Becca came into this coaching session feeling stuck, frustrated, and deeply alone in her experience:

“I’m 37. I’ve never had a relationship. It feels like I’m missing something that everyone else figured out.”

This episode is for the late bloomer who’s never really seen their story reflected in dating advice—and is tired of wondering, “What’s wrong with me?”

Together, we worked through:

– The fear that it’s too late to have what you want

– How to shift from self-blame to self-trust (without pretending it doesn’t still hurt)

– The exact first step to start dating from your real power

Becca left with a new plan—and a very different energy.

If you’ve ever thought “Maybe it’s never going to happen,” I want you to listen to this one.

🎧 The Late Bloomer Show, episode 250. Available now wherever you get your podcasts.

💥 Want more support? Start here:

→ Main Character Dating: datebrazen.com/waitlist

→ Free Essence-Based Preferences workbook: datebrazen.com/workbook

→ Read Thank You More Please: datebrazen.com/book

Follow Lily everywhere:
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📺 YouTube Channel

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Show transcript:

Lily @ Date Brazen (00:00)

Hey gorgeous friends, welcome to another episode of The Late Bloomer Show. I’m so glad that you’re here. Today I’m talking and coaching with Becca. Becca feels like a late bloomer. She’s 37. She hasn’t had a long-term relationship yet. And inside this episode, we uncover the deep fear that is underneath the surface that she’s been sort of pushing away for a while. And we talk about how to heal that fear in an unconventional way. We also talk about how to apply more playfulness to her dating strategy, to make it feel more joyful, to make her feel more connective. She identifies as more of a shy, introverted person. And so in this episode, we talk about how to navigate that when wanting to date and put yourself out there. It’s a really great coaching session. And I know that you will resonate with Becca and her story. So with that, let’s get into the episode.

Lily @ Date Brazen (01:32)

Hello, Becca. Welcome.

Becca (01:35)

Thank you.

Lily @ Date Brazen (01:36)

How are you feeling about this conversation, this session?

Becca (01:40)

Not really sure what to expect, but I’m looking forward to it.

Lily @ Date Brazen (01:43)

Okay. Awesome. So I’m asking all of the folks who I’m doing live coaching sessions with for the podcast: what is your brag—a celebration of some kind, could be on anything big or small—and your intention for this session. What do you desire to get out of this session, ideally?

Becca (02:02)

Does the brag need to be about my love life or just anything?

Lily @ Date Brazen (02:06)

It can be about literally anything.

Becca (02:08)

I started doing keto like a month ago.

Lily @ Date Brazen (02:12)

How’s it feeling?

Becca (02:12)

Good.

Lily @ Date Brazen (02:14)

Cool. I love feeling good.

What is your desire or intention for this session?

Becca (02:19)

I guess just to get like maybe a different perspective or different ideas about how to go about things.

Lily @ Date Brazen (02:26)

Okay, cool. So tell me about you. Is it okay if I read a little bit from your application?

So you shared that you’ve never been in a long-term relationship and you don’t know how to begin to get one. And that it’s been a huge ego suck.

Can you tell me about what’s been going on? How are you doing? Give me an update on your love life.

Becca (02:50)

I’m more of like an introvert and a shy person. So I have trouble initiating conversations with anyone. I don’t really get approached either. So it’s kind of just been stuff through the apps mostly.

Lily @ Date Brazen (03:06)

Okay. And you shared in your application that you have, quote, “given up on apps.”

Becca (03:14)

Yeah, for the most part, yeah.

Lily @ Date Brazen (03:17)

And that’s totally fine. It just might mean like, we need to beef up your IRL strategy and work on some confidence building around approaching people. Like, all of this is figure-outable. But I want to know, what has it been like? Have you been in any, like, a couple date situations or have you had any situationships? Tell me about your experience.

Becca (03:41)

I’ve had a couple relationships that lasted like six weeks to two months. Somewhere in there, yeah.

Lily @ Date Brazen (03:48)

Mm-hmm. Yeah. What do you notice about those relationships that are up to two months? Any connective tissue?

Becca (03:59)

One of them I worked in the same field as the person, so that was probably helpful.

Lily @ Date Brazen (04:05)

Okay. And was there a connective tissue between why those new relationships ended? Was there a similar theme there?

Becca (04:16)

No.

