I went on her podcast to talk about my book.

And we talked about this experience that she had when she started dating her current boyfriend where she texted me and was like, “But how do you deal with the fact that your partner doesn’t make as much money as you?” And I was like, “I literally don’t ever think about that or care.” And that could just be fine, you can just not care about that. That can just not bother you at all. And that was mind blowing to her. But I do think that circles back to what we were talking about, which is to me, feminist dating is not just, it is 100% and yes first, deconditioning the way you’ve been taught to think about yourself in the dating experience, and dating ‘market’ or whatever.

But also, how have you been taught to think about whoever you’re dating? I think the gender socialization of a heteronormative society hits stronger on how men and women are socialized. But whatever it is, how are you wanting, I see this in my mind all the time, I have to work on this. Especially if you have told yourself your whole life, there’s something wrong with you because you’re not in the right kind of relationship or the normal relationship or the whatever.

As soon as you get in a relationship your brain’s not like, “Good, that danger has gone.” Your brain is like, “Now I’ve got to scan all the time to make sure that he’s representing me well and reflecting on me well.”

Lily: Well, or the child, I’m an adult child of divorce is what I call myself. I don’t know. My parents got divorced seven years ago.

Kara: You’re a child of an adult divorce.

Lily: I’m a child of an adult divorce. Thank you, Kara. Yes, I’m being extra clear. And my parents did not get along for a lot of my growing up and it was a very difficult tense place to be in our house a lot of times. It wasn’t abusive, it was just difficult. And so, the scanning for, as a married person now, the scanning for, is this okay, are we okay? Is everything okay? I think that my work continues and all of our work continues.

Kara: But there is a big important shift that I feel people don’t talk about enough between what it’s like to be, I’m dating someone. And then at least for some of us, what it’s like to be like, this person’s now a member of my family. I think it kicks up a whole different set of stuff. It’s like people who have gone through having childbirth being like, “Nobody warns you about some of this stuff.”

I feel like nobody talks about the fact that there’s one set of conditioning and dating trauma you may have around dating. But then once you get into a serious enough relationship and a person becomes like a family member to you, there’s a whole other set of stuff that comes up and those things are related. Often I think we’ve been emotionally avoidant or unavailable in dating because we have unresolved family stuff.

And once someone gets close enough to that, once you are living with someone and they become your family as a whole new package. So basically, what we’re saying is, your brain’s are going to be a lot for the rest of your life. But the good news is, you don’t have to find a partner so you can be happy ever after, because your brain is going to be a lot no matter what.

Lily: Yeah, I mean, check your own, if then thinking you all, check it and then choose something different. It might be possible that my life is fulfilling now and I get to want a relationship. I think that another piece of feminist dating that I don’t hear people talking about often is this idea of as a feminist, you should know that you don’t need a relationship.

Kara: I shouldn’t even want a partner.

Lily: I shouldn’t even want one. I shouldn’t even want a partner because I should be so solid on my own. That’s such either or thinking, but it’s saying basically, desiring something new in your life.

Kara: Yeah, you wouldn’t say, I shouldn’t have friends because I should be on my own.

Lily: 100%. So, treating your desires as if the unpacking what’s going into your desires, what assumptions do you have about yourself and your desires. But then giving yourself fucking permission to want what you want can mean a beautifully freeing both and of I am whole and amazing and feminist and badass as hell. And I also want to find the right romantic partner or partners. And also, I’m going to figure out how to find them with more joy than misery.

I think that that can be a really powerful both and approach that is life changing for so many. And why I’m excited about my book and excited for people to free themselves from the patriarchal conventional norms of being miserable in your dating life and shrinking yourself into oblivion. So that you can magically land in a partnership. No, we’ve got to reframe and rewrite all of that shit.

Kara: Yeah, also then you’re going to just spend your whole marriage shrinking and keeping yourself small.

Lily: Putting on makeup in the morning before they wake up.

Kara: Oh my God. [Crosstalk]. Sometimes I have to choose to believe that those are fake because I just have so many thoughts and feelings. People need to read the book, tell them where they can get the book. It is out this week.

Lily Yeah, the book is out this week, Thank you, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love. I’m so excited that this book is out. You can buy it anywhere. It’s everywhere. And we love a local bookseller. So, if you go love on your local bookseller by buying this book, even better. And you can check out datebrazen.com/book for all sorts of bonuses when you order, to get you even more juicy results in your love life. And I’m so excited for people to read it.

You can also go to the Date Brazen podcast if you’re interested in learning more about my approach and diving into the world of Date Brazen and feminist date coaching.

Kara: I love it. And if you are now being like, “I should go to my local bookseller, but I don’t want to run there.” Just go to bookshop.org. It’s a way to purchase from the indies online. So, there’s no reason to delay. Go order the book now. First week of a book sale is a big deal.

Lily: Huge deal, and I’m so grateful for your support.

Kara: Thanks for coming and sharing with us.

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