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50. Dating After the Affair

Updated: Sep 26, 2025


Rebuilding your life after betrayal is already a monumental challenge, but what about finding love again? The idea of dating after infidelity can stir up a whirlwind of fear, hope, self-doubt, and longing. Whether you're newly single or trying to reconnect with your current partner, the emotional terrain of post-betrayal dating is complex, but navigable.


In this milestone 50th episode, I offer a deep and compassionate dive into how to date again after experiencing betrayal. This episode is filled with hard-earned wisdom, practical strategies, and personal stories that will help you date with intention, whether it's with someone new or your partner who has hurt you.


Key Takeaways:


  • How to rebuild trust in dating after infidelity through “trust calibration”

  • The right timing for dating again and what to consider before jumping in

  • Red flags to look out for (and why your gut is a powerful guide)

  • How to set healthy, evolving boundaries rooted in self-respect

  • Why your relationship with yourself sets the tone for all future love


💬 Reflection questions:


Are you thinking about dating again, or already taking steps back into the world of connection? What fears or hopes are coming up for you?


Connect with Luke:


Join the After the Affair community at www.facebook.com/groups/aftertheaffaircommunity

dating after infidelity

Episode Transcript:


The After The Affair podcast with me Luke Shillings is here to help you process, decide and move forward on purpose following infidelity. Together we'll explore what's required to rebuild trust not only in yourself but also with others. Whether you stay or leave I can help and no matter what your story there will be something here for you.

 

Let's go. Hello everybody and welcome to another milestone episode of the After The Affair podcast with myself Luke Shillings. Today is episode 50.

 

Wow, where does time go? Thank you so much for choosing to spend your time with me especially today as we delve into a topic that I know is on the minds of many of you out there and that's starting fresh. How to start dating after betrayal. If you're a regular listener you already know the exploration that I have gone into into the various elements and impacts of betrayal and of course where a relationship can be saved then that's absolutely worth fighting for and regardless of the statistics that you see and hear out there there is plenty of hope that relationships can be rebuilt and become really really strong after betrayal.

 

Of course sometimes that doesn't always happen. For some reason maybe that relationship isn't ideal and you don't want to remain in it or maybe you don't even have the choice and you've moved on you've gone your separate ways and now you're really sort of venturing into that area that often fills people with a mix of hope and trepidation. It's about finding love or connection again after the rug has been pulled from underneath your feet.

 

I want to talk about those first hesitant steps back into the dating world after betrayal has rocked your foundation. So grab your headphones or settle into your favourite chair. This episode promises to deliver valuable insights whether you're on the verge of dating again or just starting to consider the possibility.

 

So in today's episode we're going to tackle three crucial aspects of dating after betrayal. Each one of these has been carefully chosen based on what I found to be the most challenging issues faced by those I've had the privilege of coaching. First I'll look at how to navigate the dating world post betrayal.

 

How can you trust someone again without carrying all the emotional baggage from those previous relationships? Secondly I want to discuss the timing of dating after betrayal. You don't want to jump back into the pool before you're ready but how do you know when is the right time? Then I'd like to look at what red flags we need to watch out for and how to set boundaries. Because let's face it knowing what to look for and setting limits is essential for any healthy relationship but even more so when you've been betrayed before.

 

And I might even share a little bit about my own dating experience. So let's start with navigating the dating world after betrayal. Stepping back into the dating world after betrayal can feel like navigating a minefield blindfolded.

 

You're filled with anxiety, questions and maybe some bitterness. Trusting again can seem like an enormous task similar to walking on a knife's edge. It's fraught with tension and fear and the unknown.

 

However what we often forget is that trust isn't a switch that you turn on and off. It's not binary. It's more like a muscle that needs to be flexed and strengthened over time.

 

One approach to rebuilding this trust muscle is a method that I've coined as trust calibration. It involves starting with small manageable increments. You don't need to plunge headlong into deep emotional commitments start small.

