

9 Oct 2026 · 21m · 7 chapters

An “Ask Steph” episode about whether post-breakup self-doubt and second-guessing means you made the wrong choice, or whether it’s normal grief after ending a loving but misaligned relationship. Steph advises focusing on self-trust, expecting grief/doubt, and only reconciling if both people mutually want it with a real plan to change the underlying issues.
No external guests. Guest is a listener who sent a voice note describing her breakup.
Together ~8 years; long-distance; he pursued expansion (work freedom, travel, exploration) while she wanted consistency, emotional availability, and a shared future. She stepped back because the relationship felt like it was getting lost in his life.
Regret feelings often reflect grief and avoidance of pain (especially for anxious patterns). Don’t judge decisions by hindsight regret alone. Reconciliation must be mutual and substantively different, not just “pain relief.” Don’t “wait by the phone”; assume the relationship is over and focus on yourself.
Long-distance loneliness without regular touch points; holidays/birthday/trips/in-jokes becoming painful reminders; “right person, wrong time” can encourage waiting without evidence of change.
Written by AI. May contain mistakes.
Discussion about a listener's question on processing breakup feelings.
In-depth analysis of feelings after a breakup and the nuances of regret.
“Before I do, in case you missed last week's episode, I am so excited to be able to share that my book, The Secure Self, is now available for pre-order.”
Steph provides insights on distinguishing between regret and normal grieving.
“Because we were also long distance, I started feeling like the relationship was getting lost inside everything else he was pursuing.”
Learn how to navigate feelings of grief and regret after a breakup.
“but also maybe an inner knowing that things weren't working.”
Understand the dynamics of reconciling in a relationship after a breakup.
“I think more often than not, it's just the waves of grief that come for us as we're processing the loss.”
Explore how to focus on personal growth after making tough decisions.
“What's going to be the fix for that moving forward so that the unmet needs and the lack of shared vision and all of those things, is there going to be any substantive difference or do we just miss each other?”
Find out how to engage with the podcast and contribute to future discussions.
“So that would be my advice on all of those threads.”

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Automatic transcript. May contain errors.
0:00From athletic stuff like a full court pickup game, swish, to athletic stuff like a half mile stroll. Get those steps in. Head to Sierra or Sierra.com for the brands you want at the prices that let you do it all. From athletic to athletic, Sierra's got it. Propel Fitness Water with Gatorade electrolytes, zero sugar and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade electrolytes. Hey everybody, welcome back to another episode of On Attachment. In today's episode, which is an Ask Steph episode, I'm going to be playing a voice note that was received from a listener, all about processing layers of doubt and questioning and second guessing after leaving a relationship with someone that she loved but wasn't totally aligned with and felt like they we're moving in different directions and then having to process all of the layers that come with that in the aftermath and how to discern whether that doubt and second guessing is just part of the process of grieving a relationship ending or whether it's actually pointing you towards something saying that maybe the breakup wasn't the right thing.
1:17So I'm going to be playing that voice note in just a moment. Before I do, in case you missed last week's episode, I am so excited to be able to share that my book, The Secure Self, is now available for pre-order. I have been working on this book for a very long time and I really can't wait for you guys to get your hands on it. If you struggle with anxious patterns in your relationship, this book will absolutely help you. It will help you to rebuild your relationship to yourself, which I believe is the most important thing that you can do that makes everything else easier and clearer and it will transform the way that you think about relationships.
1:59It really brings together all of the things that I've been teaching and sharing about alongside more of my own personal story and relationship background than I've shared previously. The lessons that I've learned along the way. If you have been a podcast listener, if you've maybe taken one of my programs, if you get a lot out of my work, I am sure that you'll really love the book. And I hope that you'll consider pre-ordering because pre-orders make a huge difference to a book's success. They're really important in signaling interest and creating a bit of buzz and momentum around a book in the lead up to its release.
2:38And as a way to thank you or incentivize you ordering ahead of its release in February, I've put together what I hope is a really compelling bonus package. So you will get three free workshops, the first of which is instantly available. So if you buy the book and head to my website and just upload a proof of purchase, then you'll get instant access to a 40-minute or so workshop on the abandonment wound and how that forms part of the anxious attachment tapestry, where it comes from, how it manifests, all of those things, emotional abandonment, self-abandonment. So you get instant access to that when you buy the book.
