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Just Ask Her - Dating Advice for Single Men
Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
58 episodes
6 days ago
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
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All content for Just Ask Her - Dating Advice for Single Men is the property of Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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
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Relationships
Society & Culture
Episodes (20/58)
Just Ask Her - Dating Advice for Single Men
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 show
  • Listener submissions: Navigating dating with neurodivergence, overcoming “bad luck” in relationships, and embracing singlehood with confidence
  • Mindset advice for men who feel stuck or defeated in dating
  • The importance of self-awareness, communication, and taking the lead in your dating journey
  • Announcing the launch of the Self-Made Man Dating Journal—designed to help single men track, reflect, and improve their dating experiences
  • Exciting updates for 2026, including a new production team and upgraded video setup

Whether 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: @datingwithgracie

Don’t forget to rate, review, and share the show on Spotify or Apple Podcasts to help more listeners find us!

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6 days ago
45 minutes 7 seconds

Just Ask Her - Dating Advice for Single Men
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 happiness
  • The truth about texting your ex (and why it never helps)
  • How to get unstuck and start attracting the relationship you want
  • The three steps to change: Decide, Get Clarity, and Do the Work
  • Practical advice for building confidence, meeting new people, and becoming someone you’re proud of
  • A 90-day challenge to transform your dating life

You’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


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1 week ago
17 minutes 25 seconds

Just Ask Her - Dating Advice for Single Men
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 friendly
  • The power of direct communication: Why “just ask her” is the best strategy
  • Navigating texting habits, physical touch, and gift-giving in modern dating
  • Coping with rejection and building confidence after loss
  • Real listener submissions: Rekindled friendships, workplace crushes, and moving on after heartbreak
  • The best first date ideas for online matches and in-person connections
  • Are singles events and speed dating worth it? Pros, cons, and creative alternatives
  • Special 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: @datingwithgracie

If 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!

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2 weeks ago
35 minutes 35 seconds

Just Ask Her - Dating Advice for Single Men
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: @datingwithgracie

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! New episodes every Wednesday.

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3 weeks ago
45 minutes 9 seconds

Just Ask Her - Dating Advice for Single Men
Should You Approach Her When She's Alone? Ghosting, Rejection & Building Real Confidence (Ep. 54)

Should You Approach Her When She's Alone? Ghosting, Rejection & Building Real Confidence (Ep. 54)

Show Notes:

Listener submissions spark honest conversations about:

  • The right (and wrong) ways to approach women in different contexts
  • How to handle mixed signals and trust your instincts after being hurt
  • Why ghosting and rejection don’t define your worth
  • The hidden pitfalls of dating apps and how to reframe “rejection”
  • Building confidence and self-awareness for better connections

Plus, Gracie and Tracy share personal stories, Thanksgiving chaos, and announce the launch of the Self-Made Man Dating Journal—designed to help you track, reflect, and level up your dating life.

Don’t miss the practical advice, mindset shifts, and real talk that will help you date with more confidence and clarity.

Listener questions featured from: James, Kyle, Jake, and Miguel.

Resources mentioned:

  • Self-Made Man Dating Journal (available now on Amazon
  • Follow Gracie on Instagram & TikTok: @datingwithgracie

New episodes every Wednesday!

You’ll learn:

  • When (and how) to approach women respectfully—alone or in groups
  • Why ghosting and rejection aren’t reflections of your worth
  • How to trust your instincts and set healthy boundaries
  • The truth about dating apps and self-sabotaging beliefs
  • Actionable tips for self-awareness and authentic connection

Plus, hear about the new Self-Made Man Dating Journal, designed to help you track your progress and break old patterns.

Tune in for honest advice, relatable stories, and the mindset shifts you need to succeed in modern dating.

Subscribe for new episodes every Wednesday, and follow Gracie on Instagram & TikTok @datingwithgracie.

Grab your copy of the Self-Made Man Dating Journal on Amazon


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1 month ago
46 minutes 57 seconds

Just Ask Her - Dating Advice for Single Men
Gratitude, Growth, and Real Talk: Navigating Dating Challenges & Self-Trust (Ep. 53)

Episode Description:

Gratitude, Growth, and Real Talk: Navigating Dating Challenges & Self-Trust

In this special Thanksgiving and birthday episode, Gracie and Tracy reflect on the power of gratitude, embracing new chapters, and the lessons learned at 25.

