Just Ask Her - Dating Advice for Single Men

Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
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Honest dating advice for single men from two women. Dating expert Gracie Pleschourt (@datingwithgracie on IG) and certified life coach Tracy Pleschourt break down real dating questions, real struggles, and what actually works in modern dating. Each week, they dive into listener-submitted questions about their toughest dating challenges and deliver unfiltered, constructive feedback. Submit yours here: https://forms.gle/34JLMADMcxhqdb7X7

  1. 11 hr ago

    When Do You Stop Keeping Your Options Open? (Ep. 92)

    Dating with confidence isn’t about pretending you don’t care. It’s about knowing what you want, communicating honestly, and trusting yourself enough to handle the answer. In this episode of Just Ask Her, Gracie and Tracy answer three dating submissions that look completely different on the surface but share the same underlying challenge: when do you stop protecting your options and actually choose? One man is considering reaching back out to an ex after a major mistake damaged trust. Another is afraid that asking the woman he’s dating “what are we?” will make him look needy. And another has finally created abundance in his dating life—only to discover that choosing between multiple great women brings a new challenge. They break down what real confidence looks like, why clarity is better than trying to control an outcome, how to approach exclusivity, and why dating successfully eventually requires the courage to make a decision. Time Stamps / Chapters:  03:58 Why Charisma Is a Skill You Can Build 09:29 The Rise Challenge and Building Charisma 12:37 What Charisma Looks Like in Real Life 15:13 How the 30-Day Charisma Challenge Works 17:55 Three Dating Dilemmas With One Common Problem 18:46 Should You Reach Back Out to an Ex? 20:35 Why You Need to Disclose That You’re a Dad 28:59 Should He Actually Send the Message? 36:01 How to Have the “What Are We?” Conversation 38:07 What Real Dating Confidence Looks Like 43:13 Clarity, Exclusivity, and Fear of Losing Her 45:29 How to Choose Between Multiple Women 50:31 How to Know Who You Actually Want 53:23 When to Stop Dating Multiple People Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call #DatingAdvice #DatingForMen #Relationships Keywords: dating advice for men dating with confidence relationship clarity when to become exclusive dating multiple women how to choose a partner confidence versus neediness what are we conversation dating abundance mindset intentional dating for men how to contact an ex should I text my ex commitment in dating choosing the right woman relationship advice for men

  2. 26 Aug

    The Dating Mindset That’s Keeping You Single (Ep. 91)

    Dating confidence for men isn’t built by never getting rejected—it’s built by trusting yourself regardless of the outcome. In this episode of Just Ask Her, Gracie and Tracy answer three listener dating dilemmas about rejection, insecurity, self-sabotage, and approaching women with confidence. What happens when you assume women will reject you because of your height? Are you protecting yourself from dating because a past relationship hurt you? And what do you do when you’ve made huge improvements socially but still feel like you’re failing? Gracie and Tracy break down the beliefs underneath these struggles and explain how to stop making your self-worth dependent on whether a woman chooses you. They discuss vulnerability, charisma, emotional availability, approaching women, “out of my league” thinking, and learning to measure dating progress by how you show up—not just by whether you get a relationship. This episode is for single men who are tired of overthinking dating, fearing rejection, or feeling like they have to prove they’re good enough. Time Stamps / Chapters: 00:40 Welcome to Just Ask Her 00:55 The Odyssey, movies & what they’re watching 09:37 Help Just Ask Her reach more single men 09:56 JJ: Dating and rejection because of height 11:22 Stop trying to prove your worth on dates 14:29 The reality of height preferences in dating 18:28 Stop predicting rejection before you approach 20:12 Rejection vs. values and relationship compatibility 25:08 Self-made Man Dating Journal 26:16 Coach Trey: Is he self-sabotaging his dating life? 28:05 When self-sabotage is actually self-protection 37:03 Ryan: Growing socially but still feeling like a failure 40:26 Build confidence without moving the goalposts #DatingAdvice #DatingConfidence #MensDatingAdvice

  3. 19 Aug

    How to Approach Women Without Being Creepy (Ep. 90)

