“I’ve never had a relationship last a year. It feels like I missed my window.”

That’s what Jennifer told me at the start of this session.

She felt behind. Like it was too late to have the love story she wants. Like she had somehow run out of time.

And if you’ve ever looked around and thought, Everyone else got the memo on how to do this. I didn’t, this episode is going to speak directly to you.

Together, we work through:

– The fear that your best love story is already off the table

– The weight of “Nobody picks me”

– What happens when old thoughts make new dating hope feel impossible

– How to use the SOFT method to feel your feelings and rewire your beliefs, without bypassing the hard stuff

By the end, Jennifer says:

“It’s not over. I’m worth it.”

And she means it.

🎧 If you’re a late bloomer who’s still hoping it’s not too late, press play now.

💥 Ready for 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’s episode is a really special one with Jennifer. Jennifer comes on with a lot of late bloomer anxiety that we are going to talk all the way through. And I just want you to know, if you feel behind—like simultaneously your life is over and that it’s not begun because you haven’t met the right person—then you’re going to really resonate with today’s coaching session and episode with Jennifer.

Jennifer and I talk about what happens when you feel behind all of your peers, how to start dating amidst life turmoil, and figuring out big things in life alongside dating.

And I want you to know, if you resonate with this episode, that you’re not alone, that this isn’t over, and that more is possible than you currently realize. And it’s okay if you have hard, negative thoughts in the process—that’s just human of you. And in this episode, I give you a really tactical coaching strategy to move through hard feelings, hard thoughts, without making them facts, so that you can come into more empowered dating strategy, more empowered self-concept, more agency in your life and love life.

So, get into the episode.

Lily (01:17)

Jennifer, welcome.

So glad you’re here.

Jennifer (01:21)

I’m glad to be here.

Lily (01:23)

This is how we start every coaching session on the podcast. I would love to know your brag—it could be about anything—and your intention for this session today.

Jennifer (01:32)

My brag is probably the interview with a job that very aligns with where I want my future to go. I had that Monday, so… And I guess my intention is to start thinking about myself in the main character mindset. Oh, I think in the last section, like—

Lily (01:41)

Congrats.

Hmm.

Jennifer (01:54)

—workshop I attended, we got into the conversation with the main character versus the best friend. And I have often seen myself as the best friend. And I graduated from college for the second time in December, and it’s really tough. I got one in communications and one in psychology now. So it’s really, really time for me to start thinking of myself as the main character.

Lily (02:06)

Congratulations.

Wow.

Yes, 100%. That’s why we’re here. Why do you think? I have your application in front of me— is it okay if I read from it? So you shared that you feel out of sync with your age cohort. Can you tell me a little bit about that?

Jennifer (02:26)

Mm-hmm. Mm-hmm.

I’m 44. Only had one full-time job and it was really, really toxic. Never had a relationship that lasted over or made it to the year mark. Really want to be a mom and see that window shrinking. Like, most of the people in my age cohorts are sending their kids off to college, and I’m still waiting for him.

Lily (03:01)

Yeah, that sounds like a tough spot to be in, would you say? I see some emotion in your face—that’s why I’m saying that.

Jennifer (03:10)

Yeah, got a box of—

It is a hard place to—tried not to think of myself as behind, but especially with the fertility window closing, it doesn’t feel so much as closing as missed opportunities that aren’t coming back. I mean, at 44, there is no lifetime marriage. I mean, not that it happens a lot anytime, but the hope is gone. I can have an end-of-life marriage or end-of-life friendship, but no lifelong.

Lily (03:26)

You—

Hmm.

Well, I want to hold space for your big feelings around this and be really compassionate toward that version of you who has these hard thoughts and big feelings. They’re valid. They’re also not facts. What do you need from me today?

Jennifer (03:48)

Huh.

I don’t know. Like I said, I just wanted maybe some help reframing myself as the main character—or getting around that life hasn’t begun yet.

Lily (04:04)

Yeah. Well, yeah.

Mm. Mm. Okay. How hard can I be on you, Jennifer?

Jennifer (04:16)

I can take it.

Lily (04:18)

Okay. I’m rarely—I mean, it’s not my mode to be like—I want just all the good things for you, and I wanna shower you with all the kindness, and that’s my intention, that you get what you need from this session. Because I know many people listening resonate with what you’re saying. You have no idea how many DMs I get on Instagram saying, “I’m 44, I’ve never been in a relationship, I don’t know—”

Jennifer (04:34)

Mm-hmm.

Lily (04:45)

—what I’m doing wrong. Or, “I’m 54 and I haven’t been in a long-term relationship,” or, “I’m 34…” And the feelings that you’re experiencing are really common.

And why I asked how hard can I be on you is that that’s a really interesting thought that you’re having—that I can’t have a lifelong relationship. That’s like a really—like the idea that your life has somehow passed you by and that it hasn’t begun yet, that sounds like a really hard place that your brain is in.

Sounds like a rock and a hard place.

What comes up for you as I say that?

Jennifer (05:32)

Not the first time I’ve heard it. And I know I’ve done a lot of cool things. Like, I actually—trying to prep for this so I wouldn’t cry the whole way through—started just writing out some cool adventures. And they’re cool. Like, I’ve been hang gliding, and I witnessed an art theft, and, yeah, was at—yeah—but did two, what they call alternative spring breaks. I’ve went and—

Lily (05:51)

What?

That’s wild.

Jennifer (06:00)

—played with tigers and cleaned a national forest. And they’re cool stories, but they don’t feel like building blocks. I mean, it’s kind of like—people are like, “What?” It’s like watching a cool TV show. It’s like, cool, I did that, and nothing built.

Lily (06:14)

Mm-hmm. Mm-hmm.

Yeah. How are the relationships in your life beyond romantic?

Jennifer (06:24)

Got on—I’m brutally honest—got on antidepressants two years ago and they have actually gotten better. Have had a wonderful best friend for about ten years, but she was it. But since I got on the antidepressants—and out of the toxic job… So I got out of the toxic job four years ago, on antidepressants two, and the relationships have seemed to bloom.

