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. 2D AGO

    You’re Not Behind, You’re Learning How to Date

    Dating confidence starts before the date, when you stop performing to be chosen and start showing up as the chooser. In Episode 62 of Just Ask Her, Gracie and certified life coach Tracy respond to three listener submissions on transactional relationships, dating after separation, and building real first-date chemistry. If you’ve ever felt “behind,” struggled with rejection, or keep hearing “it’s not you, it’s me,” this episode gives you practical mindset shifts and grounded reminders that real connection is built, not bought, and emotional resilience is something you grow through experience. You’ll also hear how to stop relying on “safe” but stagnant connection, how to handle the grief of dating endings (even early on), and how to create a stronger emotional experience on dates without becoming performative. In this episode: Why transactional connection can reduce real-world dating initiative The difference between kindness and lack of boundaries A neuroscience-based reframe for why early rejection hurts so much How to build emotional resilience through dating experiences Why first-date “fit” isn’t enough—chemistry is physiological How playful contrast (used sparingly) can create romantic tension The “chooser mindset” exercise that changes your energy on dates The 5-minute pre-date reset to avoid “please choose me” mode Time Stamps / Chapters 00:00 Pre-date mindset: stop performing, start choosing 00:41 Welcome to Just Ask Her + “dating with confidence” mission 01:00 Minneapolis deep-freeze + “economic ice out” context 04:48 Submission 1 (Ralph): paid companionship/OnlyFans + feeling “behind” 09:11 Why transactional connection blocks real relationships 14:14 Protective narratives, dopamine spikes, and the post-date “crash” 22:05 Practical plan: pause the exclusive online tie + 90-day app commitment 25:01 Submission 2 (Chris): 65, post-separation, rejection grief + resilience 31:02 “You’re grieving the possibility”—why it hurts after 3 in-person dates 37:03 “Is it too late?” + uncertainty is part of dating (not a problem) 39:53 Self-Made Man Dating Journal announcement (Amazon link in show notes) 41:12 Submission 3 (Drew): first dates → “it’s not you, it’s me” texts 46:21 Chemistry = felt experience + playful contrast (don’t overdo it) 55:11 The chooser exercise + 5-minute pre-date reset 01:00:15 Wrap: Episode 62 closing Hashtags: #DatingAdvice #DatingConfidence #EmotionalResilience Keywords: dating with confidence chooser mindset dating stop people pleasing on dates emotional resilience in dating handling dating rejection dating after divorce at 65 dating after separation grieving the possibility dating transactional relationships dating first date chemistry tips how to get a second date playful banter on a date boundaries in dating mindset before a date

    1h 1m

  2. JAN 28

    She Doesn’t Want Marriage After 14 Years—Now What?

    If you’re stuck in mixed signals, waiting to be “reconsidered,” or navigating a relationship where marriage and long-term goals don’t match, this episode breaks down what to do next,without chasing, arguing, or negotiating your needs away. In Episode 61 of Just Ask Her, the hosts respond to three submissions: a confusing “pheromones” rejection, an 8-year relationship where ambition and lifestyle expectations diverged, and a 14-year partnership where one person wants marriage and closeness while theother doesn’t. This is for anyone who wants clarity, stronger boundaries, and a reality-based way to decide whether to stay, especially when love is present but alignment isn’t. Time Stamps:   00:00 — If nothing changes: the question you have to answer 00:31 — Episode 61 begins + submission from Steven 01:03 — “Pheromones didn’t agree”: rejection + confusion 02:39 — Why people rarely give the real reason 04:44 — “I’m not interested” is the only sentence you need 06:10 — Attraction isn’t a debate + closure is self-made 09:13 — Submission from Jay: 8-year relationship + proposal plans 12:18 — Living like roommates: provider mindset vs connection 15:20 — Love vs misalignment: wanting to co-create a life 20:12 — Resentment, pressure, and the breakup dynamics 22:08 — Stop pausing your life; release the fantasy future 23:13 — Self-Made Man Dating Journal promo (Amazon) 24:32 — Submission from Paul: 14 years together, no marriage 26:18 — Facts vs story: loneliness + competing for attention 30:07 — Is there a compromise that both people choose?     Keywords: mixed signals after rejection she said not interested pheromones dating excuse attraction is not a debate closure after breakup relationship misalignment goals love isn’t enough relationship one partner wants marriage she doesn’t want to get married loneliness in a relationship long term relationship advice resentment kills intimacy how to stop waiting for an ex dating boundaries for men self trust in relationships Hashtags:   #relationshipadvice #datingadvice #relationships #boundaries #selftrust

    35 min

  3. JAN 21

    Episode 60: Should You Take Her Back? Plus Confessing Feelings to Your Best Friend