They answer listener questions about moving on after betrayal, dating after divorce, and how to handle fast-paced connections in the digital age. Plus, they introduce the Self-Made Man Dating Journal—designed to help you track your progress and date with intention.Feeling stuck in your dating life or struggling to move on after heartbreak?

In this episode, Gracie and Tracy get real about gratitude, personal growth, and the messy realities of modern dating. They answer listener questions about letting go of toxic relationships, dating after divorce, and how to communicate your needs and boundaries.

Whether you're navigating new connections or healing from the past, you'll find practical advice and encouragement to help you trust yourself and date with intention.

Plus, discover the new Self-Made Man Dating Journal—your guide to tracking progress and building better relationships.

Listen now for a dose of honesty, hope, and inspiration!

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1 month ago
33 minutes 35 seconds

Just Ask Her - Dating Advice for Single Men
One Year of No-BS Dating Advice: Real Women, Real Answers – Anniversary Special (Ep. 52)

Welcome to the anniversary episode of Just Ask Her! Gracie and Tracy celebrate a full year of empowering single men with honest, actionable dating advice. In this special episode, they reflect on the journey so far, the growth of their community, and the impact the show has had on listeners around the world.

To mark the occasion, Gracie and Tracy take your most-asked dating questions out of the studio and into the real world—specifically, the Mall of America! Hear candid, unfiltered answers from women of all ages and backgrounds as they share what really matters in dating, what green and red flags they look for, and their best advice for men looking to improve their love lives.

Highlights:

  • The story behind the podcast’s evolution and its first anniversary

  • Why men’s vulnerability and willingness to seek advice is so powerful

  • The importance of mindset and community in dating success

  • On-the-street interviews with women answering your top dating questions:

    • Most attractive qualities in a man

    • Approaching women: what works and what doesn’t

    • Dating apps vs. real life vs. mutual friends

    • Height, self-improvement, and who should pay for the first date

    • Biggest red and green flags

    • The best advice for single men

  • Reflections on the value of honest conversations and the supportive Just Ask Her community


    Resources:

  • Self-Made Man Dating Journal – Available on Amazon ⁠

  • ⁠Submit your questions for future episodes via the show’s submission form⁠
  • Dating Differently Application


    Thank you for being part of our journey! If you’ve found value in the show, the best anniversary gift you can give is to share this episode with someone who needs it and leave us a review. Here’s to many more years of real talk and real results!

It’s our one-year anniversary! To celebrate, Gracie and Tracy take your most-asked dating questions to the Mall of America, getting honest answers from real women. Tune in for fresh perspectives, heartfelt reflections, and practical advice that will help you date with confidence. Don’t miss this special episode packed with insights, laughs, and gratitude for our amazing community. Share, review, and keep your questions coming—because no matter where you are, you can always Just Ask Her.

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1 month ago
40 minutes 37 seconds

Just Ask Her - Dating Advice for Single Men
Breaking Patterns & Building Self-Trust in Dating (Ep. 51)

Episode 51: Breaking Patterns & Building Self-Trust in Dating

Description:
In this episode of "Just Ask Her," Gracie and Tracy dive into three listener submissions that highlight the real challenges men face in modern dating. From navigating attachment styles and dating app fatigue to finding emotionally available partners and breaking free from self-sabotaging patterns, this episode is packed with actionable advice and heartfelt coaching. Plus, Gracie announces the launch of the Self-Made Man Dating Journal, designed to help single men reflect, grow, and date with intention.

Show Notes:

Intro & Halloween Banter

  • Gracie and Tracy kick off the episode with some lighthearted Halloween talk, sharing personal stories and family traditions.

Submission 1: Sal’s Story

  • Sal, a father of four and firefighter, shares his journey from anxious to secure attachment style.

  • Struggles with dating app fatigue and finding emotionally available women.

