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Just Ask Her - Dating Advice for Single Men
Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
51 episodes
4 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 (20/51)
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...
4 days 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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1 week 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 weeks 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...
3 weeks 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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1 month 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...
1 month 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.

Show more...
1 month 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!


Show more...
1 month 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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2 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!

Show more...
2 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.

Show more...
2 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.

Show more...
2 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...
2 months ago
42 minutes 33 seconds

Just Ask Her - Dating Advice for Single Men
From Public Shaming to Second Chances: Navigating Modern Dating Drama (Ep. 38)

In this episode, Gracie and Tracy tackle three powerful listener submissions about dating challenges, online reputation, and moving on after heartbreak. They offer no-nonsense advice on handling public shaming in online groups, building momentum with a newly single neighbor, and recovering from a whirlwind romance that ended abruptly. Plus, they announce the launch of the Self-Made Man Dating Journal, designed to help men reflect and grow in their dating lives.

Show Notes:

  • 00:00 – Introduction

    • Gracie and Tracy welcome listeners and celebrate 38 weeks of the podcast.
    • Quick banter about pregnancy timelines and podcast milestones.
  • 02:00 – Listener Submission #1: Anthony’s Story

    • Anthony shares his experience of being publicly shamed in a women’s Facebook group after a breakup.
    • Gracie and Tracy discuss the origins and current state of “Are We Dating the Same Guy?” groups.
    • Advice on handling online defamation, reclaiming self-trust, and whether to pursue legal action.
    • Key takeaway: Let your integrity and self-awareness guide you, and don’t let drama-filled groups define your dating future.
  • 25:00 – Announcement: Self-Made Man Dating Journal

    • Gracie and Tracy introduce their new journal for single men, available on Amazon.
    • The journal helps track dates, reflect on experiences, and build self-awareness.
  • 28:00 – Listener Submission #2: Alex’s Story

    • Alex, new to dating, wonders if he missed his chance with a neighbor after helping her through a tough time.
    • The hosts discuss the importance of momentum, meaningful interactions, and not overthinking timing.
    • Advice: Focus on genuine conversations, set healthy boundaries, and don’t attach expectations to every interaction.
  • 40:00 – Listener Submission #3: Jake’s Story

    • Jake describes a fast-moving, long-distance romance that ended suddenly after a deep connection.
    • Gracie and Tracy explain “emotional fast-tracking” and the risks of future-tripping in new relationships.
    • Advice: Let relationships unfold at a natural pace, integrate emotional lessons, and practice patience as you move forward.

    Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

    Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠

Show more...
3 months ago
42 minutes

Just Ask Her - Dating Advice for Single Men
Taking Initiative in Your Dating Life (Ep. 37)

Hosts:
Gracie Pleschourt (Dating Expert) & Tracy Pleschourt (Certified Life Coach)

Episode Summary:
In this episode, Gracie and Tracy tackle real listener questions about dating challenges, mindset shifts, and taking control of your love life. They offer no-nonsense advice from a woman’s perspective, helping single men date with confidence and intention.

Listener Submissions & Key Takeaways:

  1. Dakota’s Dilemma:
    A 31-year-old entrepreneur struggling to find quality matches while living with family and rebuilding financially.
    Advice:

    • Don’t wait passively for love—be open and intentional about meeting new people.

    • Own your journey and talk about your growth with confidence.

    • Geography matters on dating apps, but don’t let location limit your options—explore new ways to meet women.

    • Your ambition and integrity are attractive; focus on sharing who you’re becoming.

  2. Kyle’s Missed Connection:
    A 32-year-old crane operator wonders if he missed out on a romantic opportunity after a church encounter fizzled.
    Advice:

    • You did nothing wrong—sometimes timing just isn’t right.

    • Don’t dwell on “what could have been.” Stay open to new opportunities in places you enjoy.

    • Contentment is great, but combine it with curiosity and intention to avoid stagnation.

    • Emotional readiness is key to relationship success.

  3. George’s Unrequited Interest:
    A 34-year-old man questions whether to keep talking to a woman who isn’t ready to date.
    Advice:

    • When someone says they’re not interested or ready, believe them.

    • Set boundaries and move on to free your energy for the right relationship.

    • Don’t confuse hope with reality—choose clarity and self-respect.

Special Segment:

  • Product Launch: The Self-Made Man Dating Journal is now available on Amazon! Designed for single men to track dates, reflect, and build self-awareness for better dating outcomes. Limited first run—grab yours before they’re gone!

Calls to Action:

  • Rate and review the podcast on Spotify or Apple Podcasts to help others find the show.

  • Share this episode with friends who could use real, actionable dating advice.

  • Follow Gracie on Instagram and TikTok: @‌datingwithgracie

New Episodes:
Tune in every Wednesday morning for fresh, honest dating advice—no matter where you are or what your situation is, just ask her!

Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal

Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠


Show more...
3 months ago
31 minutes 12 seconds

Just Ask Her - Dating Advice for Single Men
Am I Ever Someone’s First Choice? | Healing After Rebound Heartbreak, Starting Conversations, and Breaking Old Dating Patterns (Ep. 36)
  • In this powerful episode, we hear from three men navigating dating after heartbreak, rejection, and personal transformation. Tiago, a newly single dad, opens up about falling hard for a woman fresh out of her own divorce—and the grief of not being chosen. Brady asks how to confidently start conversations in person and online. And Brandon vulnerably explores a repeating pattern of giving too much and being left behind.

    If you’ve ever asked yourself: Why does love feel so one-sided? or Am I stuck in the same cycle?—this one is for you. We offer honest answers, emotional insight, and real strategies to move forward without closing your heart.

