Is your experience of dating completely excruciating? As high-achieving, driven-focused women in most areas of our lives, you’d think we would be super confident and successful in this realm, and yet, the reality is that we don’t seem to be exempt from the insecurities, worries, and pain that often comes along with dating. 

This week, I’m sharing an interview I did over on the 51 First Dates podcast with Kimmy and Liza. If dating brings up feelings of self-loathing, makes you feel like you’re going batshit crazy, and you notice you’re spending so much time bending over backward to torture yourself, listen in. We’re diving into all things confidence and insecurities as it relates to dating, and what’s really going on in our brains here. 

Listen in as I share the true culprit of the plethora of insecurities we experience when it comes to dating, and how we can begin liberating ourselves from this mental drama. We’re exploring the reasons women often find dating so painful, and the key to approaching your dates differently going forward. 

Joining The Clutch is even easier now! All you have to do is text 347-934-8861 and we will text you right back with a link to all the information you need to learn and join. It comes with a five-week self-coaching course that will walk you through exactly how to apply this life-changing work to anything you experience. Hope to see you there!

What You’ll Learn From This Episode:

  • The story of the worst first date I ever went on.
  • Why we can’t hate our way toward the things we want. 
  • The biggest culprit of dating insecurities. 
  • How to deal with the trap of comparison in dating.
  • Why dating is often so painful and exhausting for so many people. 
  • Baby action steps you can begin taking to think about your next date differently.
  • Why you don’t need to be worried about your date not liking your body. 
  • How to stop tying your worth to your dating life. 

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Kara: Hello my chickens. How are you all? How is 2022? Seriously I don’t think any of us have recovered from the last three years yet. Thank God for thought work. So, I have a couple of important things to tell you. The first one is if you want to hear the story of the worst date I ever went on then you will need to listen to this episode. I was just revisiting this conversation which was such a joy. I recorded it quite a while ago on the 51 First Dates podcast and we never shared it with all of you.

So, we are doing that today and it’s all about confidence and insecurity which are obviously topics that apply to anyone, not just someone who’s dating. But I do also tell the story of the worst first ever date I ever went on which I just died laughing even thinking about it again. What a time in my life.

So let’s talk about insecurity from the coaching perspective. I am so excited for you to listen to my conversation with the hosts of the 51 First Dates podcast. We really get into what is going on in our brains when we are comparing and despairing, and when we are feeling insecure about dating, or our love life or anything else. And don’t worry, we get to the story of my worst first date pretty early in the interview, so enjoy.

Liza: Hi, everybody, I’m Liza.

Kimmy: And I’m Kimmy and this is a podcast called 51 First Dates.

Liza: Yay. And we are joined today by Kara Loewentheil.

Kimmy: Kara is a master coach. She’s the host of the UnF*uck Your Brain podcast and she’s the creator of the UnF*uck Your Brain: A Feminist Blueprint for creating confidence. And we are very thank you, Kara, for being here. We’re so, so lucky to have you here today and we’re really excited to chat.

Kara: I’m excited to be here.

Liza: So, let’s give everybody, all of the listeners out there, just a quick rundown of where we are in 51 First Dates land. Because we’re in a summer five of 51 First Dates. If you haven’t been listening then I’ll just tell you that Kimmy just moved to LA so we’re on two sides of the country right now which is very exciting.

Kimmy: And sad but also great, it’s really nice here.

Liza: It’s exciting. And we are as most of you guys know, Kimmy has – do you want to say this part?

Kimmy: I know. So, let’s just go – quick, very, very briefly, you guys tuned into this podcast thinking, hey, this girl’s going on a date every week, I’d love to hear it. And maybe I’ll listen to the most recent episode. Here’s the spoiler. I’m not going on dates anymore because I met someone. So, you can go back and listen from the beginning if you don’t want it to be spoiled. If you’re a listener, thank you for continuing to listen as we figure out who our next dater is going to be.

I think we’re going to have a couple of different daters so that we can expand our horizons a bit, not just single white female, that I was. And yeah, thanks for bearing with us. That was really ineloquent but I said it.

Liza: I think you did great. And yeah, so go back to the beginning, listen to Kimmy’s whole journey. By the time you catch up we’re going to at you with some new daters. But actually, don’t do it now because listen to this episode with Kara first because she’s here. And she, and I, and Kimmy are going to be talking confidence/insecurities as it relates to dating.

Kimmy: Yes. And just before we – Kara, I promise we’ll let you talk soon. But I just think this is kind of a perfect transition because if you end up going back to the beginning of the podcast at the end of this little episode here. You’ll see that I could have really used a lot of what Kara works with her mentees, would I call them, no?

Kara: Clients or students.

Kimmy: Clients. Clients or students. Mentees, I am sorry, I’m at business school so clearly in that mindset. With her students on – I could have used that at the beginning of this experience. I could still use it, let’s just be real but anyway.

Liza: I am so excited to talk about this topic with you because I think that every question that we get from any listener, every topic we talk about ultimately boils down to confidence and insecurities. And we haven’t done an episode on it yet so this is, well, a long time coming and I think really applicable for just everyone in the world.

Kara: Yeah, I think it’s the root of most women’s issues with most things but especially dating.

Liza: Yeah. And then men could maybe use a little bit more insecurities.

Kara: They don’t even know.

Kimmy: Yeah, just somewhere. But before we do that we love to ask all of our guests to share a worst first date story. Do you have any particular shitty dates you want to recap?

Kara: I don’t have any thankfully, I’ve been lucky, that were traumatizing. But I did once go on this date with a guy who was, he was 45 and seemed like a grownup in all the ways he should. He ran a magazine. He had a kid, should be a functional human being. And I went to the bathroom on the date and I came back and he was in another corner of the bar petting this dog and talking to this old guy. And I was like, okay. So, I sat down at the table, I figured he wanted to – he was next to the bar. I figured he wanted to get a drink, he’d come back.

And five minutes go by and then 10 minutes go by. And I was like, okay, maybe he’s kind of stuck there, it’s awkward. Maybe I should go over and rescue him. So, I go over and I’m like, “Hey. Can you remember me, the person you’re on a date with?” So, I go over there and make small talk with him for a minute. And then I’m like, “Okay, shall we go back?” And he’s kind of like, “I’ll be there in a minute.” He’s still talking to the guy and the dog. So, I go back to the table and then about five minutes after that I’m like, okay, I’m going to go.