Lily (06:28)

Yeah.

Wonderful.

Yeah.

Jennifer (06:51)

Since I’m not working—I’ve made, since graduation, or I’m minimally working, I’m 12 hours a week—Tuesdays are my Tuesday lunches. I drive to people, and I have no problem going to them because they’re probably working and I’m not. And since January, I counted it up, I’ve done 12 Tuesday lunches with family members I want to reconnect with, a couple of the friends that—

Lily (06:59)

Huh.

Amazing.

Jennifer (07:18)

Since I graduated in December, there were a lot of people who didn’t—so I’ve been driving back to campus and seeing them. Some of the people that I kind of put on hold, because at one point, eight months ago, I was working three part-time jobs, taking two classes, and running independent studies. I didn’t see people for six months. If you worked directly in front of me, I didn’t see you for six months. So that has been really good, because I worked nights at the toxic job and tried the same thing—

Lily (07:35)

Wow.

Yeah.

Yeah.

Jennifer (07:48)

—seven, eight years ago, and it didn’t work. Like, couldn’t get anybody to respond.

But that has actually bloomed. I actually had four people text me and ask me about the job interview. Normal relationships up to two years ago were me reaching out, me finding something to do, me coordinating everything around their schedule, and very little reciprocal. And it’s a lot more reciprocal now.

Lily (08:10)

Hmm.

Wonderful. Jennifer, that’s huge. That’s something to really be proud of. And you know what, what I’m seeing in your face as you’re talking is that you look more alive and you actually look proud of yourself, in a way that when you were talking about like the adventures that you’ve been on—as you said, it sounded like fun postcards, but maybe not building blocks. And this, by like alternative, feels—

Jennifer (08:15)

Yeah. Yeah.

Hahaha.

Lily (08:41)

—really building-blockish. Do you feel that?

Jennifer (08:43)

Mm-hmm. Mm-hmm. I am actually gonna try to host a social networking event at my home. It’s still July. Okay, still July. Next month—I went to a job networking event, but it was virtual, so there wasn’t a lot of the connections, what I felt was, because the prompts were: if you have a connection, give them a connection. If you have a resource, give them a resource. If you have nothing but encouragement, give them encouragement. And I was sitting there going, this is not gonna work to get a job, but—

Lily (08:54)

Wonderful!

Jennifer (09:13)

—it would really work to build social networks because that’s what we need. A lot of my Tuesday lunches, especially with the women, have revolved around: they feel isolated, they feel disconnected. And it’s like, well, this would be a great idea. Because sometimes you get people in the place and they don’t know what to say, they don’t know what to do. So I think the social prompts may help. So I’m gonna tweak the job networking to social networking.

Lily (09:18)

Mm-hmm.

Mm-hmm.

Great, love it. Okay, Jennifer, so here I’ve got more information. I’ve got a little bit of a lay of the land. The way that you’re speaking right now is very different than when you’re speaking about your love life, which is understandable. But it sounds like you have chosen to be the main character in your friendship and networking life.

Jennifer (10:08)

Okay.

Lily (10:10)

Do you resonate with that?

Jennifer (10:12)

Some. I guess it’s easier to feel like the main character when you’re getting results.

And I think that because I’m effort into the dating—I paused the dating website or the dating app at the moment because of the work drama, because of a couple other dramas, and it’s like—but I got dressed up last month to go to an in-person one, you know. It got canceled at the last minute, but it’s like I’m looking for the in-person dating if I can’t. Unfortunately, where I am, there’s not a lot. I’m—

Lily (10:41)

Yeah.

Yeah, yeah.

Not a lot, yeah.

Jennifer (10:52)

Yeah, I live in the outskirts of the metro area, and if I drive all the way to the closest ones, the guys are like, “I don’t want to date somebody that far away.”

Lily (11:05)

Mm-hmm.

Okay. All right, Jennifer, how consistently have you tried dating?

Jennifer (11:12)

I look weekly for in-person dating events. I have…

Lily (11:16)

Great.

Jennifer (11:20)

Before I went back to school, I was constantly on an app. I did back off the apps when I was in school because when I started talking about going back to school, because of my age group, I got a lot of negative feedback that, “I’m looking at retirement. I don’t want to date someone who’s looking to start a career.”

Lily (11:25)

Mmm.

Hold on, hold on, hold on. So you’re 44? Is that your—you’re 44? Okay. Can I be honest? I do not know many 44-year-olds myself, and I live in New York so it’s very different. But I just want to normalize. I don’t know—I have a 42-year-old friend who has a toddler. I don’t have, I don’t have 44-year-old friends who are sending their kids to college. And you sound Southern, which I appreciate.

Jennifer (11:45)

Yeah.

Mm-hmm.

Yeah.

Yeah.

Yeah.

Lily (12:08)

It’s different than New York. I’m from Alabama, so I get it. But then also, what 44-year-olds are looking to retire? I don’t—right. So, and you are some—like, I’m just saying what I’m hearing writ large, because we don’t—I want to get the most out of this time. We don’t have a lot of time together. You are doing that very human thing where you’re centering the people who were wrong for you.

Jennifer (12:15)

People who went to work at 18.

Yeah. Yeah, yeah.

Lily (12:36)

—in whether or not you believe yourself.

The men who were wrong for you, you’ve brought them up a couple times: “Well, they didn’t like that I live so far away. They didn’t like that I was going back to school. They didn’t like…” So that’s understandable why you would pause dating, because you were getting that feedback, maybe even consistently. But here’s the deal. It’s like, you’re not for everybody. In fact, you’re for the few, not for the many. And I say that all the time and some people think that that’s a little bit scarcity-inducing. Like, “Well, if I’m not for many people, then who am I for?”

Jennifer (13:02)

The meaning.

Lily (13:10)

But people who are rare still exist. Like a diamond that is rare, if it didn’t exist, then we would call it extinct.

