“More is possible than you currently realize.”

✨ Big news ✨

The Date Brazen Podcast is now The Late Bloomer Show 💜

This change is for every late bloomer who’s ever felt behind, too much, or too late. For anyone who’s been told to shrink or settle.

For everyone who needs to hear:

🌱 You are not alone.

🌱 You are not too late.

🌱 What you want is possible.

In this vulnerable episode of The Late Bloomer Show, Lily opens up about the rebranding of her podcast and what it truly means to embrace the late bloomer identity.

This conversation is more than just a name change, it’s about creating a space where late bloomers can feel seen, supported, and empowered. Lily shares why community matters so deeply, how self-compassion changes the journey, and why feminist perspectives are essential in reframing what it means to be “behind.”

Work with Lily:

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

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

Learn how to work with Lily: datebrazen.com

Let’s connect:
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YouTube Channel

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Show transcript:

Lily @ Date Brazen (00:19.32)

Hey gorgeous friends, welcome to The Late Bloomer Show. I’m so glad you’re here. Today is our inaugural episode under this new title, and I want to take you behind the scenes to share why this change is happening and what it means for us moving forward. Spoiler alert—it won’t really change anything except for the title and the intention we’re stepping into together.

I’ve tried to record this episode a couple of times, and honestly, my perfectionism kept getting in the way. But instead of letting that stop me, I’m choosing compassion—for myself and for this process—because this podcast, and you listening, mean so much to me.

When I first sat down to record, I was trying to make it this super polished update, but the truth is, I’m just deeply grateful that we’re here together. I’m grateful that you choose to listen each week—or watch on YouTube at Date Brazen. If you’re watching, you can probably see me getting emotional right now.

I want to say thank you for the last five and a half years we’ve spent talking weekly. I started this podcast in my closet just 10 feet away from where I am now, thinking, Who’s going to listen to this? It’ll be a tiny little show, and who cares? But there was always that nagging voice saying, I’m too late. That drumbeat of too late was so loud back then, and it even spilled over into other parts of my life that I had to work through.

Fast-forward to today—over 500,000 downloads later—and I am so grateful you’ve allowed me into your space, into your ears, into your home.

Lily @ Date Brazen (02:46.894)

onto your walks. Hearing that this podcast has made a difference in your life fills me with so much joy.

I love recording this podcast. I love talking to you every week. And I’ve especially loved the coaching episodes we’ve introduced over the last couple of months—coaching people live on the podcast has been so rewarding and fun. I hope you’re enjoying those episodes as much as I am.

So, why the name change? It’s part of a larger shift you’ll also notice over at datebrazen.com and on my Instagram. For a couple of years, I’ve felt something shifting in my business—something I couldn’t quite name at first. After conversations with friends, I realized a theme kept emerging: the stories I felt most excited to share were those of late bloomers.

Now, don’t get me wrong, every client story fills me with joy. But because of my own history as a late bloomer, I’ve felt a deep resonance with people who’ve joined this podcast, Main Character Dating, or my mastermind, Main Character Life—those who felt behind in their love lives, careers, or friendships. Many of them, like me, struggled with self-isolation, especially when they were the only single person in their friend group.

It’s easy to feel behind when everyone around you seems to be moving into relationships, marriage, or starting families. Add to that the patriarchal socialization that tells single women and people socialized as women that they’re behind coupled women

Lily @ Date Brazen (05:05.421)

that they need to be coupled in order to prove their worth. That mix of patriarchal socialization and the friendship isolation you might be experiencing can feel so heavy. When I think about late bloomers—about the results we co-create together here on the podcast and in my programs—those stories are truly incredible.

I used to call myself a feminist dating coach for single women and people socialized as women. But I realized I needed to claim who I support even more clearly: feminist late bloomers who are done settling, done shrinking, and who want more for their lives than the isolating, shrinking status quo.

The fact that I get to do this podcast, and coach in community with this gorgeous group of people inside Main Character Dating, is such an honor. The results we create together—the breakthroughs, the joy, the confidence—are so powerful.

About eight months ago, I finally put my finger on it: I want to claim out loud that I help feminist late bloomers. This isn’t just coaching—it’s a movement. A movement to normalize you, to normalize your experience, your timeline, your struggle.

