Good Questions to Ask Yourself When Dating After Divorce

Are you a divorced woman over 40 navigating the dating world again? While many focus on what questions to ask potential partners, the most powerful dating tool might be asking yourself the right questions first.

Why Self-Questioning Matters in Dating After Divorce

I regularly get asked by clients for good questions to ask men when dating. They want to know how to evaluate if someone is a good fit for them. While we certainly design these questions based on who they are and their vision for a relationship, what I don't hear often enough is: "What are good questions to ask MYSELF when I'm dating?"

Your brain is fundamentally a question-asking and question-answering machine. Questions are how it makes meaning of the world to fulfill its main goal of keeping you safe. You're always asking yourself questions, even when you're not aware it's happening. This is especially true when dating after divorce, when uncertainty and vulnerability run high.

The Danger of Low-Quality Questions

If you're not intentional about your internal dialogue, you'll likely default to asking yourself terrible dating questions that keep you frustrated:

  • Why can't I find a good man?

  • Why are the dating apps so awful?

  • What's wrong with me?

  • What if I'm single forever?

These questions keep you stuck in negative thought cycles. While your brain asks these questions in an attempt to keep you safe and ensure success, they actually create the opposite effect. Your brain diligently searches for evidence that supports these negative beliefs—that you can't find a good man, the dating apps are awful, there's something fundamentally wrong with you, and you'll inevitably be single forever.

This puts your focus squarely on fear, and predictably, you create fear-based results—no relationship and continued disappointment.

When Are You Ready to Date Again?

One crucial question many divorced women struggle with is: "When am I ready to date again?" This isn't just about time passing since your divorce. True readiness comes when:

  1. You've processed the emotional aftermath of your divorce

  2. You can think about your ex without intense negative emotions

  3. You're dating because you want to, not because you fear being alone

  4. You're looking for a partner to complement your life, not complete it

If you're still asking yourself "When will I be ready?", it might be a sign that you're approaching that readiness but need to build more confidence first.

Recognizing a Low-Effort Man

Another critical skill when dating after divorce is identifying a low-effort man early. These are men who:

  • Make plans at the last minute

  • Rarely initiate conversations

  • Are inconsistent in their communication

  • Don't progress the relationship forward

  • Expect you to accommodate their schedule without reciprocating

Learning to recognize these patterns early can save you considerable time and heartache. The right questions can help you identify these red flags before you become emotionally invested.

Better Questions Lead to Better Dating Experiences

In contrast to fear-based questioning, love-based questions boost your creativity and yield positive results. They help your brain find evidence that dating WILL work for you:

  • How can I create love today?

  • How can I meet more compatible men?

  • What strengths do I bring to dating?

  • What makes me an amazing partner?

  • What would be fun to do today?

  • Where have I had success in dating already?

These questions move your brain to find evidence that you CAN create love, you CAN meet compatible men, you ARE an amazing partner, and you CAN succeed at dating. By asking the right questions, your focus shifts to everything that's going RIGHT, creating the powerful result of matching you with the partner you've been looking for.

The Power of Coaching in Your Dating Journey

This mindset shift is precisely the power of coaching. A good dating coach for divorced women doesn't just help you find dates—they help you transform how you think about dating entirely.

Reflection Questions

  • What questions do you currently ask yourself about dating?

  • What results have these questions given you?

  • How might changing your questions change your dating experience?

If you're a divorced woman over 40 ready to approach dating with fresh perspective and confidence, start by becoming aware of your internal questions. This simple but powerful shift might be exactly what you need to find the loving relationship you deserve.

Want More Help? 

Click Here to Discover Your Core Values Dating Blueprint And How You Can Use It On Dating Apps, and In-Person To Attract Eligible Men Who Match You (without chasing, settling, or wasting time with low-effort men) 

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Navigating Love Again: A Guide to Dating After Divorce for Women Over 40

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Dating After Divorce: A Mindset Revolution for Women Over 40