“Why do I have to do all this work just to be given a chance?”

In this deeply moving live coaching session, Lily talks with Caleigh—a brilliant late bloomer feeling burned out and heartbroken after years on dating apps.

On the surface, it’s dating fatigue. But underneath, they uncover how internalized misogyny shows up in dating: feeling like you have to be less intense, less emotional, or hide your anger just to be seen as desirable.

In this episode, you’ll hear:

✨ Why dating can feel like Groundhog Day, especially for late bloomers
✨ How grief and shame linger around never having had a serious relationship
✨ The truth about anger—and why feeling it might change everything in your love life
✨ How perfectionism sneaks into dating and keeps you stuck
✨ Concrete tools to raise your standards without giving up hope

If you’ve ever wondered why dating feels like so much work, or worried that your big feelings make you “the problem,” this episode will make you feel seen—and give you practical ways to keep going without losing yourself.

Work with Lily:

Download the free Essence-Based Preferences Creation Guide: datebrazen.com/workbook

Get the book, “Thank You More Please”: datebrazen.com/book

Learn how to work with Lily: datebrazen.com

Let’s connect:
Tiktok
Instagram
YouTube Channel

Show transcript:

Lily @ Date Brazen (00:00.994)

Hey, Gorgeous Friends, welcome to another episode of the Date Brazen podcast. I’m so glad that you’re here. Today, I’m talking to Callie, who is an incredible human being and also a late bloomer who is feeling really, really big feelings about it. She has been on the apps for years and years and it hasn’t led to good outcomes. She feels really discouraged and burnt out. And so we’re gonna coach on all of that.

And by the end of the episode, you are going to be so, so surprised at what came up, what was underneath the surface and where we got to. So I know that you’re gonna love this live coaching session with Callie as much as I did. And I gotta let you know that this episode is brought to you by my book, Thank You More Please, A Feminist’s Guide to Breaking Dumb Dating Rules and Finding Love. In this episode, you are going to hear about

Callie’s experience in her dating life. And she also references that she read Thank You More, Please. And it helped her with overcoming hopelessness, understanding dating apps and their toxic tech bro culture from a more feminist lens. It helps to create your essence-based preferences. So you come at dating from a place of agency instead of taking a back seat with all your desires. You get to really own everything you want and start dating by being more picky.

and attracting better people than you thought possible as a result. So if you want to get your hands on my book, Thank You More Plays, then go to datebrazen.com slash book to get not only the book, everywhere books are sold, I also did the audio book, you’re gonna love it. You can also get a very special bonus called the dating life fix, which is my top 10 recommended podcast episodes from the over 200 podcast episode library of the Date Brazen podcast.

And you’re gonna find my recommendations for like every single point that you’re stuck at in your dating life. I outline 10 of them and give you 10 recommended podcasts to listen to to fix those problems within that 20 minute episode. So you’re love that bonus and you’re gonna love the book. Thank you more, please. So again, go to datereason.com slash book to get your hands on the book and get your special bonus. Now let’s get into the episode.

Lily @ Date Brazen (02:21.742)

Hey, I’m Lily Wonville, former top matchmaker and founder of Date Brazen. After setting up hundreds, I realized that with coaching, women could match themselves better than anyone else ever could. With my unconventional feminist approach, I’ve helped women around the world build courageous and self-trust-filled love lives, and now I’m here to support you. Get ready, because I’m about to share the exact steps you need to attract a soul-quenching partnership and feel amazing about yourself along the way. This is the Date Brazen podcast.

Hello, gorgeous friends. Welcome to another episode of the Deep Breast and Podcast. Today is a very special live coaching session with Callie, who is here and I am so excited to support you, Callie. Hello. Hello, I’m great. I’m excited to be chatting with you and by the end of this session, I can’t wait to see what magic we co-create. Like I ask all the live coaching session folks, what is your brag?

Hello, how are you?

Lily @ Date Brazen (03:18.646)

about anything, celebration, what are you proud of? And then what is your intention for this session? What do you really wanna get out of it?

Brag-wise is probably just a bigger one for sort of the whole year. I feel like I have really been able to develop a little bit more, I’m gonna say discipline around the things that I want to accomplish or come to fruition in my life this year.

and really be able to stick with some of the goals I’ve set in a way that still feels really balanced and sustainable. So I’m excited about that. Part of that obviously is being here signing up for this podcast. And then my intention I think is really, I think it’s really to listen maybe more than be thinking about my own responses, because I have a tendency to be.

and be able to talk really pretty stories around why everything’s not working. And I think it would be helpful sometimes to sort of like quiet that a little bit and really take in what I’m hearing and take in how I’m feeling more than be in my head.

Okay, so listen to your body more than…

Caleigh ODonnell (04:36.686)

Listen to my body.

Is that what you’re saying? Am I getting it? Yeah. Okay, great. Great. Because you were you were saying I want to listen. I was like, well, you’re on this podcast to talk. So I had to share where you’re at. but I think that you know, you can in this, you know, our together, you can really trust that I’m gonna like challenge you when I hear a pretty package on a like I’m gonna get

we’re going to get into it. So you can allow yourself to be supported in this hour as well. So your application, you indicated there were two things that were like the question marks. was some late bloomer anxiety and creating your essence based preferences, which I think like we could, I could help you do that tactically till the day is long and I can give you a resource for that. And we can talk about that, but I want to touch first on the late bloomer anxiety. Can you tell me a little bit about your dating life and where you’re at?