    💬 Topics we cover:

    • Rebound heartbreak and emotional availability

    • How to start conversations that actually connect

    • The over-functioning pattern that leaves good men feeling unseen

    • Building confidence without performing

    • When to try again—and when to walk away for good

    Whether you're fresh out of a relationship or ready to rewrite your love story, you'll walk away with tools, validation, and hope.

    Submission 1: Tiago (00:00)
    After a 14-year marriage, Tiago dives into dating again—only to fall for a woman not yet over her own divorce. We explore why emotionally available men often feel heartbreak more deeply, and how to stop trying to prove your worth to someone who isn’t ready to choose you back.

    Submission 2: Brady (21:45)
    Brady asks a common question: How do I start the conversation—on apps or in person—without being awkward or overthinking it? We break down what actually matters in first impressions (hint: it’s not cleverness), and how curiosity beats performance every time.

    Submission 3: Brandon (38:10)
    Brandon is done chasing women who don’t choose him back. We unpack the anxious attachment pattern of over-giving, why it keeps showing up, and how to lead with discernment instead of devotion in future relationships.

    Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

    Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠

  • If you found this episode helpful, please rate us on Spotify or Apple Podcasts and share it with a friend. New episodes every Wednesday!

    DatingAdvice #SingleMen #DatingApps #Heartbreak #Confidence #JustAskHerPodcast

    Show more...
    3 months ago
    39 minutes 54 seconds

    Just Ask Her - Dating Advice for Single Men
    Ghosted After 3 Perfect Dates? Here’s What Women Wish You Knew (Ep. 35)

    It’s one of the most painful dating experiences: everything feels amazing… and then she disappears.

    In this raw, relatable episode of Just Ask Her, we unpack three powerful submissions from men navigating ghosting, rejection, and confusion after what felt like real connection:

    • Luke opens up about an overseas trip that changed everything with a woman he thought he was building something real with. Now she’s gone—no warning, no clarity—and he’s still holding on.

    • Spencer shares the story of his whirlwind 4-date romance with a woman who seemed all-in—until she ghosted him after planning two more dates. What gives?

    • Conor bravely tells us what it’s like being 30, never having been in a relationship, and constantly getting close—only to be shut out. He asks: What am I doing wrong, and how do I keep going?

    💬 Gracie and Tracy go deep in this one, breaking down what ghosting really means, why it often has nothing to do with you, and what women are thinking when they pull away after connection. We also explore:

    • What to do when you still have feelings but she cuts contact

    • The truth about mixed signals and sudden disappearances

    • Why “perfect dates” don’t always lead to commitment

    • How to rebuild your confidence after being ghosted

    • When (and how) to reach out again—or let go completely

    Whether you’ve been left on read or still playing back every moment of your last date, this episode will give you clarity, closure, and hope.


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

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

    Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠

    Show more...
    3 months ago
    40 minutes 45 seconds

    Just Ask Her - Dating Advice for Single Men
    When Feelings Resurface: What to Do When the One That Got Away Comes Back (Ep. 34)

    She said she only wanted something casual… but your heart didn’t get the memo.

    In this episode of Just Ask Her, we’re diving into three real stories that hit home for a lot of men:

    • A 36-year-old man rekindles something with the woman who once ghosted him—only to find himself falling all over again. Is she just bored… or is there still a chance?

    • Another listener goes from intimate and honest connection to total silence after dating a single mom—what happened, and how do you respond to ghosting that makes no sense?

    • Plus, we talk about first-date anxiety with a guy who knows he’s a catch… but struggles to show it early on.

    If you’ve ever questioned whether you’re being patient or just played, this episode will give you honest advice, a woman’s perspective, and the clarity you need to stop spinning in circles.

    Get the Self-Made Man Dating Journal: 👉https://www.amazon.com/dp/B0F9B7SQBY?th=1

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  https://forms.gle/naT2MHcb5vPjU6K68

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  https://forms.gle/naT2MHcb5vPjU6K68


    Show more...
    4 months ago
    30 minutes 3 seconds

    Just Ask Her - Dating Advice for Single Men
    Politics, Privacy & the Girl Next Door (ep. 33)

    This week on Just Ask Her, we’re tackling three very real (and wildly different) dating dilemmas from our listeners:

    • Carlos wants to know if there’s any hope for a conservative guy dating in a liberal city—or if he should hold out for a future move.

    • Mark has rekindled things with his high school sweetheart… but there’s one big problem: she’s still best friends with his ex-wife.

    • And an anonymous bachelor is wondering how to strike up a conversation with the woman he always runs into—but never has a chance to talk to.

    We’re talking dating across political lines, what to do when the past gets in the way of the present, and how to approach a girl you barely know without being weird about it. Let’s dive in.


    Get Your Self-Made Man Dating Journal: https://www.amazon.com/dp/B0F9B7SQBY?th=1

    Get on The Dating Differently Academy Waitlist at: https://datingwithgracie.com/dda-waitlist-4055

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

    Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠

    Show more...
    4 months ago
    28 minutes 49 seconds

    Just Ask Her - Dating Advice for Single Men
    When It Feels Real… But She Pulls Away

    In today’s episode, we’re diving into three powerful stories from men navigating the messy middle of modern dating:

    💔 Luke thought he was one step away from proposing—until she blindsided him with a breakup.
    😓 Josh is tired of being the one who always initiates, and he’s starting to feel the desperation creeping in.
    🥲 Jerome had the best first date of his life… but now she’s gone quiet, and he’s left wondering if he should reach out again.

    We’ll talk about what to do when effort feels one-sided, why some women emotionally check out long before they leave, and how to find clarity when the door hasn’t fully closed.

    If you’ve ever felt blindsided, confused, or stuck on “what could’ve been,” this episode is for you.

    Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/

    Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠

    Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast Submission

    Follow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠

    Show more...
    4 months ago
    37 minutes 53 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