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!

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.

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

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.

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!

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!

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!

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.

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.

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!