How is late bloomer anxiety playing a role right now?

Yeah, I would say I, so I’m 29. I have never been in a, I’ve recently stopped trying to say I’ve never been in a relationship because I’ve definitely had relationships with people, but never anything serious where I’ve like called someone a boyfriend or a partner or anything like that. I would say my early 20s looked a lot like.

Caleigh ODonnell (06:06.382)

I wouldn’t say I was dating for a relationship. I had a lot of self-worth issues around kind of growing up in a bigger body, still being in a bigger body. I think my early twenties was a lot about me trying to prove to myself that men could find me attractive. And all of my choices were sort of around that and ended up putting myself in sort of a lot of situations that I just look back and feel kind of sad that I put myself in.

and then around 25 is when I sort of switched to feeling like, okay, I think I really do want a relationship. feel like in some ways I’ve proved to myself that, okay, yes, people can find me attractive. But then I sort of developed this other side around, sort of this other story around, yes, people could find me attractive, but behind closed doors, not attractive enough that they would want to actually be proud of dating me or be in a with me.

First year or so was me just really trying to figure out like that transition of what I was looking for. I had about three years in a row where I felt like I was making progress, but this past January, a little bit before I submitted my application, it had been the third year in a row where I realized that I had basically had to break up with myself, with somebody, with a relationship that had lasted somewhere from a three to…

six month period just based on getting into these phases where things would look really good at the beginning for the first few weeks. And then as soon as there was like any level of like, there might be some form of commitment or asking for something more, I would just start to get all those like pullback signs, have a couple months where I’m like trying to negotiate with myself, with the person, all that. And then just sort of a third January in a row where it was like, all right.

This isn’t what I want. It’s frustrating. It feels like Groundhog Day. It feels sometimes like I’m like making progress, but it is just tough when you don’t have like external, like I feel like I’m making progress internally about how I’m, each time I enter kind of a new experience with someone, I do feel like I’m a different person, but just there’s no outside progress yet that I’m seeing.

Lily @ Date Brazen (08:06.604)

What was that like?

Caleigh ODonnell (08:33.503)

any results for and then I feel like, so I kind of stopped dating in January for a little while, applied to the show and then really was focusing on sort of another round. I feel like I always have rounds of like I’m off the apps and I’m totally working on myself and I’ve read your book, through all that and I felt like so good. I was like, this time it’s gonna be so different. I’m so ready and then I got back on the apps a week and a half ago.

And like, I’m trying so hard to, it’s like, I’m really having a hard time finding my way through all of the fog that the apps cause in my mind back to some of the learning in the book. And I kind of feel like this is like the hardest round I’ve ever had on the apps. So that’s a sign of progress. Maybe I thought like,

because I felt different again, that the experience would be different. I feel like I just really, don’t know if this is true, because I only know my own experience, but I just really feel like the energy from people that I’m getting on the app, so it just feels like everyone doesn’t want to be there. I do pretty much every year that I go back into dating, I gain weight every year. I, so.

I like kind of work on, no, that’s fine. That’s not gonna impact it, but I get less and less matches. And to me in my mind, those end up being so connected. But I also know that I’m much better at making myself for the few and not for the many on the apps now. So it’s so hard to know like what’s the old stories and what are the new ones.

Yeah, this is like, literally we could take this in a zillion, a bazillion different directions. You you mentioned in your application two core anxieties that you have been struggling with. So the struggling with self-trust around when to give someone a chance, you shared. And you’ve stopped dating men that treat you poorly, which is a great, like, fresh start. Like, you deserve so much more, obviously.

Lily @ Date Brazen (10:51.16)

but you have found yourself in a pattern of attracting someone who becomes really squirrely around commitment. How are you feeling right now, doing your intention right now of dropping into your body?

Hmm. Yeah, I’m feeling a sadness come up, but I cry. So I will definitely cry. Yeah, I just I feel like there is a lot of grief around this topic. Yeah. And I’m very aware of that. And I’ve tried really hard to spend a lot of time processing that grief. But I just think it’s

Talk to me.

Caleigh ODonnell (11:32.97)

It’s so deep, it’s just gonna take like years and years and years to not ever kind of, to not have that grief feeling when really talking about it.

Hmm. Yeah. What does that grief feel like in your body? Like, where is it? We’re just doing this thing called emotional granularity, which I talk about in the book. Thank you for reading it. Dr. Lisa Feldman Barrett coined this term to say that when you have more precise emotion words to describe your experience, you can more effectively move through that experience. So I want to challenge this idea that it may take years to not feel grief. Like, what if grief was a bodily function like poop that would always come up?

Maybe you’d feel it daily, but what if it didn’t have to mean?

Mm-hmm. Mm-hmm.

Everything?

Lily @ Date Brazen (12:20.408)

What if it didn’t have to define your experience? let’s take a step back. Where is it in your body?

Usually my, it’s in my throat right now.

Okay, so I would just invite you to take a deep breath into your throat.

Lily @ Date Brazen (12:37.314)

And if it had a shape, what would that shape be?

Probably a sphere.

Mm-hmm, really common with grief and then the throat specifically from what I’ve heard from doing this with a lot of people What kind of sphere what like what weight is it? What texture?