Because here’s the truth: dating isn’t always easy. And when people try to gaslight you into thinking it should be, or ask, “What’s wrong with you?”—that’s harmful. Dating is hard. Especially if you’re holding yourself to impossible standards or applying the same rules that helped you climb the corporate ladder to your love life. Those rules don’t work here. And that’s okay.

Lily @ Date Brazen (07:07.59)

The first why for this name and website change is that this is more than a podcast—it’s a feminist movement for late bloomers. I’m calling it right now: I want to change the landscape of dating for late bloomers, to help you feel less alone and to empower you to claim everything you want. And remember—there’s no such thing as being “too picky.”

Lily @ Date Brazen (07:35.023)

I want to help you claim that you’re allowed to want what you want—and in doing so, you can settle-proof your entire life, not just your dating life. Joyful dating is absolutely possible. You don’t have to settle for a dating life that feels miserable. You don’t have to settle for feeling behind. You don’t have to settle for blaming yourself for being exactly where you are right now.

If you want something that hasn’t shown up yet, that’s okay—let’s go after it. It’s not over.

Lily @ Date Brazen (08:08.817)

I think a lot of late bloomers struggle with this thought: It’s over. Nothing’s ever going to change. And I get that. Growing up in the deep South, I didn’t have people romantically interested in me. I experienced so much bullying and rejection. Then, coming into adulthood, I tried to prove my worth—to prove that I could be attractive and interesting to men. I found myself performing this exhausting, heteronormative dance, hustling to show I was “worthy” of a relationship.

That led me to settle again and again, eventually ending up in a terrible relationship where none of my emotional needs were met.

That’s why I want to build this podcast, this movement, this community—so that millions of people who self-identify as late bloomers, or who simply feel behind right now, know that they’re not alone. I want you to know that more is possible in your love life—and in every area of your life—than you currently realize.

Because, as I say all the time: dating is a microcosm of our well-being. It’s not frivolous. Wanting love doesn’t make you less of a feminist. It simply means you desire something. And, as my friend and colleague Dr. Julianne Hauser says, desire is your birthright.

So, if you desire something that isn’t here yet—let’s f*cking go.

Over the past few years, I’ve had friends experience sudden, devastating loss. I’ve seen what it looks like when life truly ends. And that perspective has only made me more passionate about you claiming what you want—about you stepping into belonging and using real tools to change your own life.

Because here’s the truth: I know what game over looks like. And you’re not there. You’re alive. You’re breathing. And as long as that’s true, change is possible.

I get so passionate about this because, for late bloomers especially, there’s often this undercurrent of Not me though. I’m cursed. This works for other people, but not for me. Who says? Yes, you’ve tried things that didn’t work. But now it’s time to try again—differently.

Lily @ Date Brazen (10:32.593)

It’s time to try a different way forward—one that prioritizes your desires, that doesn’t ask you to shrink in order to belong, that encourages you to want more, not less. A way that says: we go faster together.

So, join this club. Join this community. And the truth is, by simply listening to this podcast, you’re already a part of it—and I love having you here.

Why not do this differently? Why not do it in a way that actually feeds your soul and spirit, instead of either denying what you want for fear it doesn’t exist, or hustling to prove your worth in order to get it? I’m not here for either of those things.

I want you to own what you want—and to have the skills to claim it, find it, and make it inevitable. That’s what we’re doing here together: through this podcast, through the tools I teach, through self-compassion. This isn’t over. Change is possible.

This is a feminist movement for late bloomers who want more, who refuse to settle, and who are ready to thrive. That’s what this podcast is for. Honestly, that’s what it’s always been for—but now we’re explicitly claiming it. And I’m so glad you’re here. I’m so grateful for your time and energy. Because more is possible than you currently realize.

I’ve coached over 400 late bloomers in my program, Main Character Dating, using the tools I share on this podcast. And here’s the truth: they work. They work to make the right relationship inevitable. They work to help you expand and deepen your friendships. They work to help you claim what you want in your work life—if that’s something you desire. And they work to help you live a bigger, more vibrant life.

I’ve told this story before, but if you’re a longtime listener, you know I’m obsessed with Gilmore Girls. Do I feel good about that being part of my personality? Yes, I feel great about it.