Jennifer (13:19)

I think I said in my application—I see your book behind you—that that phrase has helped me so much. And not just in the dating, I try to use it for the dating ⁓ but I did it for the job, I did it for—I had problems with any gratitude practice, so I even started saying “Thank you, more please.” I have 500 beautiful nature photos in my phone, three people—

Lily (13:45)

I love that.

Jennifer (13:46)

But even when I see the beautiful sunset, I started doing that. ⁓ I had some issues where I was being told—oh my God—they had an officer cuss me out with their hand on their gun. And they’re like, “Well, you’re not grateful for your job.” So it got to the point where I felt like I couldn’t say I was grateful until I had the whole. But that let me—so “Thank you, more please” let me be thankful for the little bits.

Lily (14:03)

I’m so sorry.

Jennifer, thank you for sharing that. That’s what helped me too. That’s why I wrote about it, and I join you. You know, gratitude practices when you’re struggling—and I don’t claim to know your story in full or what you’ve been through. It sounds like you’ve been through a lot. And “Thank you, more please” can be like an accessible in instead of, “I’m so grateful for everything.” It’s like, well, I am grateful, but I want more. Thank you, please.

Jennifer (14:24)

⁓ Huh.

Yeah, yeah. ⁓

Yeah, yeah. I’ve actually suggested it to two or three other people who were struggling. I’ve suggested your podcast to a lot of people. I’ve suggested your book. But that phrase, I have suggested a lot in a lot of situations.

Lily (14:56)

⁓ Wonderful. That makes me so happy. Thank you for sharing that. That means a lot to me. And I’m really grateful to be talking to you. Let’s recenter on you, Jennifer. This is about you, all about you. So I’m just identifying like, okay, there are some thought errors happening. There’s the thought error that—and thoughts, basically when you believe them, it just means you practiced them a bazillion times.

Jennifer (15:04)

Okay.

Mm-hmm.

Lily (15:23)

Like before you started this friendship journey of building reciprocal friendship, I bet you had the default thought: “People don’t like to be reciprocal with me because there must be something they don’t like about me.” Or like, “I just don’t have reciprocal friendships like other people.” Is that true?

Jennifer (15:26)

Mm-hmm.

Close. The phrase was, “Nobody picks me.” ⁓

Lily (15:47)

Nobody picks me. Okay.

How did you go from—let’s use this as a map—how did you go from “Nobody picks me” to now what you just said to me: I have four people who reached out to me to ask about my job interview, I have more reciprocal friendships? What helped you go from “Nobody picks me” to that?

Jennifer (16:05)

Believe it or not, my best dating relationship—even though it ended—when that thought came in through: he picked me. We had some issues and it didn’t work, but he still picked me. He still chose to spend time with me. He chose—and I’ll be honest, on really, really, really bad days, I guess he’s the closest person I’ve ever come to—

Lily (16:10)

Say more.

Jennifer (16:33)

Stalking on Facebook. I will, on those really bad days, look at it just because seeing his face reminds me he picked me. So that’s where it started. ⁓ Going back to college was really good. I built a really good community in there and had an awesome professor who—I put her through some crazy stuff—and she kept showing up. ⁓

Lily (16:41)

Yeah.

Yeah.

Amazing.

Jennifer (17:02)

My independent study—I went to school with a lot of research—and she said right before the last spring break, where I went to clean a national forest, she says, “I know you’re gonna be busy, but come back with a big broad topic. And she said, “Between five campuses, I’m sure somebody studies that already. And if you manage to pick something nobody studies, I’ll learn beside you.” So I come back from cleaning a forest, I sit down in front of her and go, “Environmental psychology.” And she takes a deep breath and goes—

“I guess I’m learning beside you.” I managed to pick something that no professor at five campuses of my school was studying.

Lily (17:34)

Wow.

Wow, amazing. So I’m hearing that you were chosen by somebody who you liked, and that that was significant for you and sort of was this marker of like, wow, it really can happen. And then you also had this supportive professor. You also had these helpers along the way, but I do want to point out that—

You did that. You went back, you followed your desire to go back to school. You didn’t stay for years with the person who was wrong for you but who chose you just because he chose you. You reached out for Tuesday lunches. You did all of that shit, Jennifer. And I don’t know that you are—I don’t know that that has really integrated into your identity yet as someone who has the power to change her own life.

What?

Jennifer (18:47)

That ⁓ this was supposed to be my year of harvest, 2023. I spent a whole year doing what I called “fresh soil.” The negative thoughts, like we’re talking about, I ripped a lot of them out. And dropped the phrase, “That didn’t work before.” And it’s like, well, I haven’t tried it in three years. 2024 was planting seeds. I was trying—I got back on the dating website,

Lily (19:02)

Mm-hmm.

Yeah.

Jennifer (19:16)

Graduation approached, did the independent study, I was president of a club, I did the internships—trying to plant the seeds, especially for employment. And I really had hoped 2025 would be the year of harvest. And seven months in, not getting jobs, housing situation has gotten unstable. The friendships are still good. ⁓

The dating had two—no, had one date this year and that’s it. Had one date the end of last year and that was it. And it feels like I’ve worked really hard and there’s no harvest, and I know I have power to do. I don’t know I have power to reap.

Lily (19:53)

Mm-hmm. Mm-hmm. Mm-hmm.

Okay, well you just haven’t yet. And I love these themes that you’ve laid out for your years, and I want to caution you against rigidity within those themes. Because what happens with soil—

Jennifer (20:10)

Yeah.

Yeah.

Lily (20:25)

And gardening specifically—I’m in a community garden now down my street and it’s changed my life. But what I know is that unpredictable things happen. Sometimes a bug gets in the garden and you don’t expect it. And then that season is spent working on rooting out the bug and working on getting a stable environment so that the plant can thrive next year, right? And you actually don’t know what’s gonna happen. All you can do is intentional effort.

And what I’m hearing is a couple of things, especially if you’re saying that housing is more unstable, especially if you’re saying that financially you’re working toward, you know, a new job and you are hopeful and you just had this amazing interview and you want a date. I’m hearing that there are some—and you want to find love and you want to have a family, all these things—I’m hearing that there are some foundational human safety pieces that you are working on. So of course dating hasn’t been foremost in your mind.