  • Gracie and Tracy discuss the pitfalls of over-labeling attachment styles, the scarcity mindset, and the importance of real-life connections.

  • Advice: Leverage your strengths in real-world environments, seek shared purpose, and remember that every "failed" connection brings you closer to alignment.

Submission 2: Kyle’s Question

  • Kyle wonders why it seems women don’t have hobbies and how to meet like-minded singles.

  • Discussion on generational trends, burnout, and the importance of reframing blanket statements.

  • Tips: Switch up your social activities, challenge self-sabotaging beliefs, and remember that the right partner will appreciate your diverse interests.

Submission 3: Greg’s Pattern

  • Greg, an Australian Air Force sergeant, describes a recurring pattern of women pulling away.

  • Gracie and Tracy explore confirmation bias, self-trust, and the importance of detaching from painful narratives.

  • Practical steps: Name the pattern neutrally, detach from identity, decide what you’ll do differently, and let people reveal themselves over time.

Resource Mentioned:

  • Self-Made Man Dating Journal – Now available on Amazon! Designed to help single men track dates, reflect, and grow. Limited first run—grab yours before they’re gone.

Listener Call to Action:

  • If you enjoy the show, please rate and review on Spotify or Apple Podcasts, and share with friends!

  • Submit your questions for future episodes.

Connect with Gracie:

  • Instagram & TikTok: @datingwithgracie

New episodes every Wednesday!

Show more...
1 month ago
41 minutes 12 seconds

Just Ask Her - Dating Advice for Single Men
Real Dating Questions Answered – Confidence, Signals & Starting Over (Ep. 50)

Episode 50: Real Dating Questions Answered – Confidence, Signals & Starting Over

Description:
In this milestone 50th episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about modern dating. From overcoming shyness and reading signals to building confidence and starting over after a long relationship, Gracie and Tracy deliver no-nonsense advice straight from a woman’s perspective. Plus, they announce the launch of the Self-Made Man Dating Journal and tease a special anniversary episode coming soon!

Whether you’re struggling to approach someone new, wondering how to get noticed, or navigating the dating scene after years away, this episode is packed with practical tips, research-backed insights, and encouragement to help you take control of your dating life.

Show Notes:

00:00 – Welcome & Introduction
01:30 – Listener Submission #1: Should I ask out the Home Depot girl?
05:00 – How to read signals vs. friendly behavior
08:30 – Building confidence and taking action despite shyness
12:00 – The truth about rejection and courage in dating
15:00 – Launch Announcement: Self-Made Man Dating Journal
18:00 – Listener Submission #2: Why don’t women notice me?
22:00 – The science of attraction and nonverbal cues
25:00 – How to shift from seeking validation to radiating confidence
29:00 – Listener Submission #3: Dating after a 30-year relationship
33:00 – Navigating small communities and changing your identity
37:00 – Advice for starting over and expanding your social circles
41:00 – Anniversary Episode Teaser: “Man on the Street” Q&A
44:00 – How to submit your questions for the special episode
46:00 – Final thoughts & where to find Gracie online

Resources Mentioned:

  • Self-Made Man Dating Journal – Available on Amazon

  • Submit your questions for the anniversary episode via the show’s submission form

  • Follow Gracie on Instagram & TikTok: @datingwithgracie

If you enjoyed this episode, please rate and review Just Ask Her on Spotify or Apple Podcasts, and share it with your friends!

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2 months ago
26 minutes 5 seconds

Just Ask Her - Dating Advice for Single Men
Ghosted, Blocked, and Bouncing Back — Real Dating Dilemmas & Self-Made Man Advice (Ep. 49)

Episode 49: Ghosted, Blocked, and Bouncing Back — Real Dating Dilemmas & Self-Made Man Advice

Episode Description:Are you tired of feeling stuck in your dating life, confused by mixed signals, or left wondering why she ghosted you? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener submissions about ghosting, blocking, and the emotional rollercoaster of modern dating.

From decoding sudden disappearances to reframing rejection and building emotional resilience, Gracie and Tracy offer no-nonsense advice straight from a woman’s perspective. They break down the “self-made man” mindset, share practical tips for handling heartbreak, and answer tough questions about honesty, closure, and moving forward.