So, I went to Gilmore Girls Fan Fest twice. The first time, there was a dance party, which we called the “dance marathon,” and it was so much fun. The second time, there was a karaoke night…

Lily @ Date Brazen (12:56.503)

It was so fun. The second time I went, they had a karaoke night—which was also fun, except my microphone kept cutting out. I did this full-on rendition of I Will Always Love You—the Dolly Parton version, as Lorelai does—but because of the mic issues, it ended up being only so-so. Still, everything else about the night was amazing.

After I sang, I was riding high on that karaoke glow. Spotlight on me? Yes, please. As a former musical theater girly, I live for it.

Then, this woman came up to me. She kneeled next to me and said, “Hey, I don’t know you, but I loved seeing you on stage just now. You looked so confident—like you’ve done this many times. I’ve always wanted to do karaoke, but I’ve been way too scared to do it by myself. Will you go up there and do a duet with me?”

I have never felt so honored in my life. What a gift—to be asked to stand with someone so they could feel brave enough to finally do something they’d always wanted to do. Honestly, it makes me want to cry just thinking about it.

So, we got up there together. She chose Waving Through a Window from Dear Evan Hansen. (Where are my musical theater people at?) If you don’t know it, the song is about looking in from the outside—watching everyone else live their lives while you feel stuck. Which, honestly, is so relevant to late bloomers who feel behind or too afraid to start.

We began singing side by side, but pretty quickly, she realized she was actually good. And I saw it too. So I drifted a little backstage, letting her take the lead, because she was shining. And it was the coolest thing to witness.

Lily @ Date Brazen (15:25.935)

Then the DJ—who was also a musical theater person—joined in, and the three of us started singing three-part harmony on the choruses. She knew every word, didn’t miss a beat, and I watched her become a new version of herself in real time.

Yes, maybe she’d still feel nervous the next time she tried karaoke—as most of us would—but she would never again be the version of herself who had never done it. She would never again be the version who limited her joy because of fear.

That moment, back in 2018, solidified something for me. It captured exactly what I do with Date Brazen, and what I believe I’m here to do on this planet: to help you step onto a bigger stage. To help you break through that “window” you feel stuck behind—the one where it looks like everyone else has access to love, connection, and deep friendship, but not you.

Maybe you’ve told yourself you’re cursed, or that you’re too far behind. Maybe you think it’s too late because you’ve never experienced it before—whether you’re in your 30s, 40s, 50s, 60s, or even 70s. You see others having it and think, That’s for them, not me.

But no. Your life is not over. More is possible than you currently realize—when you give yourself permission to want what you want and to try something new.

And that’s why The Late Bloomer Show exists.

Lily @ Date Brazen (17:14.159)

This place is here to help you neutralize and release any shame that you’ve built up over the years of feeling behind. And that’s why I wanted to explicitly call out the “Late Bloomer” label in the title of this podcast, because we are built for you. We are here for you. I am here for you.

I remember how isolating it felt, and I remember how much feeling isolated — and then feeling shame about how alone I felt — and like, the shame saying to me, as the liar that it is, the hijacking emotion saying: Be small. Want less. Hide yourself. Don’t tell your friends how much you’re struggling, because they’re just gonna feel sorry for you, and they’re not gonna know what to do. Or they’ll give you unhelpful dating advice.

Shrink. Want less, because you are embarrassing, right? Shame says: You are wrong. And it’s a normal human emotion designed to keep you safe. But really, what you need to release that shame as your default is to start trying new things, to start attracting more than you thought possible — which is so scary and nerve-wracking. And it’ll take a lot of courage to get up on that next stage, but I’m right here with you.

This podcast is here to help you release shame, because what helps release shame is bringing it into the light. Shame loves silence. Shame loves dark corners. And so this podcast, by claiming “The Late Bloomer Show,” I just want to bring light to a place where you might have felt shrinkiness, isolation, fear. Bring light to it in order to give you the tools and the power and the sunshine to say: Yeah, I felt like a late bloomer, and I’m going after what I want. I felt like a late bloomer. There’s nothing wrong with it. The timeline is arbitrary. All this shit is made up.

Think about this: you’re listening to something, I’m recording something, called a podcast — which is basically an old-fashioned radio show that somebody made up before televisions existed so that people had a place to listen to the news, a place to get entertainment, whatever the fuck. And then, like, all of that is made up. All of this — the dating thing, the behind thing, the you need to be in a relationship by X time or else thing — that’s all f*cking made up.