Jennifer (21:32)

I keep going back to the app, but I have made the conscious effort to not go back until some of the, like you said, safety issues have been addressed.

Lily (21:43)

Yeah, and I am—that is tough.

And what an incredible person that you are, that you’re navigating this and that we’re on this call. And so I think in terms of Maslow’s hierarchy of needs, you’re working on getting some of those needs in the foundation of the pyramid met. And that doesn’t mean that there’s anything wrong with you, Jennifer.

Jennifer (21:55)

Yeah.

Lily (22:09)

Capitalism would tell you yes, like, “Yeah, God, what is wrong?” No. But like, I know that that’s all fucking made up and ⁓ stacked against a lot of people with varying degrees of privilege and many different marginalized identities or life experiences or trauma, right? Like you are resilient, and there is nothing wrong with you.

Jennifer (22:10)

Yeah.

Sorry, “resilient.” That’s the word I’ve heard for 20 years, to the point it’s like—

Lily (22:39)

What? Why are you laughing?

⁓ Okay, got it. Are you like sick of it? You’re like, “I don’t want to be resilient.”

Jennifer (22:48)

No. “Resilient” is starting to sound a lot like “stupid.” Yeah. ⁓

Lily (22:54)

⁓ That makes me sad.

Jennifer (22:59)

But no, I don’t—I haven’t given up. I keep fighting.

Lily (23:00)

So.

I am here. We could replace “resilient” with “magical.” Like you’re sort of co-creating things that didn’t exist, like these friendships. You are attracting opportunities by showing up. You are creating a new life for yourself. You are, is what I’m hearing.

Jennifer (23:07)

No.

I’m gonna be proud, ⁓ 2016 to 2019 I applied to 200 jobs, got five interviews and no offers. ⁓ That’s when I decided to go back to school. It’s like, maybe I just need to retool. I have applied to 96 jobs, got seven interviews. Yeah, yeah.

Lily (23:44)

That’s a great increase in percentage, I think.

Jennifer (23:48)

Google is your friend and your enemy, but ⁓ that is about normal right now, a normal percentage. ⁓ But it’s a lot better than—like I said, applications and five interviews was just draining on top of working a very toxic job.

Lily (23:54)

Yeah, but yes.

Yeah.

So let’s refocus on the dating pieces because I do want to lay out a plan with you. And let’s take a deep breath together.

Jennifer (24:16)

Okay.

Okay.

Lily (24:26)

Ahhhh.

Because it is possible to pursue multiple dreams at once, right? It is possible to pursue your desired love life and be successful at that. It is also possible to find amazing, fulfilling work that you are hopefully lit up by in an environment where you’re supported. It’s possible to find housing where you feel safe and secure. Now, that’s hard work. And I want you to lean on your community as much as possible for community care, for resources, for resource sharing. I want you to allow yourself to be—I don’t think you have a problem with this, it doesn’t sound like—but I want you to allow yourself to be vulnerable with the people that love you so that they actually know what’s going on so that you are cared for, okay? Because you’ve been pouring into other people and I really want you to give yourself permission to be honest about where you’re at and what you need.

Does that sound doable?

Jennifer (25:23)

Kind of like a lot of the other things, I know I can do my piece. I don’t have high expectations on return.

Lily (25:29)

Right. And you’re never—none of us are ever—in control. It’s sort of like in the dating world, to make it a more neutral example, you can never know how a co-conspirator will show up. You never know if they’re gonna say something that’s like on my no-no’s list. It’s like, I don’t know any single people, I don’t know what to do. It’s like, you never know how someone’s gonna show up or if they can meet your needs. So I think that it’s not about necessarily—like, I think just being honest with people and making an ask

that feels aligned for you, and not making their response mean anything about you.

Does that make sense?

Jennifer (26:09)

Those things, I think it makes sense, but it is a big mountain to climb, you know? Hard, you know that.

Lily (26:09)

It’s harder, but—

Yeah, which is the same thing you probably would have said before you started Tuesday lunches.

So how did you start Tuesday lunches? One baby step at a time. One text at a time. That’s what I want you to do here.

Do you have a therapist?

Jennifer (26:33)

Not at the moment. I had a counselor through school. Graduation, lost it. On the to-do list once I get full-time employment.

Lily (26:39)

Right.

Okay, I wonder—I don’t know exactly where you live—but I wonder if you reached out to your school counselor and asked if there were any free counseling resources for folks of different income levels in your area. I wonder if you reached out and just made an ask, like, Hey, do you know of any? Like, there are places in New York where therapists are qualified, working, but they’re still getting their hours. I don’t know—thoughts?

Jennifer (27:13)

I have. Because I am living at home, my income—because I don’t pay rent—I’m earning just enough to be beyond the resources we have. I know two people who have the money and have reached out nearby, and we are so overloaded right now that if you’re not suicidal, even if you have the money, they don’t have the space.

Lily (27:26)

Got it.

Hmm, that’s hard.

Okay, okay. So I’m glad that you researched that and that you got that information. I was just checking in about how else you might be supported. And it sounds like you have some people in your life who really love you, and maybe going to lunch this week just because could be a good next step to triage support for your human needs emotionally.

Jennifer (27:47)

Mm-hmm. Mm-hmm.

Lily (28:10)

Okay, now dating. I don’t know that—okay, the dating plan if you get a job pretty quickly, the dating plan if it’s a little while, may be different. If you get a job pretty quickly, which I hope (I’m sending good vibes out for you), then I want you to start dating pretty quickly after starting your new job.

If the job… and some of my clients also are, you know, searching for jobs or were searching for jobs and it can be a slog, you know this. And so if it is a few months, then we can create a plan so you’re not like waiting for the job to be perfect before starting to date. Does that make sense? Which of those options do you want to talk about first?

Jennifer (28:58)

Let’s talk about if the job comes, because like I said, ⁓ win the job.

