One of the hardest kinds of breakups is the one where nobody did anything wrong.
There was no betrayal, no dramatic falling out, no single moment that made it obvious the relationship needed to end. There was love, care, and a genuine connection. But somewhere along the way, you started to realise that perhaps you weren't moving in the same direction.
And even when you're the one who makes the difficult decision to walk away, that doesn't mean you won't find yourself questioning it later.
Did I give up too soon? Could things have been different? What if I've made a terrible mistake?
These questions can be incredibly painful, particularly when you still love the person you've left behind.
So how do you know whether you're experiencing genuine regret about ending a relationship, or simply moving through the very normal process of grief?
Let's explore some of the layers of this experience.
When Love Isn't Enough to Make a Relationship Work
We often think of relationships ending because something went terribly wrong. But sometimes, two people can genuinely love and care for each other while wanting fundamentally different things.
Perhaps one person is focused on career growth, travel, independence, and exploration, while the other is craving consistency, emotional availability, and a clearer sense of a shared future.
Neither person is necessarily wrong.
But when your priorities and timelines are pulling you in different directions, love alone might not be enough to bridge that gap.
This can be particularly challenging in long-distance relationships, where maintaining connection requires intentional effort and a shared vision for the future.
If you're living largely separate lives, occasionally catching up over the phone, and struggling to feel meaningfully involved in each other's worlds, the relationship can start to feel incredibly lonely.
And when there's no clear plan for closing that distance or building a life together, it's understandable to begin questioning whether the relationship is truly meeting your needs.
You can love someone deeply and still recognise that the relationship isn't working for you.
That doesn't diminish the love you shared. It simply acknowledges that compatibility involves more than feelings.
The Problem With "Right Person, Wrong Time"
We've all heard the phrase right person, wrong time.
And while it might sound romantic, I think it can sometimes keep us attached to relationships that aren't actually available to us in the way we need.
Because when we label someone as the right person, we can find ourselves waiting indefinitely for the timing to change.
We convince ourselves that if we just hold on a little longer, give them more space, or make a few more sacrifices, eventually everything will fall into place.
But what if it doesn't?
What if two, three, or five years pass and you're still waiting for the same things?
There's an important distinction between making temporary sacrifices for a shared future that both people are actively working toward, and putting your needs on hold for a future that remains uncertain.
And sometimes, continuing to wait for that possibility becomes a subtle form of self-abandonment.
If someone isn't available for the kind of relationship you want and need, they may not be the right partner for you, regardless of how much love exists between you.
That's a difficult truth to sit with. But recognising it can be an important act of self-respect.
Is It Regret, or Is It Grief?
After a breakup, particularly one that you've initiated, it's incredibly common to experience waves of doubt.
You might initially feel some relief, especially if the decision had been weighing on you for a long time.
But as the weeks and months pass, the reality of what you've lost starts to settle in.
You remember the holidays you spent together, the conversations that made you laugh, the little routines, the shared memories, and the future you once imagined.
Suddenly, you find yourself wondering whether leaving was really the right decision.
And this is where grief can start to feel a lot like regret.
When we experience painful emotions, our instinct is often to find a way out of them. For those with anxious attachment patterns, that can look like overthinking, analysing, and endlessly revisiting the past.
We tell ourselves we're trying to understand what happened.
But sometimes, all that mental activity is actually an attempt to avoid feeling the sadness underneath.
We replay conversations, imagine alternative outcomes, and question whether we could have done something differently.
Yet none of that necessarily means the decision was wrong.
Missing someone doesn't mean you should be with them. Feeling sad doesn't mean you made a mistake. And experiencing doubt doesn't invalidate the reasons you chose to leave.
Sometimes, grief is simply grief.
And allowing ourselves to feel it, rather than trying to solve it, is an essential part of moving forward.
Learning to Trust the Decision You Made
One of the most important parts of navigating breakup regret is learning how to evaluate our decisions.