Plus, enjoy a fun behind-the-scenes recap of their recent trip to Ireland, complete with cultural takeaways and travel mishaps!

Show Notes:

  • 0:00 – Welcome & Introduction: Why dating feels so confusing today
  • 2:30 – Listener Submission #1: Why did she ghost and block me after a great date?
  • 18:00 – The “Self-Made Man” Mindset
  • 25:00 – Listener Submission #2: “Why do I feel like I’m preparing women for other men?”
  • 38:00 – Listener Submission #3: “Should I tell women my ex-wife is a lesbian?”
  • 48:00 – Product Spotlight: The Self-Made Man Dating Journal
  • 52:00 – Ireland Recap: Banter, culture shocks, and travel lessons
  • 1:05:00 – Final Thoughts & How to Work with Gracie and Tracy

Resources Mentioned:

  • The Self-Made Man Dating Journal (available on Amazon)
  • Application link for coaching https://form.typeform.com/to/zJkel6VK?utm_source=xxxxx
  • Follow Gracie on Instagram & TikTok: @datingwithgracie

Subscribe for new episodes every Wednesday!

Show more...
2 months ago
50 minutes 26 seconds

Just Ask Her - Dating Advice for Single Men
Dating After Divorce – Confidence, Apps & Real Connections for Men Over 40 Ep. 48

Dating After Divorce – Confidence, Apps & Real Connections for Men Over 40 Ep. 48

Hosts: Gracie Pleschourt & Tracy Pleschourt

In This Episode:

  • [00:00] Welcome & Introduction

  • [01:30] Listener Question: Starting Over After Divorce at 45

    • Breaking old routines and building new momentum

    • Is there a “market” for divorced men over 40?

    • How to meet new women and rebuild your social circle

    • The fastest-growing demographic on dating apps

    • The importance of self-awareness: knowing what you want and what you bring to the table

    • Tips for getting comfortable with dating apps

    • How to treat dating as research, not a performance

  • [18:00] The Self-Made Man Dating Journal Launch

    • How journaling can help you track progress and avoid repeating old patterns

    • Building confidence and clarity through reflection

    • Where to get the journal (Amazon link in show notes)

  • [22:00] Listener Question: Revealing a Physical Difference (Amputee Experience)

    • How to talk about insecurities and physical differences with confidence

    • Why your story and self-acceptance matter more than “the reveal”

    • The power of vulnerability and authenticity in dating

  • [30:00] Listener Question: Competing for Women’s Attention

    • Why confidence and self-value matter more than “winning” attention

    • Shifting from scarcity to abundance mindset

    • Practical tips to stand out: eye contact, conversation, and authenticity

    • How to become unforgettable by making women feel seen and at ease

  • [40:00] Final Thoughts & Where to Find Gracie

    • Follow Gracie on Instagram & TikTok: @datingwithgracie

    • Apply for 1:1 coaching (link in show notes)

    • Rate & review the podcast on Spotify or Apple Podcasts

Resources Mentioned:

  • Self-Made Man Dating Journal https://www.amazon.com/dp/B0F9B7M5B3?th=1

  • 1:1 Coaching Application https://gracie.clickfunnels.com/optin1758810316648

  • Follow Gracie: Instagram & TikTok @datingwithgracie

Subscribe for new episodes every Wednesday!


Show more...
2 months ago
22 minutes 31 seconds

Just Ask Her - Dating Advice for Single Men
How to Stop Being the Second Option: Dating with Confidence, Setting Boundaries, and Moving On Ep. 47

Are you tired of feeling like someone’s backup plan in your dating life? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about complicated romantic situations, building self-confidence, and setting healthy boundaries.

From navigating “work spouse” dynamics and emotional gray areas to overcoming social anxiety with women and learning to trust yourself after heartbreak, Gracie and Tracy offer no-nonsense advice to help you take control of your love life. Whether you’re struggling to move on from a relationship, worried about making social mistakes, or wondering if you should pursue someone who’s already taken, this episode is packed with actionable insights and tough love.

