

2 Jul 2026 · 12m · 6 chapters

Listener Q&A on how to remain hopeful after heartbreak and repeated bad dating experiences, framed through attachment and mindset.
No guests; host “Steph” answers directly.
Don’t force optimism; honor grief/disappointment first, then date from “clean and clear” integrity. If you feel bitterness/anger or still emotionally tethered, don’t rush back into dating from urgency/scarcity. Find patterns and your role; self-responsibility is empowering. Build standards/non-negotiables before attachment/fantasy. Prioritize self-worth and self-respect over “a warm body.” Cultivate self-trust and take breaks from dating to reset.
Repeated dynamics like dating unavailable people or being pursued then disappearing; mapping the trajectory of relationships to identify where you could do things differently next time.
Written by AI. May contain mistakes.
Exploring how to cope with disappointment in dating.
“So clearly it's something that a lot of people can relate to.”
Details of an upcoming workshop on anxious attachment.
“It is totally free and you can register for that in the show notes.”
Discussing the importance of acknowledging grief and disappointment.
“So time sensitive, definitely register now.”
How to recognize personal patterns in dating and take agency.
“And no wonder you feel sort of stressed and anxious by the whole thing if that's the place from which you're operating.”
Establishing relationship standards for healthier dating.
“So there's a big self-peace when we're in this energy of how do I remain hopeful.”
Using experiences to learn and grow rather than feeling hopeless.
“the points in this where I maybe could have done things differently and where is my work in all of that?”