It’s heavy, but it gets like lighter on the outside and softer on the outside and maybe like a not not soft necessarily but like a shimmery sort of texture. Yeah!

Okay. And then as you’re noticing it, has it shifted at all since you’ve been noticing it?

Caleigh ODonnell (13:25.622)

Yeah, I think so. think it’s gotten maybe a little bit like lower and less intense.

Yeah, what do you make of that?

spending time with your physiological emotional responses could change them.

Yeah.

And I think specifically when there’s a feeling in the throat, specifically that ball or like block in the throat from my anecdotal experience coaching so many people with this tool, knowing my own body, usually that signals that you’ve either said something that feels like really real and it feels like, I just said, I don’t want to say it feels like a truth that you said that feels like I don’t want that.

Lily @ Date Brazen (14:13.826)

to be the case or I said too much or I said something so real and honest that it’s scary. Or there’s something that has yet to be said that you feel in your heart you want to say that you feel like a block is there to say. Does either of those resonate?

Yeah, probably.

Probably a little bit of both, maybe. Probably more the first one.

Tell me more about it. Like, what did you say that felt like, shit?

I don’t know, just, I’ve talked about this a lot. Like I’ve done a lot of therapy around this topic and I just have the same sort of emotional reaction every time. So I’m kind of surprised sometimes that it does still feel so intense, but I think it’s just, I do just think there’s some like admitting how much grief there is around it.

Caleigh ODonnell (15:18.688)

A lot of times I think is tied to me to maybe the idea that it feels like admitting it’s hard. don’t believe this logically, but maybe in the moment I feel a little bit like it’s hard to admit the grief while also still having like a hope and a positive attitude and having that sort of like mask of like, this is going to work out.

Okay, cool. So there we have a really common, understandable, really rich dynamic happening, which is that your brain really is struggling with holding two truths, which it is want to do. is a human silly little brain who just wants to be safe. And of course the, like you’re having the feeling and experience of grief.

And it sounds like your brain is heaping a story on top of that, that it is, makes things even more hopeless or you’re admitting defeat in some way by having this human emotion.

Mm-hmm. Yeah. Or I think maybe a little bit of like shame too.

Hey, say more on that. What do you mean?

Caleigh ODonnell (16:36.906)

Yeah, I think there’s just is a little bit of shame around the idea like, it hasn’t happened for me yet. So there must, it must be a me issue. And I know like so, so, so really believe that that’s not true. and I have these times of life, like even before going onto the app where I really, really like in my body believed that that wasn’t true. Yeah. And then like, I’m struggling a little bit.

this round to, I’ve been able to hold on to it a little bit better in the past. don’t like this round of dating. feel like, yeah, I am struggling to find my way back to that actually believing it feeling rather than just the.

Yeah, gotcha. So what I’m hearing is really common in the image. I’m a very visual person. the image that I’m getting is that previously you’ve been able to hold on to the reins of hope. And it feels like you’ve been able to hold on to those reins while you ride in the dating world and holding on to those reins of hope.

means something about you that you’re more powerful or you’re actually gonna get what you want this time because you’re able to hold onto those reins of hope. Does that resonate?

Yeah, I never thought about what it would mean that maybe I felt like it meant something about me to be able to, I guess, feel that way. I just sort of thought that was like for myself, the best thing was to, yeah, to be.

Lily @ Date Brazen (18:05.122)

Okay.

Lily @ Date Brazen (18:23.213)

Hopeful.

Yeah, and are not even hopeful, like, be able to connect to a calmer state, a calmer physiological state while dating. More so than hope. like how can I keep returning to myself and not just get…

Okay.

Caleigh ODonnell (18:46.988)

washed away in the rivers of the feelings. Not that like I’m struggling to maybe.

I I’m gonna, this is gonna be one of those moments where, and you can toss it on back if it doesn’t resonate, I hear you trying to make something prettier.

Mm. Yeah, maybe.

Maybe, maybe, maybe not, I don’t know. But what I was getting at or thinking while you were sharing is that that’s a lot of pressure on you to maintain the reins of calm physiological experience, access to hope. Now, it’s good to feel good. I’m not saying it’s not. It is a more fun state of being for sure, for sure, for sure.

But the thing about life is that it’s 50-50. In the words of Brooke Castillo. And so I think that instead of thinking about dating as this experience where you got to hold onto the reins of like, I mean, in essence, I hear the desire for perfection. And in order to feel better day to day, it’s like, I want this experience to, I want to feel better in this. I want to feel better all the time about this. And when I don’t feel better about this, then

Caleigh ODonnell (19:37.41)

Mm-hmm.

Lily @ Date Brazen (20:04.498)

shame, isolation, hopelessness, circle of hell experience. I don’t want that. So I’m just going to hold onto these reins. But what if we like let go of the reins, just using the symmetry and decided that your love life is a surf experience. And sometimes you’re going to have experiences of riding a wave and feeling high as hell and like your

hot as hell and amazing. And sometimes you’re gonna have moments of crashing where grief comes up, where hard feelings come up, where you understandably are grieving for the experience that you wish that you had had already. You’re understandably grieving living in a fat phobic world that treats women and people socialized as women in larger bodies like they’re fucking less than. It’s so fucked up. And you experience that

living in a body dating that is a vulnerable experience on the whole, and then you throw in a marginalized identity or a marginalized body, and like, there you go, it’s very difficult. So what if your grief, when you feel it, was appropriate? And what if your job as a human being was to acknowledge and ride through those feelings with yourself?

