The Feminist Dating Show
The Feminist Dating Show is hosted by former top matchmaker and dating coach Lily Womble. Each episode offers practical tools, strategies, and coaching for women who want to find fulfilling relationships on their own terms. Lily shares her own dating advice along with expert interviews and live coaching sessions. The podcast focuses on feminist-leaning guidance for building confidence and navigating modern dating.
Episodes
286. Stop Freezing Around Cute People
If you want to date IRL and find your person, but you see someone cute and your body locks up, this episode is for you. Freezing is a somatic response. It is your nervous system protecting you from fears like: What if they reject me? I'm definitely not their type. They're probably coupled. Why even try? In this episode, I'm naming each of these fears for what it is, and giving you the reframes a
285. How to date men when you hate men
How do you date men when you hate men? It can be a tough question, especially if you've never seen that what you want and who you want exists. Both/and in this episode, I'm your feminist dating coach. And especially if you date men, I'm here to show you how to attract the feminist, emotionally intelligent, fights-for-women's-rights kind of man you desire. You are for the few, not the many. And
284. Make dating apps optional: A roadmap to attract the right relationship IRL
You don't have to be on dating apps to be "trying" in your dating life. This episode gives you the alternative strategy that has worked for hundreds of my clients (and worked for me to meet my husband). In this episode, you'll learn exactly how to date IRL. Inside episode 284: → Why "I don't chase, I attract" is one of my least favorite pieces of dating advice, and how it is negatively impacting y
283. My story: from people pleasing and settling in dating, to attracting more as the main character (and how you can, too)
In episode 283, I'm getting personal about how people pleasing made me settle in dating, friendship, and work, how it led to panic attacks on my lunch break, and the three-step formula I used to quit, one small choice at a time. → I thought I was and wanted "too much," and how that kept me in a relationship where none of my emotional needs were met → How people pleasing was showing up in every r
282. "It's scary to want things." How to stop people pleasing and attract what you actually want, with my client Jackie
Jackie was burnt out to a crisp. She was in a job she felt trapped in, because the story was that she had to be of service no matter how she felt. She had taken a sabbatical that was supposed to be two or three months, and it took her a couple of months just to relax. She came back and was immediately depressed. She couldn't see the forest through the trees. She had no vision. She just wanted to l
281. When is the right time to have sex? (and why you keep asking everyone but yourself)
The way you do one thing is the way you do everything. So when you're stressed about the question "when is the right time to have sex??" and outsource your answer to another dating expert or another tiktoker, I hear an opportunity to build a life changing skillset that will create clarity for this question (and all questions).... That skillset? Self-trust. When you build the skill set of self-t
280. The Sneaky Ways You're People Pleasing (and How to Stop)
The good, reliable, everyone-comes-to-me best friend. You've been praised for that role your whole life. What if it's the reason you can't get yourself to shoot your shot, ask for more, or take up space with your desires? This episode names the pattern hiding under all of it: people pleasing. Not being nice. The habit of self-abandoning in real time to avoid being misunderstood, judged, or aband
279. Decide You're the One: How to Get Over the Fear That You're Not Enough
You've been waiting to feel ready. Ready enough to launch the thing, shoot your shot, ask for the promotion you've been researching and figuring out the pitch for for months. Here's the hot take: you're stalling what you want because of the fear that you're not enough for it. The fear of failure, of judgement, of "not enoughness" has driven your car for long enough. So in this episode, I get a l
278. Stop Demoting Yourself to the "Best Friend" Role
Here are 3 signs you're demoting yourself to the "best friend" role in love, friendship, and work... You're the designated listener in your friendships, always the one reaching out first, making the plans, overgiving and caretaking. In dating, you're hesitating to ask for what you want for fear of scaring them off, settling for good enough or settling for inaction. At work, you're logging in past
Episode Spotlight: How to date in-person if you're scared to start
If approaching a cutie in the wild makes you nauseous… If you "aren't the type of person" to make eye contact with hotties in the wild… If the thought of asking someone out in-person makes your butthole clench up… If you want to try in-person dating, but feel overwhelmed and anxiety-filled at HOW to start. This episode is for you. 💎 Get the book, Thank You, More Please: https://datebrazen.com/b
Episode Spotlight: Feel undesirable? Here's what to do.