So, I started getting up to leave and he comes back and he sits down. So, I sat back down and we started having a conversation about whether or not this was weird, which obviously it was weird. So anyway, but we disagree about whether it was weird. And then he starts getting kind of hostile. And I was like, “Okay, I’m leaving.” So, I started to get up, I’m like, “I’m going to go.” It’s obviously not a proactive conversation, we’re clearly not going on a second date at this point, it’s over. And he jumps up and yells, “I’m leaving first.” And runs out of the bar.

Liza: Oh my God.

Kimmy: Wait, I didn’t – I mean that is worse than – you were like, “I don’t have anything terrible.” That’s pretty bad.

Liza: Cool, glad you’re an actual toddler, who got distracted by a dog and then had to leave first.

Kara: The bartender bought me a shot though. He was like, “I have never seen that happen before.” And I was like, “Yeah.”

Liza: Thank God for good bartenders.

Kara: Right? I can not imagine what my bartenders think. I definitely went through a period of going on a million first dates before I met my partner. And I’m sure they’re just like, “Oh, it’s Thursday, she’s back wearing one of those same two dresses with a different guy.”

Kimmy: [Inaudible] though.

Kara: Yeah, I feel like they know everything. You have your bar you take all your first dates to and you know the bartenders are like, “Well, this is 37. What is this woman doing?”

Kimmy: Yeah. No, I mean I relate to that so much. I feel like I had a couple date outfits and I kind of loved going on a lot of first dates because I didn’t have to think about, you know, after five dates with someone you’ve got to start figuring out what else you’re going to wear. But new dates, it’s great, I could wear the same things. And also, the same thing about a bar. We tried to switch up the bars for the purpose of our listeners, each week so we could talk about a new place. But in my life I love going to the same bars over and over.

And I know that I did on second or third dates over the course of this podcast. And I know some bartenders saw me, how many people is she dating? I kind of feel okay about that, just because I feel men in New York do that a lot. So, I feel empowered by it.

Kara: We’re for sure not the only ones. Also, my neighborhood bar is full of guys in their 70s with their dogs, those are the regulars. So, I just feel it’s not just the bartender. It’s all these old dudes are probably like, “What do you think about that one? Do you think she’s going to be back for a second?” Maybe they had a betting pool going.

Liza: Oh my God, that’s incredible.

Kimmy: So, wait, what was – just to go back to the dog one last moment. Did he have an explanation of why he got really involved with this older man and his dog?

Kara: He thought this was a totally normal thing to do, was like did not merit an explanation. He was being nice. He was being nice to the dog.

Liza: Yeah, I love that he wanted to be nice to the dog.

Kara: The dog, not the person he’s on the date with, but the dog.

Liza: Yeah, let’s worry about this dog who’s a stranger.

Kara: Yeah. I think that’s second only to I once went on a date with a guy who disclosed on the date that not only did he have a partner, they wanted an open relationship but okay, normally you will disclose that before you go on the date. But also, she was about to give birth the next week.

Liza: The next week?

Kara: The next week. And I was like, “No, you need to go home.”

Kimmy: It’s so interesting that he ended up disclosing it but once you’re already there. That feels really passive aggressive. I don’t like that.

Kara: I did not like it either. You’re not alone.

Liza: I mean also, and I know that people in open relationships, I’m not trying to shit on open relationships because I think that whatever works for you, works for you and it’s great.

Kara: That’s not how it works. I have been in non-monogamous relationships. You don’t wait until you’re on the date to be like, I have a partner and she’s giving birth in six days.

Liza: Well, that’s my thing, if I was that woman, it’s great, obviously she’s part of the open relationship too. I’m not trying to take away her autonomy. But don’t fucking leave my side if I’m within a week of giving birth. What if I go into labor?

Kimmy: Yeah, there’s someone joining my business school class from Japan who wasn’t there on the first day of orientation. And we were told that the guy, his wife had just had twins. But, he’s moving here and she’s not moving here. And no shade to the dude in my class who probably will never listen to this. But I was like, “Come on.” And there was a faculty member making kind of almost a joke about it. I was like, “God, [inaudible].”

Kara: Yeah. I had some law school experiences that remind me of that. There was a guy who sat in front of me in Torts or Criminal Law on my first year. And they had five children he and his wife. And he was tanned and fed, and would hang out at campus to play basketball and blah, blah, blah. And then every photo she looked like she was recovering from tuberculosis with five children hanging off of her. She just looked frail and exhausted all the time. And I was like, “Yeah, of course, because she’s trying to raise five children and you are hanging out to play basketball after school.” Go home and help your wife.

Liza: Well, speaking of that because I didn’t know you went to law school. So, tell us about all of the really cool things you did, you do, but also how you got there. So just that small very specific question.

Kara: Well, I think it’s every Jewish parents’ dream, your daughter goes to Harvard Law School and then she clerks on a federal appeals court, then she does a litigation fellowship. And then she gets an academic fellowship so she can become a law professor. And then she quits and becomes a life coach. So that’s what I did. It was the best decision I ever made.

Liza: That’s incredible.

Kara: My parents have mostly recovered. It’s been two, three years since they heard the news and two years since it happened. So, they’ve had some time to adapt. Yeah, I used to be – I have been a professional feminist one way or another my whole life. So, I worked at Planned Parenthood, then I went to law school to do reproductive rights work. And then I did reproductive rights work, I litigated. I hated all of this the whole time because I didn’t know how to manage my mind at all which is now what I teach people to do.

So, I did the thing I think a lot of accomplished women do which is you just think, I get to the next thing then I’m going to feel confident and happy. So okay, well, sure, everyone hates law school but then you get this clerkship, then you’re going to feel good about yourself. Okay, you got this clerkship, you still don’t feel good about yourself, you still don’t feel confident. Okay, what if I get this thing?  So, I was like, I got the only fellowship in reproductive rights law in the country in my year. And then shockingly that didn’t change my brain or my self-esteem.