Yeah, it’s, I guess I didn’t. It’s interesting because I didn’t connect it to that, but I definitely know I have like I did the like an inner critic exercise at one point thing I was doing and I feel like I have three around dating and one of them is actually I think I called it like the overachiever and it was sort of like I’m

I think the idea is like, I’m sorry, I’m already starting at a deficit. So I have to be the best possible version in every way to be able to, to have a chance. And so I do think I feel like, I guess I didn’t realize that I thought, I thought I was trying to take care of my self by making sure.

Caleigh ODonnell (22:20.716)

And like, I’m really not saying like the toxic positivity part. have a lot of practices around like, around like journaling and really in breathing into my emotions and all of that. I’m, I feel like this past round, it’s been so past where I can’t even necessarily access that part of myself. And so I thought it’s an issue of, I need to take care of myself better, but I didn’t think necessarily about it being.

But

Caleigh ODonnell (22:49.922)

maybe another way of sort of telling myself that if you can’t be like this all the time, where you like feel your emotions the right way, the right way, then it’s not gonna work for you.

Yes!

Lily @ Date Brazen (23:03.638)

Yeah!

Yeah.

That’s powerful. Yeah, I think that perfection isn’t just kind of snuck up in there.

Yeah.

Yeah, as it is want to do, right? It’s a protective mechanism. You want to be safe and it is a vulnerable act dating. So let’s talk about the spiral that you get into when you’re on the app itself. So tell me about that and like, let’s figure it out. What thoughts are you having?

Caleigh ODonnell (23:29.102)

I’m trying to think if I’m even having thoughts. I’m just feeling I’m just having feelings.

So there’s a circumstance, the sky is blue. could have, I could, it’s a neutral like fact of the matter. It’s the sky is blue. I could have many different thoughts about the sky is blue that I choose based on my emotional experience. Thoughts are sentences in your brain that are, that are emotional interpretations of the world around you. I could look outside and be like, my God, what a beautiful day. I’m so grateful the sky is blue. That thought, which feels true to me,

Mm-hmm.

Lily @ Date Brazen (24:04.802)

then triggers a feeling, gratitude, excitement, hope, possibility. Then I take actions in my day based on the thought I had and the feeling that I have based on the thought. So actions could be, go on a walk, smile more, or I share in every meeting that I have, my God, this day is so beautiful, whatever, the actions come. And then the result is I feel more satisfaction in my day. That’s the result.

Mm-hmm.

versus if I’m in a harder place or I’m in a place where I’m like, I really just wanna, the sky is blue. I just wanna nap today, I’m so tired. I wish that it was actually a cloudy, rainy day. That thought might trigger a feeling of disappointment and then that might trigger actions like I lay in bed all day or I work and I resent it all day, because all I wanna do is like,

just take a nap, and then that creates a result of having a worse day than I could, right? And these things just happen. It’s like life, you know? But what I’m hearing is that you have the circumstance of being on a dating app.

Mm-hmm.

Lily @ Date Brazen (25:18.584)

You are having thoughts about the stimuli of being on a dating app. Maybe the circumstance is, I didn’t get a match today. That’s a neutral fact sometimes. Then your thought about that is, fill in the blank, your feeling is shame or hopelessness or disappointment, disgust, discouragement, something. And then your actions.

are responding to your thought and feeling. And your actions might be, overwork. I try to prove that thought wrong. And so I like go and swipe more and like message more and try to push through. Or it could be shutting all of it down and getting in a download delete cycle. The result is you feel less in control of your experience and you’re having a really hard time. So thoughts or emotional interpretations of the world around you, they trigger feelings. Now,

Mm-hmm.

I think in dating this works pretty well with things like where this doesn’t work is things like racism. The circumstance of somebody was racist. You can’t choose new thoughts about you. You don’t have to choose new thoughts about that. That can just be terrible, awful needs to change. Right. But we’re talking about something that is more within your control, which is building a new neural pathway about your dating life, potentially acknowledging the current one.

So say what’s coming up for you around me explaining this.

Caleigh ODonnell (26:43.954)

Yeah, I definitely have thoughts when I’m the phone and access them because I think I try and shut them down really quickly.

So tell me your thoughts about the dating experience on an app.

Definitely. I feel like this most recent time, I feel like it’s been a lot of, I’m not getting any matches I’m particularly excited about is one thought, but like, okay, maybe if the conversation’s good or they seem really interested, you never know until you meet them.

Okay, okay. We’re gonna get into this, yeah. You never know, anything else?

Um, and then like if they pulled back, I had to this, this is not normal for me, but I had like two dates set up this week and both of them canceled. don’t normally, like, I don’t feel like the hardest part of it for me is usually the getting to date one part. I feel like it’s usually the after date one part. Um, but this time

Caleigh ODonnell (27:53.612)

feels like the getting to date one, feel like, and then I think the thought that it’s triggering is like, I must be less desirable this time around, or people on apps are more exhausted by this whole thing, so this isn’t gonna work, I should delete them, but I them because I think, and I think this is like a big thing, is I just feel like I have to be on.

I’m not gonna.