Lily (29:02)

When the job comes. When the job comes.

So we’re gonna be speaking it into existence. When the job comes, tell me—do you have essence-based preferences created?

Jennifer (29:11)

I did, but it was a while ago. They’re not coming back to the top of my head. ⁓

Lily (29:18)

Okay, did you write them out anywhere?

Jennifer (29:20)

They would be buried in one of my journals. ⁓ I know a giving heart was one. ⁓ Physically active.

Lily (29:23)

Okay.

Got it.

It’s okay, you don’t have to recall them right now. I just want you to—go ahead.

Jennifer (29:31)

Okay, yes. Yes, I have them and yes, I can go over—I can find them, I just have to find the right journal.

Lily (29:39)

Well, I think it might serve you, because you’re in a new place in your life, to do them anew. You can get my free workbook at datebrazen.com/workbook for the Essence-Based Preferences. It’s 14 pages, it’s gorgeous. And it’ll guide you step by step through owning what you want. You can do that whether the job comes tomorrow or in two months or what have you. I want you to claim what you want to recenter yourself. I also want you to brain dump

Jennifer (29:43)

Okay. Okay.

Lily (30:09)

all of the assumptions you’re making about Men don’t like to drive here, Men don’t like XYZ, and then we need to do some SOFT work around those thoughts. Are you familiar with this SOFT practice that I’m talking about? I’m gonna explain it either way. Okay, great. So when you were talking about two years ago, you were ripping these old thoughts out and really replacing them with some new…

Jennifer (30:28)

Go with—please explain it.

Lily (30:36)

…more powerful ideas, like Let’s just try. SOFT is a really powerful resource to build new beliefs about yourself—AKA neural pathways. And they’re not going to be shame-based. This process is not to shame you for having these hard thoughts. It’s to help you work with yourself to build new neural pathways. So, what’s one thought that you wanna work on about your dating life that is keeping you from trying?

Jennifer (31:06)

Nothing is keeping me from trying because I kept doing it. I did pause it when the housing situation got unstable, but I kept showing up. Doesn’t mean I don’t have negative—automatic negative thoughts, you know, ANTs, that’s… And I’ve worked on ant spray, which is when you have the automatic negative thought, come up with a positive counterpoint. Like the Nobody picks me thought, he did pick me.

Lily (31:22)

Yeah.

Jennifer (31:33)

So I can go back and start listening to my thoughts again and look for those automatic negative thoughts.

Lily (31:34)

He did. Yeah. Okay.

Well, what I’m hearing is that a thought didn’t stall you out. Like, some people struggle with a thought that is negative, and their response is the feeling of shame. And then the actions that they take are like sitting on their couch, never trying anything.

Jennifer (31:48)

Mm-hmm.

No, I decided even though I don’t always have a lot of belief it’s gonna matter, I decided I was gonna go down swinging.

Lily (32:09)

Okay, great.

So I hear in that an assumption that it probably won’t work out.

And so I don’t hear that that thought stopped you, but I do hear that that assumption probably created some hard feelings and maybe some hustling action. So what we’re doing here is going from hustling action—which is I’m going to go down swinging, let me try everything, let me go after it, let me try throwing spaghetti against the wall—to more intentional action rooted in your essence-based preferences and your desires.

So intentionally working on the belief that It’s not gonna work out is what I wanna help you with, with SOFT. Does that make sense?

Jennifer (32:59)

Yes, I think I may have something to lean in on that. ⁓ Been a gardener for years and years and years, but never could grow anything from seeds. And that’s what my life always felt like. Like one year, me and my niece got 24 little squash plants, but they all died before we got squash. I watered them and I slowly just watched them wither. This year, just…

Lily (33:04)

Tell me.

Jennifer (33:25)

I tried again and I have four beautiful sunflowers staring at me. And I am trying to lean into that—into like, things are blooming.

Lily (33:30)

Wonderful.

Lily @ Date Brazen (33:36)

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Jennifer (35:51)

I like, yeah.

Lily (35:51)

Yes. Yes. Okay.

So let’s take this idea that you—what’s a default thought, like an automatic thought that you were having when you were dating that you would like ideally to pivot away from?

Jennifer (36:05)

I’ve passed the window of connection, I guess. That people my age are too set in their ways and…

Lily (36:11)

Okay. Okay.

That’s a hard thought. It’s done, right? It’s over. And my life hasn’t begun, it’s passed by. Like, when you said I’m past the window of connection, I was imagining you were in a car and there was a window that you saw through, when you were driving through a street. There was a little store window and you’re like, Wait, the window is back there. It’s gone. I can’t even see into the store anymore. Okay. Okay.

Jennifer (36:16)

Yeah, that word, that… yeah.

Yeah. Yeah.

Yeah. Yeah.

Lily (36:46)

S of S-O-F-T: Self-compassion. Do you know about self-compassion? Can I share more?

Jennifer (36:54)

Yeah. I mean, I’m familiar, I’ve listened to a lot of the podcasts and, like I said, I just made it through a psychology degree.

Lily (36:58)

Mmm. Yeah, great.

What do you think self-compassion might say to the version of you who really struggles with that belief that the window of connection has passed? What might self-compassion say?

Jennifer (37:20)

The sun is still shining. Something like that.

Lily (37:23)

Maybe.

So I want to ground in. OK, so I’ve talked about this example a lot in the podcast recently, but I don’t think those episodes have dropped. So I’m just saying, if people have listened to all the episodes, you will have heard this story before. I had a client who was struggling with the idea that she wasn’t desirable. And we acknowledged it, we really held space for that, and I said—

Jennifer (37:34)

Okay. Okay.

Lily (37:51)

What might self-compassion say to that version of you who doesn’t think they’re desirable? And her response was, I am desirable. You are desirable. And I said, cool, cool, cool. That’s a great thought. It’s true, I believe it. But you don’t believe it yet. Self-compassion is meeting you where you are and radically getting on your level and saying something like, Of course I’m struggling with this. It makes total sense why I would have this default thought. That’s really hard and human of me.