And then I thought I hated litigation because litigation’s academia. And it was around the time that I switched academia, I was still working in reproductive rights and LGBT rights. And around that time I found my teacher, the person who taught me cognitive work and how to change my thoughts. And I started doing that work on myself. It just really changed my life. I mean honestly, I changed my life from listening to her podcast. I listened to her podcast for a year and used the tools. And it totally changed my life.

And then I decided I was going to quit the law and become a life coach. And that’s what I did. And now I work with high achieving feminist women who are experiencing anxiety and self-doubt, who kind of feel they have accomplished all the things and gotten all the brass rings. And maybe a lot of them also have even gotten married and had kids, done all the things you’re supposed to do. They still don’t feel confident, they still feel like an imposter. They still do a lot of imposter syndrome, or feeling fraudulent.

And what I really teach women how to do is overcome, I call it the toxic brew, evolutionary biology and patriarchal conditioning creates a ton of insecurity and kind of self-doubt. And so, I teach women how to overcome that by literally rewiring their brains, changing their thought patterns and produce authentic confidence which has to come from inside of you, will never come from anything outside of you.

No matter how many dates you go on, how many jobs you get, how many gold stars you get, how many people tell you your great, it’s never going to matter, it has to come from inside. So, I teach women how to actually create that.

Liza: That’s so fucking cool. I’m always really impressed by people who identify their current trajectories as unhappy and actually change it. I feel most of my friends complain about their jobs a lot. And it’s hard to do obviously. I’m not trying to shade anyone who doesn’t do it. I myself am kind of in that place right now where I’m like, [inaudible], not about the podcast, about other stuff I do. But what do I like doing? And how can I get more into what I want to be doing and less of what I don’t want to be doing and whatever? It’s very hard to make those changes.

So, when people have said, “I am going to light it all on fire and go towards the thing that actually brings me joy.” That’s one of the things that impresses me most in the entire world.

Kara: But I think that’s actually a big – it’s not a misconception but I think a lot of people get stuck in that place. And one of the things that I teach people and I did in my life was you actually can’t motivate. We all think that we can motivate ourselves to make a change by hating where we are. And it really doesn’t work because when humans create anxiety, or guilt, or shame for themselves we just want to hide. We just watch Netflix, or eat, or drink, or smoke, or take pills. We do whatever we can to get away from the feeling.

So, the way that I actually was able to leave is actually not by hating where I was but by learning to love where I was. And then being able to leave. And that’s a lot of what I teach women because I think we are all raised with the social idea. People just in relationships, this is a dating podcast, people drive their relationships into the grounds. They can have a reason to leave, where they think that focusing on what’s wrong with the relationship or what’s wrong with the partner will motivate them.

Or they think focusing on why they hate being single will motivate them to find a partner. And it really doesn’t work. When you think about how much you hate your life being single, you do not become magnetically attractive to other people who are going to want to hang out with you. It feels terrible, and that’s what you give off also. So, I think in a funny way it’s actually the opposite. You have to learn to love the life you have then you can change it.

Liza: Listeners, if you hear something weird, we had a little audio problem. So, Kimmy’s switching to recording on her iPhone, we promise we will sort it out. Mercury’s in retrograde. Yeah. And also, as Kara has just told us, we’re making a podcast.

Kara: You’re welcome.

Liza: Oh my God, that feels so uncomfortable for me to say.

Kara: I know, right.

Liza: I’m such an apologetic white girl.

Kimmy: And Mercury is in retrograde because it just disconnected, I didn’t hear you. But I think, Liza, did you just say, did you own it?

Kara: Yes.

Kimmy: Yeah, okay, good. So, you were being coached on it.

Kara: She tried to own it but then she, yeah.

Liza: [Crosstalk], argh, this sounds weird. Anyway, okay. So, let’s talk a little bit about insecurity and dating. Like you said, you work with a lot of women who are really high powered, really they’re on serious career tracks. And obviously I think a lot of women in New York are really driven focused people who seem on paper they should be super confident. But how do you find a lot of your, not clients.

Kimmy: Your coachees.

Kara: My coachees, they are clients or students is fine.

Liza: Yeah. So how do you find – what do you see as some really common insecurities related to dating?

Kara: Oh lord, I mean everything. I think for a lot of people, dating actually has nothing to do with the other people. They’re just – it’s like the other person’s – the other people are like a green screen on which people are projecting their own insecurities. And they’re just basically going on a date with their own thoughts about themselves. So, they don’t even know anything about the other person. So, it’s almost, it would be easier to ask the question, how is dating not about people’s insecurities?

I mean what I generally find is – this is true in any area, not just dating. You have ideas about yourself and then your brain, confirmation bias, is your brain’s tendency to look for evidence to support stories it already has. So, your brain has something called confirmation bias, which means it’s always looking for evidence, so stories it already tells itself. So, if your story is good guys are never into me, or guys just want to have sex with me but they don’t ever want to date me. Or I can always get to the third date but then no one wants to go on a fourth date with me.

You’re always looking for evidence of that. And you’re actually creating more and more of that pattern. And so, what I see with dating is that people are driven so much by the desire for validation which is not a criticism of anyone because our whole fucking society tells women that the thing that’s the most important in the world is male validation. And that being in a romantic relationship is the pinnacle of life validation. Some random average Joe chooses you and now you can finally feel good about yourself. And that’s the thing that matters most.

So, if you teach women that and they hear that for 20, 30, 40 years, of course they are going to be just crazed by the desire for validation and by that insecurity. And so, I think the thing, if I had to boil it down in one sentence, the thing that fucks most people up in dating is that they take dating personally. They take all the people’s behavior and they filter it through, their story about themselves, that they’re already worried is true. And then they make it match. So, they make it mean something about them. And I would say that that’s the biggest thing.

And then that ends up reproducing their problem both because they kind of seek out people who confirm those patterns, and because they take a passive role. I mean I love the title of this podcast because people will come and then be like, “I just don’t know. I’ve been dating so much, I can’t find anyone.” I’ll be like, “How many first dates did you go on last year?” And they’ll be like, “Five.” What are you talking about? You can’t go on five dates and be mad that your soulmate hasn’t shown up yet.