Lily @ Date Brazen (04:17)

That’s fine. Great. Is there one that sticks out to you? Like someone that got away or someone that was really meaningful to you—maybe that you’ve been thinking about more often—or is it more like it doesn’t feel like anybody in your past has met the mark? Tell me about that.

Becca (04:17)

No. Yeah. Well, I met someone organically last year, like IRL. We weren’t a good match, but just the difference between that and the apps really stood out to me.

Lily @ Date Brazen (04:48)

Yeah. I want to touch down on what’s going on for you right now. How are you feeling?

Becca (04:55)

I’m okay. This is just… I don’t talk about it a lot.

Lily @ Date Brazen (04:59)

Yeah. What is it like for you to be honest—like, to be talking right now about it?

Becca (05:04)

It’s weird, but it’s good.

Lily @ Date Brazen (05:06)

I know you probably know this, but you can take anything that you need. Like, if you needed to step away and take a break or whatever, you tell me what you need in this time. Because it’s really normal to have big feelings about this, because you care about this and you want something and it’s not here yet.

So tell me, in thinking about doing this episode and doing this conversation and having this session, what has been on your mind to ask or get perspective on, as you shared at the beginning?

Becca (05:41)

Build a strategy for meeting people in person.

Lily @ Date Brazen (05:45)

Okay. If you wouldn’t mind sharing, what is the sort of geography of your brain on this subject? So when I’m sitting here asking you questions, what’s going on in your brain? Any fears or doubts pop up that feel familiar?

Becca (06:03)

I guess just the… nothing will change.

Lily @ Date Brazen (06:08)

I sensed that fear, and I don’t think it will be effective to not look at it before we talk about the strategy.

Yeah, how do you relate to that fear that nothing’s going to change or that doubt?

Becca (06:26)

I mean, it’s been true so far, so…

Lily @ Date Brazen (06:32)

So it feels like undeniable.

Then why—I’m just curious, and there’s no judgment either way—then why apply for this and talk to me? Tell me about that.

Becca (06:44)

I don’t really get input. I just try to figure it out on my own.

Lily @ Date Brazen (06:46)

Mmmmm. Yeah.

You shared in your application: this affects my confidence because I’m embarrassed to talk about my personal life. Luckily, I have friends who don’t judge me, but I do feel like there are things they can’t talk to me about and vice versa. So do you talk to anybody in your life about this?

Becca (07:07)

I have a girlfriend I talk to a little bit about it. Just like, how should I deal with this particular situation?

Lily @ Date Brazen (07:16)

And how often would you say you’re talking about your love life with that friend?

Becca (07:23)

Not very often.

Lily @ Date Brazen (07:25)

So this is new.

Becca (07:27)

Yes.

Lily @ Date Brazen (16:18)

Self-compassion. So what I’m hearing right now and what I’m seeing in your body is that there’s maybe some stress. Does this feel stressful talking about this?

Becca (16:28)

Yeah. Yeah.

Lily @ Date Brazen (16:29)

Yeah, normal. So normal. Cortisol is high, you know, stress is happening. Cortisol, stress, tough.

Also, I would imagine because you’re saying like, I tried dating, I stopped, it doesn’t seem like anything’s gonna change. Your resilience is kind of low right now. Because it feels like, I’ve tried… I’m hearing, maybe it feels like I’ve tried everything and nothing has worked. And maybe that means nothing will work.

So the good news about self-compassion is that in a 2014 study out of Stanford, it found that a regular self-compassion practice—like brushing your teeth, that kind of regularity—decreases cortisol and increases resilience. So instead of shoving that fear into a closet, or instead of trying to avoid the fear that you have that nothing will ever happen, I think it would actually serve you to take a really big deep breath and to practice self-compassion right now. Are you willing to do that with me?

Okay, so I’m going to ask you to take a really big deep breath, eyes closed. I’m not looking at you, I’m going to close my eyes with you. So we’re going to do five beats in, hold at the top for three, ten beats out. We’re going to do it two times. Five beats in, hold at the top for three, ten beats out. I’m going to count with you.

Breathe out all your air and breathe in… two, three, four, five. Hold… two, three. Exhale… two, three, four, five, six, seven, eight, nine.

Last one. Inhale… two, three, four, five. Hold… two, three. Exhale… two, three, four, five, six, seven, eight, nine, ten.