So often, we judge the quality of a decision based on how we feel about it afterwards.
If we feel relief, we assume it was right.
If we feel sadness or uncertainty, we begin to question ourselves.
But that's not necessarily a fair or helpful way to assess our choices.
Instead, it's worth considering the circumstances and information available to you when you made the decision.
Were you honest with yourself about what you wanted?
Had you spent time reflecting on the relationship and what wasn't working?
Were your needs consistently going unmet?
Did you make the decision thoughtfully, rather than impulsively in the heat of an argument?
If you made a considered choice based on your values, needs, and the reality of the relationship at that time, you can trust that decision even if it continues to hurt.
Self-trust doesn't mean never experiencing doubt.
It means recognising that you can make thoughtful, self-honouring decisions without having certainty about how everything will unfold.
When Does Reconciliation Make Sense?
Of course, sometimes people do find their way back to each other after a breakup.
But if you're considering reconciliation, there's an important question to ask:
Has anything actually changed?
It's one thing to miss someone and want relief from the pain of losing them. It's another to recognise that the circumstances that led to the breakup have meaningfully shifted.
For reconciliation to create a healthier, more sustainable relationship, both people need to genuinely want to try again.
There needs to be mutual willingness, clarity about what wasn't working, and a shared commitment to doing things differently.
If one person is pleading for another chance while the other remains hesitant or resistant, it can create an imbalance from the very beginning.
The person who fought to restart the relationship may then feel responsible for keeping everything together, becoming overly cautious about expressing their needs or doing anything that might push their partner away.
And that's not a particularly secure foundation to rebuild on.
Before revisiting a relationship, consider whether you're both aligned on the future you want and whether there's a realistic plan for addressing the challenges that previously existed.
Because without meaningful change, getting back together might simply provide temporary relief from grief before returning you to the same painful dynamic.
Why Keeping the Door Open Can Keep You Stuck
One of the trickiest parts of ending a relationship with someone you still love is figuring out how to move forward when a part of you remains hopeful.
Perhaps you've told your ex that you still care about them and would be open to trying again.
They've responded kindly, but they haven't taken any meaningful steps toward reconnecting.
So what do you do?
Do you keep the door open, just in case?
While that might seem harmless, it can leave you emotionally tethered to someone who isn't actively choosing the relationship.
You might find yourself checking your phone, interpreting their silence, or quietly waiting for the day they change their mind.
And in doing so, you risk putting your own life on hold.
If you've already communicated how you feel, there's nothing more you need to do to prove your willingness.
You can allow the relationship to be over without needing to know what the future holds.
Moving forward doesn't require you to predict the future. It simply means choosing not to organise your present around the possibility that someone might come back.
You deserve to build a life that feels meaningful, fulfilling, and aligned with what you want, regardless of whether that person ever returns.
Moving Forward Without Having All the Answers
There's something incredibly painful about letting go of a relationship that still contains love.
It's much easier to walk away when someone has clearly mistreated us or when the relationship has become undeniably unhealthy.
But when the ending comes down to different priorities, unmet needs, or incompatible visions for the future, the grief can feel especially complicated.
You might never get absolute certainty that you made the right decision.
And that's okay.
The goal isn't to eliminate every doubt or convince yourself that the relationship meant nothing.
It's to recognise that you can love someone, miss them, appreciate what you shared, and still honour the reasons you chose a different path.
You can grieve the future you imagined while making space for a future that may be more aligned with who you are and what you need.
And perhaps most importantly, you can learn to trust yourself through the uncertainty.
Because sometimes, the most loving decision you can make for yourself is also the one that hurts the most.
A Final Thought
If you're questioning a breakup, try not to interpret every wave of sadness as evidence that you've made a mistake.
Instead, give yourself permission to grieve.
Remember why you made the decision, acknowledge what you've lost, and resist the urge to turn every painful feeling into a problem that needs solving.
You don't need to make your ex the villain to justify leaving.
You don't need to stop loving them to move forward.