You’ve got to take some responsibility for this process and take the action that’s going to be required. So that’s why I love the title of this podcast. And I was like, “Yeah, 51 is a good start.” You got there faster. But if you were my client, I’d be like, “Okay, you got to 51, maybe it’s 100. I don’t know, we’ve just got to keep going.” But the reason can’t is because they take it personally and that’s why it’s so painful for them.

Liza: Yeah. And I think that we’ve said this before but I think that the biggest thing Kimmy found on her journey was that going on a lot of dates helped her to understand that it wasn’t about her. It helped her clear that filter. And be like, it’s about if I like someone.

Kimmy: Yeah, I think – I feel like – my therapy actually recommended I go on 100 dates. I was kind of like your clients, oh, dating is so hard. But I think the numbers game wasn’t even – even if I was still dating now, which honestly would have been easier for the podcast, like as we grew, like LA dating. It wouldn’t be easier for me necessarily but it would have been very cool to keep doing. I think I still would feel – even before I met someone I started feeling differently about what a date was, well before it was, but you were speaking to it was, let’s see, confirmation bias.

Can I confirm what I believe about myself is true? I’ve told myself the story I know I’m telling myself but still can’t shake. Can I not do that anymore? And I stopped doing that pretty – not pretty early on but – I don’t know – I want to say 15 to 20 dates in. When I go back and listen, the early dates they weren’t all magical. But I was beating myself up afterwards even if it wasn’t crazy sparks, I was like, “Well, I didn’t get the second date ask so it means this.” I was really using kind of the numbers game and the tally in the wrong way.

So, I don’t know, that just rings really true for me. And that’s where, yeah, you don’t have to – going on 10 dates does not mean you’re automatically going to meet someone. But if it can reframe the way you think about it or if it can reframe the way I think about it, which it did, then I think it opened me up, if that makes sense.

Kara: Totally. My clients are acting like a first date is – it’s like an Olympic trial for their worthiness. What placard is the judge going to hold up? And the judge is some dude you met on Tinder three days ago. You don’t know anything about but now he’s in charge of all of your feelings about yourself. And that’s craziness, wildness. And that’s why people find dating so exhausting. If dating is just snacks and conversation to see if you want to hang out with someone again, which is what I tell my clients to think of it as. It’s not that big of a deal.

It is certainly exhausting if every time you go on a date you are going to run through a litany of self-criticism, take everything personally, make everything mean you’re going to be alone forever. Yeah, that is exhausting. And frankly, has nothing to do with that guy. He could be anyone. You do this on every date. And you don’t even know who’s there because you’re so in your own head about it.

Liza: Yeah. And I feel for a while in the beginning of this experiment, Kimmy, wasn’t giving herself room to just not like someone and not be interested in them romantically because it was, yeah, you were seeing people as a reflection of [crosstalk].

Kara: Right, you can’t, if what you care about, if you are telling yourself that if you don’t get a second date, or the third date, or whatever, you’re not good enough and you’re never going to find love and no one will ever like you. You can’t even think about whether you like them. It’s not even a question. You’re just trying to get the approval. I talk about it as like you’re using somebody else as an emotional vending machine, a validation vending machine. So, you’re just like, “Where are my Cheetos? Where’s my validation?” You can’t even tell if you like the other person.

Liza: That was literally all I did till I was 24.

Kara: Listen, if you stopped at 24 that’s early.

Liza: I mean was like therapy, 24 was when I started to stop. And still, I’m still having moments where I’m like…

Kara: Yeah, we all do that. We’re taught to do that.

Kimmy: Yeah. And also I’m having a moment I remember when I first started therapy being like it was literally because Liza and my acting teacher way back when we were 22 year old babies was like, “You should go to therapy.” So, I was very worried to my therapist about, is this self-centered? I didn’t even grow up in a house that was weird about therapy. I just had never been and I was like, “Is this really self-obsessed of me to do? And there’s nothing I really am working on.” But really, it was really self-obsessed for me to be thinking – doing a lot of the other things that I did in an insecure place in my life.

For example, going on a date and actually not paying that much attention to the other person because I was just worried about whether they liked me, or things like that. It’s just funny, I used to have this moment where I was like, “Therapy’s the least selfish thing you can do because it benefits you and the world.”

Kara: Totally. I just did a podcast episode about this, of one of the misconceptions about coaching or working on yourself is that it’s selfish, it’s self-centered. I’m like, do you know what’s self-centered? When you hate yourself and all you do is thinking about what did I say in that meeting? Or what does that person think of me? And do I look fat today? And why don’t why my pants fit? And what did my mother think of me? That is self – not in a moral way, self-centered. But just people who hate themselves spend way more time thinking about themselves than people who love themselves.

Kimmy: Certainly. And putting a lot of burden – I don’t know if burden is the right word, but putting a lot of that responsibility on the people around them. It’s not up to them. And just like you said, a gold star from anyone.

Kara: It doesn’t work.

Kimmy: It doesn’t do anything.

Kara: We just keep going back to the vending machine being like, “I don’t know, I just ate but I’m hungry again.” And you want so badly to get that validation and then what I see sometimes with clients in the beginning before we really solved it, is they’re going for the validation. The guy goes for it, wants to date them and then they’re not interested because it wasn’t about him. They just wanted the validation but they’re stuck in that Groucho Marx problem of don’t want to be a member of any club that would have them.

So, the minute a guy likes them he’s immediately like, well, there must be something wrong with him, he doesn’t count. I don’t get my hit anymore, this isn’t a good fix. Now I need a new one.

Kimmy: Right. So, let’s say a listener right now is really relating to what we’re talking about and what you’re speaking to more specifically about dating and they have a date lined up some time this week. Are there any – and I’m kind of putting you on the spot with this, what are some of the kind of actionable steps or ways you can just start in baby ways? Obviously coaching would be ideal to think about that next date, what might you recommend?

Kara: Yeah. Other than go listen to my podcast.

Kimmy: Yes, that’s true.

Kara: I mean even if you – you don’t have to hire a coach to do this and I teach you about this in my podcast. But what you want to do is become aware of what your thoughts are and see if those are the thoughts you want to think about this. Most of us don’t even pay any attention to what we’re thinking. We just assume it’s all true up there, carry on. And so, I would say write down everything you’re thinking about this date. And then look at those thoughts and see do I want to be thinking this?