If you've ever feared that you're not attractive or desirable because it's never happened before, this episode is a must-listen. Lily breaks down the internalized fears many late bloomers carry—and how to reframe those thoughts with compassion, context, and confidence using her signature ACK mindset tool (Acknowledge, Compassion, Kind Reframe). You'll also get a powerful challenge to reconnect wit
277. The Flirting Ladder (from frozen with fear, to flirting irl)
You want to flirt IRL. But you're scared to start... The Flirting Ladder is exactly how you will build the skills to become an expert, confident flirter! This is the exact tool Lily teaches inside Main Character Dating to take you from frozen with fear to flirting with confidence. In this episode: → Flirting is joyful, courageous connection. Not a performance, not a personality trait some people a
276. The Impossible List: The Exercise That Proves Your Love Story Is Possible
Today we're talking about making the impossible happen. So if you think finding love is impossible for you, this is the episode for you. You've done it before. The friendship you didn't know you needed. The job that used to be a pipe dream and is now a no-duh. Your love life is next. Work with Lily: ■ Get the book, Thank You, More Please: https://datebrazen.com/book ■ Join the Main Character D
Episode Spotlight: Get over the fear of rejection (rejection resilience side quest!)
If rejection makes you want to hide under the covers and never date again—this episode is your roadmap back to brave action. In this Episode Spotlight, Lily shares one of her most painful rejections from her dating life, how it nearly derailed her belief in love, and the five-step Rejection Resilience Side Quest she created to help late bloomers build the skill of shooting their shot without spi
Episode Spotlight: "How to move through hopelessness in my dating life?"
This episode of The Feminist Dating Show is a juicy one-- I'm responding to a listener's voicemail about feeling completely hopeless after being ghosted... And after validating the hell out of her (because getting ghosted SUCKS), I got down to answering her question with a tactical action plan: How do you build hope in your dating life after so much disappointment? Is it even realistic to be hop
Episode Spotlight: "I'm a late bloomer, will men think that's a red flag?" - Live Coaching Session
If you feel like a late bloomer, and you're fearful that will come off like a "red flag" when you start dating, this is for you. This is a live coaching session with Dana, a healthcare worker who's never been in a long-term relationship and is wondering if it's too late for her. In one hour, Lily helps her build a full dating system from scratch. Inside this episode: 💎 Why you're for the few,
Episode Spotlight: The Most Anxiety-Relieving Dating Advice
You know that spiral where you replay a conversation for hours, convinced you said the wrong thing to the wrong person at the wrong time? Lily's got one sentence that ends it. This week's Episode Spotlight revisits the piece of advice that went viral for a reason: you cannot say the wrong thing to the right person. Inside this episode: ✨ The exact moment on a first date Lily talked about her e
275. If I Was Your Dating Coach This Summer, Here's What I'd Tell You to Do
If you've never been in a relationship before, or never been in a good one, and you identify with feelings of anxiety, hopelessness, or overwhelm when it comes to dating, and you just feel like it's impossible for you to find love and it's all over. This episode is for you. This is exactly what I would do if I was your dating coach in the next three weeks, so you could build a joyful dating life
274. Three Reasons Finding Love Is More Possible Than You Think
Your brain is convinced it knows how your love story ends. It's gathered all the evidence from your past and decided: this is just how it is. But your brain is not a fortune teller. It's a safety mechanism. And it is working with about 1% of the data. In this episode of The Feminist Dating Show, Lily breaks down three reasons you might just be wrong that finding love is impossible — and why more i
273. How to become lucky in your love life
Okay, let's say finding love is 100% all luck. A few weeks ago I shared my take: finding love is proximity to opportunity plus courageous behavior in the face of it. I got a lot of comments that said, "You're wrong, it's just 100% luck." So let's run the thought experiment. If finding love is 100% about luck... what creates the conditions for luck to occur? What even is luck? And how do you bec