    RIZZ CHALLENGE WAITLIST: https://datingwithgracie.com/rizz-challenge1 How do you approach women without being creepy? The difference often isn't whether you approach—it's how you handle the moments leading up to it. In this episode of Just Ask Her, Gracie shares a grocery-store encounter that started with prolonged staring and eventually turned into an approach in the parking garage. She explains exactly what was going through her mind as the interaction unfolded—and why the man's hesitation made an apparently well-intentioned approach feel increasingly unsafe.  Gracie and Tracy use the experience to break down a better way to start conversations with women: stop searching for the perfect line, pay attention to context, read the situation, and learn how to have normal conversations with new people. This episode is for men who want to become more confident approaching women without making interactions feel forced, rehearsed, or uncomfortable. Time Stamps: 00:31 Welcome to Just Ask Her 01:10 Why This Approach Story Matters 11:27 The Grocery Store Encounter Begins 13:19 How to Make Eye Contact Without Being Creepy 15:17 The First Red Flag 18:33 When Awkward Attention Starts Feeling Unsafe 21:07 The Self-Checkout Encounter 23:28 He Approaches Her in the Parking Garage 28:29 Why Waiting Too Long to Approach Backfires 33:20 What He Should Have Done Instead 36:35 There Is No Perfect Opener 39:49 How Women Actually Want Men to Approach 42:41 Approaching Is Really a Social Skill #DatingAdvice #DatingForMen #SocialSkills Keywords: how to approach women approaching women without being creepy how to talk to women how to start conversations dating advice for men conversation starters with women confidence approaching women how to meet women social skills for men charisma for men natural conversation starters approaching women in public how women want to be approached dating confidence for men become more charismatic

  4. 12 Aug

    What Women Actually Want: Real Dating Advice for Men (Ep. 89)

    What do women actually want when dating? We asked real women the dating questions men want answered—from how to approach women to first dates, texting, dating profiles, and more. In this special episode of Just Ask Her, Gracie and Tracy take the podcast to Country Jam 2026 to hear real, unscripted answers from women of different ages. If you're a single man trying to date with more confidence, this episode gives you a firsthand look at women's perspectives. You'll hear what women notice when a man approaches them, what makes a positive impression, what turns them off on dating apps, and how they want a guy to take the next step. One of the biggest themes? Context matters. Preferences aren't universal, but the conversations reveal recurring themes around confidence, respect, authenticity, effort, intentionality, and actually getting to know someone. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call Time Stamps / Chapters: 00:00 What women actually think about dating 11:20 Taking Just Ask Her to Country Jam 13:56 What surprised Gracie and Tracy 24:42 Where women prefer to meet men 27:50 Small things that win women over 30:56 How to approach a woman with her friends 35:13 Dating profile mistakes women notice 39:59 Should you ask for her number? 43:19 How long should you wait to ask her out? 47:08 What makes a good first date? 54:09 Final thoughts on the special episode #DatingAdvice #DatingTipsForMen #WhatWomenWant

  5. 5 Aug

    How to Handle Relationship Conflict Without Losing Connection (Ep. 88)

    Looking for summer first date ideas that actually help build attraction? In this episode of Just Ask Her, Gracie and Tracy share creative date ideas before diving into two powerful listener questions about repairing relationship conflict and dating after heartbreak.  Whether you're struggling to communicate during conflict, wondering how to validate your partner's emotions, or questioning why dating feels emotionally flat after a breakup, this conversation offers practical mindset shifts and relationship advice. If you're a man who wants healthier relationships, stronger communication, and more confidence while dating, this episode is for you. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web 20%off coupon code = JUSTASKHER Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://datingwithgracie.com/application?utm_medium=YTepisode Time Stamps:  00:35 – Welcome back to Just Ask Her 00:51 – Summer first date ideas 02:30 – Picnic dates, breweries, and game nights 05:57 – Live music, fairs, and memorable summer dates 12:11 – Volunteer opportunities as unique date ideas 16:18 – Listener Question #1: Repairing a relationship after conflict 27:35 – Misunderstandings, communication, and relationship repair 35:12 – Self-Made Man Dating Journal 36:18 – Listener Question #2: Dating after a painful breakup 43:09 – Why your first heartbreak isn't your last 45:22 – Final thoughts and where to submit questions #DatingAdvice #RelationshipTips #FirstDateIdeas Keywords: summer first date ideas dating advice for men emotional validation relationship communication dating after heartbreak healing after breakup relationship repair emotionally available dating healthy relationship advice first date conversation tips dating confidence conflict resolution in relationships intentional dating vulnerability in relationships relationship mindset

  6. 29 Jul

    Are These Dating Red Flags... or Are You Overthinking Them? (Ep. 87)

