EP 51: You've Been Asking the Wrong Questions After Every Date: The 4-Question Dating Checklist

EP 51: You've Been Asking the Wrong Questions After Every Date: The 4-Question Dating Checklist

You went on the date. You texted your friends. And immediately, every question was about him — did he like you, did he text, does he want a second date? But here's what we almost never stop to ask: Did you even like him? In this episode, Madden introduces a dating checklist that has nothing to do with his behavior — and everything to do with yours. Fresh off hosting her very first in-person dating event (the Love Lab!), Madden brings the energy of summer dating season with a framework that puts you back at the center of your own experience. This checklist isn't about being pickier or playing games. It's about breaking the cycle of performing and auditioning your way through dates — and finally dating like someone whose experience actually matters. WHAT YOU'LL LEARN: * Why even the most self-aware daters default to outsourcing their experience — and how to catch yourself doing it in real time * The subtle but important difference between performing and auditioning on a date (they overlap, but they're not the same thing) * How to tell if you were actually present on a date or just managing the conversation * Why your body language during a date is some of the most honest data you have — and how to start reading it * The one question that should anchor every post-date debrief that almost none of us are asking * How to use this 4-question checklist to keep yourself at the center of your own dating experience — not just this summer, but every date going forward "This checklist exists for one reason: to put you back in the center of your own dating life." - Madden Zappa CONNECT WITH YOUR HOST MADDEN ZAPPA: Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making. Madden's Instagram: ⁠@maddenzappa⁠ [instagram.com/maddenzappa] STAY UP TO DATE WITH WE'RE DATING THE SAME GUY: We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠ [instagram.com/datedifferentlyco] Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠ [https://www.speakpipe.com/datedifferentlydiaries] ✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.

EP 50: Pelvic Health, Shame & Intimacy: What Your Doctor Isn't Telling You ft. Dr. Sarah Oreck

So many women are silently navigating pelvic pain, chronic BV, UTIs, and other symptoms — feeling embarrassed, dismissed by doctors, or completely disconnected from their own bodies. And what we don't talk about enough? How much this affects your confidence, your intimacy, and your relationship with yourself. In this episode, Madden is joined by Dr. Sarah Oreck, a Columbia-trained reproductive psychiatrist and co-founder of Mavida Health, for one of the most validating and important conversations we've had on this show. Whether you're single, dating, in a relationship, or married — this one is for you. WHAT YOU'LL LEARN: * The real (and often ignored) women's health issues: BV, pelvic pain, vaginismus, vulvodynia, perimenopause, chronic UTIs * What medical gaslighting actually does to your nervous system and your trust in relationships * How pelvic health symptoms quietly erode your confidence and make you avoid intimacy * Why you don't need to apologize — not to your doctor, not to your partner, not to anyone * How to start rebuilding your connection with your body (and why your skincare routine counts) * What emotionally supportive partners actually do (and what's a red flag) * The importance of leading with curiosity "The pelvis holds a lot. I actually think it's a place that stores a great deal of trauma and a great deal of anger. That's why the mental health piece is always so important to link with the physical. A lot of people are just running to OBs and urologists trying to figure it out — but mental health support in all of this is essential."— Dr. Sarah Oreck CONNECT WITH DR. SARAH ORECK: Dr. Sarah Oreck is a Columbia-trained reproductive psychiatrist with a practice focused on women's mental health across every life stage — from fertility and pregnancy to perimenopause and beyond. She is the co-founder of Mavida Health, a virtual mental health platform making specialized reproductive psychiatric care accessible and affordable. Mavita is currently serving patients in California, New York, New Jersey, and Texas, with rapid expansion underway. Dr. Oreck's Instagram: @sarahoreckmd [https://www.instagram.com/sarahoreckmd/] Dr. Oreck's TikTok: @drsarahoreck [https://www.tiktok.com/@drsarahoreck] Mavida Health Instagram: @mavidahealth [https://www.instagram.com/mavidahealth/] Learn more about Mavida Health HERE [https://www.mavidahealth.com/?utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQPOTM2NjE5NzQzMzkyNDU5AAGnxGZbu_UvWA0_qNLkWZ4JPfa8ZGZfvxwLdKK9QSKKZWT5v0kCHECwxQJf5fE_aem_LrbtXmMADKRsUVrQ3YjBtQ] CONNECT WITH YOUR HOST MADDEN ZAPPA: Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making. Madden's Instagram: ⁠@maddenzappa⁠ [instagram.com/maddenzappa] STAY UP TO DATE WITH WE'RE DATING THE SAME GUY: We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠ [instagram.com/datedifferentlyco] Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠ [https://www.speakpipe.com/datedifferentlydiaries] ✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.

