Today’s podcast episode is a coaching session with Michelle. She’s in her 50s, divorced after a 24-year marriage, and getting back into dating after being with one person her whole adult life.

In this raw and powerful coaching session, we unpack the overwhelm of dating apps, the anxiety of being “naive,” and the pressure late bloomers feel to already know how dating is supposed to work.

Michelle shares how:

→ Dating apps make her feel panicked in 3 minutes or less

→ She’s afraid she missed the memo on how to flirt or date

→ All she really wants is a partner to laugh with at a family campsite, but dating feels like an IMPOSSIBLE way to get there.

We talk about self-compassion, letting go of judgment, and what it means to stop settling—not just for the wrong relationship, but for a miserable dating life.

 

Or watch the video version on YouTube! (@datebrazen)

 

Work with Lily:

Free Live Training on June 17th: datebrazen.com/lets-go

Learn about Main Character Dating: datebrazen.com/waitlist

Book: Thank You More Please

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Show transcript:

Lily @ Date Brazen (00:00.046)

Hey gorgeous friends, welcome to another episode of the Date Breason Podcast. I’m so glad that you’re here. Today, I am coaching Michelle. Michelle is a badass who also identifies as a late bloomer. She is in her 50s. She got divorced a few years ago and since then dating has felt like a really punishing experience. One that she feels like she can’t figure out. It feels like she’s so behind and she describes dating as feeling like a punishing class that she

has to take in order to get the right course credits. And so if you resonate with any of that, you’re gonna love my conversation and coaching session with Michelle. We are gonna dive into why dating feels so dang hard. Not because you’re wrong, not because Michelle’s wrong, not because you’re missing some grand master plan for your dating life that everybody else seems to have that you don’t. No, no, no. Because the dating world is a hotbed of patriarchal nonsense.

because the way that you were taught to date fundamentally does not fit with you and your place in life and your desires. I’m gonna coach Michelle through feeling behind and help her feel like the badass that she is in her dating life. And you’re gonna love this episode. It’s a really powerful coaching session. And by the end, she has some really awesome aha moments. In this episode, we unravel why dating feels so hard, not because you or Michelle is doing it quote wrong,

but because the world has not made space for people who feel like late bloomers to date with compassion, self-trust, and joy. That is exactly why I coached Michelle today on this episode and why I created my program, Main Character Dating. In this 12-month group coaching program for feminist late bloomers, I take you through exactly step by step how to attract the right partnership with a joyful dating life, both online and in person. This is the room for you if you wanna stop settling.

Stop judging yourself for wanting what you want. Take up more space with your desires. Start dating in a way that is magnetic to the right people and really disqualifies the wrong ones with ease. So you can start attracting more with unshakable clarity and confidence, whether you are 65 or 25. This program was built for you. The doors to main character dating open tonight, June 17th, 2025, and we open periodically throughout the year. So if you wanna learn more or you wanna join us,

Lily @ Date Brazen (02:23.97)

go to the link in the description of this episode or datebrazen.com. Now let’s get into this episode.

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. Hey, Michelle, welcome to the Date Brazen podcast. So glad that you’re here. Here. So how are you feeling about this?

Yeah, I’m glad to be here.

Michelle Johnson (03:12.172)

Yeah, a little bit nervous, a little bit nervous, but excited to do it. Yeah. Okay.

normal

Cool. Well, so I’m asking everybody before we get going, what is a brag? So a little celebration, a big celebration, something you want to acknowledge about yourself. And then what is your intention for this session?

Ooh, those are good questions. Well, I think a break is that I’m actually doing this. So I’m feeling proud of myself for putting myself out there and trying to figure out maybe next steps or something to change something. So I’m pretty proud of myself for doing this, I think. Yeah, that’s a break. I think an intention is…

Yeah, I think I’d just like to know a little bit more about maybe why I’m stuck. So if I could like, like figure out just maybe another piece to that puzzle or maybe something that will help me get a little bit movement, that would be my intention, I think, for the question, I guess, or our time together. Yeah.

Lily @ Date Brazen (04:22.338)

Great, awesome. So tell me about, now I have for those listening, have a form that Michelle filled out, so I have a sense of what’s, you know, some of what’s going on, but I want to hear from your words. Tell me about your love life so far.

Okay. On the form it said, it asked you something about your dating life. And I was like, that might be a generous term for where I’m at with things. I don’t know if I would use the terms dating life. Like that seems a little bit extreme, but let’s see. I have been single for about five years now. I was married quite very young.

And I was married for 24 years and then my husband and I separated and divorced. So, and I basically haven’t dated since, well, when I met him when I was 19. So, and even then, I don’t know if know if technically you would call it dating. kind of were friends that turned into a relationship. So I don’t know that I ever feel like I’ve dated. So this is also a tricky scenario, but yes.

So I guess that’s it in a nutshell. I’ve tried dating apps and that’s a lot.

What happens there tell me about your experience

Michelle Johnson (05:45.422)

Well, the first time I think I just like was totally overwhelmed and I don’t know that I was ready. I mean, you feel like you should be ready a couple years after being single. You just feel like, okay, it must be time to do this. And so then I did it. But I just found it like, I just, it made me almost sick inside. I was just so overwhelmed. So we stopped that. then, and then I tried it again.

Just actually this last January, February, I went on to the dating apps again and made a little bit more forward movement. Actually was like had some chats or you know some phone calls that kind of thing but I just I really like your bless and release thing but I think I release real real fast and I almost feel relieved. I almost feel relieved when I was just like this was not going to work out and and then and so you know.

go on them, try to set a time and go on them a certain amount every day until you’re activated but it takes about three minutes. I’m activated, I’m like, I’m done. And so then I’m like, why am I doing this?

to ask about that. So tell me about what’s happening in minutes one through three. Like take me through what’s going through your brain, what feelings are in your body. Are you aware of those things?