    Episode 60: Should You Take Her Back? Plus Confessing Feelings to Your Best Friend Welcome back! After a brief hiatus to upgrade our studio setup, Gracie and Tracy are back with real talk on navigating tricky dating situations. In This Episode: Question 1: Should I Give Her Another Chance?Rick shares his story about a woman who ghosted him after two months of dating, only to reach out months later with an apology. Should he take her back? We discuss: How to separate facts from fear-based interpretationsThe difference between compassion and accommodating bad behaviorWhat to watch for if you decide to give someone a second chanceWhy confidence comes from trusting yourself in uncertainty, not predicting outcomesQuestion 2: How Do I Tell My Best Friend I Have Feelings?Dan writes in about having romantic feelings for his lifelong best friend (who also happens to be his boss's daughter). We cover: Why the real fear isn't "weirding her out"—it's facing potential rejectionHow 68% of relationships actually start as friendshipsThe difference between a dramatic "confession" and a mature conversationHow to handle the situation professionally regardless of the outcomeQuestion 3: Why Should Men Listen to Women's Dating Advice?An anonymous listener challenges why women should give dating advice to men. We address: The difference between facts and the stories our brains tell usHow contempt and defensiveness make you undateableWhy expertise comes from observing what creates results, not genderThe importance of filtering the information you consume onlineKey Takeaways: You're not here to be chosen—you're the chooserConfidence is earned by doing hard things and surviving any outcomeThe risk isn't rejection; it's self-abandonmentYour job is to become a man you trust, then learn to choose wellResources Mentioned: The Self-Made Man Dating Journal - available on AmazonConnect With Us: Rate us on Spotify or Apple PodcastsShare this episode with friends who need to hear itNext Episode: More real dating questions, more honest answers. See you next week!

    35 min

  4. JAN 14

    Laid Off and Dating: What to Say (and What NOT to Put on Your Profile)

    Chemistry and availability aren’t the same thing—and that’s a key reason dating can feel confusing. In this episode of Just Ask Her, Gracie and her mom/co-host (certified life coach) Tracy answer three real submissions about mixed signals at work, dating after a layoff, and why first dates from apps often get canceled last-minute. If you’re dating with intention and you keep wondering “What did I do wrong?”, this episode helps you separate the facts from the story your brain is trying to write—so you can move forward with more confidence and less overthinking. You’ll hear practical scripts and mindset shifts for navigating modern dating dynamics (especially on the apps), plus how to protect your time and self-respect while still staying open to connection. In this episode: Why “chemistry” doesn’t equal “availability” (and how faith/values can change outcomes) Friendly vs. flirty in work settings—and how to get clarity without spiraling Should you mention unemployment on your dating profile? (Spoiler: no) How to talk about a recent layoff on a first date with confidence Why app dates get canceled so often—and how not to take it personally The better response when someone cancels (so you don’t carry the whole reschedule) Why comparison is wrecking your confidence (and what to do instead) Time Stamps / Chapters: 00:00 — Welcome to 2026 + new studio setup 00:02:21 — Submission #1: Mixed signals at work + mini golf invite “180” 00:05:56 — Friendly vs. flirty: how to get clarity (especially at work) 00:10:42 — Faith/values + “two truths can coexist” 00:13:02 — Lesson: you can do everything right and still not control outcomes 00:15:44 — Submission #2: Laid off—how it affects dating + your profile 00:19:06 — Why you shouldn’t disclose unemployment on apps (and what to say instead) 00:24:11 — Mind drama, shame, overexplaining: what actually hurts your dating life 00:28:49 — Submission #3: Dates keep canceling + confidence crash from comparison 00:32:05 — App reality: most matches don’t meet + lots of day-of cancellations 00:37:49 — What to text when she cancels (and why “pick a new time” backfires) 00:45:00 — Stop over-texting before the date: save conversation for in-person 00:47:32 — Episode wrap: Episode 59 + what’s next Keywords: chemistry vs availability dating friendly vs flirty at work mixed signals workplace crush how to ask her out clearly dating after being laid off unemployed and dating advice should I mention unemployment dating profile what to say when she cancels date dating app dates cancelled last minute why dating apps ghosting happens stop over texting before first date confidence after rejection dating dating apps decision fatigue how to reschedule a date text modern dating advice for men Hashtags: #DatingAdvice #OnlineDating #Confidence

    50 min

  5. 12/31/2025

    Dating Mindset Shifts, Spotify Wrapped Wins, and Real Listener Advice (Ep. 58)

    Are you ready to take control of your dating life and attract the women you want? In Episode 58 of the "Just Ask Her" podcast, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt celebrate a year of growth, share their impressive Spotify Wrapped stats, and answer real listener questions about dating challenges, mindset shifts, and self-confidence. In this episode: The Just Ask Her podcast’s first full year recap and top Spotify Wrapped achievements (Top 5% of videos, most shared show, and more!)Meet Noodle, the adorable new dachshund puppy joining the showListener submissions: Navigating dating with neurodivergence, overcoming “bad luck” in relationships, and embracing singlehood with confidenceMindset advice for men who feel stuck or defeated in datingThe importance of self-awareness, communication, and taking the lead in your dating journeyAnnouncing the launch of the Self-Made Man Dating Journal—designed to help single men track, reflect, and improve their dating experiencesExciting updates for 2026, including a new production team and upgraded video setupWhether you’re struggling with dating setbacks, wondering how to be the “chooser” in your love life, or just want to hear real, no-nonsense advice from women who get it, this episode is packed with actionable tips and inspiration. Resources mentioned: Self-Made Man Dating Journal on Amazon Follow Gracie on Instagram and TikTok: @datingwithgracieDon’t forget to rate, review, and share the show on Spotify or Apple Podcasts to help more listeners find us!