EP 49: Social Media Is Killing Dating: How Your Phone Is Sabotaging Your Love Life

We have more ways than ever to meet people, communicate, and see how others are living their lives. And yet — research shows we're in the middle of a loneliness epidemic. More than 6 in 10 adults in the U.S. report feeling disconnected. So what's actually going on? In this solo episode, Madden gets into three specific ways that living in a digital world is quietly wrecking how we date — and what you can actually do about it. WHAT YOU'LL LEARN: * Why constant texting early in dating creates a false sense of intimacy — and what real connection actually requires * How your social media algorithm is secretly setting impossible relationship standards (and why we never see the messy middle) * The truth about dating apps: they weren't designed to help you find love — they were designed to keep you on the app * Why every swipe and match is really just an ego hit dressed up as dating * Three practical things you can do right now to start dating with more presence and intention "We are living in a time where we have more ways than ever to meet people and connect. And yet, research is showing time and time again that we're actually potentially the most disconnected generation. More than six out of 10 adults in the U.S. report feeling disconnected or lonely. That is not a coincidence. That is a pattern worth paying attention to." - Madden Zappa LOVE LAB & MORE: * 🎟️  Love Lab LIVE Dating Event- Minneapolis, May 4th [https://partiful.com/e/IPypfXO1HldeMYZTLMR3?c=5tEEirmI] * 📥 Free PDF Guide: The 9 Dating Personalities [https://preview.mailerlite.io/forms/2157581/180924007548192609/share] (deeper breakdown of every pattern) CONNECT WITH MADDEN: Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making. Madden's Instagram: ⁠@maddenzappa⁠ [instagram.com/maddenzappa] STAY UP TO DATE WITH WE'RE DATING THE SAME GUY: We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠ [instagram.com/datedifferentlyco] Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠ [https://www.speakpipe.com/datedifferentlydiaries] ✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.

EP 48: Great at Dating, Terrible at Relationships: A Celebrity Matchmaker's Unfiltered Truth ft. Alessandra Conti