272. The secret to magnetic dating? Unbothered CEO Energy.
You want dating to feel like something you're in charge of, that is going your way, not something that's happening to you. That shift-- from anxious hustle to magnetic momentum-- is what this episode is about. This week on The Feminist Dating Show, Lily breaks down the three levels of dating energy and exactly how to move from bothered and stressed to unbothered in your love life. Inside episod
271. Why now is the BEST time to date
This episode gets into why now is the best time to powerfully date — and why how you show up in your dating life is already changing the rest of your life, whether you realize it or not. Inside this episode: Your brain fears rejection the same way it fears death. That's not a dramatic spiral. It's neurobiology, and understanding it changes how much you let fear stop you. Women are socialized no
270. How to Meet People IRL (Even If You're Shy, Anxious, or Starting from Zero)
If you want to meet someone IRL, but the "how" feels like a total mystery.... This episode tells you exactly why it hasn't happened yet and what to do about it. Inside episode 270: → The two things that determine whether you meet people IRL: proximity to opportunity and courageous behavior in the face of it → What joy building is and why it works →What shooting your shot looks like when you're sh
Episode Spotlight: How to believe the best-case scenario in your dating life
You already know what the worst case scenario looks like. Your brain has mapped it out in extraordinary detail (in its attempt to keep you safe from rejection and vulnerability). This episode is about what happens when you let the best case scenario take up some of that space too. In this episode, Lily walks you through a best case scenario practice designed to open your brain up to possibility t
Episode Spotlight: What to Do at 1am When Your Brain Asks "Will I Die Alone?"
In this episode, Lily unpacks the fear, "Will I just die alone", that showed up dozens of times in her Instagram DMs, and walks you through what to actually do with it. Inside this episode: Why this fear feels too shameful to say out loud, and why that shame is exactly the reason you need to say it The seesaw dynamic keeping you stuck between hope and hopelessness, and how to step off it for go
Episode Spotlight: How to Flirt with Zero Experience
If you want to walk into a coffee shop, a bookstore, or a comic book store this summer and actually know how to say hi to someone you find cute, this episode gives you a step-by-step flirting framework you can use the next time you leave your house. Flirting is a buildable skill — not a secret language, not a personality trait. Here is the exact process. Step one: how to open a conversation with
Episode Spotlight: How to Start Dating When You Have Zero Experience
If you have zero dating experience and you want to find the right partner, this episode gives you six tools for late bloomers to start dating successfully. From zero experience to finding the right partner, without the patriarchal nonsense or the spiral. Step one is dropping the shame — and the actual skill that makes that possible (hint: it's not positive thinking, and it's not logic) Step two