The sun is shining—that’s, you know, true. Both/and. But I don’t know that you believe that. I don’t know that that feels true in your dating life yet.

Jennifer (38:32)

Yeah.

Lily (38:41)

What’s coming up for you?

Jennifer (38:43)

The evidence that proves that I’m not desirable, but not wanting to go into it because I can’t. I can’t grow from there, and I know I can’t grow from there.

Lily (38:53)

Yeah.

Yeah. The thing about the human brain is it just wants to be safe.

And so of course, when I use that story as an example for a different thought that you’re dealing with, I hear that that really brought up a lot for you in terms of the fear of not being desired.

And I think that what I heard you just say is, I can’t go there, because if I go there, then I’ll have way too much evidence, I’ll give up.

And there’s a perfect example of why dating feels really arduous—because all of that experience feels like proof that what you want isn’t possible, when in actuality you just haven’t had experiences. You have had one with somebody who chose you, and you haven’t had experience with the right person yet, or else you’d be with them.

What’s coming up for you as I say this?

Jennifer (39:51)

Echoes that it’s not—I want to stay in dating—but the echoes that I’m not desirable echo through so many fronts of my life. You know, the career is…

Lily (40:02)

Yeah.

Jennifer (40:06)

Like I said, two years ago I would have said friendships, and like I said, like we’ve talked about, I’ve made strides. I’ve been in places where, like I said, I’ve already had seven RSVPs to my social networking events. Yeah.

Lily (40:14)

Yes.

Yeah, amazing. Yeah.

But let’s pause here. We’re working with a struggle place. And that doesn’t mean that you are wrong. That doesn’t mean that you are not valuable or valued. You are. It’s a both/and. Both: I have created change in my life in other areas, and I’m still struggling with another area. And so we’re just going to work on that area.

Jennifer (40:26)

And go back to dating. Yeah. Yeah.

Lily (40:51)

It doesn’t make you less than. I think that a lot of this—what I’m hearing is a lot of fear that acknowledging these dark, scary thoughts makes them more true and invalidates your brilliance in some way.

Jennifer (40:51)

Mm-hmm.

It also makes it more sticky. Like it feels like mud. Yeah. Yeah.

Lily (41:11)

Uh-huh, uh-huh, uh-huh, yeah.

And I would imagine if you’re using the ant spray technique that it would be like, well, let’s just spray all this and get it over with and move on. When I think that that’s giving your thoughts a lot of power.

They’re just little sentences in your brain that you’ve practiced a bazillion times.

And so we’re getting to know them. Let’s move on to the SOFT. I think that’ll be helpful. So let’s actually move to: I’m not desirable as the default thought that you have, like in the back recesses of your brain, that feels really scary. Self-compassion would say: Of course I have that thought. I’ve had a lot of hard experiences, not feeling chosen. That is hard. And this is a moment of suffering, and that’s just really human of me.

Jennifer (41:39)

Okay.

Lily (42:06)

Instead of rushing to fix, we’re just… like a child on a playground who stubbed their toe or who got rejected by their friends. Instead of looking over them and saying, Get over it, it’s not that big of a deal, it’s not that big of a deal, you get on their level and you say, Hey, what happened? I’m so sorry that happened. That’s really normal, to feel big feelings about it. Do you need a hug? Does that make sense?

Okay. Now moving on to O—S-O—own your needs. What might a need be that you have in this moment, physically or emotionally, that you can own? Do you need a deep breath? Do you need to take a second with your eyes closed? What do you need in this moment to resource yourself?

Jennifer (42:51)

Deep breath.

I need time outside. That’s what’s the most recharging for me.

Lily (42:58)

Okay, great. So right after this session, can you go outside?

Jennifer (43:02)

I think it stopped lightning.

Lily (43:05)

Great, even if it was, maybe stand under a little awning.

But yes, owning your needs means: What emotional or physical needs do I have in this moment? Let me triage support for them so that you don’t get… like, if you’re in fight or flight, you can say, Okay, maybe I need to lay on the ground. Maybe I need to take a walk. Maybe I need to text a friend. Maybe I need to insert—what do you need here?

Okay? F, feel your feelings. S-O-F, feel your feelings.

So when you said it was like mud, what feeling and where is it in your body happens when you are having the thought, I’m not desirable?

Jennifer (43:53)

Feet and my chest. Feels like something is trying to pull me down.

Lily (43:58)

Okay, so let’s close our eyes together. Are you open to that? So let’s do this practice that I call How to Feel Anything. So I’m gonna ask that you put your hand somewhere compassionate, maybe on your chest or on your belly.

Take a big deep breath. And I want you to hear these sentences that I’m gonna say. You can let them wash over you or say them silently to yourself. They’re quotes by Simone Sol:

There is nothing that you could say, do, or feel that would make me wanna stop being your friend.

I am willing to feel anything to be with you.

Breathe into your body and where feels most tender or big—in your chest or your feet or somewhere else.

Jennifer (44:49)

Belly.

Lily (44:51)

Okay, so breathe into that and let me know: What shape is this feeling? Just let your brain populate an answer. Doesn’t have to be logical.

Jennifer (45:06)

I think the gummy, muddy feeling is sticky.

Lily (45:11)

Yeah. Does it have a color?

You just keep breathing into it.

How big is it?

Jennifer (45:24)

Shrinking, but it can get very big.

Lily (45:28)

Yeah, like how big? Like a field size, or like a gymnasium size?

Jennifer (45:37)

Can’t tell how big. It’s just encapsulating.

Lily (45:40)

Mm, okay. So take some deep breaths into it.

It might get more intense as you breathe into it, and that’s okay—that’s part of this process. You’re processing this emotion like a bodily function. You’re allowing it right now. What else do you notice about this sticky brown feeling?

Jennifer (46:06)

That it hasn’t quite made it to my mouth and nose. At my worst, I couldn’t breathe around it.