I think like it starts off like, know, you’re swiping, which in and of itself is, I mean, I feel like I’m shopping for another human being. So there’s that interest, you know, like looking at all the canned goods, trying to figure out which one you want. But it’s like I can do the no’s very easy. The yeses, you know.

Michelle Johnson (07:33.846)

I tried to be fairly, but it’s like when I come to ones that I can’t, I can’t, I don’t know if they should be yeses or nos, which I know it shouldn’t be such a big decision, but just, you know, and then I just start getting in my own head and thinking about it. And then I start feeling like, like, why am I doing this? And it’s just too much. then it just all like, it’s down. And so then I just turn it off for the day. That’s it. So.

I think I get probably too much in my own head.

So I think that this is a beautiful example of what I talk about when I say that dating is a microcosm of every hope, joy, dream, fear, insecurity, desire that we have as humans. Dating actually matters to our wellbeing. And so what I’m hearing from you, Michelle, is that a dating app is actually a lot deeper than a dating app and that it’s coming along with it, like a lot is coming along with the

practice of being on a dating app that we need to slow down and examine with compassion instead of judgment. Because what I’m hearing is that you’re judging yourself for having this intense emotional experience on a dating app, true or false?

Yes, I would say I do judge myself for that. True.

Lily @ Date Brazen (08:50.804)

Yeah, what does that self judgment sound like?

of like, are you making this such a big deal and why is this, you know, like why can’t you just like do this? Why can’t you just, why can’t I just, you know, be a normal person, do some swiping, do some chatting, go for a coffee, like what’s the big deal kind of thing.

Yeah, I’m gonna challenge you to answer your brain’s question. So you’re having the question in your brain, why is this such a big deal with a tone of like judgment, a tone of like, should, it shouldn’t be this big of a deal. But let’s take that question that your brain is serving up, which is a thought, let’s take it seriously and answer honestly. Why do you think giving yourself the benefit of your context and your life experience

Why do you think this is a big deal?

Well, I guess because I’m doing, I’m actually, actually having to date. That feels like a big deal. Like that’s not something I thought I was signing up for to do again in my life. So that probably is part of what my brain is. Like that in itself is like maybe not a life stage. thought I’d have to be.

Michelle Johnson (10:14.338)

be approaching or dealing with. Yeah. And I think just feels like a big deal because I just don’t have experience doing it. It feels like new. It’s new, scary. And just don’t. Yeah.

How are you feeling right now, Michelle?

Mmm, sweaty.

Okay, where are you sweaty? Is it all over? Is it localized? Just hot. Hot, okay, yep, hot, okay.

I’m just…

Michelle Johnson (10:47.362)

Nervous, not nervous. Yeah, just trying to really think about what, why I feel those things when I’m on a dating app is, and not just the judgment, but like why, why I feel that way is, it’s activating again, like it just.

Okay. Activating how? Tell me about that.

feel.

Like just kind of takes me back to that spot where I feel like a little bit young, unsure, like, right? You know what I mean? Like I’m just, I’m trying to put words to things that are very like our feelings and I’m just feeling a little bit. Okay. Just a little bit worked up. So deep breath.

Well, let’s take a deep breath together.

Lily @ Date Brazen (11:46.126)

So you mentioned your 16 year old self in your form. And you mentioned just now that it feels a little bit like your younger self is present with us. And I wonder when you were 16, was there ever a teacher that made you feel really safe to like learn something new, ask questions?

Yes.

Michelle Johnson (12:08.514)

Yeah.

What was that experience like to have an adult really hold space for your like messy, awkward, sometimes growth? What was that like?

I think it felt like really safe, right? And then it made you feel a little bit more like interested in what they were teaching you as well, like, because he felt like, like felt their passion may be on the thing, but also then that they were excited to see you learn and grow in that area too. So

Yeah. And what expectations did that teacher have of you?

She just really wanted, I think she wanted me to show up. And I think, I mean, that was an expectation. then, yeah, just to grow into my potential. She probably, that was kind of looking back now. Okay. I see what you’re doing here. see what you’re doing here. I like her.

Lily @ Date Brazen (13:10.638)

Well, now we’re gonna talk about a teacher that you actively disliked or even disdained. Like, did you have a teacher ever that made you feel dumb or like made you feel wrong?

Yes, of course, yeah.

Yeah, what was their expectation of you?

I don’t even know if they, it’s almost like they disdained that us kids, we were there, right? Like, it’s just kind of like, okay, your job is to teach us, but you just seem really like disgusted that we actually are even present in your, you know, like, don’t bother me, don’t ask any questions, just sit down, do the work, get out of my hate face, you know, like that kind of, that kind of feeling.

Do you see a similarity between how you might be speaking to yourself right now about dating and how that teacher that was unkind and expecting perfectionism from children, how that teacher might’ve talked to you? Do you see the diff- the similarity?

Michelle Johnson (14:16.416)

Yes, yes I do.

What’s coming up for you is I point that out.

Yeah, I guess I want to treat myself as kindly as, right? The teacher who’d want us to learn would teach, would… I want to talk to myself like I would talk to my daughters who are dating, right? And I want to talk to myself like how I would talk to a friend. And I’ve done that in so many areas in my life, but it just feels like when it comes to dating, it seems like I’m, I don’t know. Yeah, there is just those repeated messages that seem to get stuck in there.

Why do you think, like what does the should voice in your head sound like in regards to dating that makes it so difficult to be compassionate towards yourself?

feel like I should, I think the should on myself is like it shouldn’t be such a big deal, right? Like it shouldn’t be, or I should on myself in that I should be able to figure this out. Like this isn’t rocket science. This is like going out and meeting someone. Like those are the shoulds that I think I end up.

Lily @ Date Brazen (15:26.732)

Yeah, those make sense. They’re very common. I wonder though, I want to back it up to your past relationship with your ex. Did you, and you can share if you feel comfortable. You don’t have to, if you aren’t comfortable. But did you initiate the separation? Did he initiate it?

initiated the separation. Okay. But my my like sisters and friends would say he initiated it well before I initiated it in that.

Sure, you were unwilling to take something that had been going on.