269. It's not luck or timing. It's these two things.
Finding love isn't just luck or timing. It comes down to two learnable skills. Episode 269 of The Feminist Dating Show breaks both of them down so you can start practicing today. Inside this episode: ✨ The reason going on more dates won't get you closer to the right person. Dating is not a numbers game. It's an act of self-trust. ✨ Proximity to aligned opportunity: why most people are either p
268. Can You Date Men and Still Decenter Men? (yes, here's how)
If you want to date men AND you want to decenter men... This week's episode of The Feminist Dating Show (episode 268) is a giant permission slip. Because most dating advice is telling you to go on more dates, give more people a chance, stop being so picky. And all of that is designed to exhaust you into settling. (and you deserve more) Decentering men doesn't mean never dating a man again. It me
267. Your Rejection Resilience Plan: The tactical guide to becoming unstoppable in your dating life
Dating in your main character energy means more access to everything you want. More connection. More aliveness. More of the good stuff. It also means more rejection. BOO. Rejection doesn't have to mean anything about you. It's a filter, getting the wrong people out of the way. And the fear of it is one of the top forces stopping people from going after what they want. This episode is your reje
266. "I'm embarrassed to want partnership after fighting so hard for my independence" live coaching session
Cora left an unhealthy marriage, deconstructed her entire evangelical upbringing, bought her first house, and raised two 16-year-olds solo. Then she met someone really good on Hinge. Who met all of her essence-based preferences. And she almost talked herself out of it. Not because he did anything wrong. Because she felt ashamed for wanting partnership after working so hard to become independent
265. "Is it even worth it to try dating?" — When dating doesn't feel like part of your great life (and how to change that)
If you have a great life and dating just doesn't feel like part of it — this one's for you. In episode 265, I'm coaching Christina live. She's 36, has a great life, one long-term relationship under her belt, and is asking the question a lot of you are quietly asking: is it even worth it to try dating after so much disappointment? She's frustrated by the single tax — the emotional and financial cos
264. How to Flirt When You're Socially Anxious with Flirt Coach Benjamin Camras
Here's the secret of flirting... Every single person you've ever wanted to talk to — the cute stranger on the subway, the guy at the coffee shop, the woman you keep seeing at the farmers market — is also in their head. Every. Single. One. And yet most of us walk around convinced that WE are the only ones who are awkward, anxious, and completely clueless about flirting. This week on The Feminis
263. "I can barely open a dating app" Live Coaching Session (and a concrete plan for dating with anxiety)
If you've ever opened a dating app and immediately wanted to throw your phone across the room — this one's for you. In episode 263 of the Feminist Dating Show, I'm coaching Kayla live. This episode is for you if you relate to any of this: You open a dating app and immediately spiral into, "What if they make me uncomfortable?" or "what if I say something stupid?" You avoid swiping because judg
262. "I feel like my picker is broken." live coaching session
This one's for you if dating has started to feel like a hamster wheel of painful experiences… and you keep thinking: I've done so much work on myself—why is this still so hard? In this live session, I coach Quinn through: the loop of type vs. essence-based preferences the fear of being "too much" in dating what to do when uncertainty triggers a full-body spiral how to tell if your "picker is br
261. "I thought I was too late at 39—and I'm dating with hope now" with my client, Liz
Have you ever wondered if you're "too late" because dating has never worked the way it seems to work for everyone else? My client Liz joined Main Character Dating at 38 having never been in a long-term relationship. She felt behind, alone, and unsure how to even do dating. What shifted for Liz inside Main Character Dating was hope. No more dating shame. And an action plan that helped her m
260. The 10 Rules of Feminist Dating
In this episode, I'm sharing my 10 rules of feminist dating—the principles I know actually lead to an equitable, joyful partnership. No matter your past experience (or lack of experience), your age, or your sexuality, these rules are here to help you magnetize the right partner and feel amazing doing it. These 10 rules are a response to outdated, patriarchal dating advice that teaches you to shri