As much as you can, breathe into any tension in your body—whether that be in your forehead, your jaw, your shoulders, your butt, your hips. Breathe into any tension and release it as much as you can.

And come on back to the room so we can do a little self-compassion TLC. There are three steps to self-compassion as defined by Dr. Kristin Neff. Step one is kindness over judgment.

So if we took one of the stickiest, scariest thoughts that you have about your dating life—for example, nothing will change—and we use that to model self-compassion in response to… how do you usually respond without self-compassion to this thought, nothing will change? Do you shove it into a corner, or do you say like, it will, and it doesn’t feel true? What happens?

Becca (18:59)

Okay. Yeah. I think I probably just shove it into a corner.

Lily @ Date Brazen (19:25)

Yeah. So I’m going to ask that we open the… we sort of dust off the corner and we gently reorient ourselves to just be with this fear for two minutes. We’re going to be with this fear. Know that it’s always safe to… My hunch is it does not feel emotionally safe to look at this fear right now. So I want to remind you of your resources—your breath. You can always say, I need to take a break.

Becca (19:53)

Okay.

Lily @ Date Brazen (19:53)

You can always turn off your video, take a deep breath. So we’re just gonna, with emotional safety, look at this fear together. I’m here with you.

Becca (20:02)

Okay.

Lily @ Date Brazen (20:04)

So what might kindness say to this fear, this version of you who is deeply afraid?

Becca (20:16)

You don’t know that?

Lily @ Date Brazen (20:19)

Maybe. Maybe. Here’s what I’m surmising: it’s very easy to try to go to the opposite, to try to go to the more positive thought because you want to believe something positive. It’s good to feel good. But you don’t yet.

Becca (20:33)

Yeah. Great.

Lily @ Date Brazen (20:36)

It’s like, we need to work with what is right now before we go to what you hope is true, okay? So we’re looking at this with emotional safety. It’s very similar to a kid on the playground who had a social rejection. Their friend told them, you can’t play with us, and they’re crying on the playground. And there’s a teacher who comes over and looks over the kid and says, What’s wrong? What happened? That’s not true. It’s not true that you were rejected. It’s fine. It’s fine. Go. You’re fine. Go play.

That child might feel more rejected because that teacher didn’t affirm that it hurts. Whereas the other teacher comes and gets on the kid’s level, gets on their knees, says, What happened? I’m so sorry. That’s really hard. Do you need a hug? Gives the child a hug. And the vibe is, I’ll be here as long as you need me to be. And then inevitably what happens? Decreased stress, increased resilience. That child is more likely to go play quicker because of that kindness that they received in a hard moment.

We’re doing the same for you. So once again, what might kindness say to this fear?

Becca (21:54)

It must be really hard to feel that way.

Lily @ Date Brazen (22:01)

Of course I don’t want to look at this fear. This is really painful. This is not frivolous, this is hard. I’m not wrong for feeling this way. It doesn’t make a feeling true, but I’m not wrong.

Because what I’m sensing is that you’re making yourself wrong for still being single and you’re making yourself wrong for having this fear that nothing will change.

So what if you just didn’t make yourself wrong here? It’s okay to have this fear. It’s like a human function. Doesn’t make it true, makes it like a bodily function—like poop.

Becca (22:37)

Yeah, right.

Lily @ Date Brazen (22:39)

How is this feeling, this kind portion of self-compassion? Again, there are three steps. We’re gonna get to each of them, but how is the kindness feeling?

Becca (22:47)

I mean, it feels good. It’s something I do a lot at work. It’s just a matter of like turning it on myself too.

Lily @ Date Brazen (22:57)

Exactly. Exactly, Becca. Do you like what you do?

Becca (23:03)

Yeah, I do.

Lily @ Date Brazen (23:04)

Yeah. Do you feel good at what you do?

Becca (23:07)

I just started, so I’m not… well, it’s been like two years, but I’m getting there. I’m good at parts of it and I’m learning about the other parts.