Caleigh ODonnell (28:21.932)

the apps in order to meet someone, even though I don’t want to believe that that’s true. do like deep down, do believe that’s true. My head knows it’s not.

Well,

Yeah. Okay. Great, great raw material that we’re going to work with. So I want to start with the dating apps. Are they necessary? Peace.

Mm-hmm.

You read my book. talk a lot about dating apps and how they’re a fiery hellscape and they’re like, they’re not the answer to anything. They’re just a little silly little tool. The multimillion dollar mark. I don’t, I know your age. shared it at the top. So I know about the year that you were growing up and, how deeply, uh, marketing messages around thinness. mean, for me too, in a different era moment, like

Lily @ Date Brazen (29:13.132)

those marketing messages around thinness really fucked me up as they did, you know, most everyone, if not everyone. Marketing affects us, especially mass marketing on a national, if not global scale. It affects us. The messages that we perceive unconsciously, consciously affect us. So why wouldn’t it be the same with that? Like if you think about how much marketing has affected how you feel about your body, how I feel about my body,

Why wouldn’t the same be true for a dating app that has a multi-million dollar, they are multi-billion dollar corporations that own these dating apps that have giant marketing budgets, that their job is to convince users that you need to be on a dating app to retry.

Yeah, and I think it’s really tied also to…

like the time of my life and like my history with dating apps. was 19 when I was on the first time I was on dating apps. I’ve used them my entire dating life. And I think being in a bigger body, like in high school, getting kind of no romantic attention and in college too. And then I get on the apps and I like feel so desirable. Like, I feel like I’m getting so many swipes. I think it really started to create this dynamic in my head. like,

people might be attracted to me, but they’re maybe not willing to show it in public. So I have to be in this place that like allows people to feel safe enough to like, like say that, like show that they like me. Yeah.

Lily @ Date Brazen (30:47.406)

That sucks.

And with other, know, I went on the Swipe Fat podcast with Nikki and Alex. I don’t know if you’re familiar with them. They talked a lot about this in their experience of being kept a secret by dates and that that is a reality with some people who are absolutely wrong for you. But of course, that can be a traumatic experience.

Mm-hmm. Yeah.

And it’s understandable. It doesn’t mean that it’s over and nobody exists that is right for you. It just means that like both hands, that sucks. And of course your brain would make that correlation and then practice the thought in order to keep you safe in the future. moving like really, what might self-compassion say to you in this moment? Can you access that or do you need a little help?

Yeah.

Caleigh ODonnell (31:37.238)

I think it would say that the experiences that you’ve had have been really challenging and have caused a lot of grief. Yeah, you’ve lived in a world that while you’re fighting really, really, really hard to believe something different is constantly telling you to believe this one thing about you. Yeah, you know it’s not true, but.

Hmm

It’s really, really hard to hear past what everyone else is indirectly telling you.

Mm-hmm. That is really hard. And everybody struggles with it. Everybody. In different ways, of course. Different levels of privilege, but like, you’re not alone. So you’re not alone. Three tenets of self-compassion is defined by Dr. Kristin Eff, by the way. Beautiful job. How did it feel to offer yourself that?

Good.

Lily @ Date Brazen (32:38.466)

Yeah, good. So the three tenets of self-compassion and this for everybody listening as defined by Dr. Kristin Neff, kindness over judgment. So that’s like, this is really hard. Of course I’m struggling. Like offering yourself a reality check, not in a doom and gloom way of like everything sucks, it’s all over because this is hard. But it’s a hard human experience and it makes sense. Of course, right? Like your best friend being like, you’re sharing, you know, and I don’t know if you have this experience, but I do when.

I share, I’m kind of struggling, but I’m okay, but I’m really struggling. And I share my contacts with my best friend and she’s like, no, no, no. It actually makes sense why you’re feeling this way. It’s like, what a relief. That validation. Then common humanity over isolation. So you’re not alone, like picturing yourself in the collective of people who have this experience and, and that you’re, you’re not alone in feeling this way. Finally, mindfulness over over identification. So identifying like, wow.

My brain is having a lot of kooky thoughts, a lot of really intense hard thoughts about this. And it’s possible those are thoughts, not facts. So, do you wanna take a deep breath before we move on to the next, or you were gonna say something?

Yeah.

Caleigh ODonnell (33:53.588)

I was just gonna say I feel like it’s that last part that like this time around more than other times and the perfectionism is coming in but like that’s the part I’m just really struggling to hold on to. I keep telling myself like these are facts not feelings. Yes, yes, yes, yes. Feelings not facts but I think I just go really underwater in the feelings and so.

feeling’s not facts.

Caleigh ODonnell (34:23.085)

It’s been harder to like I’m saying it but it’s not like I’m saying it, you know, but it’s not reaching. Yeah for recently

Yeah. Okay.

So I think that that’s a sign that there are some, there’s just like a deeper permission you need to give yourself to have a moment.

Yeah, okay.

that you don’t have to be okay.

Caleigh ODonnell (34:44.694)

Yeah, that makes sense. I do feel like I’ve been sitting down and I kind of want to journal about it and I’m just like, I’m so sick of journaling. Feelings are like breathing into it. Like, can’t I just be done?

Yeah!

Lily @ Date Brazen (34:58.54)

I hear anger. Yeah, like what if you just like allowed yourself to be pissed?