The Feminist Dating Show: Why the podcast name is changing and what comes next
In this episode, I'm sharing a transparent update about the podcast: why I decided to rename it The Feminist Dating Show. I talk through the intention behind the previous name, what I heard from listeners over time, and why I want the podcast name to immediately feel inclusive and clear—especially for people who are new to this work. Feminist dating has always been the value system underneath ever
Episode Spotlight: Holiday dating survival guide
If the holidays bring up nerves about being single — the questions, the pressure, the comparisons — this episode is your Holiday Dating Survival Guide. It's a warm, grounding replay packed with self-compassion, boundaries that protect your peace, and real scripts for handling conversations about your dating life. Inside, Lily shares: how to release the self-judgment we've all internalized from pa
259. From dreams in a drawer to doing the thing: How Laura finally started her business with main character energy
Laura sat on her dream for years. She had already moved abroad, left her marriage, rewritten her book, built a whole new life in a new country… and yet the next thing she actually wanted to build — a business supporting women after divorce — stayed in a drawer. In this conversation, you'll hear exactly how she went from: • paralyzed by fear of judgment • hiding the work she'd been doing for year
258. From "I'm So Behind" to Main Character Energy: How Abby got promoted, found community, and attracted her first healthy relationship in her mid-30s
In this episode, Abby shares her late bloomer story with so much honesty and clarity. We talk about what it was like to be in her mid-30s, never having been in a serious relationship, carrying a loud "I'm behind" and "I'm weird" narrative, and feeling totally unsure how to talk about her dating history without spiraling. Abby opens up about moving to a new city, trying to date while feeling embar
257. Self-Trust for Anxious Overthinkers: How to stop dress rehearsing tragedy
If you're stuck in a spiral of overthinking — replaying conversations, asking 15 friends what to do, imagining every worst-case scenario — this episode will feel like a deep exhale. Overthinking isn't you being "careful." It's a self-trust deficit. And that is a skill gap, not a character flaw. In this episode, I break down: • Why anxious rumination feels so real and so urgent • How patriarchy
256. 10 Seconds of Courage: The Secret to Becoming the Main Character of Your Life
Feeling like the supporting character in your own story? This episode is your plot twist. We unpack Main Character Energy (MCE) as a buildable skill set—not a personality type—and show how tending to your needs heals burnout and expands your capacity to show up for the people and causes you care about. In this episode, you'll learn: The 3-part MCE framework: Permission → Self-Trust → Massive, Mes
255. How to heal burnout, release perfectionism, and be the main character everywhere: Maureen's story
If you've ever found yourself doing everything right and still feeling exhausted, this conversation is for you. In this episode, Lily sits down with Maureen, a writer, educator, and book coach who transformed her life from chronic burnout and perfectionism to joyful, sustainable main character energy. They dive into: ✨ How perfectionism becomes emotional armor (and how to take it off safely). ✨
Episode Spotlight: "Am I doing enough to find love?" Checklist!
Ever catch yourself thinking: "Am I doing enough to find love?" That question sounds productive—but it's usually fear in disguise. Fear that time's running out. Fear that what you want might never happen. In this week's episode of The Late Bloomer Show, I walk you through the 10-step "Am I Doing Enough?" checklist—the one I give my clients when they start to spiral. You'll learn how to: 💗 Pra
Episode Spotlight: Slow Burn vs. The "Spark"
Should you wait for the slow burn? Or chase the spark? This question keeps so many late bloomers stuck in overthinking, second-guessing, and dating people who aren't right for them. In this episode of The Late Bloomer Show, Lily breaks down the real truth about attraction and connection, including: The pros + cons of both the spark and the slow burn Why both approaches can lead to wasted time
Episode Spotlight: Body image and your dating life with Bri Campos
