Just Ask Her - Dating Advice for Single Men20 Aug 2025

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!

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