Yes, yes. So then I removed myself, right? So yes, but yes, would, would, technically it would have been me initiating. He would have been quite happy to stay in that scenario.

What did that decision teach you about yourself?

Michelle Johnson (16:29.82)

that I can do hard things. And it taught me, yeah, that I could do something that I didn’t think I’d ever would do or could do. Feels good. I feel like I can hear myself and I know I can do good things and hard things and things that, but yeah. And I’d like to think I could do this too, but.

that feel to say?

Michelle Johnson (16:59.534)

Just seemed to get stuck on that hump.

Well, here’s the good news. You’re not gonna do it alone. I’m here with you. There’s like, I hear you. Maybe your brain is doing that very common brain thing, which is thinking that it’s over. It’s over. It’s already so hard. It’s never gonna change because your brain has recency bias saying the way that it’s been most recently is the way it’s always going to be.

that your brain’s just trying to be safe amidst something that is so incredibly vulnerable. It’s sort of like being put into an acting class when you’ve never been in a drama class ever and the teacher is yelling at you, why don’t you have this memorized yet? This monologue memorized yet when you’re like.

Hmm.

Lily @ Date Brazen (17:54.602)

I just showed up to this class out of nowhere with no prior experience or context. And then you’re going home and blaming yourself for not having the knowledge already.

Yes.

acknowledged like you’re learning something new.

Hmm, that feels good. I like that.

Okay, I’ll buy it. I like that you like it. Now let’s integrate some of that like, so when you think about how activating dating is, or when you think about how I should be better at this by now, where is sensation in your body happening?

Michelle Johnson (18:18.701)

Yeah.

Michelle Johnson (18:30.7)

Sweaty palms, definitely. Usually upset, like my stomach starts just like, in on itself. Like having to speak public speak in front of someone. Like that was a great analogy. Cause that’s exactly like those kinds of, that kind of the tight, know, tight shoulders, just, yeah, definitely. Definitely.

that nervous doing, doing something going to go on stage and you haven’t memorized your lines. Like definitely those kinds of, yeah, that kind of feeling for sure.

Yep. Yep. Totally normal. So one of my favorite human beings in the world, her name is Susan Blackwell and she was a mentor of mine and a teacher of mine and she used to, she’s an artist and a creativity coach. She and her business partner, Laura Kamian were on my podcast like two years ago because they helped me write my book. So

Susan Blackwell was on Broadway and she, not only was she on Broadway, she helped write the Broadway show. And she’s so, so cool. And I would never think of her as somebody who was stage fright, but she talked about how deeply, intensely she felt stage fright almost every time she got on stage and she would teach and talk about how to navigate stage fright.

The way to navigate stage fright effectively is not by judging yourself and wanting to shut the stage fright down. The way to navigate stage fright and actually do the thing that you want to do, get on stage, perform, do what you like, connect with people, connect with the audience. The way that you effectively move through stage fright is by acknowledging it, breathing into your body as your stomach is doing flips, saying to yourself,

Lily @ Date Brazen (20:41.814)

I’m safe with you right now. I feel a lot of intense feelings, but I’m here with you and I’m actually safe. This is just really hard. Like saying that instead of being like, shut up stage fright, get away from me, you’re the problem. It’s just actually a bodily function in response to a vulnerable stimuli. There’s actually nothing that has gone wrong. How does that sit with you?

Hmm.

Michelle Johnson (21:06.146)

That makes a lot of sense. I really like that. Just like compassion, right? I have compassion for myself in other areas. It’s like just putting it into practice maybe and…

Why do you think, now I know that you have the voice of like, should be, I shouldn’t be dating anyway. I wish that this isn’t what was happening.

Right? Yes, exactly. Yes.

Is that why you think it’s so hard to practice compassion for yourself? Or like, what do you think that’s about?

Yeah, and I think like I resonate a lot like with like your late-blamer stuff. Like I just feel like I shouldn’t feel so naive or I shouldn’t feel so like awkward or vulnerable or like, I don’t know why I feel like I’m 50. I should like, you know, kind of like, like I feel like I’m a, I feel like I’m a confident, competent woman in so many areas of my life. And then it’s just like, yeah, I, I don’t, I just don’t feel like

Michelle Johnson (22:04.916)

I should feel these things in this area. Like, guess that’s maybe, does that, does that make sense? I don’t know if I’m being too kind of, yeah. Okay.

It makes total sense. In fact, it’s very common whether the whether somebody I’m talking to is 25 or 65. It’s very common. The stories, issues, the self judgment is the same whether someone’s never been in a romantic relationship or whether they just got out of a 24 year marriage. It is the fear that you are wrong for being where you’re at.

It’s also, yeah, like that piece of feeling like, yeah, maybe like, yeah, like that. I don’t know if naive is the right word, but you know, that, like kind of, I don’t know, like inexperienced, like, right? Like, like to just be like not knowing, feeling like maybe there’s like a set of rules or there’s like.

these things out there that I should know or have figured out or like there was a manual somewhere or something and I just like missed the boat, missed the memo, missed, I don’t know, just, I don’t know. That’s how it kind of feels inside, yeah.

Yeah, yeah. I hear that there is a fear of something here that I want to get curious about. like what, okay, so sure, you’re naive. Let’s just go down, let’s believe your brain for a second and go down this thought experiment rabbit hole. You’re naive, you don’t know what you’re doing. And so then this happens. Like what happens in your brain when you’re spinning out because you’re so naive, therefore.

Michelle Johnson (23:57.336)

like what’s going to be that potential bad end result or something? Is that what?

Right, like what’s the fear about being naive? Why does that matter that you are naive? Tell me.

I know, I think I just feel like I don’t know maybe how to play the game. I don’t know, I don’t want to say dating’s a game, but it kind of feels like a game sometimes. And it feels like maybe there’s rules or ways of doing or speaking or flirting or whatever that I just don’t seem to… I feel like I missed the memo. I don’t know. Like on the dating app or like, you know, I don’t know how to be… don’t… Like, they’ll make a…

comment or a text or something and I’ll be like, I don’t know how to read that or I don’t know how to respond in the like manner maybe. And so I’m trying to be genuine and just myself but I feel like I’m a little bit like, weird.