Lily @ Date Brazen (23:08)

Congrats. Yeah. When you feel in flow, like, my God, this is a great moment at my job, do you imagine, like, does it feel like there’s a light in the room? Or do you feel like when you’re in flow, when you’re in a moment of like, wow, I’m doing really well… what I’m imagining is that there’s like a light that is connecting you and this other person when you’re talking and you’re connecting and you’re having a great moment where you feel…

Becca (23:34)

Thank—

Lily @ Date Brazen (23:43)

…aligned with your value. You feel like you’re adding value to this moment. I want you to imagine that warm light that you are shining on other people in these moments where you’re holding beautiful space. I want you to shine it on yourself and literally imagine this moment where you’re in flow, things are going well. Imagine that light, that beam of light is coming back on you.

You need to give yourself the same energy that you so generously give others. I’m getting bossy because I want you to really own that you do a good job and that now you get to shine it on yourself. So kindness: giving yourself that energy you give other people all the time.

Great. Let’s move on to the second step of self-compassion.

Becca (24:13)

Yeah.

Lily @ Date Brazen (24:30)

This episode is brought to you by my upcoming live training called Three Steps to Attract the Right Partner as a Late Bloomer. Inside this room, I’m going to help you release any of the shame or stigma that you’re carrying around being a quote late bloomer.

You’re going to get a feminist dating detox so you can release any of the old-fashioned or patriarchal dating rules that have been keeping you playing small, shrinking yourself, settling again and again. And you’re going to get my Matchmaker Protocol so that you can start dating effectively, vetting people quickly with confidence instead of self-doubt.

Finally, in this free training, you’re going to learn my Main Character Dating Strategy—what you need to do online and in person as a late bloomer to start putting yourself out there and attracting better matches, better dates than you thought possible, as quickly as within the next month.

So go to datebrazen.com/lets-go to sign up for this free live training coming up on October 7th. Again, that’s datebrazen.com/lets-go to sign up for this free training. You’ve got this and I’ve got your back. Now let’s get back to the episode.

Lily @ Date Brazen (25:38)

Common humanity over isolation. This is something that I see you’re really struggling with, which is the feeling of being alone.

So self-compassion is here to remind you that you are a part of a collective. That you’re… it’s, I’m not alone in this moment. A lot of people feel this way.

I had an interview with another person who felt this exact same way a couple hours ago. You’re literally not alone.

Can you offer that to yourself? What might that sound like?

Becca (26:08)

Yeah. Reminding myself that just because I don’t see other people struggling with it doesn’t mean that they aren’t.

Lily @ Date Brazen (26:16)

Yeah. Yeah.

I created this podcast because I wanted people to understand that they weren’t alone.

And so you can just imagine the thousands of people who listen to this podcast—or, I don’t want to freak you out now because we’re talking on the podcast and you know people listen—but I think like imagining the people that are nodding.

Becca (26:40)

Yeah.

Lily @ Date Brazen (26:45)

…And thinking, What courage Becca has to share something that I’ve been thinking alone in my room for years.

You’re not alone. So that’s the second step in self-compassion. What’s coming up for you right now?

Becca (26:58)

I do tend to get stuck in thinking that, or like counting all the people around me who are in relationships and being like, and then there’s me. So, sort of changing that thought pattern.

Lily @ Date Brazen (27:13)

Absolutely. And not in a way of like, I’m wrong. Like you could… this could be a moment where you own the need to make more single friends. It could be a moment where you recognize, I want to be talking to people who are in a similar place as me more, to bring more belonging into my life. You can change that. That’s figure-outable.

But I also think that it’s a really common experience to be like the quote only single friend left. That’s a really common experience. It’s one of the many reasons that I have a job—because people feel so isolated. And isolation begets isolation. Shame breeds in isolation.

And so what we’ve got to do is bring it into the light, which is what we’re doing right now. Number one: kindness over judgment—you’re sitting beside yourself on a park bench offering yourself what a close friend would offer you. Number two: common humanity over isolation. Number three: mindfulness over over-identification.

Over-identification, for those that don’t know (maybe you know), is when you’re having a thought and you identify with that thought as a truth about you. Or it’s a thought that you don’t want to have, but you’re like, well, this is the truth because I’ve practiced it a billion times. It feels like a belief at this point. There’s no changing it. It is over. Nothing’s going to happen. And it’s a self-protective mechanism.

But mindfulness says, I’m having a thought that is really hard, instead of shit, I’m having a thought. Better not have that thought because if I do then I’m cursed.

Becca (28:49)

Mm-hmm.

Lily @ Date Brazen (28:58)

Does this resonate?

Becca (29:00)

Yeah, it does. Sort of the idea of taking that thought out of the story you tell yourself about yourself.