Show Notes:

  • [00:00] Welcome & Updates: Gracie and Tracy share personal updates, including an upcoming trip to Ireland and behind-the-scenes podcast planning.
  • [04:00] Listener Submission #1: “Am I the Second Option?” — Advice for men caught in complicated relationships, why pursuing someone who’s unavailable is a losing game, and how to protect your self-respect.
  • [18:00] The Self-Made Man Dating Journal Launch: Introducing a new tool for single men to track, reflect, and improve their dating experiences.
  • [20:00] Listener Submission #2: “Social Mistakes with Women” — How to handle awkwardness, why confidence is really about self-trust, and why women care less about your blunders than you think.
  • [35:00] Listener Submission #3: “Trust Issues After a Breakup” — Rebuilding trust in yourself, letting go of relationships that no longer serve you, and why your future happiness depends on your own decisions.
  • [50:00] Key Takeaways: Why boundaries, self-awareness, and emotional resilience are the real keys to dating success.
  • [52:00] Call to Action: Rate, review, and share the podcast; follow Gracie on Instagram and TikTok @datingwithgracie.

Resources Mentioned:

  • The Self-Made Man Dating Journal:
  • Follow Gracie on Instagram and TikTok: @datingwithgracie

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! Got a question for Gracie and Tracy? Submit it for a chance to be featured in a future episode.

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2 months ago
33 minutes 36 seconds

Just Ask Her - Dating Advice for Single Men
Why Dating Apps Aren’t Working for You: Real Advice to Attract Women & Build Confidence Ep. 46

Are you tired of feeling stuck in your dating life, striking out on dating apps, or wondering why nothing seems to work? In this episode, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt answer real listener questions and share no-nonsense advice to help men attract the women they want and build lasting confidence.

What You’ll Learn:

  • Why dating apps might not be working for you—and what to do instead

  • The mindset shifts that turn “invisible” guys into irresistible partners

  • How to break free from self-sabotaging beliefs and rewrite your dating story

  • Practical tips for meeting women in real life (and why it’s often more effective than apps)

  • How to stand out at speed dating events and make a memorable first impression

  • The truth about confidence, self-worth, and why women are drawn to men who trust themselves

  • How to handle rejection, scarcity mindset, and the pressure to “have it all figured out”

Listener Questions Answered:

  • “I’ve been on dating apps for 20 years with no luck. What am I doing wrong?”

  • “How do I prep for a speed dating event and avoid the friend zone?”

  • “Why do I feel like every woman is already taken, and how do I stop feeling average?”

Special Segment:

  • Introducing the Self-Made Man Dating Journal—your new tool for tracking dates, building self-awareness, and making real progress in your love life. Limited batch available on Amazon—grab yours before they’re gone!

Join the Conversation:

  • Take our poll on Spotify and let us know: Do you love the personal banter, or do you prefer us to get straight to the dating advice?

  • Share your thoughts and questions for future episodes!

Connect with Gracie:

  • Instagram & TikTok: @‌datingwithgracie

  • Check out Gracie’s membership for hands-on coaching and support https://form.typeform.com/to/zJkel6VK?utm_source=xxxxx

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with a friend!

No matter where you are or what your situation is—just ask her.

Timestamps:

  • 00:00 – Welcome & Listener Feedback

  • 06:00 – Why Dating Apps Aren’t Working

  • 18:00 – Mindset Shifts for Dating Success

  • 30:00 – Real-Life Dating Tips & Speed Dating Advice

  • 45:00 – Overcoming Scarcity and Building Confidence

  • 55:00 – Introducing the Self-Made Man Dating Journal

  • 60:00 – Final Thoughts & Calls to Action

Resources Mentioned:

  • Self-Made Man Dating Journal https://www.amazon.com/dp/B0F9B7M5B3?th=1

  • Gracie’s Membership https://form.typeform.com/to/zJkel6VK?utm_source=xxxxx


Show more...
3 months ago
44 minutes 36 seconds

Just Ask Her - Dating Advice for Single Men
Break the Cycle: Real Advice for Dating Confidence, Moving On, and Finding Love (Ep. 45)

Break the Cycle: Real Advice for Dating Confidence, Moving On, and Finding Love
Episode 45 – Just Ask Her Podcast

Episode Summary:
In this episode, Gracie and Tracy tackle some of the most common and challenging dating dilemmas sent in by listeners. From navigating on-again, off-again relationships to overcoming self-doubt and building confidence, this episode is packed with real talk and actionable advice for anyone looking to level up their love life.