 

For instance you could let a new date choose the restaurant for an evening or you could trust them to call when they say they will. These might seem like trivial things but these tiny acts can serve as building blocks for trust. Think of it as a ladder where each rung on the ladder represents a new layer of trust.

 

As you climb higher you're not trusting them you're also trusting your own confidence in your own judgement. It's essential to distinguish between learning from your past and being chained to it. You see your past experiences can serve as a useful textbook but they shouldn't be a prison.

 

They shouldn't be the restrictive rules that you can't step outside. It's really important to avoid viewing new relationships through the lens of past betrayal because that's how we see it. We become you know trapped inside our own restrictive box and we can only see the new relationship through that tainted lens.

 

Yes you've been hurt before but this is a new chapter it's a fresh start. You might now have the wisdom to recognise red flags and sense you know untrustworthiness and in a way that maybe you hadn't done before but it's very easy to allow those little markers to shine much brighter than they really need to and that can then therefore restrict you from making better choices. So rather than using it against you utilise this this newfound wisdom this new awareness as a wall to sorry not as a wall to keep others out but more of a filter to let other ones in.

 

Equally vital in this journey is the element of self-compassion. I've spoken about this many times before. If you stumble if you find it hard to trust someone or even if you experience another betrayal remember it's okay you're human and your emotions are valid.

 

Healing is neither a sprint nor a marathon. It's more like a series of sprints and stops and sometimes you move forward and other times pausing to catch your breath. Your path will have its set of ups and downs.

 

It'll have these obstacles the trips and falls and it's perfectly fine to be that way. It's never going to be a straight line. So be gentle with yourself.

 

You're doing the best you can and each step you take however tentative is a move in the direction of healing and growth and when we apply this to going out into the world and meeting new people for the first time especially when we're afraid of being hurt again which is a very real feeling. It's a very real fear that many people have. The pain of betrayal as many of you listening will be able to attest to is overwhelming and unexpected and up there with one of the most painful things that somebody can experience on an emotional level.

 

So having your guard up makes perfect sense but by having your guard up not only you preventing yourself from letting other people in, you're also preventing yourself from seeing what other people have to offer. So there needs to be some room for manoeuvre. Imagine it a little bit like peeking over a wall that's a little bit too tall.

 

You know you can start by putting your hands on the brick wall and lifting your eyes just above it so you can take a peek over. You're still fully protected by that wall and the problem with that is you can only see part of what's beyond the wall. You're not exposing yourself to the full view so maybe you could get a little box and you could stand on that box and lift yourself a little bit higher giving you a slightly better view which exposes you to more things which you can then make more judgments from and you can continue on this journey eventually to the point where you are like Humpty Dumpty and you are sat on top of the wall and okay maybe Humpty Dumpty fell but you know that's a different story.

 

The point is you get to view everything but you're still on the wall so you still got that element of safety. If things do become too much for you you can just jump straight back down again and build it back up but by staying behind the wall and peeking through a little hole that you've made in the cement in the mortar is never going to allow you to rebuild that connection and rebuild that trust in a future partner. Okay so you think this sounds all well and good but you're now wondering well yeah but when when's the right time you know what is the perfect time to date after betrayal and how do I know when I'm ready? Well deciding when to jump back into the dating pool after betrayal is a delicate balancing act.

 

There's a temptation to rush and move on and find someone better we might completely overlook the need for that internal healing. Often actually the pain that we experience we want to get rid of that so quickly that seeking pleasure whether that just be hookups or just human interaction or communication can really be damaging to future relationships by mistakenly believing that the new relationship will erase the scars of the old and of course they don't. The truth is jumping in too quickly can be like pouring salt on an open wound.

 

It stings and it completely stops and halts the natural healing process. Understanding your emotional readiness is quite important here. Have you taken enough time to grieve the loss of your previous relationship? We often think of grief as being only if somebody passes but of course grief can be described as the loss of anything that was important or had meaning or significant value to us and particularly when it comes to the loss of our identity, the loss of the role that we had within the relationship and of course the loss of our partner.