And you don't need to know exactly what comes next to trust that you're capable of creating a fulfilling life beyond this relationship.
Sometimes, moving forward is simply about knowing that even in the midst of heartbreak and uncertainty, you can continue to show up for yourself.
And that's a powerful foundation for building a more secure relationship with yourself and, eventually, with someone else.
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[00:01:00]:
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 were moving in different directions, and then having to process all of the layers that come with that in the aftermath. And, you know, 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. So 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 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.
[00:02:21]:
That makes everything else easier and clearer, and it will transform the way that you think about relationships. It 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 programmes, 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 signalling interest and creating a bit of buzz and momentum around a book in the lead-up to its release. And 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 3 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.
[00:03:46]:
So you'll get instant access to that when you buy the book. And then in November and December respectively, you will get access to 2 additional workshops on the fear of rejection and its role in anxious attachment, and then the unworthiness wound. So it's a 3-part workshop series on on the core wounds or the core beliefs at the heart of anxious attachment. That's all brand new and exclusive to people who preorder the book. And in addition to that, you'll also get an invite to 3 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. And 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'll have, cuz I've already received it a few times, I will be reading the audiobook.
[00:04:39]:
So I really do hope that you will preorder the book. You can just look it up directly on Amazon, The Secure Self by Stephanie Riggs. Or if you would like a full list of retailers, you can find that on my website at stephanieriggs.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. you in advance for your support. I'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.
[00:05:20]:
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.
[00:05:29]:
Hi, Stephanie. I'd really love your perspective on something I'm struggling with after my breakup. My ex and I first met about 8 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. Because 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.
[00:06:19]:
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. So how do you know whether you're experiencing genuine regret because you made the wrong decision versus the normal bargaining that happens after losing someone you deeply love? And if you've already made it clear you'd be open to trying again, how do you keep the door open without standing in a doorway waiting?
[00:06:55]:
So there's so much in that question. So thank you to the person who sent it in. I'm gonna pick apart a few threads and then kind of give advice along the way. So first, I wanna 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 When 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.
[00:07:36]:
Mm-hmm.
[00:07:37]:
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 butting 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, but 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 recognise and validate that that'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.
[00:08:57]:
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. But 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 touchpoints 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. If 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 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.
[00:10:26]:
So you may have heard me describe this previously as a structural incompatibility where you just want fundamentally different things. This 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. But 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.
[00:11:39]:
And when you play that out, if in 2, 3, 4, 5 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 It isn't meant to be. And 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. It'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 in.
[00:13:09]:
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 are 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. And 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.
[00:14:08]:
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. It sounds like you did that in a really mature and self-responsible way coming from No doubts and 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 realising 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—
[00:14:59]:
Yeah.
[00:14:59]:
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. I 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 That's why I really always emphasise 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 realise 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 realise 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. So 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.
[00:16:35]:
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 realised 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? I 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. There'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.
[00:18:30]:
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. 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 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 were because 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. And 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 chapter's closed.
[00:20:13]:
You'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. So it's 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.
[00:21:23]:
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. So 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 gonna leave it there, guys. Thank you so much for joining me. Please do consider pre-ordering the book.
[00:22:00]:
I will be eternally grateful to you and hope that I can return the favour by giving you access to the presale bonus package and maybe see you on some live Q&A calls over the coming months. Okay, thanks so much for joining me, guys, and I look forward to seeing you.
[00:23:16]:
Again next time.
Keywords from Podcast Episode
self-abandonment, anxious attachment, inner relationship, attachment patterns, self-worth, romantic relationships, relationship dynamics, The Secure Self book, pre-order bonus, core wounds, fear of abandonment, fear of rejection, unworthiness wound, workshop series, self-compassion, self-regulation, self-advocacy, self-trust, codependency, emotional safety, nervous system, relationship boundaries, overgiving, people pleasing, inner child, communication skills, relationship conflict, breaking unhealthy patterns, personal growth, self-development