Just Ask Her - Dating Advice for Single Men

Break the Cycle: Real Advice for Dating Confidence, Moving On, and Finding Love (Ep. 45)


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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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Just Ask Her - Dating Advice for Single MenBy Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men

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