Yeah. So let’s go down this rabbit hole even more. So, okay, so you’re awkward. Like, let’s believe your brain, you’re awkward. And so therefore that means what? In this default brain.

Michelle Johnson (25:10.67)

That I’ll just never find my person. Like, because of that. I’ll not be able to do what, how… So like, I don’t know how to play the game. So then I end up not playing the game. So then I’m never going to end up finishing the game, which, you know, to play this out, this analogy out is like winning, you know, the life partner or whatever, right?

Yeah

Yeah, so like that would be like probably where the train like that’s where stops is like saying, okay, like, you don’t know how to do this. So therefore you’re not going to achieve.

So then why even try?

Yes.

Lily @ Date Brazen (25:59.051)

Yeah. Yeah. So let’s answer that question. Why even try? What do you want? Yeah.

So like I have a picture in my head of like, you know, I’m at a camping site and my kids are there and know, future grandkids, that kind of thing. We’re all camping, family camp out or whatever. And a guy comes up beside me and he puts his arm around me and he just like puts his head by mine and he’s just like, you know, like, you know, makes a joke or something. And it’s just laughing at the chaos that’s happening that is.

the family, you know, or whatever. And it’s just like, I really want that. So.

That’s a beautiful vision.

Mm-hmm. So then I feel like obviously brings emotion. That’s something I think I really want, but I would just like to magically get there without doing any of that. So if we could just make that happen, that would be great.

Lily @ Date Brazen (27:04.718)

Yeah, sure. I can try to rave my magic wand and deliver him to your side. I can try.

I would like that very much. Yeah, that would be great.

My, that is such a beautiful vision. feel it viscerally with you. It is so beautiful. It’s belonging. It’s calm. It is loving. It is day to day. It is like living life with somebody I hear and partnering with them and having them adore you and you adoring them. Like what a beautiful vision. I believe that your desire

is evidence that what you want exists. Just like the Wright brothers didn’t know that a plane could exist. They were just like, I think that this thing should exist. And so we’re going to go after it and we’re going to fail, fail, fail, fail, fail. And then one day we’re going to emerge with an airplane.

I would just like to skip the whole fail fail fail fail part. That would be great.

Lily @ Date Brazen (28:09.806)

That’s the thing is that you have an opportunity right now as a human being, Michelle, to learn something new in so, like this isn’t a frivolous dating, it’s not a frivolous task because it gets to be an expression of your self-trust, of your confidence.

of skills that you are built of your nervous system care, of the practice of self-compassion. The reason we’re speaking today is not to help you skip over like skip over dating to find the partner that you want. It’s to actually learn how to be kinder to yourself, how to trust what you want, how to ask for it out loud, how to feel confident in yourself as you’re asking for it out loud, even if you want to vomit. How to stop judging yourself for being awkward as like a deal breaker.

because all of those things that you’re getting stuck on are directly corollary to having a better relationship with yourself and with a future partner. To have the partnership that you want in the future with yourself and a partner, you’ve got to learn these skills of like being kinder to yourself, trusting yourself, knowing what you want, asking for it out loud, even if you want to vomit. How is this landing with you?

Yes, I hear you because I feel like those are practices I put into place in other areas of my life. It’s just interesting to hear it in this context and recognize that for whatever reason, I haven’t done that in this area of my life. don’t have maybe not even seeing that saying that I feel awkward or naive is even putting a judgment on myself is for some reason I haven’t even like, it’s like, it’s like a

Missing that for some reason and yeah going hmm that’s interesting.

Lily @ Date Brazen (30:12.344)

Well, it’s also like you’re not dead yet.

Thank you.

You are gorgeous. You are vibrant and alive right now. This is not over. And learning these skills is just on the other side of trying imperfectly and having your own back. So let’s talk about it. Are you game to talk about your dating strategy?

my dating strategy. Alright, sure, let’s talk about my dating strategy. Let’s see.

Okay, because we’re centering the vision. And you know what also strikes me about that cookout or the campsite with your future partner is you didn’t describe feeling nervous. You didn’t describe feeling like out of place or awkward or worried about saying or doing the right thing. That version of you is also the vision.

Michelle Johnson (31:10.348)

Yeah.

She is not tied to being in a relationship. She gets to exist right now. Your best self is standing on the other side of you learning just a few skills and learning how to trust yourself more. And the relationship gets to be the bonus. This is about you standing in your power.

Yeah, I like that. Yeah, I like that a lot. I just think that’s exactly something I’d want to say to my daughter, right? Like, that’s exactly what I’d want to say. I’d want to say, this is about you. This is about you, like, feeling so damn good about herself, right? And like, and just, yeah, owning that. Yeah, I like that. Owning that power and not, and I just don’t, yeah.

what’s coming up for you about it.

Michelle Johnson (32:01.376)

I don’t want to see her settle for anything and I don’t want to settle for anything either and I just…

Yeah. So I think this is about becoming saddle proof.

Mm-hmm. Yes. Well, yeah, I… That I don’t feel like I would have a problem with, because I think I’ve… Sounds bad, but I’ve been there and done that, so I’m not going to do that again. Yeah.

But I’m gonna challenge you, Michelle. You’re currently settling for a really miserable dating life. You’re currently settling for a lot of self judgment. These things matter too. Yeah, you’re settled proof in terms of you’re not gonna choose the wrong partner. Done, dusted, good job. A lot of people struggle with that and need to do that work and climb that mountain. You’ve done it.

You’ve done it. You’re subtle proof. I’m so proud of you. You have done so much work, hard work. You can do hard things, but now it’s about looking at like, where else might you be settling in ways that are kind of sneaky?

Michelle Johnson (33:03.886)

Yes.