Dating while struggling with body image fears can feel like an impossible task. In this episode, Lily is joined by Bri Campos, LPC, and body image coach, to explore the idea of body grief—the distress and loss we feel when our bodies change—and how it impacts dating. Together they cover: → The 4 aspects of body image you need to know → Why rushing to "body love" skips over the real healing work →
254. Dating with a disability, setting boundaries, and dating post breakup - Live Coaching Session
In this powerful live coaching session, Lily sits down with Veronica for a live coaching session—a listener and Main Character Dating client—to explore what it really looks like to start dating again after a painful breakup…while also navigating chronic pain, a disability, and a world that often is deeply ableist. They explore: ✨ How to know if you're really ready to date again after a breakup ✨ N
253. 10 Sex Questions Every Late Bloomer Has—Answered by Sex Therapist, Dr. Juliana Hauser
What do late bloomers most want to know about sex? In this episode, Lily sits down with Dr. Juliana Hauser—sex therapist, TEDx speaker, and author of A New Position on Sex—to answer the top 10 questions late bloomers have about sexuality, intimacy, and pleasure. They cover everything from starting with little or no experience, to disclosing your sexual history (or lack thereof), to navigating body
252. How to end emotional outsourcing and date with self-worth with Beatriz Victoria Albina
If you've ever felt behind in love or life, this episode is for you. On pub day for her new book, End Emotional Outsourcing: A Guide to Overcoming Codependent, Perfectionist and People Pleasing Habits, Beatriz Victoria Albina joins me to talk about how to stop centering everyone else's needs at the expense of your own—and start dating with self-worth. We unpack: 💎 What "emotional outsourcing" is a
251. "Hope is scary", here's how to build it - Live coaching session
Taylor hasn't been in a relationship since she was 19. Now, at 31, after eight ghostings and countless near misses, she's wondering: "Why not me?" In her words: "Hope is scary." Because every time she's let herself hope, she's been let down—and she's started to believe maybe she's just not worth the effort. In this raw and powerful live coaching session, we unpack what's really underneath that fea
250. "Nothing Will Ever Change… Right?" Coaching Through Dating Doubt as a Late Bloomer
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
249. "I've never been in a relationship. Are men going to see that as a red flag?" Live coaching session
Today on The Late Bloomer Show, I'm coaching Dana. Dana is a badass who's never been in a relationship—and she came to our session asking the question so many late bloomers carry: "Are men going to see that as a red flag?" In this episode, we go deep and get tactical. 💎 We create her Essence-Based Preferences in real time (including the exact words she'll use to vet potential dates) 💎 Build a clea
248. "I'm 44 and It Feels Too Late" to "I'm worth it" Live Coaching Session
"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. To
Don't call yourself a "Late Bloomer"? This is still for you.
When I renamed the podcast The Late Bloomer Show, some of you may have wondered: "What if I don't feel like a late bloomer — is this still for me?" I recorded a mini podcast episode talking about exactly that:) Listen here. Here are my hot takes: 🌱 "Late bloomer" to me means feeling "behind" in any way. To me, late bloomer isn't about the amount of experience or inexperience— it's about the fe
247. "I Stayed Long After I Knew It Was Over… Now I'm Starting From Scratch (Again)" Live Coaching Session
Are you afraid that raising your standards means you'll be alone forever? Today on The Late Bloomer Show, I'm coaching Marissa, who stayed long after she knew her relationships were over—because she thought starting from scratch would be worse than settling. In this episode, we dig into: ✨ Why we shrink our needs to keep relationships ✨ The guilt that keeps us stuck for years ✨ How to believe what
246. Behind the scenes of our name change- ("The Late Bloomer Show"!)
"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
245. "Why do I have to do all this work just to be given a chance?" Live Coaching Session
"Why do I have to do all this work just to be given a chance?" In this deeply moving live coaching session, Lily talks with Caleigh—a brilliant late bloomer feeling burned out and heartbroken after years on dating apps. On the surface, it's dating fatigue. But underneath, they uncover how internalized misogyny shows up in dating: feeling like you have to be less intense, less emotional, or hide