Lily @ Date Brazen (29:07)

Yeah. Really just like being curious about it and kind toward it as a squishy human trying to be safe, coping mechanism.

Very similar to the thought like, You haven’t… What’s a good analogy? For people that are struggling to find a job, for example: the thought, I should never apply to those jobs because I’m not qualified. I’m never gonna get them. I should just apply to jobs that I’ve gotten before—at the level that I’ve gotten before. I shouldn’t try because that’s too vulnerable. If they reject me, then that’ll make it true that I’m a fool. I shouldn’t be trying harder. I shouldn’t be reaching for something different. I should just keep it, right? Those thoughts.

If left unchecked, they’ll keep that person in a spiral of hiding.

It’s much more vulnerable to try. It’s much more vulnerable to acknowledge: That’s a thought, not a fact. Let me open up to possibility. It might be true that I haven’t experienced everything yet. It might be true that I’m not dead yet and therefore I don’t know what’s going to happen next.

How is this landing?

Becca (30:24)

It makes sense. And it’s something that I’ve heard in yoga class before. There’s a part of your mind that’s noticing the thought. So then your mind must not be the whole thought.

Lily @ Date Brazen (30:39)

Yeah. I am not my thoughts is a really cool mantra to integrate into your week this week. I am not my thoughts.

I have thoughts. Sometimes they’re fun thoughts, sometimes they’re shitty thoughts.

And the more you practice self-compassion, the more accessible positive thoughts will be. This is not about never trying to integrate positive beliefs about yourself—in fact, quite the opposite. Self-compassion is about accessibility.

With trying to replace the negative thought with a positive one, what I surmise is that you (and so many other people, myself included sometimes) are just trying to jump over a fence without a ladder. You need a ladder to make the jumping over the fence accessible. The ladder is the self-compassion. It’s the baby step reframe.

Instead of being like, I’m a failure because I’m having this thought and even the positive thoughts that I try don’t stick, it’s like, well, then you got to make it more accessible.

How’s this landing? What’s coming up for you?

Becca (31:57)

There has been a lot of like just trying to change the thought by force.

Lily @ Date Brazen (32:03)

Yes. Yes. And that’s not, no. That little version of yourself who just is in pain and wants something that’s not here, like that younger version who felt rejected for the first time or who felt unworthy for the first time, that little version of you who first felt that way is crying out for your support and love and understanding.

Becca (32:04)

And it’s not really changing.

Yeah.

Lily @ Date Brazen (32:27)

So this is bringing belonging to yourself instead of shoving a part of you into a corner who is afraid.

So knowing all of this, knowing that we’ve laid this bedrock of self-compassion—which I talk about all the freaking time—how might you be curious about what’s next in your dating life with this model of self-compassion in your toolkit?

Becca (32:51)

Just starting to look at my beliefs and tweak them a little bit.

Lily @ Date Brazen (32:55)

Yeah. Yeah. I think like throwing the blanket of self-compassion is practice. I dare you to do it once a day for five to 10 minutes a day this week. I dare you. ⁓ Self-compassion.org, Dr. Kristin Neff’s website, has some great resources and free meditations. But I give, you know, I tell everybody like these are great, great resources. I have a couple of very tactical—

Becca (33:01)

Yeah.

Okay.

Lily @ Date Brazen (33:26)

—recommendations for you and questions for you.

Have you owned your preferences? Like have you done any of that essence-based preference work that I talk about? Do you know about that? Tell me.

Becca (33:38)

I know about that and ⁓ I know what I want. Yeah.

Lily @ Date Brazen (33:43)

Okay, cool. What do you want? Tell me about it.

Becca (33:46)

I want someone who’s like funny and playful.

Yeah. Someone—

Lily @ Date Brazen (33:54)

Love it. Anything else? What else? What does that mean to you?

Becca (34:00)

It doesn’t mean that they have to be seeking higher education all the time, but just be interested in learning new things and taking in new information.

Lily @ Date Brazen (34:08)

Mm-hmm. Cool. How would you know that somebody is curious in the way that you desire?

Becca (34:16)

You know, if they’re actively studying something, whether it’s like, you know, trying to figure out a better workout routine or learning more about Palestine.

Also like being curious about other people. So if they’re in conversation, they’re like, “Tell me more about that. What is that like?”