Get the gist, explore an idea or ask about something said.
On On Attachment, what are the key points of this episode?
Automatic transcript. May contain errors.
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1:13That's lemon propaganda right there. But now 7up is fighting back with their new lime lemon soda. Join the 7up rising. Hey everybody, welcome back to another episode of On Attachment. In today's episode, I am answering the listener question of how do I remain hopeful after a string of heartbreaks and poor dating experiences? So this is one, it's actually a question that I've been asked multiple times in the past week by people in different forums. So clearly it's something that a lot of people can relate to. And of course, that makes so much sense because as much as we can really want to date more intentionally to shift our patterns and maybe you've been doing the work, it is naturally very disheartening to feel like everything keeps unraveling despite your best efforts.
2:03And so I want to share some thoughts today on how you might approach that from a mindset point of view and how you might approach it practically if you're coming off the back of a series of heartbreaks, disappointments, situationships that never turned into anything, anything like that where you're feeling a bit worn down by your dating and relationship experiences and you're trying to remain hopeful, but that's feeling a bit forced or a bit disingenuous just by virtue of the experiences that you've had recently. So I'm going to be sharing some thoughts on that today. Before I do, a quick reminder that next week is my free workshop on understanding anxious attachment protest behaviours.
2:43So if you are someone who has a hard time with conflict and communication in relationships, if you struggle to be vulnerable and direct and advocate for yourself from a grounded place, and you know that actually when you've got needs or concerns or worries, that they tend to spill out in less than helpful ways, this workshop will really help you to understand yourself, to be more compassionate towards yourself rather than blaming and shaming yourself for those patterns and ultimately to shift into something healthier. So I would love for you to come along. It is totally free and you can register for that in the show notes.
3:18And it is a one-off live workshop. So time sensitive, definitely register now. That's not something that I have any plans to repeat in the near future. Okay. So let's talk about how to remain hopeful when you've had this string of heartbreaks and disappointments and And dating, relationships are just feeling really hard. I think it's really important to acknowledge at the outset that just trying to force yourself to feel bright and cheery and optimistic and hopeful when that's just not how you're feeling is probably not helpful. And if anything, I would give myself a wide berth if I were in this situation.
3:55I'd give myself a wide berth to actually just feel into the grief and the disappointment. right? I think we tend to try and keep clear of those heavier emotions because we designate them as bad or low vibe or how am I going to find someone if I'm just moping around feeling sorry for myself, right? And that makes sense. I get that. And I'm certainly not encouraging you to just stay at home feeling sorry for yourself for months on end. But I think there's a middle ground there that allows you to honor the disappointment and the grief and actually be with those feelings so that you can come out the other side of the tunnel in an honest way, rather than just trying to sweep all of those things under the rug and pushing yourself to get back out there, so to speak, when actually you're still in a place that feels kind of emotionally heavy and bogged down with all of those experiences.
4:46Because really, I think the instinct there that I don't want to date from that heavy place is probably a wise one, but the solution is not to then just suppress it and keep dating. The solution is, okay, well, I need to work through those things so that I can date from a lighter energy, an energy that feels kind of clean and clear and in integrity. And I think particularly if you're really feeling a lot of bitterness or anger or blame or whatever other stories you might have towards the people who you've had these relationships with, who have broken your heart, the breakups that you've been through, all of that stuff, if you still feel emotionally tethered to them and you're still really in the trenches of that, it's not a good idea to just try and get back out there from this place of urgency and scarcity and, well, I need to find someone so I've just got to keep pushing.
5:41I don't think that's a good idea because when we're not giving ourselves the time and space to process whatever has happened, both our emotions around it, But also, frankly, like looking at how am I participating in this pattern that I say I don't want and that I really don't want, but clearly I keep gravitating towards things that are going a similar way. Maybe it's people who end up being unavailable or who are really into me at first and then they sort of disappear. Like, what's the pattern and what's my role in the pattern? If you don't know that, then the likelihood that you're just going to keep repeating it is pretty high.
6:21And I know that that's hard to hear, particularly when it's just not what you feel you want. It's the opposite of what you want. I think we need to find, almost find hope and agency in the fact that we are a contributor to that pattern, because that's the part that we can change. If we really cling to the story that this keeps happening to me and I have no part in it, that's a really, really disempowering, I would say pessimistic story because then you are just this sort of passive character in your own life. And no wonder you feel sort of stressed and anxious by the whole thing if that's the place from which you're operating.
6:55I think once you step into more self-responsibility around, okay, clearly things have not been going very well for me. Can I get curious as to what might be driving that? And for a lot of people who I work with, and just as a side note, this is a very, very common experience. It's so many people that I support, particularly in my breakup course, but also in my anxious attachment program, doing the work to build your self-worth so that you stop pining after people who don't want you. so that you stop persisting in relationship dynamics that feel really insecure and then end up sort of unraveling and yet you're holding onto this story that it all happened really suddenly and unexpectedly.
7:38There's a lot in that that is actually us, even though it feels like the other person made all the decisions and they held all of the power. The way that we respond to those dynamics and the fact that we keep participating in them even when they're not working, that's our stuff. And so something that I teach in my breakup course is to get really, really clear on what your standards are, what your non-negotiables are, what your deal breakers are. Before you have a person in front of you that you're really excited about and attached to, and you've already latched onto them and started building this fantasy around them, you need to have something a little bit more objective that's coming from your clear-headed self.
8:22These commitments to like, here is the kind of relationship that I am interested in being a part of and anything less than that isn't going to cut it. The reason that I emphasize self-worth so much in everything that I do and teach is because you have to reach a place where you are more committed to your well-being, to self-respect, to taking care of yourself than you are to just having a warm body next to you, right? Because for as long as you are more interested in just having someone to give you some attention, just having a partner because you don't like being alone, you don't like what that means or the stories that you craft around it, then, you know, something will always be better than nothing, but that something's probably going to be way less than what you really want and deserve.
9:08So there's a big self-peace when we're in this energy of how do I remain hopeful. I think you've got to do the work to radically up level, like, what do I believe I am worthy and deserving of? And that can't just be like an affirmation you repeat in the mirror. It's got to be a deeply embodied belief such that you will not be interested in something that isn't that, right? That's how we change our patterns is that we stop doing the old thing and we actually hold the line, even when our feelings are pulling us towards the thing that is familiar but unhealthy. Right. So remaining hopeful. I think a big part of that is cultivating self-trust by saying like, I know that that's not going to keep happening because I won't let it keep happening.
9:55And to be clear, that's not to say that you have control over whether someone breaks up with you, right? Heartbreak and grief is part of life and relationships, but the way that we become not just hopeful, but resilient in the face of those really challenging experiences is by knowing that we will have our own back and that we are a really trusted person to carry ourselves through those experiences. Because most of us, and particularly those of us with anxious attachment patterns, when something hard happens, we feel deeply, deeply alone because we don't really trust in our own company. And our inner environment tends not to be a very safe place.
10:37And that's why we're so accustomed to like looking out there for someone or something to make us feel better. But of course, that then leads us back into the pattern. So I think if you're feeling this way, taking a break from dating is a really good idea because just, you know, rushing back into it and expecting to get some different results as if it's just a lottery and you've got to keep buying tickets and eventually you'll luck out. I don't think that's realistic. If you keep coming up against similar patterns, similar people, similar dynamics, you've got work to do. And again, like to me, that is encouraging.
11:13Even now in my own life, I'm always really willing to be shown where something is my work because that is empowering to me. I feel much better about something that I can exert agency over rather than sitting in the story of this keeps happening to me and it's so unfair. So take that invitation into self-responsibility and greater standards and self-respect and self-trust. Like that's a beautiful thing to gift to yourself so that you get to really re-enter dating and relationships whenever that may be from a different place within yourself. Because wherever you go, there you will be. And if you've got some patterns, you've got some burdens, you've got some wounds, as we all do, there's every chance you're going to keep coming up against them in your dating and relationships, because that tends to be where they're most acute.
12:08So to recap, give yourself time to greed. Don't try and just like be your little cheer squad and get back out there and force yourself to feel hopeful and cheery and optimistic when that's just not how you feel and fair enough. Allow yourself the space and the time to feel into the sadness and the hurt and the disappointment and the grief. And then when you feel like you have more capacity, start to reflect on your role in it. And what is it within me that keeps tolerating these sorts of dynamics? Or how does it usually go? Can I map out like the trajectory of how my relationships tend to unfold?
12:42Because you'll probably notice some common themes and then go, okay, where were the points in this where I maybe could have done things differently and where is my work in all of that? What would I do differently next time? That's how we turn regret into a teacher and we actually learn from our experiences rather than just collapsing into shame and hopelessness and despair around it. Okay. And I should mention this is absolutely the kind of work that I support people with in my programs. So if you are looking for some more support and accountability, you can check those out on my website. Okay.
13:17Sending you lots of love if you're in this. I know it's hard, but I hope that today's episode and the thoughts that I've shared have given you something to orient towards rather than just feeling like you're at war with yourself because I know that's not a particularly nice experience. And as always, grateful for your support. Thank you so much for joining me and I look forward to seeing you again next time. Thanks, guys. Want to be the one who's always in the know about the game, the scores, the plays? Here's a tip. The Apple Sports app. Just pick your favorite teams and get automatic live updates without even knowing their schedules.
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When you've had a string of heartbreaks, disappointments, and bad dating experiences, remaining hopeful can be a big ask of your system. In today's Ask Steph episode, I'm sharing some thoughts on why forcing yourself to feel hopeful might not be the thing you need, and why it might be best to give yourself the time to grieve, reflect, and grow before forcing yourself back into the dating arena.
Register for my Anxious Attachment Protest Behaviour Workshop