Yeah.

Caleigh ODonnell (35:06.304)

Yeah, that’s true. Yeah, I am very angry.

Yeah, makes sense. What does that anger feel like?

Like physically or?

I don’t know whatever comes up for you. No perfect way to do this.

It feels a lot like why do I have to do all of this work to be like so ready for something for someone like why don’t you do all of this work for someone to just give me a chance when like I don’t like going into this mind space because I don’t think it serves me but like when all these fucking men don’t get you get to just like

Lily @ Date Brazen (35:28.344)

Hmm.

Caleigh ODonnell (35:51.662)

And I know this isn’t true, like float through their dating experience for just when they’re like absolutely perfectly ready and something just hits them over the head and it’s like, oh, well, I’d still have to be like, I don’t know. feel like there are women are always told that they’re the romantic ones and the delusional ones, but I feel like I’m constantly tempering that and find myself surrounded by.

Like all the single men I feel like I’m interacting with are just like, oh, well, I don’t have to put in any effort. It’ll just like happen for me when it happens. And if it’s not perfect, then I don’t want, like, I don’t know. It feels like they’re the torsional line sometimes around what it takes to have a relationship where you have to, you know, 1 % of the time not do exactly.

exactly what you want to do in that so yeah get a little bit angry

I guess.

Lily @ Date Brazen (36:52.962)

Yeah, I hear that and your feelings are valid. My friend Megan Saxelby says your feelings are your feelings and you get to have them.

Yeah, yeah, I’m feeling a big need to like, asterisk that like I know that that’s not

You don’t have to, you don’t have to, I’m gonna do my job. You don’t have to, you don’t have to. I’m just like, I think that this is a great model of a moment where like you get to have your big feelings, like you get to fucking have your big feelings and acknowledge the anger that you feel, acknowledge the like lack of, like society treats single women as behind coupled women. That sucks. They do not treat single men the same.

as compared to coupled men. We can draw that. That’s a totally under, like totally.

Fine conclusion to draw.

Caleigh ODonnell (37:48.906)

Mm-hmm. Yeah.

And I also think that the patriarchy has fucked all of us over.

Mm-hmm.

and that there are a lot of men who are wrong for you who you have been interacting with who sucks.

Mm-hmm. Yeah.

Lily @ Date Brazen (38:08.618)

All of those things I’m incredibly comfortable saying.

Me too.

Great. How are you feeling now checking in, doing your original intention, dropping in.

I think I’m feeling a little bit vulnerable.

Mmm.

Caleigh ODonnell (38:29.996)

Yeah, I think I don’t love to show the anger part because I think…

Caleigh ODonnell (38:44.438)

I’m worried that if I come across as angry, then it will be confirmatory that I must be the problem.

Mm-hmm, mm-hmm, mm-hmm. Yeah, so that’s actually the problem here. That’s why you feel stuck. One of the reasons. That’s why you feel stuck. Do you hear it?

Not yet.

Okay, so that one feeling of anger that has been happening, you have been choosing to avoid or put in a closet or go like, like go take a walk anger because I can’t be angry because then I’ll be an old shrew.

who nobody wants to be with, that’s fuckin’ patriarchal socialization right there, misogyny 101.

Lily @ Date Brazen (39:37.258)

internalized misogyny that you can’t feel anger in order to be attractive.

Lily @ Date Brazen (39:49.708)

You ready to keep going?

Yeah.

How are you doing?

Good.

Yeah, what’s what’s what’s coming up?

Caleigh ODonnell (39:59.5)

Yeah, I don’t think I maybe fully realized. I think I spent a lot of time working on like the sadness part of it. do think I’ve been ignoring the anger part of it. And I don’t really know like, I guess I don’t feel like I know as much what to do with the feeling of anger.

Yep.

Lily @ Date Brazen (40:27.998)

Yeah. This is actually not to be hyperbolic. really do think this is a turning point for you. In general. Because by the way, if you were in when you are in, if you were in right now, the most loving partnership, you would be doing this fucking work of allowing anger. This is life shit.

It’s not like I have to do all of this heavy work in order to be worthy of a relationship to be chosen. The relationship just hasn’t happened for you yet.

Lily @ Date Brazen (41:05.962)

you have an opportunity right now to create more wholeness and integration with yourself for yourself so that when the relationship does come along, you are a planted tree who feels just like so full of yourself in a great way and you’re ready to embark on that adventure when it comes. You’re ready now, you’ve been ready. But I think that this is like,

Mm-hmm.

Lily @ Date Brazen (41:33.186)

Life work that you are gonna have you would have to do anyway, no matter where you fucking were does that make sense?

It’s work I see my mom doing right now at like, in her 60s.

There you go.

Lily @ Date Brazen (41:47.214)

You’re coming to this so early.

Yeah.

and you are gonna be served so well. It might even impact the partner that you choose. Allowing anger.

Yeah. Because I like to say, like, I don’t care about you finding a dusty crusty relationship. I want you to find the best relationship of your life where you feel like you are 100 % chosen and you 100 % choose them. And there’s no, like, feeling that you’re not willing to feel to be with yourself. And that creates deeper intimacy with yourself to create safety, ultimately, in every relationship in your whole life.

Does that make sense?