Lily (46:15)

Okay. Well, so just dealing with right now, taking this moment and really sitting beside it as the oldest and wisest you’ve ever been—your future self—sitting beside this feeling, just witnessing it. I’m here with you.

Take another deep breath. Is there anything you notice about it before we come back to the room?

Has it shifted at all since we started focusing on it?

Jennifer (46:44)

It’s shrinking.

Lily (46:48)

So I want you to take one more deep breath and thank your body for showing up for you and giving you this information so that you can better care for yourself.

And wiggle your fingers and toes and come on back to the room. I want you to point out three things in your physical environment that you either smell, see, or hear to sort of reorient your nervous system in this room. And say them out loud.

Jennifer (47:15)

I see paintings that me and my mom did at a paint, bring-your-own-bottle painting place.

Lily (47:21)

Mm-hmm.

Jennifer (47:23)

Luckily I don’t smell anything, because we have a very unhealthy dog. So I cleaned him up. He’s very large, very elderly, and very sick. He doesn’t—he—it’s gassy, but I cleaned. So I don’t smell anything, which is good. And I see a giant stuffed tiger.

Lily (47:28)

Okay? Okay?

I’m sorry. Yeah. Yeah. Great. Great.

Great, okay, so what did that experience of breathing into your stomach teach you?

Jennifer (47:54)

That I can see around some of these really big feelings—that they don’t…

Lily (47:58)

That you… can—go ahead, go ahead.

Jennifer (48:01)

That they don’t have to block my vision.

Lily (48:06)

And they actually can block your vision if you’re not willing to breathe into them and feel them. It’s sort of counterintuitive, right? It’s like when they have a big response, I think the fear around feelings and feeling them is that you’re gonna have to do it forever, it’s gonna be wallowing in them. But in actuality, it’s sort of like when you’ve got to poop. And if you’re like, Nope, I don’t need to poop, I don’t need to poop, I don’t need to poop—more painful, more painful, emergency bathroom situation.

Whereas if you listen to your body and you’re like, Okay, my body’s sending me signals. I need to address this bodily function. Let me go take care of it. You pass it, you feel better. But here’s what happens with poop: I get that it’s gross. I don’t care. It’s a bodily function and it’s a visceral one, so everybody gets what I’m saying. You’re gonna need to poop again. That’s what the body does. You will have this feeling again.

Having it again is not a failure—it just means that you have some maintenance to do.

Having hard feelings doesn’t make you a failure, it makes you a human being. And I think what you’ve been facing is this assumption that having these hard, old feelings come up again and again makes you a failure, when in actuality, you just need the tools to move through them effectively to become more empowered in this experience of growth and getting more of what you want. Does that make sense?

Is this resonating? Tell me what’s coming up for you.

Jennifer (49:38)

It is resonating, but almost like I’m feeling it, not thinking it.

Lily (49:45)

Good, because your body is separate from your mind. You don’t have to overanalyze everything. You can just have the pros. Like, feelings aren’t facts. It’s not like feeling the feeling of shame means, Shit, I am bad. I am wrong. Though that’s what the feeling is there to sort of help protect you from, because it’s a hijacking emotion. It makes you go into hidey-hole safety mode.

But if you’re willing to say, I’m feeling shame, and it feels like a sticky tar pit in my chest. Ugh, this really sucks. I’m willing to feel anything to be with you. Suddenly shame is an emotion in your body. It’s not a fact of your being.

Just like these thoughts that you’re having are thoughts that you’re having to try to protect yourself. They’re not actually facts.

So let’s get to the final of the T, S-O-F-T. At the beginning, you were struggling with the thought, I’m undesirable, I have so much evidence to prove it. We did self-compassion, we did owning your needs—you’re gonna go outside after this. We did feeling your feelings.

Now, I hope that you feel a little more accessible to a baby-step reframe, a new baby-step thought that you can practice out loud and often.

In the moment when you catch yourself having the thought or fear, I’m undesirable—quick, self-compassion, acknowledge it. You can use this quicker version, which is like ACK: acknowledge, compassion, kind reframe, if you’re kind of on the go.

What might be a useful and true thought about your personhood, about your desirability, that you can start practicing? And I can help if you need it.

Jennifer (51:26)

First thought is I’m worth it, but I don’t know if that’s where you’re going.

Lily (51:30)

Does that feel true?

Jennifer (51:32)

Yes.

Lily (51:35)

Cool.

Jennifer (51:37)

Doctor Who’s enemy, the Cybermen, they always talk about—the Cybermen seem confused why people are running away. I don’t know if you’re familiar with Doctor Who, it’s one of the villains. It’s one of the villains that take people over. But they always seem confused why people will run away because they’re so great. And sometimes I feel like Cybermen. It’s like, I know what I bring to the table and I know what I’m worth and I know my life doesn’t reflect that.

Lily (51:46)

Yeah. I’m not. Yeah.

Yeah.

Yeah.

Yeah.

You’re worth it.

It’s possible that the right person and people will be so delighted that you exist and that they met you. And I don’t think you’ve spent enough time thinking about the people that you haven’t even met yet. You met your best friend 10 years ago, is that correct? You were 34. There are a lot of 34-year-olds right now who I know,

who are looking around saying, I don’t have any close friends, the close friends that I’ve met, like I don’t know anybody new, people have such a hard time making new friends in their 30s, I don’t know what to do. And here you are, living proof that you met somebody at 34 who became your best friend 10 years later. What an incredible piece of evidence that you have that there are people in your life who you have not met yet who are gonna be obsessed with you.

So it might be possible that I haven’t met everyone yet. It might be possible that I am desirable to the right people, full stop. Friendship, love life, job search, all of the above. It might be true that I’m desirable to myself. I desire myself. And I want you to kind of get off on yourself in that way and make a list after this session,

of maybe 10 to 20 reasons why you think you’re awesome.

And that can be a regular practice, I call it 20 in 2. So set a two-minute timer, try to write 20 reasons you’re awesome on a list just for yourself.