3:19And then in November and December respectively, you will get access to two additional workshops on the fear of rejection and its role in anxious attachment and then the unworthiness wound. So it's a three part workshop series on the core wounds or the core beliefs at the heart of anxious attachment. That's all brand new and exclusive to people who pre-order the book. And in addition to that, you'll also get an invite to three live Q &As with me over the coming months. So you can come along and ask me a question, connect, get my advice on your situation, all of that for the cost of a book. and you also get the book when it comes out in February.
3:55And you can take advantage of that whether you order the hardcover, the ebook or the audiobook version, which to answer the question that I'm sure some of you will have because I've already received it a few times, I will be reading the audiobook. So I really do hope that you will pre-order the book. You can just look it up directly on Amazon, The Secure Self by Stephanie Rigg. Or if you would like a full list of retailers, you can find that on my website at stephaniereed.com book. And that URL is also the page that you'll go to, to claim that bonus package once you've purchased the book. So thank you in advance for your support.
4:32I've already been so touched and humbled by all of the love and support that I've received since announcing last week that the book was available for pre-order and also that I'm pregnant in case you missed that announcement. So there's been lots going on. And as always I'm so so grateful for all of your support in all of the ways so I hope that you'll get behind the book as well okay with that out of the way I'm gonna hit play on this voice note all about processing breakups and second thoughts hi Stephanie I really love your perspective on something I'm struggling with after my breakup my ex and I first met about eight years ago lived completely separate lives for years and then he reached back out and we eventually fell in love and became a couple so the relationship already felt like this unexpected second chapter in our story it was a very loving relationship and it didn't end because we stopped loving each other or because of betrayal it ended because our timelines and priorities started feeling increasingly misaligned he was very focused on building himself work freedom travel and exploration while i wanted more consistency emotional availability and a clearer sense that we were building toward a shared future.
5:39Because we were also long distance, I started feeling like the relationship was getting lost inside everything else he was pursuing. And I was ultimately the one who stepped back because I didn't know how to make it sustainable. Since then, therapy and a lot of reflection have helped me understand his perspective much more deeply. And now I sometimes wonder whether I ended something that could have evolved if I understood that sooner. I've since told him I still had loved him and that if there was still a path, I'd be open to exploring things differently. He responded kindly, but hasn't actively tried to reconnect.
6:08So how do you know whether you're experiencing genuine regret because you made a wrong decision versus a normal bargaining that happens after losing someone you deeply love? And if you've already made it clear you need to be open to trying again, how do you keep the door open without standing in a doorway waiting? So there's so much in that question, so thank you to the person who sent it in. I'm going to pick apart a few threads and then give advice along the way. So first I want to acknowledge how hard it is when the breakup is not some big watershed moment of betrayal or a big fight happens or something that makes it really clear.
6:49When you actually just have to look at the situation, it's probably been a slow drift apart and a sense of maybe loneliness, maybe misalignment and feeling like despite your best efforts, nothing's really changing there. I think that's so much harder to make that call. And I really applaud your courage in being able to own your desires and your priorities and to see his as not wrong, but different. He's not wrong for wanting to be in a season of expansion and freedom and ambition and all of those things. But when that's budding up against your very valid desire for stability, for building a shared future, for laying down roots, it seems like you were maybe just on different trains heading to different places.
7:49But that doesn't make it any easier. I do think it makes it harder when there's otherwise a lot of love and goodwill and care and history there. so I do just want to really recognize and validate that it's a really brave call to make and it's a really self-aware one to actually be able to say like I love you and also this doesn't feel like it's working and the long distance layer on top of that I'm not surprised that you would have felt a bit detached from his world and I think that's often a struggle with long distance I have done an episode on it a while ago that anyone else who's long distance can go back and find in the archives.
8:34But I do think that's part of the challenge of long distance. While it can work, it's really hard if you don't have regular touch points and a sense of being involved in one another's world. And I think when you feel like you're just living separate lives and then chatting on FaceTime every so often and having really perfunctory conversations and you don't really feel like you exist in each other's world in any meaningful way or you have insight into that, then I think it can start to feel pretty lonely. and particularly where there's no end in sight, where it's not a temporary period of long distance that is maybe a necessary evil on the way to building that shared future together.