What You’ll Learn:

  • How to recognize and break free from unhealthy relationship cycles

  • Why you can’t “save” someone else—and how to set healthy boundaries

  • The truth about attraction, self-image, and why confidence matters more than looks

  • How to handle rejection, negative comments, and the pressure of dating apps

  • Practical tips for moving on after heartbreak and getting back into the dating scene

  • When to follow up (and when to move on) in online dating conversations

  • Why chemistry on the first date isn’t everything—and what to focus on instead

Listener Submissions Featured:

  • Todd: Struggling with an on-again, off-again relationship and wondering if he should wait or move on

  • Drew: Battling self-confidence issues and negative feedback while re-entering the dating world

  • Anonymous: Unsure about next steps after a breakup and facing challenges with dating apps and first dates

Special Segment:
Gracie and Tracy announce the launch of the Self-Made Man Dating Journal—designed to help single men track their dating experiences, reflect, and grow. Limited quantities available on Amazon!

Resources & Links:

  • Self-Made Man Dating Journal on Amazon

  • Connect with Gracie on Instagram and TikTok: @‌datingwithgracie

Support the Show:
If you enjoyed this episode, please rate and review us on Spotify or Apple Podcasts, and share with your friends!

New episodes every Wednesday. No matter where you are or what your situation is—just ask her.

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3 months ago
41 minutes 26 seconds

Just Ask Her - Dating Advice for Single Men
Living at Home, Gym Love, and Mixed Signals (Ep. 44)

Episode 44: Living at Home, Gym Love, and Mixed Signals

Hosts: Gracie Pleschourt & Tracy Pleschourt

Struggling with dating while living at home? Unsure if you should make a move at the gym? Confused by mixed signals from someone you like? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest questions with no-nonsense, real-world advice.

We answer listener submissions about:

  • How to date confidently when you’re not financially independent or still living with your parents
  • Navigating the tricky world of gym romance and whether you should look for love outside your workout routine
  • What to do when someone gives you mixed signals after turning you down


Key Takeaways:

  • Confidence and clarity about your life path are more attractive than financial status.
  • Don’t apologize for your situation—own your story and values.
  • Mixed signals usually mean “no”—don’t wait around for someone to change their mind.
  • The gym isn’t the only place to meet active partners; try apps, clubs, and social events.
  • Focus on what you can control and keep your dating mindset positive.

Connect with Gracie:

  • Instagram & TikTok: @datingwithgracie

Support the Show:

  • Rate and review on Spotify or Apple Podcasts
  • Share this episode with friends


Purchase the Self-Made Man Dating Journal:

  • https://www.amazon.com/dp/B0F9B7M5B3?th=1


New episodes every Wednesday!


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3 months ago
32 minutes 18 seconds

Just Ask Her - Dating Advice for Single Men
Stood Up Again? Real Talk on Dating Disappointments, Blind Dates & Building Confidence (Ep. 43)

Episode 43: Stood Up Again? Real Talk on Dating Disappointments, Blind Dates & Building Confidence

Show Notes:

  • Why do people keep getting stood up on dates? Gracie and Tracy break down the stats, share real listener stories, and offer practical advice for handling rejection and disappointment in the dating world.
  • Blind dates in 2025: Are they still a thing? The hosts discuss the anxiety of not knowing what your date looks like, how to handle awkward first impressions, and why short, low-pressure first dates are the way to go.
  • Special segment: Navigating dating with ADHD and social anxiety. Listener Jack from England shares his experience, and Gracie and Tracy provide mindset shifts and actionable tips for building confidence and social skills.
  • Launch announcement: The Self-Made Man Dating Journal is now available! Learn how this tool can help you track your dating experiences, reflect, and grow.
  • Listener Q&A: How to avoid getting cynical, set healthy standards, and know when to walk away.
  • Plus: The importance of self-awareness, communication, and not taking rejection personally.