Caleigh ODonnell (42:33.184)

It does, it does. I’m feeling like it makes a lot of sense. I’m also feeling like maybe confused around like how I guess a little bit how and a little bit like I think the feeling of if I feel that anger, how do I like actually express that in a way? Like I feel like I have anger about

all of these different experiences over 10 years. Yeah. How do I not put that on one person who I barely know who like maybe really hasn’t even done anything and maybe is a total, you know.

to you start to like rage journal or like scream into a pillow when it feels authentic literally stomping your feet and shaking your arms physically have a tantrum for a moment that’s okay be like this fucking sucks I hate this in my journal instead of trying to keep it buttoned up in case somebody somebody reads this you know what I’m saying

Yeah. I just, I think I definitely do that. Um, even when I’m during it’s not for like any, really want else, but I have to, I have to like put that cherry on like, but I know blah, blah, blah, blah, blah. It’ll all work out.

you

Lily @ Date Brazen (44:00.05)

No, I totally, totally resonate with this and something that I’ve practiced doing is literally just journaling. Like I’m having a hard day. I do not feel good about anything. I hate how I feel right now. I don’t like, like literally putting the journal away, like ending it. It doesn’t have to be wrapped up in a bow. And I really struggle with things being wrapped up in a bow because I have the thought like that makes it, that makes me more moving forward than not. Like with therapy, my therapist has to be like,

Lily, we don’t have to wrap the session in a lesson. We’re in the process and I’m like, fuck you, I hate this, but that’s okay. So in terms of how to process anger, you’re just learning how to, and I gave you some menu options. Like sprinting can be, like if that feels available or like literally stomping against screaming into a pillow, thrashing around, laying in your bed and literally being like,

your body needs to close that stress cycle. And I think what will happen as you allow it is that it will start to transform and shift and move through your body instead of being constipated.

Yeah. Okay. I’m liking this. I feel more energized already. What the heck do I do with like, I feel like both versions I’m sick of. I’m sick of, okay, well, I just need to push through on the app while I’m doing all this. And I’m also sick of, I need to delete the app and come back later. I’m of both options.

So number one you need to up your standards for connection. No more like you never know until you meet them. No more of that. No no no. What? What’s your face? What’s happening?

Caleigh ODonnell (45:54.478)

That’s…

Okay, well so you’re asking how I’m good. This is really So Do you are you musical theater? Lover like me nothing comes from nothing nothing ever could so sound music Somewhere in my youth or childhood So I think nothing comes from nothing if you’re getting nothing from a profile if you’re getting nothing from messaging then no nothing comes from nothing so bless and release

I’ve.

Caleigh ODonnell (46:29.622)

It’s not nothing. It’s like not a hundred percent.

Do curiosity? Do you feel curiosity? Like, oh, I want to learn more.

See, I would say yes, but then you said it in that way and I don’t feel- I want to more!

I want to learn more then it’s nothing then it’s nothing then it’s somebody that you don’t need to meet It’s like it’s like if you were on bumble BFF looking for friends and you’re like you seem nice I’ll go on a friend date with you with literally no Interesting topic of conversation that was interesting to you that came up before you fed up It’s like like think about it like you have enough friends I would imagine you would say or maybe you want to make more friends, but you have a like

She’s a little lark, though.

Lily @ Date Brazen (47:15.508)

I need to feel some level of connection before we meet up if you’re doing Bumble Bee a huff. Let’s apply the same standard to your love life. You need to have curiosity that sounds something like, I want to learn more. Kind of a little bit of a leaning forward. It doesn’t have to be like, I’m sold on this person 100%. It just has to be curiosity.

Yes, I agree. Logically.

But what? But…

That’s just us. I think then I struggle with like when I have those moments where it’s like it is a lean forward I want to learn more Then I feel like I really latch on to them too much and sometimes having the mediums help me like Temper, but maybe that’s not true. I don’t know I in my head I get my head sometimes because I’ve had experiences where it’s been like

and then like I meet them and I really liked them, but obviously it wasn’t the person.

Lily @ Date Brazen (48:19.118)

I believe the universe is taking care of you. So if you meet somebody on a dating app and you’re like, no curiosity, bless and release, you’ll meet them IRL. Or you’ll meet somebody else who is amazing for you. There’s not one person. And so I don’t want you to get in the land of maybes and be caught up in, that’s one of the reasons why dating apps are so exhausting is that you’re trying to make something work for fear that nothing exists. And I think that…

What you can see from your own experience is that, okay, there are people with whom I connect that has happened before. There are people that I’m attracted to who are attracted to me. What hasn’t happened yet is mutual long-term intention. I’m learning how to believe that that’s out there for me. In the process, I am not settling for less than curiosity. That’s what I want you to put in your pocket and start dating with. Now, you might have one interesting match in a month.

Yeah.

Lily @ Date Brazen (49:15.086)

One every other month. That’s not a fucking problem.

Yeah, I think that’s a mindset set shift that I need to make again, given that I was like 20 when I started on the apps and like.

You were also searching because of another reason. You were searching to prove to yourself that you were okay.

the lowest of lowest of standards at that time too. So I see the numbers, the number game I get caught up in and it’s not reflective of the difference in what I’m looking for and who I am now as opposed to when I was 20 and I sometimes forget that.

Yeah.