Judging yourself is a version of settling. If you’re just being human, just like stay, if you had the choice to stay in that teacher’s class who was so punishing and like so mean, that would be settling. If you had a choice to leave that class, but you chose to stay in that punishing environment because maybe you had the thought, punishing myself means I’m moving forward. But you get an option to opt into.

Yeah.

the classroom where you’re actually learning something in an environment where you’re cared for and really like understood.

Yeah. I think sometimes you feel like, like it’s a, that subtle message is also that that’s the only choice you have. Right. Is that class with that punishing teacher? Like you have to check off this box. You have to be in that class, that, that course credit or whatever.

Lily @ Date Brazen (34:00.27)

What in your mind does dating have to look like, feel like, in order to meet a person?

It just has to feel hard. And has to feel like you have to do the dating apps and weed through profiles that tell you nothing about a person and you have to try to guess if they’re someone you wanna potentially, like even just crack open your life a little bit too. You have to like decide from a picture and a sentence and then you have to start with these like awkward backs and forths and it’s just like.

There’s nothing about it makes me feel good. And then I just like, again, that’s when I just start to like pile those things. So, but it just feels like there’s no, like, doesn’t seem to be like a very good solution.

Great, got it, got it. Putting it into my brain. I hear you. So here’s what we’ve got to do together, Michelle. I want you to take a deep breath. Release. One more. We’re taking you out of school.

I have you have suddenly graduated from school. You don’t exist in school anymore This has become an unhelpful metaphor that we are now great. I understand your brain more now, but now we’re gonna grab you out of school We’re taking you out of school. Imagine it leaving school feeling so proud of yourself. You did it rah rah rah now you’re in the adult world and it can be a little scary place to be or you’re in the job market for the first time or whatever like you’re doing something that you haven’t done before

Lily @ Date Brazen (35:39.918)

that people around you are doing that you’re gonna learn from and that person, like I’m here with you. I’m here to help you figure this out. Why do you think you’re so bothered by the people who are wrong for you? Because when I hear you say, don’t know how to gauge whether or not this person is right for me if they don’t have answers in their profile or just a few pictures, my response to that is, well, they’re an immediate no, period. And.

It is a waste of your time to be bothered by them because they will and have always been wrong for you. Thoughts?

Hmm. Well, I think I just, I think part of it is like, well, I mean on the dating apps or whatever, it just, feels like, I don’t know. I feel like maybe I’m being like too picky then or too like, right?

There you go. That’s the issue. You’re not giving yourself permission to want what you want and you’re using the assumption, I’m just naive. How could I know what I want against yourself?

I actually don’t think you’re that naive and I actually don’t think you are such a beginner or so awkward at this. I just think you haven’t yet given yourself permission to want what you want without apology.

Michelle Johnson (37:00.718)

Okay, I can see that. Well, I’m just picturing myself on the dating app and I just feel like, yeah, I’m gonna end up smiping on like one out of a thousand, it feels like, right? And I think there’s part of me that’s always like, I don’t wanna be too picky, I don’t wanna have, know, like dating apps are hard, it’s hard to put yourself.

show who you are on a dating app, think sometimes, right? But I mean, I know what I’ve put on my dating app and I guess I just want to see that kind of similar effort. And sometimes I just feel like, yeah, right? I just feel like that’s somehow expecting too much. don’t, I don’t know, right? Yeah, you’re right. Message in there that’s just being, being too picky or being too, but I don’t need all the guys. just need one guy.

Correct, correct. And the dating app, I’m not a dating app apologist. If you’ve read my book, I like, don’t like them. think that they’re difficult to use. think they’re difficult on our brains and bodies and nervous systems. I think that they are just a little silly tool that I want to help you use with CEO unbothered energy, Michelle. Because that’s where you’re going in your dating life. The vision is the version of you

who knows what she wants, who is unbothered by the wrong people, who knows that it only takes one person, and who is not willing to settle in any fucking way how she speaks to herself, who she goes on dates with, who she swipes on, right? You swipe one out of a thousand. I would imagine it’s going to be more than that if you actually counted. A lot of people have a distorted view of like the numbers there because of default patterns of thought.

So, so what if it’s one in a hundred people? Most men are going to be absolutely wrong for you. And what a gift that is because you didn’t need to go on a date with them anyway.

Michelle Johnson (39:01.046)

Right. Yeah.

But this is re-centering, this is actually a coming home to yourself, Michelle.

Yeah, I like that. And I want that, like that. feel that, right? Like that resonates with me because I do, I do want that for myself. I want this part of my life to align with all the other parts of my life that I’ve been working on, right? I do, I want, I don’t like that this is a part of my life that feels out of alignment or out of sync with like who I want to be and how I want to speak to myself and…

Right? just, I think you’re right. It’s sneaky and I don’t feel like I see that I’ve been being so not, not just like not judging men, but judging myself about how I’m looking at it. But I did, you know, I did try to listen to some of your podcasts. Like I like the idea of not being on the dating apps like that. I’d love

for real life scenarios to happen, but realistically where I live, the part of the world I live in, the circles that I run in, you know, for work, it’s not really a very good environment just for meeting people.

Lily @ Date Brazen (40:17.012)

Yeah. So I think that it’s a two pronged approach. I want you to do this summer a lot of joy building IRL. So I want you to get outside your house if you can go to go to music festivals or or like potlucks or gatherings that where you know people it’s like not like you’re gonna meet a bunch of potential it sounds like you live in a smaller place. So it’s not like you’re gonna meet a bunch of hot hot guys at the potluck necessarily.

But I just want you to experience more joy and expand your nervous system’s capability to feel good while you connect with people. And maybe even talk about like, I’m dating. If you know any single cuties who move here, let me know. You know how many men are moving or getting a divorce themselves who are great people or who may have, you know, not had partners but not been, I don’t know. There are so many people that exist.

so many people. It’s true.

Yeah. So, joy building big, big, big in-person dating strategy, but not in the way you think it’s just to increase your level of joy and connection and maybe even tell people, I’m dating or like, Hey, if you know anybody cute who moves here, let me know. Okay. Dating apps. I think have you ever done essence based preferences?