9:17If it's just open-ended and particularly where it's not what you want, I think it's really fair and understandable that you would feel a growing restlessness around where is this going and is it really working for me? And when he's been maybe resistant to those conversations, or maybe that's just not where he's at because he is in a season of freedom and expansion and maybe focus on himself, which again is fine, but maybe just incompatible with where you're at and where you want to be going. So you may have heard me describe this previously as a structural incompatibility where you just want fundamentally different things.
10:05This is probably a little less clean cut than some others where one person never wants to get married or have kids and the other absolutely does. This feels like it's more a timing point than a clear black and white incompatibility. But even still, I think timing is something we have to take seriously, particularly when you are the one holding out for the possibility of a future that you really desire, but in the meantime, really going without a lot of your relationship needs being met. And again, I think those sacrifices can make sense where we know that it's relatively short term and that we're very clearly aligned on the bigger picture.
10:53But without that, without that light at the end of the tunnel or without that clear agreement and joint vision, I don't think it is wise to just keep holding out hope for a maybe because that is, I think, a more subtle form of self-abandonment. abandonment. And when you play that out, if in two, three, four, five years, you're still in some version of the dynamic that you're in, I think you'll feel really disappointed in yourself for clinging to that hope when maybe all signs were pointing to the fact that you were heading in different directions. Again, not for lack of love or care, but just that sometimes it isn't meant to be.
11:37And that can obviously come with a lot of grief and it can feel so unfair. You always hear like right person, wrong time thrown around. And I think those sayings are maybe unhelpful because in saying this is the right person, it's just the wrong time. I think that implicitly encourages you to just keep waiting and that it'll all be worth it because this is your soulmate, your person, the person you're meant to spend your life with. But from my point of view, I think if the timing's wrong and there's no sign that that's going to resolve, then it's not the right relationship. And there are many, many people who could be great partners to you, but if they're not available for the kind of relationship that you want, then that's kind of irrelevant.
12:24It's sad and disappointing and frustrating and unfair, but it doesn't mean they're the right person for you if they're not available for a relationship with you of the kind that you are wanting and needing, particularly when you've already invested so much and you are where you are. So to your point around how do I know when regret is pointing to having made the wrong decision or is it maybe just grief that you're experiencing as regret? I think it's a beautiful question. It's actually something that I touch on in my book. I have a chapter on self-trust and within that I speak about the fear of regret and the complexity of our relationship to regret.
13:09And a lot of us will try and judge our decisions and our decision making in hindsight based on whether we feel regret. And then we decide that we can't trust ourselves because we're not really certain about our decisions. And I think that's a very fraught way of approaching decision making and self-trust. And really we should be judging our choices at the time that we're making them. And from what I'm hearing, you made a brave, scary, aligned choice that was really self-honoring and still respectful of him. It doesn't sound like you had to make him the villain in order to feel justified in stepping away from the relationship.
13:56It sounds like you did that in a really mature and self-responsible way, coming from no doubt some fear and trepidation, but also maybe an inner knowing that things weren't working. And I think when you, in the aftermath of that, are processing and realizing what you've lost in that process, then the sadness and the grief can often feel like regret because so many of us, I would say most of us, are really inexperienced with grief and sadness and we have a strong aversion to it. And so when it comes up, we scramble to try and get away from it. And particularly people with anxious patterns tend to try and get away from it by thinking a lot.
14:42I talk about this often in the context of breakups that ruminating and spinning around in the what ifs and the second guessing. Oftentimes we think that we're processing, but we're actually just spinning our wheels trying to get away from the depth of pain and hurt and fear that sits underneath all of that. And that's why I really always emphasize having realistic expectations around breakups and expecting there to be grief and expecting there to be doubt and expecting there to be sadness as you do process all of the layers because I think when you step away initially there's probably some sadness but also a bit of relief particularly if you knew for a while that you probably needed to do that but then in the weeks and months afterwards you start to realize what does that mean for holidays and my birthday and that trip we took together which was actually really fun and those in jokes that we have or whatever it might be, we start to really realize that there is a lot that we're letting go of even at the same time as it could be the right decision based on all of the circumstances.
15:54So I don't think that missing them, I don't think that grief, I don't think that doubt or sadness, any of those things are signs that you've made the wrong decision. I actually do just think that they're part of the process and particularly so when the decision was one that you came to presumably after a lot of reflection and soul searching and honesty and courage. It's not like it was a reactive heat of the moment thing in conflict and you realize that actually you didn't mean what you said. It sounds like this was maybe a long time coming. So I think framing all of the feelings that you're very understandably feeling as, oh God, is this regret telling me that I've made a terrible mistake?