Do I want to think, do I want to go on this date with the thought, I hope he likes me, I hope he doesn’t think I’m fat, I hope somebody approves that I’m worthy of love? Is that the mindset you want to be in? Or do you want to try to make it – with my clients I do tell them, think about it like snacks and conversation, that’s all a date is. You’re just going to have a conversation and see if you want to have another conversation. And then see if you wanted a third conversation. That’s really all it is without this huge amount of pressure.

But really, honestly, whether you do it on your own or with a coach, it is sustained work. You can’t do it in one week for the next date, all of it because it’s truly about building up your own self-confidence. I mean self-love which is such, everybody wants to be about self-love now. But let’s just start with self-neutrality. Most of us are so far over here and self-loathing. So even just creating some self-acceptance before you even get to self-love.

All the dating work is about that because what people end up doing is think you abandon yourself in favor of some dude whose last name you don’t even know. You become so obsessed with what this person thinks of you who you barely know anything about and has real no importance in your life and whose not even thinking about what’s going on. And I think it makes women feel crazy because they’re like, “Why can’t I stop thinking about this? I’m upset.” They know rationally they don’t even know the guy’s last name and they just met him on Tinder last week.

And they know it shouldn’t be so important. But what they’re missing is it’s so important because of what they’re making it mean about themselves. So that’s the work you have to do. When you clean up that work then you just see it for what it is. I mean I have a partner now but after I’d done this work when I was dating, it was just a totally different world. It was like if somebody was interested, great, if they weren’t, they weren’t. When I started this work the idea that I could not care if somebody rejected me was that seemed impossible.

That was, rejection was like death, now it’s not. And by the end it was like, yeah, well, that person doesn’t want to go out with me again, okay, who’s next? Totally chilled, that’s the journey.

Kimmy: Yeah. It’s so interesting how similarly I feel to what you were just describing. There’s a lot more work I have to do. There’s so much more insecurity left in my life. But interesting that I felt the same way. I went from rejection is death to a very different mindset when it came to going on a date. And you mentioned – and this is a specific question a listeners asks and it might just be more of the same. But about feeling uncomfortable about your body, or what someone might think of your body on a first date.

A listener specifically asks that for this week. And I mean yeah, give me your thoughts. I mean for me it feels it definitely falls into everything you’ve said but just more specifically.

Kara: Yeah. My thought about that is with the internet, any man you’re on a date with has looked at the bodies of women clothed and naked 10 million times. So, if you met your person, he saw your photos online then he’s already imagined what your body looks like and he’s into it.

Kimmy: It’s such a good point, yes.

Kara: Right, because I used to do that because your listeners can’t see but I’m a plus size woman. And I used to have this insane thought that was like, but then they’ll see I’m fat. And I finally was like, wait, a 35 year old man who lives in New York City with access to the internet probably has watched porno fat women. If he’s into fat women he probably knows what my body looks like.

I mean, yeah, you should be worried if you put up photos that are massively different than what you look like, which is also this crazy thing people do where they’re like, I’ll put up these photos that don’t really look like me. This is how we replicate these problems. We’re like, I believe my body’s unacceptable so I put up photos that don’t look like me so that I can create the experience of going on dates and people not liking my body because I didn’t show it to them.

If you show people what you look like, men spend a lot of time thinking – well, not everybody’s dating men, but anyone, women too. If they saw what you look like, they know what your body looks like. They have seen bodies that looks like yours. They know what’s coming. And if by chance you take home someone who’s like, “Oh, I thought you’d had a breast job and I don’t like anyone who has.” I mean it’s such a bullet dodged. It’s not something to be upset about.

Kimmy: That’s such a good point, yeah. And I feel like I think I represented myself pretty honestly on dating apps. But I remember having moments, Liza, to you where I was like, “Did I accidentally catfish?” It’s really easy to go to the looks thing if a date doesn’t work out. And again, but you explained it perfectly. It’s another way to beat yourself into the same old thought pattern.

Kara: And you’ll notice that whatever your brain’s thing is that you think people don’t like about you, magically that’s always the thing that’s the problem in your brain. If 10 people don’t want to go out with you again, my brain would be like, it’s because you’re fat. And your brain would be like, it’s because this eyebrow I have I don’t like. Whatever your thing is that you’re obsessed with about yourself and criticize yourself about, you just magically think that’s the whole reason that everybody else would make that decision.

And you really have no idea, it could be you remind him of his third grade teacher, or he’s in love with his ex, or he got hit by a bus. You have no idea.

Kimmy: Yeah, it’s such a good point.

Liza: And actually, speaking of exes, so another listener question we had was just about exactly that. How do you deal with comparing yourself to someone’s ex?

Kimmy: Which I think, yeah, we’ve touched on this which that yes, but still.

Kara: Well, my clients, I always say to my clients, “I’m only ever telling you one thing which is your thoughts cause your feelings.” I’m just telling you in a 100 million different ways until it sinks in. Yeah, I mean if you’re comparing yourself to someone’s ex, it’s a perfect example. You’re totally going to only look at the thing that you have decided is the problem. So, if you think your weight is the problem then when you compare yourself to someone’s ex you’re just looking at their weight and thinking about your weight.

You’re not even thinking about all the other things that could be going on or the ways you might be – I mean that isn’t the right word in this context. But just things you might possess that they don’t. Your brain is just like a homing pigeon to its thing that it hates about itself, that it’s looking for evidence of. I think that when people get obsessed with looking at somebody else’s ex, is the question they’ve broken up and it’s a new person? Or it’s the person’s other – they’re with the person, it’s that person’s exes?

Liza: Yes, their current person’s ex, yeah.

Kara: Exes. I think it’s just a beautiful example of if you don’t manage your mind, how much it will bend over backwards to torture you. They are no longer with that person. They’re with you and instead of enjoying your relationship you are spending time worrying about whether the person they’re no longer with is prettier than you. It doesn’t make any sense. And it’s this weird – I think this example is going to seem relevant. We’ll see.