Yes. Well, I, how was that for you? I, I got part, like, I think I had a hard time. it was easier for me to like picture, like the picture I had, I told you, right? Like the picture. And I felt like that was in the alignment with what you were trying to say. Like what kind of feelings does this person create in me? What do I like feel when I’m with them?

Michelle Johnson (42:09.238)

And so that was kind of where I ended up going with it. So like the things you said, like how I felt with that person, like I felt treasured and I feel like we’re enjoying simple things together and there’s humor there together and you know, and yeah, capacity to do those things together, like stage of life. like, so like there, was those kinds of things that came out of that.

Cool, I love that. So here’s what I’m, I’m just gonna cut right to the chase, because it’s sexy summer and I want you to start going on sexy fun dates with sexy fun men. Okay, I see you getting red and that’s okay.

Yeah. Okay.

Okay? I want you to have sex life this summer.

Hmm. Yeah.

Lily @ Date Brazen (42:54.582)

Yeah. That is fun and consensual and it’s possible. Tell me.

Very uncomfortable.

Just breathe into your stomach.

Well, do you want that is the first question. I say that because you put it in your form.

Well, I do because I do want to be comfortable with that part of my life and I want it to not be such a big fucking deal. And I just would like to be… Not… I’m nervous. Maybe if I’m with the right person that won’t be a big deal. But I think that’s part of that feeds into that awkwardness. It’s like…

Michelle Johnson (43:43.662)

I’ve flippin’ kiss the new person since I was 19. I’ve only ever been with my husband. I’m not this siren, he’s like, la la la, and very casual about, there’s remnants of that upbringing in those years, that this is very, that’s just not something you do. Right?

Like, or it’s not casual. It’s very like, and I, and I don’t, I don’t think I feel that way anymore, but there are still pieces of that, that sit in me. yeah, right. That, that this is, and so I think that’s part of what makes me so sweaty is like the idea of, of maybe there being kind of expectations of that out there and me not.

Yeah.

Michelle Johnson (44:42.594)

like feeling very like, yeah, very suave or very. So like, yeah, when you talk about having a sex life this summer, like, that like.

It really brought up a lot for you.

Super uncomfortable!

That’s okay, because remember the stage fright conversation that we talked about with Susan Blackwell? What do you do? You literally just breathe into your body. Breathe in, it’s okay to feel this way. It is a normal human reaction. There’s nothing, nothing has gone wrong.

I just like honestly can’t even picture that. Like it’s like so out of the scope of, yeah. It would be like you saying, this summer you’re gonna be in a Broadway show. You’re gonna be on stage. like, no way. There’s no, that is not, Yeah, that was.

Lily @ Date Brazen (45:43.682)

Yeah. Well, I will offer this to you. It’s not actually like a Broadway show because you’ve had sex before.

Yes.

whether or not it was the sex that you want to continue having, you’re not going to with him ever again, right? So like, lesson released. He’s like, but it’s sort of like, I’ve done it once, I can do it again. I’m not dead yet.

So am I going to allow myself to dream a little bit more? Not even talking about doing sex. I’m talking about allowing yourself to dream a little bit more about what it might feel like to kiss somebody cute. Allowing yourself to dream a little bit more about what it might be like to be in a booth and like touch each other’s hands at a restaurant. Like.

allowing yourself to dream a little bit. Does that resonate?

Michelle Johnson (46:46.402)

Yes, it does resonate. I guess I’m just like trying to think and make sure that I’m being integral with my words, like honest with myself, not to say to you, yeah, that sounds like something I really want. And then I’d be like, is it something I really want? Maybe I need to think about this. But I think like I do want, I want that, but like I say, I want to like jump and be in that relationship where it’s already like comfortable and known and.

with that trusted person and it’s safe and all those things. I think it’s that whole like leading up to that. just have a lot of that. I have like a lot of anxiety and a lot of like, yeah. So it’s like, it’s not that I don’t want that, but I just, want that comfortable you’re my person stage already. I don’t want all the like, yeah.

Yeah.

Okay, so you’re feeling anxious, so I’m gonna ask you to do something. I’m gonna ask you to stand up and go out of frame. I don’t care, I don’t need to see you. And I want you to jump around for like 10 seconds. That’s all I want you to do. Literally like jump around, move your arms, like shake your arms like for 10 seconds. Can you do that for me?

Yep, I can do that.

Lily @ Date Brazen (47:59.118)

10, 9, 8, 7, 6, 5, 4, 3, 2, 1. Come on back.

Okay.

All right, take a deep breath. How do you feel now as opposed to like 30 seconds ago? There you go. So anxiety is your body asking for movement because neurobiologically anxiety plays a function of run away from the lion. And so to complete the stress cycle, because you had a stressful thing, we’re talking about sex and dating, then you had some thoughts about it, then you had an anxiety response.

Do you feel better?

Lily @ Date Brazen (48:39.03)

And you can get stuck, I can get stuck in the anxiety response unless you respond to it and close the stress cycle in the words of the Nagoski sisters who wrote the book Burnout. So what you did just then by like, you acknowledge the anxiety, used emotional granularity to name the feeling, a term coined by Dr. Lisa Feldman Barrett that found when you have emotion words to describe an experience, you are that much more equipped to move through said experience, you have that information, you.

You shared it with me, and then I was able to say, okay, cool, this isn’t gonna fix everything, quote unquote, but moving your body, shaking for a second is really gonna help you to get clarity. Does that make sense?

Yes, I just picture myself going on a date, feeling a little anxious, and be like, this guy’s going to think I have some bladder control issues. He’ll be like, I just got to go to the bathroom. I’ll be right back. Shake, shake, shake, shake.

I love a bathroom boundary for that reason because you can go and take a deep breath or like shake your body or whatever. Who the fuck cares if he thinks you have a bladder issue? The right person is going to be so excited to have met you. A bladder issue is not going to be a reason for them to break it off with you. Who the fuck cares?