Lily @ Date Brazen (34:36)

Yeah, I’m hearing empathy too. Somebody who’s really empathetic and like cares about the world and cares about what’s happening in it. Tell me about how you know if someone’s playful in the way that you want.

Becca (34:39)

Yeah. I think that they’re willing to be silly and make jokes and kind of banter.

Lily @ Date Brazen (34:56)

Yeah, what kind of silly? Like what comedians, podcasts, TV shows sort of exemplify this level of silly that you’re looking for?

Becca (35:04)

I think Pete Holmes is a comedian I really like.

I binged the Ted Lasso show a while ago.

Lily @ Date Brazen (35:13)

Are you religious at all or spiritual?

Becca (35:16)

I mean, a little bit. I do like a yoga practice and I’m sort of learning more about the spiritual part of that. Yeah.

Lily @ Date Brazen (35:23)

Yeah, cool. Just, Pete Holmes—I know him from when I was in sort of the… I learned about him and his religious background because I grew up religious as well. So I think Pete is so great.

Ted Lasso also is this like deeply—to me—has this spiritual feeling of like this community, this love, this like the opposite of toxic masculinity, just like such cool—

Becca (35:48)

Yeah.

Lily @ Date Brazen (35:50)

—storytelling that is grounded in relational health as a concept.

Becca (35:56)

Yeah. Well, and I like that both of them sort of like easily transition between like silly and serious.

Lily @ Date Brazen (36:05)

Yes, silly and serious. Like there are moments where it’s like, that’s ridiculous and hilarious, and moments it’s like, I’m in tears. So I would imagine you want that sort of fluidity of conversation.

Becca (36:13)

Yeah. Yes. Yeah.

Lily @ Date Brazen (36:21)

…on a date, in a conversation. Amazing. Okay. So learning more, curiosity, empathy. I would also imagine—I’m guessing—you know, somebody who is… what kind of values do they have? Progressive values? Tell me. Progressive? Yeah, let’s own that. Yeah. You mentioned Palestine. So I’m just going to assume like progressive values that embody—

Becca (36:35)

Progressive, like very progressive. Yeah.

Lily @ Date Brazen (36:46)

—a way of thinking about the world and a way of wanting to care about others, micro and macro.

Becca (36:53)

Yes. Yeah.

Lily @ Date Brazen (36:53)

Does that make sense? Okay.

How are you feeling as we talk about this? You seem different.

Becca (36:59)

Good. I mean, it’s more fun to talk about the things that you want, you’re excited about.

Lily @ Date Brazen (37:05)

Yeah, I’m excited to hear that you… I’m excited to hear you giving yourself permission to go there. Because we can do both. We can talk about the fear and acknowledge it and like hold space for it. And then I hope you felt—and I don’t know, I know you, like, I want to hear more from you. I want to like, I want to know everything in your brain. But what I’m hearing is that this might feel a little more accessible because we did the self-compassion practice to care for the fear. Does that resonate or no?

Becca (37:35)

I think it’s partly that and partly that I’ve already, I’ve already done this work and figured this part out. So this is just like an easy answer.

Lily @ Date Brazen (37:43)

Okay, an easy answer. Okay, great. Okay, so when you’re talking about vetting people, you said that you might be not giving enough people a chance or you’re sort of cutting things off before they progress. Tell me about that.

Becca (37:49)

Just coming up with any excuse to not get to know someone better or…

Lily @ Date Brazen (38:06)

Yeah. What’s the latest excuse that you can recall that you gave?

Becca (38:10)

I don’t want to date someone I work with.

Lily @ Date Brazen (38:13)

Okay. How closely are you working with somebody?

Becca (38:14)

Not that closely, but… I mean, I started a new job a couple of months ago, so just deciding that everyone at the job is off-limits is sort of… reductive. Prohibitive. Yeah.

Lily @ Date Brazen (38:31)

Potentially, yeah. Depending on your workplace dynamics and policies, you might be onto something in terms of like, “don’t need to do that.” Or it might be like, “I work at this giant place. I don’t have to limit myself that way.” Thoughts?

Becca (38:46)

I mean, I think I’ve used it to not really get to know much of anyone.

Lily @ Date Brazen (38:51)

Okay, there we are.

Becca (38:54)

Yeah.