244. Get Over The Fear of Rejection (Rejection Resilience Side Quest!)
If rejection makes you want to hide under the covers and never date again—this episode is your roadmap back to brave action. Lily shares one of her most painful rejections from her dating life, how it nearly derailed her belief in love, and the five-step Rejection Resilience Side Quest she created to help late bloomers build the skill of shooting their shot without spiraling. Inside this episode
243. "Why would they like ME?" Busting This Late Bloomer Myth
Ever catch yourself thinking: "Why would they like me? What's wrong with them for wanting me?" This sneaky belief keeps so many late bloomers stuck in self-doubt, playing small, and avoiding the very love they crave. In this episode, Lily gets personal about how this thought showed up in her own love life—even when she met her now-husband—and shares the powerful mindset shifts and tools you need
Episode Spotlight: The Complete Guide To Finding Love On A Dating App
Think dating apps are the only way to find love—but secretly hate them? Same, friend. In this episode of the Date Brazen Podcast, I'm sharing my complete, no-BS guide to using dating apps in a way that protects your sanity and increases your chances of finding the right relationship. Inside, you'll learn: → Why deleting and re-downloading apps keeps you stuck → The exact rules for stress-free s
Episode Spotlight: How to get over the fear of dating
Dating can feel like a rollercoaster of emotions—excitement, hope, fear, and sometimes, pure panic. In this episode, we're tackling the fear that keeps so many incredible people stuck on the sidelines. If you've ever thought, What if I get rejected? What if I say the wrong thing? What if I'm not enough?—this one's for you. I'll walk you through how to move through dating fear with self-compassion,
Episode Spotlight: Your Mid-Year Dating Plan: From Late Bloomer to Main Character
This episode is your mid-year reset, late bloomer style. Whether you've been dating with no luck, stuck in swipe fatigue, or haven't dated in 15 years, this seven-step feminist dating plan is your guide to attracting the best relationship of your life. In this replay of one of our most popular trainings, you'll learn: ✨ How to create your Essence-Based Preferences to vet potential dates ✨ The IRL
Episode Spotlight: Finding love as a queer late bloomer, building self-trust, and healing after heartbreak
In this vulnerable and wisdom-packed episode, Lily sits down with Liz, a former Main Character Dating client, to talk about what it really takes to come back to yourself after a heartbreaking, sudden breakup—and how that healing work can lead to the most aligned love of your life. Together, they discuss: Why we feel "behind" in dating (especially as queer late bloomers) The emotional labor we
242. "I Want Love—But I'd Like to Skip Dating, Please"-- Live coaching session
Today's podcast episode is a coaching session with Michelle. She's in her 50s, divorced after a 24-year marriage, and getting back into dating after being with one person her whole adult life. In this raw and powerful coaching session, we unpack the overwhelm of dating apps, the anxiety of being "naive," and the pressure late bloomers feel to already know how dating is supposed to work. Michelle s
241. "I Stayed for a 4-Hour Date I Didn't Want to Be On" — Live Coaching Session for Late Bloomers
In this very first live coaching session on The Date Brazen podcast, you'll meet Ellie—an amazing, big-hearted late bloomer who's never had a romantic relationship, and who thought dating was something she missed the memo on. Sound familiar? Together in this episode we explore: Why Ellie stayed on multiple 4-hour dates she didn't even want to be on How to process feeling behind in your dating
Episode Spotlight: How to Shoot Your Shot (Even If You Feel Awkward)
Does the idea of making the first move in dating make you feel awkward AF? You're not alone. In this episode, I'm breaking down exactly how to shoot your shot as a late bloomer—without spiraling into self-doubt or waiting for someone else to make the first move. You'll learn: ✅ The mindset shifts that make it easier to take bold action in dating ✅ Why making the first move 100% of the time is a ga
240. Late Bloomer Series: Feeling undesirable? Here's what to do about it
If you've ever feared that you're not attractive or desirable because it's never happened before, this episode is a must-listen. Lily breaks down the internalized fears many late bloomers carry—and how to reframe those thoughts with compassion, context, and confidence using her signature ACK mindset tool (Acknowledge, Compassion, Kind Reframe). You'll also get a powerful challenge to reconnect w
239. Late Bloomer Series: How to Flirt
If flirting feels awkward, forced, or like a foreign language—especially because you feel "behind" in dating—this episode is your new playbook. Lily breaks down her step-by-step approach to flirting IRL with courage and ease. You'll learn how to strike up a conversation, gauge interest, and shoot your shot—without spiraling or second-guessing yourself. 📺 Want the visual breakdown? Watch it on YouT