I know, it’s just very, very, it’d be like lots of anxiety, lots of shake breaks.

Lily @ Date Brazen (49:58.722)

There you go, shake breaks, there you go. But here’s the deal, Michelle. Awkwardness is the price of admission for connection. Awkwardness is the price of admission for connection. The problem with awkwardness is not the awkwardness, it’s the judgment that you heap on top of it. Awkwardness is the price of admission for connection.

You think if you met the love of your life, a man who showed up in front of you tomorrow and they were a little bit awkward when they asked you a question, or they stumbled over their words, or they didn’t know exactly what words to use and they took a second to answer, or they said something a little out of left field that you had a question about, you think any of that would be a fucking deal breaker to you?

No.

No, your awkwardness is not a deal breaker for the right people. But what? You were gonna say but.

But I have a lot more grace for others than I ever would for myself, right?

Lily @ Date Brazen (50:52.204)

And there we have the growth edge. It is possible to grow your capacity for grace for yourself. That is what we’re doing here is really like even you giving yourself permission to shake just now. You didn’t shut down the opportunity for growth because of the fear. You didn’t shut down your opportunity for growth because of self judgment. You allowed yourself to try something new. It felt awkward and you felt better for it. And so even in doing that micro moment, you’re saying,

it’s actually normal to feel this way. It’s actually okay that I feel this way. It’s not a deal breaker. I’m not wrong for feeling this way. I’m just a human being who needs to shake or whatever it is. So this is about expanding your capacity to have grace with yourself as you do this thing.

Right.

Michelle Johnson (51:37.773)

Mm.

And if I were to hear what you want in your, in that vision at the, at the campsite, if I were to take what you want from the established relationship that you’ve cast for me of like what that looks and feels like, if I were to take the information that you shared with me about your future sex life with that person, when you’re in an established, safe environment, here’s what I would say you want. And you can toss any of this back if it doesn’t resonate, but I’m going to cut right to the chase.

your essence-based preferences sound like they are, yes, you want to feel adored, you want to feel cherished, you want to feel treasured and really safe with this person. You need them to have done emotional work. You need, it sounds like, you need them to be aware of their emotionality. Maybe they’ve gone to therapy. And that also means that they need to have language to self-describe, which means that anybody who doesn’t know how to describe themselves, at least a little bit, or

somewhat is a deal breaker on a dating app, on a date, somebody that is not asking you questions that are interesting is a deal breaker. Someone that is not doing equal emotional labor in a conversation is a deal breaker. So if we back up your EBPs, you could, if you gave yourself permission to fully want what you want using this session as an example of the breadth of like this person is emotionally mature, they are

groundedly confident They are excited to build a partnership with someone exactly like you they are looking for emotional safety, which means that they Listen, well, they ask follow-up questions The the vibe is very grounded. It’s not erratic or chaotic The vibe is right all of these things are in for all these pieces or information of your preferences that you can then use

Michelle Johnson (53:09.484)

Mm.

Lily @ Date Brazen (53:36.6)

to vet people on dating apps more easily, giving yourself permission to want what you want, giving yourself permission to be awkward if needed, or if you are, that’s fine, because you’re now doing the things you need to do to meet the right kind of people instead of being like, I don’t know, am I asking for too much? I don’t wanna be too picky. This is your one wild and precious life, so let’s go.

Yeah, I like that. Thoughts? wild and precious life. I love that.

This is Mary Oliver. Brilliant, beautiful.

I just, I, it just makes it so clear when you say it, I’ll like that. Like then it just feels, it’s like you’re giving me permission, but it’s just like giving permission to myself, right? To, yeah, go with my gut and listen to those things. And maybe that’s part of what causes those dating apps to be so much trouble because I’m fighting with my own, my own instincts that are saying, no, these are people for you. And I just keep trying to sit there and.

waffle on them and then I get all worked up.

Lily @ Date Brazen (54:43.65)

And you aren’t probably closing the stress cycle. You’re just sort of lingering there in self-punishment. When closing the stress cycle can look like shaking your body, can be like doing a stretch, going on a walk, calling a friend, doing a self-compassion meditation, taking three deep breaths even can really help to, we’ve done that too in this session. These are examples of how to tactically,

yeah.

Lily @ Date Brazen (55:10.894)

dating in a way that doesn’t rob you of your peace. Yeah. And it actually centers your desire for the right relationship instead of fearing that what you want doesn’t exist and judging yourself for being too picky. My thing about your fear about I’m too picky is who cares? So you want what you want. Who cares if somebody else would label it as picky? They’re not for you. Who cares? This is about you centering yourself this summer and beyond.

and beyond.

So what do you think you are from all of this? We’ve talked about so much. You’ve been so, so beautifully vulnerable and open with where you’re at. I think so many people are gonna resonate. I know they will. I resonate with your story. And I just hear that you’re on the cusp. You may have even stepped over the threshold today, I feel, but like, what do you think you’re taking away? What are you taking away from this session? And what do you think your best next step is?

Like you say, it’s been a lot, but I think I want to put in, I definitely wanna, I feel like a blinder came off in that I’m seeing how I had sneakily let a lot of negative self-talk and not very good self-compassion come in, especially in the area of dating and the dating app. So I definitely wanna catch myself when I’m putting all those self-judgments on myself. I definitely.

want to change that dialogue for sure. And even if it’s like you say saying, okay, I am awkward and naive. Like, so what? Like, I liked when you said that. Like, so what? That’s like valid. Like, look at my history. Look at my story. Yeah, like, so what? That’s okay. That’s… And so I really like that. So I’m definitely taking that away. I definitely, I feel like I’ve given…

Michelle Johnson (57:05.998)

I think I’m taking away renewed permission to listen to myself on the dating app and not worry about why I feel like that’s a person’s a no. They’re just a no, it’s okay, like move on. There’s just, yeah. I don’t know if I’m gonna jump right on the dating app, but I do like the idea of just doing joyful things for myself this summer. like that, but.

but maybe through the lens of being a little more, like, I mean, I’m trying to do the whole, you know, I think you’ve, I listened to one of your podcasts and it was like flirting in real life or whatever, but it’s the thank you more, thank you more please challenge, right? Like just the eye contact with someone or a smile or something. I, so I mean, I’m trying to be more intentional in that way, but maybe, maybe trying to be a little more steady with that this summer might be a good, as I’m doing.

things that are fun for myself.