You've been on the dates. You've felt the spark — or you haven't. You've told yourself you have a "type." You've stayed friendly with your ex "just because." And you've done all of it while genuinely believing you're ready for a relationship. But what if most of what you've been taught about dating is quietly working against you? This week, Madden sat down with Alessandra Conti — Celebrity Matchmaker and co-founder of Matchmakers In The City in Beverly Hills to talk about the single biggest mistake daters make (going for chemistry instead of character), what a man's Instagram following actually tells you, and the real reason why men who are great at dating are usually terrible in relationships. Then we go fully off-script — into whether men and women can actually just be friends, and why staying in contact with your ex isn't harmless, it's self-sabotage. This one is going to make you want to text your group chat immediately. WHAT YOU'LL LEARN: * Why chemistry-chasing is keeping you in the same loop — and the question Alessandra says to ask instead * The one Instagram red flag that tells you a man isn't ready for a relationship * Can men and women actually be just friends? (We have opinions.) * Why staying friends with your ex is an avoidant attachment pattern — not just a personality trait * Hyperindependence as a trauma response and how to start letting people in "People are going for chemistry and not going for character. And this is where we are — welcome to 2026 and the wild, wild west of dating. It's not that chemistry doesn't matter. It's that character is the thing that sustains a relationship once the butterflies quiet down. And most people aren't vetting for character at all." - Alessandra Conti CONNECT WITH ALESSANDRA CONTI: Alessandra Conti is a Celebrity Matchmaker and co-founder of Matchmakers In The City, a personal matchmaking firm based in Beverly Hills. She has served as the matchmaker for Real Housewives of Beverly Hills, NBC's Access Hollywood, TLC's My Big Fat Fabulous Life, and two seasons of MTV's Are You The One. Her advice has been featured in Forbes, The New York Times, The LA Times, and Fox News. Over nearly 14 years, Alessandra has worked with clients ranging from royalty to young professionals, leading a team of six matchmakers responsible for hundreds of marriages. Alessandra's Instagram: @matchmakeralessandraconti [instagram.com/matchmakeralessandraconti] Matchmakers In The City: @matchmakersinthecity [instagram.com/matchmakersinthecity] Matchmakers In The City Website [www.matchmakersinthecity.com] LOVE LAB & MORE * 🎟️ Love Lab Live Dating Event – Minneapolis, May 4th [https://partiful.com/e/IPypfXO1HldeMYZTLMR3?c=hfiknbc9] * 📥 Free PDF Guide: The 9 Dating Personalities [https://preview.mailerlite.io/forms/2157581/180924007548192609/share] (deeper breakdown of every pattern) CONNECT WITH YOUR HOST MADDEN ZAPPA: Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making. Madden's Instagram: ⁠@maddenzappa⁠ [instagram.com/maddenzappa] STAY UP TO DATE WITH WE'RE DATING THE SAME GUY: We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠ [instagram.com/datedifferentlyco] Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠ [https://www.speakpipe.com/datedifferentlydiaries] ✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.

EP 47: You Don't Have a Type, You Have a Pattern: 9 Dating Patterns Quietly Sabotaging Your Love Life

Have you ever looked back at everyone you've dated and thought… wait, why does this keep happening? This week Madden breaks down something that's been living in her head for months — and honestly, it cracked something open for her in a really big way. It started with a simple comment from her best friend: "He's totally your type." And she couldn't let it go. Because she's always said she doesn't have a type. But here's what she realized — it was never about her type. It was about her pattern. In this solo episode, Madden walks you through 9 dating personalities she's identified from her own experience, her coaching practice, and the stories of so many women navigating dating. These aren't diagnoses. They're not labels. They're tools — for awareness, for self-understanding, and for finally starting to spot the behaviors that aren't serving you. WHAT YOU'LL LEARN * Why your "type" is actually your pattern in disguise * The 9 dating personalities: The Saleswoman, The Chameleon, The Bargainer, The Detective, The Dreamer, The Runner, The Project Manager, The Performer, and The Affirmation Junkie * The unique strength inside every single one of these patterns * The one shift each personality can make to start showing up differently * Why awareness alone isn't enough — and what comes next "Awareness is everything. And also — awareness is just the first step. What you do with your awareness, that's where the change actually starts to take place. That's the work. So which one hit home for you? Because knowing your pattern is one thing. Choosing differently is another." - Madden RESOURCES MENTIONED * 📥 FREE 9 Dating Personalities Guide [https://preview.mailerlite.io/forms/2157581/180924007548192609/share] (deeper breakdown of every pattern) * 🎟️ Love Lab Live Dating Event [https://partiful.com/e/IPypfXO1HldeMYZTLMR3?c=tW5jR_xA] – Minneapolis, May 4th [LIMITED SPOTS- BOOK BEFORE IT FILLS UP] * 📲 Follow Madden on Instagram: @maddenzappa CONNECT WITH MADDEN ZAPPA: Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making. Madden's Instagram: ⁠@maddenzappa⁠ [instagram.com/maddenzappa] STAY UP TO DATE WITH WE'RE DATING THE SAME GUY: We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠ [instagram.com/datedifferentlyco] Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠ [https://www.speakpipe.com/datedifferentlydiaries] ✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.