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5 Questions That Lead to Deeper Conversations in Early Dating

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How do you have deeper conversations on a first date? These 5 questions will open up lively, informative, and connecting conversations. — Early dating doesn’t have to feel like an interview or a performance. The most meaningful connections grow when conversations move beyond small talk and into curiosity, values, and things you have in common. If you’re dating and craving something real, these five questions can gently open the door to deeper conversations. They’re not about pushing intimacy too fast or interrogating your date to see if there are red or green flags. They’re about listening, noticing, and seeing whether there’s room to grow together. 1. What feels fulfilling to you right now? This question reveals priorities. Some people light up talking about family, creativity, travel, volunteering, or even slowing down. Pay attention not just to the answer, but to the energy behind it. If you want to learn if their vision aligns with where you are in your life today, this...
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Reinventing Love and Life After 40

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Have you thought about reinventing your love and life after 40? Wendy Valentine did, and here’s her inspirational story! — Wendy Valentine reinvented her love and life after 40. She’s the author of Women Waking Up: The Midlife Manifesto for Passion, Purpose, and Play and the host of The Midlife Makeover Show , a top-rated podcast for women in midlife. After her divorce at 45, she learned to “marry herself” first—rebuilding her life from the inside out. Now she empowers women to embrace self-love, rediscover joy, and attract relationships rooted in authenticity and alignment. In this episode of Last First Date Radio: What it means to marry yourself before dating after divorce The FREEDOM Framework for transformation, and how to use it to heal from heartbreak How to design your ideal relationship and have an amazing life after 40 EP 694: Wendy Valentine – Reinventing Love and Life After 40 You’ve said that one of the best things you ever did was “marry yourself.” What ...
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5 Steps to Bust Limiting Beliefs in Dating

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Your limiting beliefs could be keeping you from the love you want. Here are 5 ways to bust those beliefs and finally find your person! — If dating has felt discouraging, confusing, or exhausting, it may not be because you’re meeting the wrong people. More often than not, it’s because old, limiting beliefs are quietly running the show. Limiting beliefs are those deeply held stories we tell ourselves that feel like facts, but are actually assumptions shaped by past experiences, heartbreak, cultural messaging, and fear. By midlife, we have had enough lived experience to collect quite a few of them. The good news is that beliefs are just thoughts, which means they can be questioned, softened, and replaced. And when they are, dating starts to feel lighter, more empowering, and more aligned. Here are five steps to help you bust the limiting beliefs that may be holding you back from love. Step 1: Identify the Story You Keep Repeating The first step in changing any behavior patte...
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How She Went From Purity Culture to Polyamory

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She went from purity culture to polyamory, and her husband stayed monogamous. Find out more on this episode of Last First Date Radio! — What happens when you go from purity culture to polyamory? My guest, Courtney Boyer, became polyamorous while her husband stayed monogamous. She is a relationship coach, writer, and speaker focused on love, desire, and authenticity. A former therapist, she blends mental health and sex-therapy expertise to help women release shame, reclaim their voices, and build honest, autonomous relationships. She lives in Germany with her husband and three children, endlessly learning and writing her next chapter. In this episode of Last First Date Radio: The beliefs from purity culture that shape our understanding of relationships and sexuality How Courtney realized polyamory felt aligned with who she now was The impact of polyamory on motherhood How to better understand mixed-orientation relationship structures EP 693: Courtney Boyer – From Purity Cu...
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Should I Stay or Should I Go? Relationship Advice

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If you’ve ever asked yourself, “should I stay or should I go” when in a relationship, here are 5 tips to help you decide. — Should I stay or should I go? Early dating can feel surprisingly confusing. One moment you’re hopeful and excited. The next, you’re questioning everything. You like him, but something feels off. Or maybe nothing specific is wrong, yet you’re not ready to go all in. This back and forth is called relationship ambivalence. It’s the mental tug of war between staying open to the relationship unfolding and wanting to walk away and find a better fit. For women in midlife, ambivalence can be especially tricky. You’re wiser now. You know yourself better. And you’re far less interested in wasting time. But discernment and fear can sometimes feel very similar. I’m sharing five tips to help you sort out whether your ambivalence is information worth listening to or anxiety asking for reassurance. Should I Stay or Should I Go? 5 Tips to Help You Decide 1. Separate di...
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Why Hope Might Be the Real Secret to Lasting Love

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What’s the real secret to lasting love? My podcast guest, Dr. Julia Garcia, has a hunch it might be something that surprises you… — What’s the real secret to lasting love? My podcast guest, Dr. Julia Garcia, is a psychologist, author, and renowned speaker dedicated to empowering people through the science of mental health. She weaves her real, lived experiences with behavioral science to create practical, transformative strategies for lasting change. Whether through her TEDx presentations, her interactive workshops, or her book The 5 Habits of Hope, Dr. Garcia’s mission remains the same: to prove that hope isn’t just something you feel—it’s something you practice, one habit at a time. In this episode of Last First Date Radio: The secret to lasting love Why people struggle to hold onto hope in romantic relationships The 5 Habits of Hope Feeling Detours, and how they show up in our lives How to train yourself to have more hope EP 692: Dr. Julia Garcia – Why Hope Might Be t...
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5 Questions to Ask Before You Become Exclusive

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How do you know if you’re ready to become exclusive? Ask yourself these important five questions before you stop dating others. — Exclusivity can feel exciting. It often comes with relief and hope. Finally, you’ve found someone great. But just because something feels good, it doesn’t necessarily mean it’s right. If you’re a woman in midlife and beyond, it’s important to slow down and check in with yourself. Before you agree to become exclusive, ask yourself the following five important questions. These are not questions for your date. They’re about taking care of yourself and honoring your values, your nervous system, and your future. 5 Important Questions to Ask Before You Become Exclusive 1. Do I feel emotionally safe with this person? Emotional safety is foundational. Do you feel calm, seen, and respected around them? Can you express a concern without being afraid of dismissal or defensiveness? Do their words and actions line up over time? Butterflies can distract you fr...
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