So your next steps are to clean—you’ve done it with friendship, now you’re doing it with love life. Clean up the thoughts, clean up the assumptions. Because you actually, you’re not dead. You don’t know what’s gonna happen. You really don’t. And of course you’ve been through a lot. There’s complex trauma, there’s experiences that you have that you’re healing from. There are rejections that you’ve experienced that you’re healing from. And those do not define you, Jennifer.

Your life is far bigger than the people that have rejected you.

Truly, this is about re-centering yourself.

Thoughts?

Jennifer (54:26)

Funny that you said I’m not dead yet. On the bad days that’s what I fear. That I just haven’t stopped.

Lily (54:33)

That you’re over, that

it’s over.

Jennifer (54:36)

I’m just still breathing, but it’s over.

Lily (54:39)

Yeah, and that would be a normal thought in response to vulnerable desire.

Doesn’t mean it’s true.

Your brain is a human brain. It is not an oracle. It does not tell the future. If it did, we’d be having a very different conversation.

You don’t—

Ooh, and you’re doing so much for yourself right now. I think that you get to give yourself a lot more credit, which is why I’m prescribing the 20 in 2 challenge for you. 20 reasons you think you’re awesome in two minutes. If you don’t get to 20, that’s okay, just keep practicing.

And another baby step thought that you can integrate, and I would choose one that feels most useful and true and practice it out loud and often. Another baby step thought is I’m learning how to—fill in the blank. I’m learning how to believe that I’m desirable. I’m learning how to get a job that is aligned with my values. I’m learning how to ask for help from my friends.

This is just a new chapter.

So what I told you to do: do your essence-based preferences to claim what you want and get off a little bit on the best case scenario. Give yourself—you’ve done a lot of worst-case scenario planning. I think that’s covered, okay? You’ve done enough. Now I want you to suspend disbelief for like an hour. Put on your favorite music, print off that free guide that is at datebrazen.com/workbook. Print off the free guide and get it. Journal out,

What does it feel like to be in the right relationship? And if you need help, I have a podcast episode, Episode 63 of the podcast is the Envision Your Future Partner meditation. So you can even couple it with that.

Quick meditation to—like I can guide you through the experience of getting in best-case-scenario brain.

Jennifer (56:42)

Is that the one where you’re at your third date and they bring the little gift?

Lily (56:47)

Yeah, yeah. I want you to do it again.

Jennifer (56:50)

I haven’t done that one in a while. I’ve done it, but I haven’t done it in a while.

Lily (56:54)

And you’re gonna do it coupled with this workbook and I think it’ll be really powerful. So that’s the next step, center your desires. The other step is SOFT. I want you to try doing SOFT every day for a week, for 20 minutes. Self-compassion—if you need help with that, you can go to self-compassion.org and do like a five-minute self-compassion meditation by Dr. Kristin Neff to get you in that brain. You don’t have to do it all alone, Jennifer.

Five-minute self-compassion meditation, then journal out: What might I need right now? Then feeling your feelings, using this episode as an example of like, how can I breathe into my feelings like a bodily function, not make it a fact, and really honor it, process it, move through it effectively. Then for three minutes, you can do that. Then thoughts, not facts. What else might be true? What’s a useful and true baby step thought instead of jumping to like the aggressive opposite?

I am desirable. If that doesn’t feel true, it’s not gonna serve you right now. It might be true that, it might not be impossible that, it might be that I’m just learning that, right? And there you have it, your SOFT practice. Rinse and repeat. The more you practice, the more this will become your default. Like you did with the ant spray, this is just a new practice to integrate, to be on your own side and get more. Third and final homework assignment, 20 in 2. 20 reasons you love yourself in two minutes. Though,

if you can get to five reasons, I’ll be happy. All of that will create more of a fertile soil from which you can start dating. Okay? Because it sounds like you’ve listened to the episodes on dating app practices, your dating profile, you’ve listened to the episodes on—do you have my book?

Jennifer (58:43)

No, at the moment. That is on my list of stuff to buy as…

Lily (58:49)

We’re sending you

the book. We’re sending you the book. So you’re gonna give us your address after this and I’m gonna send you the book. And I’m excited for you to read it. Go ahead.

Jennifer (58:58)

I’m

excited to read it, I wanted to—

Lily (59:01)

Yeah, I’m gonna send it to you and I really want you to read it and I’m gonna do a little note in the front of encouragement because you deserve what you want. You are worthy of what you want and your story is not over. I wrote this book for you. So I think like you’ll have the strategy pieces of the dating profile, of in-person dating, of the bingo card in the book. So you will have the fertile ground with these practices that I think are more important to coach on first, to then—

Jennifer (59:03)

Okay.

Lily (59:30)

Ignite your dating strategy.

It’s gonna be easier because of this foundation you’re laying. Does that make sense? Okay, great, Jennifer. I am so excited for you to take these resources and run with them. And how are you feeling?

Jennifer (59:48)

Okay, like I was on a boat on choppy water and the water is still rough but it’s calming down.

Lily (59:58)

Great, I’ll take it. I’m really excited for you. This is not the end. This is just the beginning of a new chapter.

All right, Jennifer, thank you so much.

Jennifer (1:00:08)

Thank you for having me.

Lily @ Date Brazen (1:00:10)

Thank you so much, Jennifer, for coming on the podcast and sharing your story with us. I know that it resonated with so many people, and I am really excited to hear where this next chapter leads you, because this is just the beginning. Everyone, if you resonated with this episode, then please share it on Instagram and your stories, or DM me @datebrazen. Tag me if you share it on your stories. I know that this experience of feeling like a late bloomer can be so isolating.

And that’s why The Late Bloomer Show exists—to help you shed any stigma, reclaim your timeline, step into your power in your love life and everywhere. And I hope that this episode empowered you to start rewriting those stories that it’s over, because it’s not. And more is currently possible than you think.

I’m so grateful again to Jennifer for coming on and sharing her story. It takes courage to be vulnerable and ask for help. So I’m so excited that you took that step, Jennifer. And for all of you listening, this is just the beginning of your love story too. And I am so honored to support you. Talk to you next week.