Lily @ Date Brazen (38:55)

Becca, I think this is a greater call to action, which is a “get to know people” challenge.

Becca (39:01)

Pfft.

Lily @ Date Brazen (39:08)

What if you—I would imagine you enjoy learning more, because what people want in their essence-based preferences are generally what they like to give or want to give ideally in their day-to-day life. So what I’m hearing is that you currently have a gap between what you value, what you want, and what you are giving out in the world because of fear.

So that’s actually a really easy fix. Which is that you need to give more of this learning, more curious empathy, being willing to be silly a little bit with new people—Ted Lasso energy—giving a little bit more of that and being willing to receive it in return.

Becca (40:02)

Definitely.

Lily @ Date Brazen (40:03)

Yeah, so when you said at the beginning, “don’t get approached,” I actually wonder if practicing this level of openness that still feels emotionally safe for you will allow you to be approached in the near future.

Becca (40:16)

I mean, it’s very possible.

Lily @ Date Brazen (40:18)

I think it’s probable. What will help you get over the hump of trying this level of openness?

Becca (40:28)

I think just trying little bits. Like not necessarily with the goal of dating anyone, but just getting more comfortable talking so that when I do meet someone I want to approach or be approached by, I know what to do.

Lily @ Date Brazen (40:43)

100%. I don’t even think you need dating apps right now. I think you need to spend a month doing a connection challenge. I want you to write down 10 dares that you have for yourself around connecting—with coworkers, connecting with friends, connecting with new friends, connecting with people that you’ve met tangentially but you want to get to know more. 10 dares.

Including things like: asking somebody on a coffee date at work that I really like, that I could see being friends with; asking a friend for a phone call when I normally would feel like a burden, but I’m gonna actually reach out and ask for a connection call to vent or to laugh or to be playful together, whatever.

Does that feel doable? 10 dares around connecting and openness. Does this feel scary, or how does this feel?

Becca (41:41)

I mean, it’s a little scary, but I think that means I need to do it.

Lily @ Date Brazen (41:45)

I think you need to do it. And I want you every time you do something connective—when you go for connection instead of isolation—I want you to say to yourself, thank you, more please. Thank you, more please. Connection versus isolation. I am building a life that I love. I am learning how to receive more joy, more connection on every level.

That’s the thought that I want you to work on: I’m learning how to receive more joy and connection at every level, including dating.

Because I don’t want you to shut off from opportunity because of the ego suck that you’ve experienced in the past. This is a new moment. You’re learning something new. You’re learning how to date. If we apply this skillset that you’re going to build over the next month with this dares challenge to your dating life, what kind of version of yourself will you be if you’re just more comfortable giving and receiving affection, attention, connection?

Becca (42:44)

Yeah.

Lily @ Date Brazen (42:43)

What do you think?

Becca (42:45)

I think that’s something that I would want to, and that will help my dating life too.

Lily @ Date Brazen (42:52)

Do you have a therapist?

Becca (42:55)

Not at the moment, I’m gonna try looking again.

Lily @ Date Brazen (42:59)

Okay. The fear thing—looking at that fear—would be a really positive thing to get ongoing support around. But in the meantime, self-compassion. I challenge you to do a daily five-minute self-compassion practice with a meditation or a self-compassion journaling exercise. You can find them online. I really think that practice will help you get more in the light.

Instead of staying isolated, you deserve to be in belonging right now with yourself and others. That’s why I’m really excited for you. Like, I think we identified that—you said it’s constant work to not let the negativity of missing out make me feel inferior. Okay. Hello, default thought. Hello, old coping mechanism. And now I’m going to try something different. I’m going to try connecting with people proactively and see what happens, and say thank you, more please when I do.

And then in terms of like, “When am I going to meet my partner?” I do know that you don’t know what’s going to happen. I do know that there are relationships that you don’t know will exist in your life yet. And I do know that when you show up with this level of self-compassion, self-trust, massive messy action—which I call main character energy—those three things: permission, self-trust, massive messy action—when you show up with those things and try imperfectly, you make the right relationship inevitable.

Becca (44:06)

Yeah. Okay.

Lily @ Date Brazen (44:30)

So this is just the beginning. I think this month-long connection challenge, then I want you to dive into Thank You, More Please for sure and use those strategy pieces to reignite your online dating life with more boundaries and more connection.

