Just Ask Her - Dating Advice for Single Men

Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • 4.8 (63)
  • Relationships
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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. 12h ago

    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

  2. Aug 12

    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

  3. Aug 5

    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

  4. Jul 29

    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

  5. Jul 22

    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

  6. Jul 15

    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

  7. Jul 8

    Confidence Isn't Something You Find, It's Something You Build (Ep. 84)

    Confidence with women isn't something you're born with—it’s something you build through action. In this episode, Gracie and Tracy break down dating confidence, rejection, social anxiety, and why trying to become "what women want" is holding so many men back. If you've ever overanalyzed a rejection, struggled to approach women in person, or wondered why dating feels so confusing, this conversation offers practical advice that focuses on becoming confident in yourself instead of chasing external validation. The episode also explores how to rebuild confidence after painful relationships, why your dating history doesn't define your value, and how trusted friends and family can become one of the best ways to meet compatible partners. 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 Confidence comes from taking action 00:00:32 Welcome to Just Ask Her 00:01:14 Community dating success stories 00:06:36 Submission #1: She rejected me after a great second date 00:15:06 Talking about never having a serious relationship 00:23:08 Self-Made Man Dating Journal 00:24:16 Submission #2: What do women actually want? 00:33:34 Submission #3: Fear of rejection and social anxiety 00:36:14 How confidence is really built 00:41:24 Should family set you up? 00:47:08 Why your network is your biggest dating asset 00:49:53 ADHD, anxiety, and building confidence 00:51:30 Final thoughts #DatingAdvice #Confidence #JustAskHer

  8. Jul 1

    How to Know When a Relationship Isn't Right (Ep. 83)

    Ever wonder whether you're reading the signs correctly—or holding onto a relationship that's no longer moving forward? In this episode of Just Ask Her, Gracie and Tracy answer three real dating submissions from men navigating complicated relationship dynamics. From mixed signals with a coworker to becoming someone's emotional rescuer and exploring unconventional relationship structures, this episode helps you separate emotion from reality so you can make healthier dating decisions. If you're dating after heartbreak, divorce, or years of being single, this conversation will help you build confidence, establish stronger boundaries, and focus on relationships that genuinely align with what you want long term.  Self-Made Man Dating Journal -  https://www.amazon.com/dp/B0F9B7M5B3?th=1 Use Coupon SMMAN20OFF when purchasing Journal for 20% off. 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 Opening Thought: Sometimes the Right Relationship Isn't the Next One 00:00:26 Welcome Back! Fourth of July & Birthday Celebrations 00:02:18 Family Traditions, Minnesota Lakes & Summer Plans 00:05:22 Memorial Day vs. Labor Day (And the White Clothes Debate) 00:09:21 Dating Dilemma #1: Mixed Signals From a Coworker 00:10:40 The Signs That Made Him Think She Was Interested 00:13:06 Did She Friend Zone Him? Reading the Situation Clearly 00:15:18 Why Flirting Doesn't Guarantee a Relationship 00:16:32 Stop Giving Your Best to Someone Who Isn't Choosing You 00:18:35 Rejection Doesn't Define Your Worth 00:19:00 Dating Dilemma #2: Love, Rescue, or Emotional Dependency? 00:22:28 Are You Trying to Save Someone Instead of Dating Them? 00:25:25 Why Financial Support Can Hurt a New Relationship 00:27:03 Trauma Bonds, Therapy & Taking a 90-Day Pause 00:31:00 The Self-Made Man Dating Journal Announcement 00:32:11 Dating Dilemma #3: Can a Poly Relationship Actually Work? 00:35:24 "If I Was Coaching Him..." Tracy's Honest Take 00:39:01 Are You Truly Okay With This Relationship? 00:42:14 Scarcity Mindset After Divorce & Dating Again 00:44:03 The Most Important Question to Ask Yourself 00:46:31 Final Thoughts & How to Submit Your Dating Questions #DatingAdvice #Relationships #DatingCoach

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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
    90
  • Rating
    Explicit
  • Copyright
    © Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • Show Website
    Just Ask Her - Dating Advice for Single Men