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: From Heartbreak to Healing – Real Advice for Men Ready to Date Again

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!

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

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