Links Mentioned:

  • Self-Made Man Dating Journal - https://www.amazon.com/dp/B0F9B7M5B3?th=1
  • Follow Gracie on Instagram and TikTok: @datingwithgracie


Episode Description:

Ever been stood up and wondered, “Is it me, or is this just modern dating?” In this episode, Gracie and Tracy get real about dating disappointments, blind dates, and the mindset shifts that can help you bounce back stronger. They answer listener questions about being stood up, navigating first-date nerves, and dating with ADHD or social anxiety. Plus, they announce the launch of the Self-Made Man Dating Journal—a must-have for anyone serious about improving their dating life.

Tune in for honest advice, practical tips, and a reminder that you’re not alone in the dating game. Whether you’re tired of ghosting, anxious about blind dates, or just want to build more confidence, this episode is for you!

New episodes every Wednesday. Don’t forget to rate, review, and share!

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3 months ago
31 minutes 11 seconds

Just Ask Her - Dating Advice for Single Men
Real Stories, Real Advice: Overcoming Dating Struggles (Ep. 42)

Episode 42 – Real Stories, Real Advice: Overcoming Dating Struggles

In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about the challenges men face in modern dating.

You’ll hear three honest stories:

  • Jacob, a dedicated teacher who feels invisible in the dating world, gets advice on shifting his mindset, leveraging his network, and building confidence through daily habits.
  • Nick, a single dad and school administrator, opens up about the struggle to find lasting love and the impact of first-date hookups. Gracie and Tracy break down the importance of pacing, setting standards, and running a “dating experiment” to find deeper connections.
  • Anonymous shares the pain of being friend-zoned and dealing with height insecurity. The hosts offer practical tips for setting boundaries, moving forward, and reframing self-doubt.

Plus, discover the new Self-Made Man Dating Journal—designed to help you track your progress, reflect on your experiences, and become more intentional in your dating life.

If you’re ready to take control of your dating journey, this episode is packed with actionable advice, mindset shifts, and encouragement. Don’t forget to rate the show, share it with friends, and follow Gracie on Instagram and TikTok @datingwithgracie for daily tips!

Resources mentioned:

  • [Self-Made Man Dating Journal – Available on Amazon]
  • Free guide to optimizing your dating profile at datingwithgracie.com

New episodes every Wednesday. No matter where you are or what your situation is—just ask her!

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3 months ago
36 minutes 28 seconds

Just Ask Her - Dating Advice for Single Men
Breaking the “Just Friends” Cycle: Flirting, Ghosting, and Setting Standards (Ep. 41)

Episode 41 – Flirting, Ghosting, and Setting Standards: Real Dating Advice for Men

In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle some of the most vulnerable and confusing moments in modern dating. They answer real listener questions about:

  • How to show romantic interest without falling back into toxic masculinity or getting stuck in the “friend zone”
  • What to do when you’re ghosted after a promising connection—and how to separate facts from painful stories your mind creates
  • Why chemistry isn’t always enough, and how to set and hold your dating standards even when things don’t work out

Gracie and Tracy share research-backed flirting tips, advice for building confidence, and practical strategies for moving on after rejection. They also discuss the launch of the Self-Made Man Dating Journal, designed to help single men reflect, grow, and date with intention.

Whether you’re struggling to make the leap from friendship to romance, reeling from a sudden ghosting, or just want to date with more clarity and confidence, this episode is packed with honest insights and actionable advice.

Mentioned in this episode:

  • The Self-Made Man Dating Journal (now available on Amazon)
  • How to use self-compassion to recover from rejection
  • The importance of being direct, setting boundaries, and choosing yourself first

If you enjoy the show, please rate us on Spotify or Apple Podcasts and share this episode with your friends!

Follow Gracie on Instagram and TikTok @datingwithgracie for more tips and updates.

New episodes every Wednesday. No matter where you are or what your situation is—just ask her.