So, when I’m teaching women about body image, one of the things I talk about is you’re going to feel great about yourself on the beach and if a super model walks by suddenly you feel shitty about yourself. The super model existed before, she was already around she just wasn’t in front of you so you weren’t comparing yourself to her. And I think kind of the same thing happens with the exes. If you think – I don’t know what are people – people are usually upset about someone being…

There’s a million models in the world who are conventionally more attractive than you probably. You don’t mostly walk around agonizing over it. But then when you have this one particular person to fixate on, you are constantly comparing yourself.

Liza: Totally. Or success, I feel I’ve had issues with people I’m dating having really successful exes. And it’s an insecurity of mine. I have a very non-traditional career.

Kara: It’s just a mirror for you.

Liza: It’s a measure of success for me. And it’s something that it’s very clear that that’s the reason I hang my hat on that.

Kara: Yeah. It’s just a mirror for you of whatever work you need to do for yourself because they’re not with the person. So, I mean I just don’t think it’s useful to think about your ex’s new partners either. But it’s definitely not – thinking about somebody who’s chosen to be with you now and what their last person who they’re no longer with is like, is totally just a way to be. It’s a creative way to beat yourself up.

Kimmy: Yes, very creative. And I’m saying that as one who’s done that and continues to do that because even when things are working out with someone, you can find a way to make yourself, yeah.

Kara: Well, that’s why you have to manage your mind because you think, well, once I get a boyfriend then I’m going to feel secure. Suddenly you get a boyfriend and suddenly you’re like, “Well, his ex from third grade, she looks like she’s won an Emmy”, or whatever. So, you have to manage your mind on purpose. That’s what happens when you just assume, okay, well, as soon as I get this thing then I’ll feel good. If you don’t change those thoughts, your brain will just find something else to use.

Kimmy: Yeah, it’s such a good point because I feel I was single forever and ever. And yeah, I really like the person I’m dating, I really care for him and he’s really great. It’s not that I feel better because I have a boyfriend. I don’t feel any better about those things. Those things are still so real. My body stuff, all my complexes because I have a lot of them, they’re all still there. And yeah, it would be scary. I know some people can, for a minute fix themselves by being with someone. That would be scary for me if I suddenly…

Kara: It doesn’t work long term.

Kimmy: No, it doesn’t. And I have seen that not work out for people. And that’s another, yeah, so while I’m still beating myself up I can relate to that listener, yeah.

Kara: Well, I think we’re sold this bill of goods. Women are taught that falling in love and having male validation is going to be this transformative experience. And so, this is the other thing I see with my clients a lot too is I’m always saying, “Listen, I have a partner, they’re just not the person who’s around a lot.” It’s nice but it’s like they think, like the world, it’s like a black and white film turned to color. The world becomes a technicolor, and then there’s a unicorn. And you live in a whole other dimension now.

That’s what people, when you’re fixated on getting a partner for validation, that’s what you think it’s going to be like. And it’s really not, you’re still you. You still have all your same shit. It’s nice to have regular orgasms and snuggling but it’s not all of a sudden your life is in technicolor. You’re on acid, it’s a totally different dimension, you live in a different universe. If so, everybody around you with partners would be gleefully skipping down the street being happy all the time. And if you notice, they’re not, they still have their own shit and their own problems.

Liza: Totally. And I think funnily enough I’m realizing in this conversation, the way that my boyfriend makes me feel better about things is by being like, “Liza, why did you think that?”

Kara: Yeah, he’s like coaching you.

Liza: It’s not him being like, “No, you’re not, you’re perfect, you’re this, you’re that.” It’s him being like, “Why are you telling yourself this? It’s bullshit.” Which is shit anyone can also do for themselves.

Kara: But I love that because it’s like, because I do teach that other people don’t cause our feelings. So, when your partner is helping you it’s because he’s basically unofficially coaching you, to be like, “You’re thinking this. You don’t have to. You could think this other thing.”

Liza: Yeah. You’re wack, [crosstalk].

Kara: Right, but it’s not because he can make you feel any given way. And I just think about, when I was doing this work on myself one of the thoughts I had all the time was – I forget who it was. It was some super model. Now I use Beyonce with my clients. But I’m like, “Even Beyonce got cheated on.” It doesn’t matter how beautiful you are, or how successful you are, or how talented you are, or how in love with you someone is. There’s no human life that does not involve suffering, that’s just part of the human condition. And there’s no one who’s perfect enough that this shit doesn’t happen.

Liza: Yeah, I almost feel I’ve seen some – I’ve heard people be like, “Even, Beyonce’s life isn’t perfect.” But that just really resonated with me when you just said that. It’s true. Not that I’m happy she got cheated on but…

Kimmy: She sits at the top of the pyramid of [crosstalk].

Kara: Right, because women are like, “It happened to me because I should have lost the baby weight faster.” Whatever, it’s like, no, you can look like Beyonce and have that many Grammys. It happens to everyone. I think what I was doing was like Christie Brinkley, some super model had been cheated on recently. It was in the news. That’s the person I used. Because it’s so easy, we all just drink the Kool-Aid that we’re taught which is conventional attractiveness will get you male validation and then you’ll be happy forever and that’s not how it works.

Kimmy: And that Kool-Aid is so powerful and I just hope it becomes less powerful for younger generations because [crosstalk].

Kara: Well, that’s why I think to me managing – like I said, been a professional feminist for my whole life. But to me, the work I do now is the most powerful, even though I did abortion rates work, I did a lot of different kinds of work. The true liberation is inside your own brain. And there’s no way to do that without changing your thoughts. The only way – I mean we can try to change society but it’s going to take a while and we’re going to be better at it if we manage our own minds.

So, to me learning how to undo that socialization in your own head, that is the true liberation, that’s the revolution.

Kimmy: Yeah, that’s incredible and I think so important because we, you know, in a lot of ways, women are achieving all these milestones and also having shit taken away from us.

Kara: We’ll see how the next 18 months go.

Liza: [Crosstalk]. Progress is on a straight line but we have come a long way. But I do think this is the next frontier is how do we make our thinking patterns, how do we make that an equal playing field?

Kara: Right. And there’s so much feminist energy, I’m going to totally get shit for this. But there’s so much feminist energy right now that’s like the way we fix this is yell at everybody whose around still not doing it the way we want. Which I just, especially in online feminist spaces, I just feel like use some of that energy to change. We can’t control other people. Yes, I think we can move society over time and certainly if you’ve kids you can try to raise them a certain way. But yelling at your boyfriend is not going to change his mind or how you feel.

