On Attachment

#212: How & When to Start Dating Again After a Break-up


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One of the most common questions after a break-up is: when will I be ready to start dating again? Sadly, there’s no hard and fast rule, no magic timeline, and no moment where you’ll suddenly feel 100% confident and never wobble again. Readiness isn’t about the calendar — it’s about how you’re feeling, the work you’ve done, and the mindset you're bringing with you. 

In this episode, I’ll share:

  • Signs you may not be ready yet (like still being in the thick of grief, rumination, or longing for your ex)
  • Signs you might be moving toward readiness (like curiosity about meeting someone new and clarity around your standards and patterns)
  • How to approach dating again with intention and self-compassion
  • Why dating itself can stir up new layers of grief — and how that doesn’t mean you’ve failed or gone backwards

If you’ve been wondering whether to dip your toes back in the dating pool, this episode will help you manage your expectations, recognise where you’re at, and approach the process in a way that feels grounded and intentional.

Highlighted Links

  • Free Break-Up Training: The 3 Shifts That Help Anxiously Attached People Heal After a Break-up
  • Free Training: How to Heal Anxious Attachment and (Finally) Feel Secure in Life & Love

Additional Resources

  • Download the FREE Anxious Attachment Starter Kit here
  • Join my email list 💌
  • Explore my library of free guides, classes & meditations
  • Visit my website
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On AttachmentBy Stephanie Rigg

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