231. How to Ask Dating Questions

In this episode, I dive into why asking questions is both an art and a crucial skill on your dating journey after divorce. Most women I work with struggle not because they lack intelligence or communication skills, but because the drama attached to dating turns question-asking into self-sabotage.

You might think asking questions is straightforward, but are you using them to protect yourself or to people-please? Both approaches block authentic connection and prevent you from gathering the information you need to make wise decisions about potential partners.

Key Insights

• Curiosity is your superpower: Approach dating with curiosity—not just about your date but about yourself. Your reactions hold valuable information about your patterns.
• The protection trap: Going into dates with a rigid checklist of questions turns dating into an interview. You miss crucial nuance and context when you're focused on checking boxes rather than truly connecting.
• The people-pleasing pitfall: When you avoid asking important questions because "you don't want to be nosy" or "you don't want to chase him away," you sacrifice your needs for a stranger's comfort.
• Reclaim your authority: Dating involves meeting a stranger, knowing them for months, and potentially committing to them for life. This requires active participation, not passive acceptance.
• Your dating rights: You have the right to know about people who want access to you. You deserve to have potential partners earn your trust through honesty and transparency.

Practical Takeaways

• Start with broader questions about lifestyle, career goals, and weekend activities before diving into deeper topics
• Design questions based on your core values rather than using generic lists
• Pay attention to how someone responds—defensiveness, vagueness, or dismissal tells you something important
• Recognize when you falter in asking important questions and get curious about what's happening within you
• Remember timing matters—questions should match the relationship phase you're in

Dating After Divorce Wisdom

Think about it: we've known our siblings, cousins, and best friends our whole lives. Yet romantic relationships expect us to meet someone, know them for months, and commit to them forever. That's wild! Since this is our collective social agreement, we need to approach it with intention and courage.

Your Next Step

If you don't know what questions to ask, that's a sign you need clarity on your core values and relationship vision. This isn't just about having a list of questions; it's about knowing which answers matter specifically to you.

Ready to transform your dating experience? Book a consultation call with me where we'll discuss how working through your core values and dating patterns can help you find clarity and confidence. Stop outsourcing your safety to a checklist and start leading your own journey to love.

Schedule your Dating Consultation Call with Sade 

The Dating After Divorce Podcast with Sade Curry helps smart, accomplished women navigate dating with confidence after divorce. New episodes every Tuesday.