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4 months ago
37 minutes 50 seconds

Just Ask Her - Dating Advice for Single Men
How to deal, think about and learn from rejection, and what to do now (Ep. 40)

Episode 40: How to deal, think about and learn from rejection, and what to do now

Welcome back to Just Ask Her, the no-BS podcast for real dating advice straight from a woman’s point of view! In this milestone 40th episode, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest questions about moving on, healing, and dating with confidence after heartbreak.

In this episode:

  • Submission 1 (Chris, 32, UK Firefighter):
    Chris finds himself repeatedly attracting women who are fresh out of relationships and struggling emotionally. Gracie and Tracy break down the “rescuer” dynamic, discuss the difference between chemistry and true connection, and offer practical steps for setting dating standards, recognizing patterns, and staying in the “chooser” role.

  • Submission 2 (Anonymous, 27, Med Student):
    After a nine-year relationship, Anonymous is back in the dating world and wonders if a recent date didn’t work out due to timing or lack of interest. The hosts share how to separate facts from stories, process rejection, and keep moving forward without waiting for a “maybe.”

  • Submission 3 (Matthew, 28, Law Student):
    Matthew is healing from a recent breakup and wants advice on both moving on and planning a new date. Gracie and Tracy discuss the importance of not waiting until you “feel ready,” making decisions ahead of time, and taking small, confident steps forward.

Special Segment:
The Self-Made Man Dating Journal is now available on Amazon! Gracie and Tracy introduce their new journal designed to help single men track their dating experiences, reflect, and grow with intention. Limited first run—grab yours before they’re gone! (Link in show notes)

Key Takeaways:

  • Don’t let past experiences define your worth or what you deserve.
  • Set clear dating standards and stay in the chooser role.
  • Rejection is a normal part of dating—use it as a learning opportunity.
  • Healing is an active process; don’t wait for closure to move forward.
  • Take small, actionable steps to rebuild confidence and momentum.

Resources & Links:

  • Self-Made Man Dating Journal on Amazon https://www.amazon.com/dp/B0F9B7M5B3?th=1
  • Follow Gracie on Instagram and TikTok: @datingwithgracie

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! New episodes drop every Wednesday.

No matter where you are or what your situation is—just ask her.

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4 months ago
39 minutes 21 seconds

Just Ask Her - Dating Advice for Single Men
Dating After Divorce, Overcoming Insecurities & Navigating Workplace Romance: Real Advice for Men | Just Ask Her (Ep. 39)

Episode 39: Dating After Divorce, Overcoming Insecurities & Navigating Workplace Romance

In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt answer real listener questions about the challenges men face in modern dating.

Topics Covered:

  • Dating After Divorce: Daniel, a recently divorced dad living in the Caribbean, asks how to navigate dating with kids, a limited dating pool, and emotional healing. Gracie and Tracy discuss emotional availability, redefining relationship goals, and the importance of self-awareness.
  • Overcoming Insecurities (Height): Lucas from Canada shares his struggles with dating as a shorter man and feeling stuck in the friend zone. The hosts offer practical tips for building confidence, expressing romantic interest, and leveraging your unique strengths.
  • Workplace Romance: Shane wants to know how to tell if a coworker is interested or just being friendly, and whether it’s appropriate to ask her out again. The conversation covers reading signals, respecting boundaries, and balancing professionalism with personal interest.
  • Bonus: Gracie introduces the Self-Made Man Dating Journal, designed to help men track their dating experiences and grow in self-awareness.

Key Takeaways:

  • Emotional readiness and bandwidth are different—define what you want in this season of life.
  • Confidence comes from action and self-acceptance, not just external validation.
  • Flirting and expressing interest can be learned skills—start with small, bold steps.
  • Workplace relationships require extra care and respect for boundaries.

Resources Mentioned:

  • Self-Made Man Dating Journal on Amazon
  • Free guides on dating apps, starting conversations, and building chemistry at www.datingwithgracie.com

Connect with Gracie:

  • Instagram & TikTok: @datingwithgracie

If you enjoyed this episode, please rate and review on Spotify or Apple Podcasts, and share with friends!

Show more...
4 months ago
42 minutes 33 seconds

Just Ask Her - Dating Advice for Single Men
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