Change your own mind, liberate yourself and then it doesn’t fucking matter. You are going to be in a better position to deal with structural inequalities if you are managing your own mind. It’s a lot harder to try to control other people’s brains.

Liza: Totally. And people are drawn to that energy. People who walk through life confidently, it’s that big dick energy thing. People who walk through life confidently just attract good things to them, good people to them, the right partners, the right jobs, the right, like all that shit.

Kara: But they may, and they may still get cheated on because listen, the Buddhists are right, suffering happens to everybody.

Liza: Yeah, it’s true.

Kara: Because I see women use that almost against themselves. It’s like, well, if I just had done enough thought work, and I was confident enough then this wouldn’t have happened. You can control yourself, and you can control the results you create in your own life. And there’s always going to be speedbumps, the question is how do you deal with them? Do you make them mean something about you or do you just rise again and keep going?

Liza: Totally. So just as a way to wrap up, if there’s people out there, they’re going on first dates. We have a lot of listeners who have not been big daters and they’re dipping their toes in the water. They’re going out, they’re going to their first date, they’ve written down their negative thoughts and they’re trying to shed some of those insecurities. What’s the first step towards getting your brain in that place that you want it to be, unfucked?

Kara: I mean I’ll say, no, this isn’t that picky, but awareness is the first step. I mean this is why meditation works for people is that even just by itself over time, awareness will shift your thoughts. I was like, I can’t spend 20 years doing this, I want to do this faster. So coaching is much more of an active intervention in changing your thoughts. But just even, I think it’s too much to say to someone, “You hate your thighs, you think no one will ever love you, you’re scared to date. So just love yourself on this first date. You’re not going to be there yet.”

I think even just starting with a really neutral thought like the outcome of this date doesn’t determine my worth. Or I’m open to believing that what I think about myself matters more than what this guy thinks about me. Or I’m going to try to focus on whether I like this person. Or how would I approach this if I knew I was going to find my perfect partner, how would I approach this date?

If your listeners go back and listen to my podcast I teach a concept called the thought ladder which is to help you get to neutral thoughts before you get to positive ones. If I were organized I would know the episode number but I don’t.

Kimmy: We’ll find it and link to it because it will be very helpful.

Kara: I think the episode is called How to Think New Thoughts or something, or something. Who knows what I do?

Liza: We’ll put it in the description for people listening, in the episode description.

Kara: So, I think that’s probably where I would start. I mean I think the reason that the 51 dates works so well is in the absence of thought work, volume is actually useful because it does some of that work for you. Because you just go on enough that you’re like, “Alright, that one didn’t work out. There’s another one. That one didn’t work out. There’s another one.” It just can’t be such a big deal. You can’t get yourself so worked up if you’re going on one or two first dates a week.

Liza: Yeah, that exposure thing too.

Kara: Yeah, taking massive action. I mean I think the other thing, one of the ways I think is very helpful for people to try to think about dating that you can practice now is take an area of your life where you just do what needs to happen to get something done. If it’s work, if you’re a marathon runner, whatever. There’s some area of your life where you’re like, I just do what I need to do to get the result I need. That’s what your dating life needs to be like too. You want a partner, you’ve just got to keep taking action until you get one.

As opposed to making it like, if you don’t have a partner all that means is you haven’t taken the actions you need to get a partner. It doesn’t mean there’s something wrong with you. It doesn’t mean you’re unworthy. It doesn’t mean there’s no one to love you. It doesn’t mean your town is too small. It doesn’t mean online dating sucks. It doesn’t mean that men are terrible. It means you have not taken the actions yet to get the result you want. And when you turn it more into a project like that it takes some of the moral and worth stuff out of it.

Liza: I feel we should have talked to you at the beginning when I was so insecure about this project because you’re saying everything that I just experienced is true. I was like, it’s never going to happen for me. I’ll be alone forever, unlovable, everything. I was staying in half relationships too long. I wasn’t going on dates. I would go on five in a year kind of like you mentioned earlier. And then obviously even if I was doing the good thoughts or feeling positively about myself, one bad thing and it was all over. So that, it’s just such good advice.

Some of our listeners have started doing experiments of their own. But make it a project, that’s the only reason, because then you keep going on the dates too and you can’t put pressure on if it does work out.

Kimmy: It’s not a problem.

Kara: Right. And you don’t make it mean anything. If I could tell you, listen, you’ve got to go on 125 first dates to meet your person. You’re not going to get to them before that, you’ve just got to go on 125. You would just fucking do it. It wouldn’t be such a fucking drama. You would just be like, “Alright, that was date seven, I’ve got to find an eighth person now. I’m not allowed to get my partner until I get to 125 so I’ve just got to keep doing it.” It’s all about your mindset and what you’re making the process mean.

Liza: Yeah, because I was really trying to get to 51. I made it to 32, and I met him at 13, so I really pushed it. And then I was like, now, it’s time to really make a decision. But yeah, that’s such – it’s so – it’s great that you’re confirming what I now believe, it really is.

Kara: No, but I love that you were able to start through the actions. I mean I do think in the absence of anything else, committing to a number and just – I have someone on my program right now. I told her she has to go on 10 dates by the end of the program and then she just found a boyfriend. I think she just didn’t want to go on the dates.

Liza: That’s hilarious, I think that’s amazing.

Kara: She’d gone on one date in the past year and I was like, “Alright, we’ve got two months left, you’re going on 10.” And then by the next week she was like, “Okay, I went on a first date, we’re already going on a second date. Does that count?” She just didn’t want to do it.

Liza: Oh my God. And she’s online dating.

Kara: I fixed it, I solved it. But it’s because her thought – the thought process changed, it was like, alright, I’ve just got to do what needs to be done to get it, I might as well just get it now as opposed to using it as a green screen for all my self-inflicted trauma.

Liza: Yeah. Well, I think that basically super exposing yourself to things that make you uncomfortable are a way of very tangibly doing the kind of mental work that you’re used to doing. Because the more times you do those things, the more times you feel those feelings of discomfort and have to dispel them. I felt this way with standup, or whenever we screen any videos we make.