    45 min

  6. 12/24/2025

    Why You’re Alone on Christmas (And How to Change It) Ep.57

    Feeling alone this Christmas Eve? You’re not the only one. In this special holiday episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt get real about why so many men find themselves single during the holidays—and what you can do to make sure next year is different. We’re not here as coaches or experts, but as your family—your older or younger sister, your mom—ready to tell you the truth you need to hear. We’ll talk about the real reasons you’re stuck in your dating life, the stories you tell yourself that keep you from moving forward, and the steps you can take to break the cycle of loneliness. Key topics include: Why comparing yourself to others on social media is sabotaging your happinessThe truth about texting your ex (and why it never helps)How to get unstuck and start attracting the relationship you wantThe three steps to change: Decide, Get Clarity, and Do the WorkPractical advice for building confidence, meeting new people, and becoming someone you’re proud ofA 90-day challenge to transform your dating lifeYou’re not broken, and you’re not alone. Tune in for honest, no-BS advice, encouragement, and a promise: next Christmas can be different—if you decide to do the work. Subscribe for weekly episodes with actionable tips, real talk, and the support you need to change your dating life for good. Merry Christmas from Gracie, & Tracy

    17 min

  7. 12/17/2025

    Unlocking Dating Clarity: Real Advice for Men, Navigating Mixed Signals, and First Date Success (Ep. 56)

    Welcome back to Just Ask Her, the no-nonsense dating advice podcast for men who want real answers from a woman’s perspective! In Episode 56, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest dating dilemmas, from decoding mixed signals to making the most of first dates. In this episode: How to tell if she’s interested or just being friendlyThe power of direct communication: Why “just ask her” is the best strategyNavigating texting habits, physical touch, and gift-giving in modern datingCoping with rejection and building confidence after lossReal listener submissions: Rekindled friendships, workplace crushes, and moving on after heartbreakThe best first date ideas for online matches and in-person connectionsAre singles events and speed dating worth it? Pros, cons, and creative alternativesSpecial announcement: The Self-Made Man Dating Journal is now available on Amazon—track your progress and level up your dating life!Plus: Rapid-fire Q&A, reality TV talk, and why being the chooser (not just the chosen) is the key to dating success. Resources & Links: Grab your copy of the Self-Made Man Dating Journal on Amazon Follow Gracie on Instagram and TikTok: @datingwithgracieIf you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends. Your support helps more men find real, actionable dating advice! Tune in next week for a special holiday episode!

    36 min

  8. 12/10/2025

    Why She Didn’t Text Back: Real Talk on Dating Apps, Instagram DMs, and Moving On (Ep. 55)

    Show Notes Episode 55: Why She Didn’t Text Back: Real Talk on Dating Apps, Instagram DMs, and Moving On Welcome back to Just Ask Her—the no-nonsense dating advice podcast for men, hosted by dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt. In this episode, Gracie and Tracy tackle three listener submissions that highlight the most common struggles men face in modern dating: ghosting, mixed signals, and the frustration of online dating. In this episode: Submission 1: A listener wonders if an ex’s Instagram like means she wants to reconnect, and Gracie and Tracy break down why social media signals are rarely what they seem—and how to move forward with confidence.Submission 2: Tyler asks why women don’t respond to his Instagram DMs, despite his best efforts and a strong profile. The hosts explain the hidden variables of online messaging, why your worth isn’t tied to replies, and the “Rule of 100” for building dating resilience.Submission 3: Dan shares his story of heartbreak after divorce and struggles to find connection on dating apps. Gracie and Tracy offer advice on reframing rejection, increasing your “reps” in dating, and why your past doesn’t define your future.Plus: The launch of the Self-Made Man Dating Journal—designed to help single men track their dating progress, reflect, and grow.Why mindset is the most important factor in dating success.How to separate facts from stories when facing rejection.The importance of volume and persistence in online dating.Key Takeaways: Don’t read too much into social media interactions—focus on real communication and alignment.Your value isn’t determined by how many replies you get; it’s about choosing yourself first.Dating is a numbers game—get more reps before drawing conclusions.Healing from heartbreak is a journey, and every experience is a step toward the right relationship.Resources Mentioned: Self-Made Man Dating Journal on Amazon Follow Gracie on Instagram and TikTok: @datingwithgracieIf you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! New episodes every Wednesday.

    45 min
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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
    62
  • Rating
    Clean
  • 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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