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On Attachment

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

On Attachment

Stephanie Rigg

Relationships, Society & Culture

4.91.2K Ratings

🗓️ 28 October 2025

⏱️ 20 minutes

🧾️ Download transcript

Summary

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.

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Transcript

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0:00.0

You're listening to On Attachment, a place to learn about how attachment shapes the way we experience relationships and where you'll gain the guidance, knowledge and practical tools to overcome insecurity and build healthy, thriving relationships.

0:19.7

I'm your host, relationship coach Stephanie Rigg,

0:22.8

and I'm really glad you're here.

0:28.7

Hey everybody, welcome back to another episode of On Attachment. In today's episode, we are talking

0:34.2

about how and when to start dating again after a breakup. So if you've been

0:40.1

through a breakup in the last few months, maybe even longer, and you've had a period of time to

0:46.1

turn inwards, to focus on yourself, which by the way, certainly what I recommend after a breakup,

0:52.5

rushing back into things as a way to distract ourselves

0:56.0

or bypass the pain and the grief is probably just kicking the can down the road and

1:02.5

delaying the inevitable because whatever wounds we're carrying, we're going to have to face

1:07.0

eventually. But in any case, if you've been through a breakup and then you've had some time and

1:12.6

you're feeling like maybe I'm ready to start dating again, but you're not really sure,

1:18.0

I'm going to be offering some thoughts in this episode as to signs that you might be ready,

1:22.8

signs that you might not be ready, and just some tips around managing your expectations of what it's likely

1:28.1

to look like as you dip your toe back in as you venture out into the world of dating so that you

1:34.6

can do that in a way that feels really supported and not rushed and not pressured while also,

1:41.5

as I said, managing expectations around possible grief that might come up,

1:45.9

anxiety, all of those other feelings which I actually think are really normal and not necessarily

1:49.8

a sign that something's wrong. And I think really like at the heart of everything we're going

1:54.4

to talk about today is knowing how to attune to yourself and be really honest about where you're

1:59.8

at and what you're needing

2:00.8

and what feels right for you and continually checking in with that because of course

...

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