Where it’s a surge of anxiety and then every time you feel that surge you’re like, “Well, I have to move forward because I’m already here.” I have to, I know this will pass because it always does. There are these ways that your body and that adrenalin, [crosstalk].

Kara: Yeah, be willing to factor it.

Kimmy: Yeah, standup is such a good example, Liza, I was thinking that when you were saying that earlier. It’s similar because you’re going to – and you can have bad nights and have the bad feelings or you can have something in that and it doesn’t work out. It doesn’t mean you’re like I quit it all. And you can be sad for a night, you can be happy for a night.

Liza: I was leaving a show, I had to bum a cigarette from a stranger. And I was talking to this stranger and was like, “I’m never doing comedy again. I’m quitting tonight.” And no, I needed to go home and take a nap.

Kara: Yeah, cry it out and then…

Liza: And then just fucking do it again.

Kara: Totally. I was thinking about doing the 50, oh, here’s what it is. I think also when you go on a lot of dates, when you think about your romantic history. If your story is nobody ever loves me, it never works out. You filter out all the people who did like you that you didn’t like. It’s like they don’t count.

Liza: Oh my God, I was always telling Kimmy. I was like, “Dude, if you wanted to have a boyfriend, you could have a boyfriend.”

Kara: Yes, I say this to my clients all the time. “If your main goal in life is being married, you’d be married by now.” So, it’s true for all of us. So, one of the things I like about going on a whole bunch of dates at once is it’s just more – you just start to see all the data together of, right. Often I go on a date and I like the person, they don’t like me. And often I go on a date and they like me and I don’t like them. And we’re just trying to get to that date where we both have the same opinion about it. It’s like musical chairs except there’s enough chairs for everyone.

That’s what we’re trying to get to, and when you think about it like that, it’s yeah, it’s just math, I’ve just got to go on enough, eventually we’re going to be on the same page. So, I think it’s another benefit of that because women come to me and be like, “Well, I just never had a real boyfriend.” I’m like, “Okay, tell me your relationship history.” And they’re like, “Well, I dated this guy for five years when I was in college and I lived with this guy.” And I’m like, “What are you talking about?” But because that’s their story, they have just completely filtered it all out somehow. Dates are great, really powerful.

Kimmy: They are really powerful, it’s scary, yeah, there is a lot there. Okay, I want to get really specific, Kara, about where all our listeners can find obviously your podcast, but everything. I want them to go on your site, I think there’s a lot that they’re going to be looking for in the immediate future to start practicing these things.

Liza: I feel fucking loved up right now.

Kimmy: Me too.

Kara: You want to manage my mind.

Liza: Yeah, totally.

Kimmy: I want to unfuck my brain because my brain is already fucked, just being in business school because I feel like such an imposter. I’m just like, this was so helpful.

Kara: Alright, here is your first piece of free coaching. Are you ready?

Kimmy: Yes.

Kara: I’m an imposter is not a feeling, it’s a thought. So, we do this thing in English where we say I feel and then we just put a long string of thoughts. Like I feel if my husband respected me he would take out the trash and remember my anniversary. None of that is a feeling, it’s a thought. And the reason it’s important is you can’t change a feeling once it’s happening but you can change a thought, a thought is optional.

Liza: Mind blowing, yeah.

Kara: Yeah, just notice how often you’re saying, I feel like an imposter. I feel like I’m not good enough. I feel like I’m this. None of those are feelings, those are all thoughts.

Liza: Totally. Especially because women are so often, I think, taught to express our feelings, which is great, but also to apologize for what we want by contextualizing it as a feeling.

Kimmy: Yeah, and I just feel like you’re not listening. It’s like, no, I want you to listen.

Kara: Well, and express your feelings. You’re not expressing your feelings, you’re expressing your thoughts. My feelings would be like I feel sad. I feel anxious. I feel angry. I feel like an imposter because all these other people have already worked at Goldman Sachs. That’s a thought.

Kimmy: Yeah, that’s the thought.

Kara: Yeah, that’s the thought. It’s almost like I’ve done this before. And differentiating…

Liza: What?

Kara: Differentiating between thoughts and feelings is actually a big important first step, but there you go, practice that. That’s your first assignment.

Liza: I love it. Yay. Thank you, Kara.

Kara: Where can people find more of this? The podcast is called UnF*ck Your Brain. There’s an asterisk instead of the second U. You can also find my name probably on the show notes and search that. It’s If you spell it out all the way you will go to a website that forwards to someone called the Intimacy Doctor and that is not me. I don’t know, I don’t know who that is and I should buy that website. But that’s not me, so if you end up at the Intimacy Doctor you’ve taken a wrong turn,

The podcasts is everywhere you get your podcasts, Spotify, iTunes, android, whatever.

Kimmy: And we’ll link it in the bottom thing for this episode, the show notes.

Kara: Yeah. So, I’d say the main thing your listeners should do if they want to do some of this work is I have a free download, that’s called a Confidence Cheat Sheet but it actually is a tiny eBook. That makes it sound too overwhelming. It’s three written exercises that are actually really great that I use with my private clients. So go to the good stuff that usually people have to pay for. So, if you go to, it’s unfckyourbrain and it will be linked on the episode.

But that’s a good way, if listening to this has made you be like, wait, I think I should manage my mind, that makes sense, download that and try those exercises.

Liza: I’m going to. I have to admit that I haven’t done that so I’m going to.

Kara: Well, there’s no reason you would have yet. You didn’t know about it but now you do.

Liza: Yeah, I feel very grateful.

Kimmy: Thank you, Kara.

Liza: [Crosstalk]. I want to go for [crosstalk].

Kara: Right, we’re going to go and vandalize some patriarchy after this episode’s over.

Liza: Or at least just – I don’t know – do a bunch of shots or something, no, I don’t know.

Kara: Your boyfriend’s going to come and you’ll be like, “I want to talk about feminist history.” And he’s going to be like “What happened?”

Kimmy: Like, damn, again.

Liza: What thoughts, sit down, shut up.

Kimmy: Thank you so much for joining us, Kara.

Kara: A pleasure.

Liza: Thank you for bearing with our little technical difficulties snafu.

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