    What are the biggest dating red flags in women—and which ones actually aren't red flags at all? In this episode of Just Ask Her, Gracie and Tracy break down common assumptions men make while dating and explain why context matters more than quick judgments. They also answer real listener submissions about mixed signals after a promising first date, overcoming the feeling of being "behind" in dating, and navigating modern dating while blind. Whether you're rebuilding confidence after rejection or trying to date with more intention, this episode offers practical advice and mindset shifts that can help. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call?utm_medium=spotify Time Stamps / Chapters 00:00 Intro & today's dating topics 00:42 Welcome to Just Ask Her 02:17 Podcast updates & listener feedback 03:23 Red flags in women discussion begins 20:10 Is hating every ex a red flag? 28:42 Submission: Should he reach back out after declining a second date? 37:50 Submission: Feeling left behind in dating 48:23 Self-Made Man Dating Journal 49:36 YouTube listener: Dating while blind 59:58 Episode wrap-up #DatingAdvice #DatingForMen #Relationships Keywords: dating red flags red flags in women dating advice for men dating confidence first date advice dating mixed signals relationship communication feeling behind in dating dating after rejection dating coach advice modern dating tips dating mindset confidence in dating dating podcast healthy relationships

  7. 22 Jul

    You're Not Behind: The Truth About Dating, Breakups, & Commitment (Ep. 86)

    Wondering whether to text your ex, when to commit, or why dating feels so difficult? This episode explores healthy dating, emotional growth, and dating confidence for men navigating modern relationships. Gracie and Tracy answer three thoughtful listener questions covering breakups, dating uncertainty, and healing from childhood experiences that continue to affect relationships today. Whether you're returning to dating after heartbreak, struggling with dating apps, or wondering if you're "behind" compared to everyone else, this conversation offers practical mindset shifts that can help you build healthier relationships. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call Time Stamps / Chapters:  00:26 Welcome Back to Just Ask Her 00:40 Celebrating 100 Community Members 05:09 How to Join the Dating Community 06:14 Netflix Recommendation: The Four Seasons 08:11 Leave a Podcast Review 08:28 Jason's Breakup and Unanswered Text 12:27 Why Her Silence Is the Closure 18:49 Brett's Dating Dilemma: When Do You Commit? 23:09 Commitment Creates Certainty 29:10 Brandon's Story: Childhood Trauma and Dating 33:00 You're Not Behind—You're Healing 38:07 Stop Trying to Create Attraction 39:46 Final Thoughts & Outro #DatingAdvice #Relationships #DatingConfidence

  8. 15 Jul

    Why Your Dating Mindset Matters More Than You Think (Ep. 85)

    Are your dates feeling one-sided? In this episode of Just Ask Her, Gracie and Tracy tackle one of the most common dating frustrations for men: feeling like you're doing all the work in conversation and wondering whether women actually want to get to know you. They also answer a listener's question about whether women have an advantage in modern dating, discuss why mindset matters more than keeping score, and celebrate an inspiring listener success story after years of struggling with dating. Whether you're trying to build confidence, communicate better, or date with more intention, this episode offers practical advice that can help you approach dating in a healthier way. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call Time Stamps / Chapter:  00:00 Opening message: Don't date with negativity 00:00 Welcome back & Tracy's 31st wedding anniversary 07:08 Listener Submission #1: Emil's dating conversations feel one-sided 09:36 Are you asking questions for the right reasons? 12:07 Stop using dating "strategies" and communicate honestly 18:11 Listener Submission #2: Do women have it easier in dating? 20:08 The realities of dating for men vs. women 27:44 Why a victim mindset won't help your dating life 30:05 Self-Made Man Dating Journal announcement 31:17 Listener Success Story: Chris finds a healthy relationship 36:07 Staying grounded after entering a relationship 38:16 Final encouragement and where to submit questions #DatingAdvice #Relationships #DatingConfidence Keywords: dating advice for men one sided dating conversations women asking questions on dates dating confidence tips healthy dating mindset dating communication skills intentional dating modern dating advice dating coach for men relationship communication dating expectations building confidence in dating dating after heartbreak healthy relationships dating self improvement

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About

Honest dating advice for single men from two women. Dating expert Gracie Pleschourt (@datingwithgracie on IG) and certified life coach Tracy Pleschourt break down real dating questions, real struggles, and what actually works in modern dating. Each week, they dive into listener-submitted questions about their toughest dating challenges and deliver unfiltered, constructive feedback. Submit yours here: https://forms.gle/34JLMADMcxhqdb7X7

Information

  • Creator
    Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • Years Active
    2024 - 2026
  • Episodes
    92
  • Rating
    Explicit
  • Copyright
    © Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • Show Website
    Just Ask Her - Dating Advice for Single Men

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