Yeah. What are your thoughts? How are you feeling?

Becca (44:49)

I guess I’m just wondering how to do the online dating with more connection.

Lily @ Date Brazen (44:56)

You first put more of yourself in your profile and more of your preferences in your profile. And this is all in the book, so you’ve got that resource. Chapter six is the online dating piece. You put more of yourself in your profile. So I give exact examples in the book of how to take something that’s maybe a little more surface level or a little more safe…

Becca (44:59)

Okay.

Lily @ Date Brazen (45:19)

…into something deeper that exemplifies the playful energy that you want, that talks about how much you love Ted Lasso and why. That helps you show people who you are more in your profile. Then you swipe with your boundaries and you bless and release anybody that doesn’t have a profile filled out, who you don’t have any curiosity for. You, without mind drama, bless and release them.

But then in conversations, your goal is to get to know new people and allow them to get to know you too. And then from there, go on some “fuck-around dates” to have more fun in your love life.

So this is like taking it from “Do I need to do this? This all feels terrible” to “Let’s be more playful. Let’s use your own values and your own desires in your dating strategy to make this whole thing more playful.”

Becca (45:59)

Okay.

Lily @ Date Brazen (46:13)

Does that make sense? Does this feel distinct from what you were doing before? Does it feel similar to what you were doing before?

Becca (46:14)

Yes. Yeah. Well, I think the idea of like taking a break with goals while I’m taking the break, instead of just taking a break and going back to the same thing. This is—yeah.

Lily @ Date Brazen (46:32)

100%, yeah. So this is taking an intentional pause to do more connection in your life. Then in a month, put a calendar invite—in a month you’re gonna have read chapter six in Thank You, More Please. You’re gonna have your dating app of choice. I recommend Hinge or Bumble just to start with.

And then I recommend you look at your dating profile and really take it through the rubric that I put in the book, of like: does this showcase my preferences? Does this showcase my joy? Does this showcase what I’m looking for?

Becca (47:09)

Okay.

Lily @ Date Brazen (47:09)

And then from there, it’s about doing self-compassion through the process so you don’t get stuck in the fear as often. And connecting with people more freely. Blessing and releasing more freely the people who are not co-creating the conversation. That’s how you do dating apps more effectively and with more joy. And the connection challenge is stretching your in-person dating muscles.

Becca (47:35)

Sounds like a plan.

Lily @ Date Brazen (47:37)

Yeah. How are you feeling after this session, if you were to compare to an hour ago?

Becca (47:42)

Better. Feels like I have a plan.

Lily @ Date Brazen (47:47)

Great, I’m excited. You do have a plan and this is just the beginning. Who are you gonna reach out to to connect with after this session? Is there anybody in your life you can talk to?

Becca (47:58)

I could talk to my friend.

Lily @ Date Brazen (48:00)

Yeah, what might you say to them if you were sending a text?

Becca (48:08)

Like, “Guess what I just did?”

Lily @ Date Brazen (48:11)

Yes, I love that. You need to celebrate this. This is really courageous and exciting and like, this is not over.

You’re not over. What you want isn’t over. You’re just going to learn some new skills.

So I want you, even in this moment, challenging you to connect, challenging you to reach out, say “Guess what I did,” so that you can bring belonging to this conversation after we get off the phone.

Does this feel complete for now, Becca?

Okay, great. Do you feel like you got perspective—your original intention?

Okay, great. Well, it’s been an honor talking to you, and thank you so much for being honest and sharing your story with us and with me. And I’ll talk to you soon.

Becca (49:00)

Okay, thank you.

Lily @ Date Brazen (49:03)

Thank you, Becca, for sharing your story and for being so vulnerable and honest with us. I know that so many people resonate with where you’re coming from, what you’ve been through, and I hope that they feel inspired by how you’re showing up differently—for yourself, for your connectivity, for your joy, and for what you ultimately desire, which is deeper relationships with the right friendships and the right partner eventually as well.

I’m so grateful that she decided to join us. And now let’s get a quick update from Becca after this session.

Be sure to subscribe to The Late Bloomer Show everywhere you get your podcasts and leave a review if you feel that it really helps the show get into more hands. Five-star reviews are always welcome. I love doing this podcast for you. It is such a joy. I built this space for you. I hope you feel that and you belong here. So let’s keep it going.

I’ll talk to you next week.