Lily @ Date Brazen (19:36.025)

It’s time to ditch that shame and start reclaiming your timeline — the one that you are in right now. It is your timeline, and it is right for you. And in this timeline, things can change when you give yourself permission to want what you want and permission to try something new. So I hope that today you felt my excitement for you. Whether or not you can believe it for yourself, that’s okay.

You can believe that I believe it for you. And you can borrow my belief anytime — that what you want exists. And it’s on the other side of you trying something new and being in belonging. And I hope that you’ll go over to datebrazen.com to see our rebrand, to see the amazing pictures of my clients who came together on this day to celebrate one another, to own what they wanted — bananas, to own what they want. It was one of the best days of my life, this photo shoot with some of my clients.

I have so many amazing clients. Like, I would have invited you all. We rented a little space, and it was up there with my wedding and my book launch because it was all of these people who were sharing their brags and really celebrating one another for all of what they’ve created in their lives — creatively, work-wise, and romantically. They’ve all co-created so much goodness by showing up for themselves and their desires.

And I got to see people who I started working with seven years ago, some of my first clients ever, who are living such a different life now because they gave themselves permission to prioritize what they wanted. And they gave themselves permission to receive aligned support, to learn something new, to get on a bigger stage. I was so emotional. I cried a couple of times on that day. And those clients, who didn’t know each other before, left with each other’s phone numbers and left in belonging and community with one another.

And they showed up on camera and these…

Lily @ Date Brazen (21:48.591)

These photos of my clients are just so beautiful, and you’ll see on my website some video, and it’s such a party vibe. And that’s what I wanted to bring to this rebrand — this like, you’re not alone, let’s fucking go, feminist movement-for-late-bloomers energy. So I hope that you’ll check out my website that is beautiful and rebranded. I’m so grateful for the support of everyone I had to make that happen. High Flyer Powerhouse did my rebrand. They’re amazing. And yeah.

It’s just—I’m so excited for you to see it. And I’m excited for this new season of the Late Bloomer Show. Here’s to another five years together. You’re gonna hear more coaching episodes, you’re gonna hear more opportunities to apply to get coached by me on the podcast, and we’re going to keep growing our YouTube. I really want this to become a show—like a show-show—for late bloomers who are done shrinking, who want more,

and who are ready to reclaim their timeline and step into their most epic lives. So that’s what I’m building toward over here behind the scenes. It’s like: how do we build a YouTube show or a TV show that showcases this movement and helps even more people to show up for themselves, claim what they want, and attract it with more confidence? So I’m so excited.

The other piece of news that is so fun is that as of this recording—well, I’m recording this earlier, but it’s dropping on August 20th—I’m going on my belated honeymoon in a few days. And I’m so excited for that. So I’ve batched a lot of episodes that are so good that you’re gonna hear, but as you are listening to this, I might be on my honeymoon. We’re going to France, and I’m so grateful. I’m very excited to celebrate our

relationship and ourselves individually on this fabulous trip, about two and a half years after we got married. So thank you—more praise to that. And I am really excited that you’re here. I could sit here and ramble and talk in this catch-up for another hour and a half, but we gotta go. We gotta keep it pushing. So here’s the next step that you can implement after listening to this podcast to start claiming what you want.

Lily @ Date Brazen (24:08.879)

To start releasing the shame, start stepping into this new timeline where you are the main character. You can fill out your Essence-Based Preferences workbook if you haven’t already. I want you to claim everything that you want in such specificity that you never have before. I want you to claim how you want to feel in the right relationship, what you want—give yourself permission to take up space on the page. And I have a free workbook for you at datebrazen.com/workbook. It is totally free.

The sponsor of today’s episode is a 14-page guide that’ll help you create what I call your Essence-Based Preferences, which is how you want to feel in the right relationship. This is going to help you settle-proof your choices and learn how to vet people more quickly. It’ll also be the language that you use to describe what you want to your loved ones and friends. It’ll help you magnetize the right people to you. My clients who create Essence-Based Preferences find that even that practice alone grows their main character energy.

And they use them in the future when they meet people to know whether or not they’re the right fit—on date one, two, three, four, five, onward. It is a settle-proofing force, your Essence-Based Preferences. And I can’t wait for you to create your own at datebrazen.com/workbook. You’ve got this, and I’ve got your back. Talk to you next week.