Amazing. I love all of this, Michelle. And I would say, I want you to celebrate yourself more. So if you have somebody in your life who you can text celebrations to or micro wins to, want you to, the brain neuroplasticity loves micro wins, loves small wins. And so the more, and what you’re doing is changing your brain to be more compassionate towards yourself as the default.

to give yourself more permission to want what you want, to trust yourself more. So that change will happen by making small inflection point changes and then celebrating them because the brain loves small wins when it’s changing because otherwise it’s like, no, I don’t wanna change, I don’t wanna grow. You need to celebrate these micro moments. I really want you to celebrate the session afterward, writing yourself a celebration letter or.

Lily @ Date Brazen (58:57.944)

texting a friend, I just did something scary and I’m proud of myself. Like, that is awesome. Can you do that?

I am, I am going to text, I’m going to text my sissies after, be like, okay, I did a session on dating.

Amazing, amazing. So I think that getting on the dating app will be much easier once you have your complete essence-based preferences. So I would encourage you to finish that workbook if you haven’t already and re-listen to this for the words that I used, if they resonate, on like, groundedly confident, self-aware, emotionally mature.

like other pieces that help you feel safe, help you feel alive in the presence of someone. You can even use your friendships as sort of a blueprint of like what qualities did they have that make me feel safe in their presence? And how did I know that from the beginning to use as your vetting resource? Because I think you’ll overthink your decisions so much less when you have your essence-based preferences as the organizing principle of your love life.

I like that idea.

Lily @ Date Brazen (01:00:08.492)

So Michelle, I’m so excited for you. This is just the beginning. And I am honored to have been your coach in this session and I want to hear your updates. All right, Michelle, congratulations on a beautiful set, on a beautiful set of breakthroughs. I’m so excited for you. This is just the beginning.

That conversation with Michelle was so dang powerful. I loved every moment of it. I really appreciate how honest and vulnerable Michelle got with us. She named the fear that I know so many of you carried. I know I carried it when I was dating and felt like a total late bloomer. I’m fill in the blank age. I’m 35, 45, 55, 65. And I am not with the right person. Am I too late? Is it over?

And then I love how we got to unravel that story in real time so that she could be more compassionate to herself and start stepping into this new dating season powerfully and magnetically. I also think it’s really powerful that Michelle realized that she was speaking to herself so unkindly, like with so much pressure and behind, you’re behind energy. And I want you to think about where in your love life might you be going really hard on yourself because you’ve been taught

that to go hard on yourself is to excel, but really that mean teacher energy that you’re giving yourself is just slowing you down. It’s like muck in your wheels. Michelle realized that she deserves the same kindness that she extends her daughters, the same compassion that she speaks to them with. She is precious, you are precious, and you deserve that love and compassion too. This is your call to action to stop settling.

Even if you’re sure that you won’t settle for the wrong relationship, it’s time to stop settling for a miserable feeling dating life. It’s time to stop settling for self-talk that feels punishing. This is our one wild and precious life, in the words of Mary Oliver. Like, your dating life matters to your overall wellbeing because it’s a microcosm of every hope, joy, dream, fear, insecurity, desire that you have as a human being. It matters to your wellbeing. And so stop talking to yourself like…

Lily @ Date Brazen (01:02:15.666)

You are the villain in your own story. You’re the answer to getting what you want, right? I’m sure you’ve seen that in other areas of your life. And now it’s just time to apply a more self-compassionate framework to how you speak to yourself, how you move forward so that you can build that resilience and decrease stress to move forward toward that which is highest for you faster. Michelle has sent us an update. So let’s go listen to what happened after our session.

Just doing little follow up from our session a week and a half ago. I didn’t want to do it too soon. I wanted to kind of give myself time to think through some of the things we talked about. I think my biggest takeaways in the last little bit was to have more self-compassion, especially around the dating areas where I was feeling really judgmental on myself for being so triggered.

in different areas. And so I’m really thankful that I’m just being more curious about why I’m being triggered and not being so judgmental around that. So I’m really happy about that. And I think another thing I took away was just that permission to be picky and want what I want. And so that led me to actually completing the essence based preferences thing that I had started, but it never finished. So I was able to kind of go in and

really think on those things a little bit more and give myself permission to, yeah, want what I want. And I think I just feel really proud of myself for also just looking for some ways to be really intentional about finding some things that bring me joy and hopefully to get out of my house a little more and meet some people. And so I’ve just been kind of trying to put myself out there a little more and just talk to people, not for dating reasons, but just for joy reasons.

Yeah, I appreciate the encouragement and I really enjoyed meeting you and thanks for that opportunity.

Lily @ Date Brazen (01:04:16.268)

If you resonated with this episode, please let me know by screenshotting it and sharing it on Instagram and tagging me at datebrazen. I would love to hear from you. My DMs are always open and it’s a delight to get your DMs and to connect with you. If you’ve been feeling anxious and overwhelmed with your dating life, if you’ve been feeling like a late bloomer and that behind pressure and maybe some shame has been keeping you really stuck, that’s exactly why I created my program, Main Character Dating, which is open for enrollment, right?

Now you can check the link in the description of the episode for the link to join us or just go to datebrazen.com. Inside of this program, you’re going to learn how to attract the right partner with a joyful as fuck dating life, making the right partnership inevitable with a joyful dating life. This program has worked for over 400 clients around the world and next it’s your turn. So again, go to the link in the description of this episode or go to datebrazen.com to learn more and join us. I cannot wait to see you inside.

And I’ll talk to you next week. Bye.

And be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back.