16:45I think more often than not, it's just the waves of grief that come for us as we're processing the loss. And so I wouldn't be making too much meaning out of that. And as far as having reached out and said, there's still love there and I'd be open to trying. I mean, I think that that's okay to have done that certainly, but my advice as far as reconciling is always that it has to be really mutual because if it's one person kind of pleading against another person's resistance, it's really hard for the relationship. If you do then reconcile, it's really hard for the relationship that comes from that to feel balanced and steady.
17:32There's usually a bit of a power asymmetry there where the person who has wanted the relationship to resume then feels like they have to really hold onto it very carefully and they have to be very mindful of anything that could rock the boat or push someone away because there is that knowing that the other person was okay with the relationship having ended and sort of had to be convinced to come back. And so I do think that any consideration of a reconciliation should be both people coming to the table, both really wanting it and wanting to try again and being really clear and aligned around what led to the relationship ending and why that's going to be different.
18:19What's going to be the fix for that moving forward so that the unmet needs and the lack of shared vision and all of those things, is there going to be any substantive difference or do we just miss each other? And we're scratching the itch so that we can relieve the grief and the pain. Because I do think that in that scenario where it's just pain relief, then you'll end up right back where you work as nothing's really changed. And if there was a good reason for the relationship ending, which again, it sounds like in this case there was, even though it wasn't a big, dramatic watershed moment, the circumstances were such that it made sense for you to step away.
18:58And unless those circumstances have meaningfully, substantively changed, then I think you can feel comfortable that you made the right decision for you, which of course doesn't mean easy and doesn't mean smooth sailing, but means a decision that you can stand behind and know came from a place of integrity and honesty and self-respect. And I should add, you mentioned at the very end of your question, what does it look like to keep the door open without just being there waiting for them? I think that's a really astute question to ask. And frankly, I would caution you against that. I would proceed on the assumption that the relationship is over and the chapters close.
19:43You've made your position clear. But I think given that he knows where you stand and hasn't taken action to reach out and to say, yes, I want to try again and sort of following from what I was just saying around really wanting clear mutual buy-in as far as trying again, I don't think that you should be checking your phone every day to see if there's messages from him. If today's going to be the day that he reaches out to say, let's do it. I think that that's tantamount to you sort of chaining yourself to him, even at the same time as you have stepped away to honour yourself and what you really desire for your life.
20:24So it sort of defeats the purpose of this big brave act that you've taken to then sort of keep that foot in the door, keep the door open and be holding out hope that he's going to walk through it. I think that having made your position clear, you do have to proceed on the assumption that things have ended and that you're going to go your separate ways and your focus now should be on you and what the next chapter looks like and how you can take great care of yourself through that. So that would be my advice on all of those threads. And again, thank you for the very thoughtful, considered question with so many layers that I'm sure even in different circumstances, many people will be able to relate to bits and pieces of that.
21:07So thank you for sending in the question. If anyone else is listening and wants to send in a voice note, I'll pop the link in the show notes for you to do that. And also feel free to let me know if you enjoy this format of me answering a longer form listener question in more of a coaching and advice style. Okay, I'm going to leave it there, guys. Thank you so much for joining me. Please do consider pre-ordering the book. I will be eternally grateful to you and hope that I can return the favor by giving you access to the pre-sale bonus package and maybe see you on some live Q &A calls over the coming months.
21:43Okay, thanks so much for joining me, guys, and I look forward to seeing you. Coca-Cola. For the big, for the small, the short, and the tall. Peacemakers, risk takers. For the optimists, pessimists. For long distance love. For introverts and extroverts. The thinkers and the doers. For old friends and new. Coca-Cola. For everyone. Pick up some Coca-Cola at a store near you.
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Pre-order my book, The Secure Self on Amazon
In today's episode, I'm giving advice to a listener who recently stepped away from a long-term, long-distance relationship, over concerns that she and her partner were wanting different things. Despite having been the one to end things, she is grappling with the loss and having second thoughts about whether stepping away was the right choice.
I touch on a lot in my advice to her, including what's "normal" after a breakup, the courage it takes to walk away when nothing big happened, why the fear of regret can cloud our judgment, and under what circumstances a reconciliation is a good idea.
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