238. Late Bloomer Series: How to Start Dating (If You've Never Dated)
Are you a late bloomer wondering, "How the hell do I even start dating?" In this episode, Lily breaks down the exact 6-step roadmap to go from anxious and avoidant to confident and aligned in your love life. You'll learn how to drop shame, claim your essence-based preferences, use dating apps with boundaries, and build your IRL dating strategy—messy and awkward and powerful. Here's how to work w
237. Late Bloomer Series: How to Tell a Date You've Never Been In A Relationship
In this kickoff to the Late Bloomer Series, Lily gets real about how to tell a date you've never been in a relationship—without spiraling, oversharing, or self-abandoning. If you've ever felt behind in love, this episode will help you embrace your story, communicate with confidence, and stop making your dating history mean something it doesn't. ✨ Grab Lily's book Thank You, More Please + get the
236. How To Stop People Pleasing (And Build A Stupidly Joyful Life)
Are you tired of living for everyone else's expectations... and ready to step into your own dang spotlight? 🎬✨ In this behind-the-scenes episode, I'm sharing practical tools to stop people-pleasing for good — and start building the stupidly joyful, self-trusting, main-character life you're meant for. Inside this episode: What people-pleasing really is (it's deeper than being "too nice") Why re
235. You Deserve More Than "Fine"- Katie's Story of Wanting More—and Getting It
RSVP for my new training- Stop People Pleasing & Build a Stupidly Joyful Life HERE Apply for Main Character Life Mastermind HERE Order my book, "Thank You, More Please": https://www.datebrazen.com/book Follow me on ✨ Instagram ✨ Tiktok ✨ Youtube
234. Go From Shrinking To Confident Main Character Energy
In this episode, we're diving deep into Main Character Energy — what it is, why it matters, and how to start building it (even if you're shy, introverted, or feeling wildly behind). You'll learn: - Why Main Character Energy is even more important in unstable times - The three essential skills at the heart of a Main Character Life - The truth about people-pleasing, perfectionism, and "best friend
233. How Jackie Went From Burnt Out Background Character-- to a Magnetic, Joyful AF Life
She Moved Abroad, Quit Her Job & Took Her Life Back: Jackie's Main Character Energy Story Burned out, stuck, and shrinking herself to stay safe—Jackie thought joy was out of reach. In this powerful episode, she shares how she went from emotional exhaustion to building a joy-filled life abroad with purpose, friendship, and bold-ass moves. If you're craving your own main character energy moment, th
Episode Spotlight: My Qualifying/Disqualifying Questions Strategy So You Never Go On A Bad Date Again
In this episode, Lily shares the ONE question that will revolutionize how you vet potential partners, ensuring you never waste time on lackluster dates and conversations again. Grab your notepad because this episode isn't just about strategy - it's a journey into reclaiming control of your dating narrative and steering towards the relationships you truly desire. Links: ✨ Order Lily's book, "Tha
Episode Spotlight: "How Can I Stop Being Lazy In My Dating Life?"
In this week's episode of the Date Brazen Podcast-- Episode Spotlight: "How can I stop being lazy in my dating life?", I'm teaching you exactly what you need to do instead of falling for the productivity myth. (which will lead to better outcomes for your dating life!) What you'll learn in the episode: ✨ How to ditch the idea that "doing more" will get you better results in dating. ✨ How to do
Episode Spotlight: How to Bless and Release The Wrong People Without Mind Drama
In this episode, I walk you through my Blessing and Releasing strategy: a powerful step-by-step method to let go of the wrong people and make space for the right ones. Because holding on to what isn't meant for you? That's keeping you from what is. Here's what you'll learn: ✨ How to identify who to bless and release (and why it's essential). ✨ The mindset shift that will help you actually move o
Episode Spotlight: Where Do I Even START With Dating?
In this episode, I break down exactly how to start dating with confidence, self-care, and intention.-- especially if you've never dated before! You'll get a step-by-step guide to move past fear, own your desires, and create a joyful dating life on your terms. Here's what you'll walk away with: ✨ How to start dating from a place of power (not pressure). ✨ Why your thoughts are not always facts—
Episode Spotlight: Owning Your Preferences is a Feminist Act
If you've ever been told you're too picky or need to be more open, this episode is for you. Your preferences aren't the problem—they're the key to dating with more joy and ease. I break down how to define your essence-based preferences so you can stop wasting time on the wrong people and start attracting the right ones. ✨ Get free "Create Your Essence Based Preferences Guide" HERE ✨ Order my boo
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