Lily @ Date Brazen (49:52.962)

Yeah, you’re looking for something different, more meaningful, deeper now, and you’re not, you’re working to detach your self-worth from these apps. Cause they’re going to let you down every single day of the week. So I think in terms of building up self-worth, building up self-confidence, that is about practicing more self-compassion. That’s about allowing your anger. That’s about going and doing joy building IRL outside of your house and

Yeah.

Lily @ Date Brazen (50:17.934)

talking to people and giving compliments and receiving compliments and having a good ass summer outside of your house and celebrating every win no win is too small. So that’s how you create a more fertile ground in your dating life for opportunities to emerge. Set more boundaries, ask deeper questions earlier and in terms of the situationship pattern I think that that can be pretty easily cleaned up by

asking or maybe you did this you can tell me but asking earlier on hey what what’s your hope for your dating life and then they ask you back and then you can say if you’re looking for a relationship I’m looking for a relationship with the right person that’s why I’m dating like center your desire don’t worry so much about whether or not what you’re saying is too intense if you’re coming from a place of here’s my truth then you can’t fuck it up with the right person thoughts

I feel more permission to be pickier. I do like, even though I knew you were going to say that, I just like, knew obviously you were going to say that I’ve read your book. It does help to like actually have you say it to me versus just knowing. And I also feel relief that I can like go on less dates. Cause honestly it is exhausting. Time out of my week.

I know.

does feel kind of relieving if it is like, no, it might only be like three dates a year, but I’m gonna be excited about it.

Lily @ Date Brazen (51:52.792)

And you can always go on fuck around dates. That’s something that’s always available to you. If you meet somebody and you’re like, I’m feeling a vibe, but I don’t know if we’re long-term compatible, you can go on a fuck around date. If you want to hook up with somebody and that feels aligned for you, go on a fuck around date, hook up, whatever. Like it doesn’t have to be so serious and you can.

hold this lighter and with more joy. And the way that you get there is by allowing anger. I know it’s so counterintuitive, but I think it’s also about like allowing your anger is really about validating yourself as a human being. And that drawn out is about validating your own desires, validating your preferences, validating your wants and needs and blessing and releasing anybody who is messing around, you know? So the wrong men for you.

the

Lily @ Date Brazen (52:45.996)

are not doing their work. Guess what the right men are? The right men are, you’re dating only men, yes? The right men are going to therapy. The right men are also sick of dating apps and excited to get off them for the right people. I know men in my life who have struggled in their dating lives and who are doing this work and who are asking me to coach them specifically. You know what I’m saying? So I know that they exist. I know that they’re for the few, not for the many too. Sure, there’s like,

fucked up shit that you have every right to be angry about in terms of the difference between how men and women are allowed to date and exist in the world. And you can hold that and hold that the right man for you might just possibly exist and you haven’t met him yet. I believe he does, but I’m just giving you a baby step thought so your brain can latch onto it and practice it. How is this feeling?

Good. I was just gonna say I feel a little like lighter. I’m angry.

Yay!

Yeah, there you go. No problem. You get to feel that and move through it when it feels accessible to do so. Not negating it, but being like, okay. Like when you have a big cry, you know, it’s like, okay, I’m ready to, I’m ready to move on from that moment and let’s figure out what’s next. That’s what you’re doing right now. Yeah. By allowing it and not minimizing. Great job. This is powerful stuff.

Caleigh ODonnell (53:57.506)

Yeah.

Caleigh ODonnell (54:20.408)

Yeah, I’m excited.

I am too. So your next steps are to do some anger work, anger processing. And your next steps are also to do kind of a cleanse in your messaging, in your dating app. So if there are people who you’re like, nothing comes from nothing, this is nothing, let’s delete and move on, or bless and release and move on. If there are people that you are curious about, ask them out. Okay, see if they co-create a date.

really, I think we didn’t get into this like, two dates canceled, I must be less desirable. Or they were never right for you and it sucks that they canceled.

Yeah, I don’t really believe that. think it was just like, I was already having all of these big feelings around being back on the apps. And it was just like confirmatory in the moment in a way that was sort of like, like I really don’t believe it. I’m just having all the feelings, know.

Yeah.

Lily @ Date Brazen (55:21.806)

Yeah, absolutely. So confirming my strategy and go back to the book if you need it, but like 20 minutes a day, no notifications. Ask an intentional question to open, maybe even before a date asking what are you hoping to find in your dating life, just a vet for that if you want that. Focus on your joy building outside the house this summer and you’ll be good. All right, thank you so much.

Thank you so much. This was so fun. Thank you.

That conversation was so powerful. I am so grateful, Callie, that you came on and shared a bit of your story and allowed yourself to be vulnerable, allowed yourself to be supported. I know that you are not alone and that you sharing your story probably inspired thousands of people to be honest about their emotions, to move through them with agency and to believe their own desires in the process.

If you want to get my book, Thank You More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, you can go to datebrazen.com slash book to get your hands on your copy and get an extra special bonus as well at datebrazen.com slash book. Thanks for listening to the Date Brazen podcast. If you liked this episode, then you’re going to freaking love my book. Thank You More Please. It’s my proven step-by-step feminist guide to breaking dumb dating rules and finding love.

You can buy it anywhere books are sold and then get a juicy bonus at datebrazen.com slash book. The bonus is the dating life fix. My top 10 podcast episodes to get unstuck right now. And be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back.