Ask These 5 Questions to see if he’s worth pursuing!
Perspectives With Sherry27 Juni 2025

Ask These 5 Questions to see if he’s worth pursuing!

In this episode of Perspectives with Sherry, we’re diving into 5 intentional, thought-provoking questions every woman should ask a man early in the dating process. These aren’t surface-level icebreakers — they’re designed to help you gain clarity, assess compatibility, and save yourself from wasting time. Whether you’re newly back on the dating scene or just trying to date with more purpose, these questions will help guide your heart and your standards.

💬 In this episode, we discuss:

  • Why the right questions early on can reveal emotional intelligence
  • How to gauge values, priorities, and self-awareness in a potential partner
  • Red flags and green flags to listen for in their answers
  • The power of dating with intention in midlife
  • What not to settle for just to feel “chosen”

📝 The 5 Questions:

  1. What does a fulfilling relationship look like to you at this stage in life?
  2. How do you typically spend your weekends?
  3. What’s something you’ve worked on personally over the past few years?
  4. What role does love, faith, or personal values play in how you choose a partner?
  5. What’s one thing you’ve learned from past relationships that you carry with you now?

💡 Takeaway:

You don’t need to be a relationship expert to date with wisdom—you just need the right lens. Start asking better questions and get closer to the connection you deserve.

📲 Connect with Sherry:

Instagram: @perspectiveswithsherry

YouTube: Perspectives with Sherry

TikTok: @perspectiveswithsherry

🗣️ Join the conversation:

Have you asked any of these questions on a date? What answers were revealing? DM or comment and let us know what resonated with you!

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