 

Have you spent quality time in your own company learning who you are outside of the context of a relationship? One of the most common things I experience with my own clients is that they have identified as this person that they have this role that they have played throughout their lives and now all of a sudden they don't know who they are anymore because they only ever thought of themselves in the context of the relationship, in the context of the marriage or in the role as a parent. Many people completely underestimate the power of self-reflection and solitude and I've spoken about this in episodes before so I highly recommend if this is the first episode that you've discovered me then please go back and have a look at a list of the episodes that talk on these sections in more detail. This time alone serves as fertile ground for self-discovery.

 

It's like a perfect opportunity which in turn creates a more secure foundation for future relationships. I can't stress enough how important it is not to skip this phase. You need to embrace it and allow yourself the gift of self-introspection.

 

It really is the, you know, for the sake of the metaphor, it's the soil in which your future love will grow. But how do you know when you're ready? Well one indicator is the absence of what I call emotional echoes from your past relationship. These are the kind of residual feelings of anger, betrayal or even lingering love that bubble up when you consider dating someone new.

 

If these feelings are still strong you might want to give yourself more time. On the flip side, if you can think about dating without being overwhelmed by these emotional echoes then that's a strong sign you are ready to move on. Now there is no definitive timeline that tells you when this is ready or how long this will take.

 

So looking externally or asking other people, it doesn't really create any framework for you as an individual. You really need to pay attention to how you feel in the moment, whether you feel right to move on to the next stage and just be open and honest with yourself about your motivations. Another aspect to consider is that motivation.

 

Is that motivation for dating again? Are you seeking companionship because you feel whole and are eager to share your completeness with someone else? Or are you just trying to fill the void? The latter almost always leads to what's generally considered a rebound. A rebound relationship which are usually not fair or healthy for either party involved, yourself or the person that you're dating, and can often extend the recovery process rather than accelerate it. And then finally, trust your intuition.

 

Now I know for some of the guys listening, intuition, it's like, really? Intuition? Isn't that a bit touchy-feely? Isn't that a bit woo-woo? It's like, well hang on, maybe that's the word that you may be more familiar, your wife or your mother or the other females in your life to use. But when we think of it as guys, think of your gut feeling. Gut feeling and intuition are essentially interchangeable.

 

You've weathered the storm of betrayal and that experience has granted you a form of emotional intelligence that you just didn't have before. You're more in tune with your needs now, your boundaries and your limitations. They're there, they're more prominent.

 

Listen to that inner voice. It's been fortified by your experiences and refined by the reflections that you've taken to date on this journey. And if it tells you that you're ready, then you probably are.

 

And if it advises you to wait, then maybe you should pay some attention to that too. But you need to ask it that question. You need to ask yourself that question.

 

Is there a part of you that just isn't ready? And in which case, there's no rush. Tinder is not going anywhere soon. Okay, so you have established that maybe you are ready to start going back into the dating world.

 

And you now have some idea about how and what exposing yourself... That's a really inappropriate choice of phrase. Sorry. But what... Oh, reset.

 

So now you have decided that you want to reintroduce yourself into the dating world. And you want to go out there and start to... Oh my god, why can't I think of a word other than expose? I'm gonna stick with it, but I don't mean it. I don't mean get naked, okay? Right, let's carry on.

 

Well, not straightaway, at least. Okay, sorry, back to the point. You're at this point, you're going out into the dating world, but you're still wanting to know, well, what red flags are there that I should look out for? And what kind of boundaries can I set to navigate myself through this this new field? So if betrayal has taught you anything, it's the imperative need for vigilance.

 

Not just in your partner, but also in yourself. This is your moment to redefine what is acceptable for you in a relationship. We're not looking at how you were in your previous relationship, we're looking at what can you take from what you've learned in your previous relationships and utilise those in the relationships going forward.

 

The red flags you might have ignored in the past, let's say. You know, we all have these questions of ourselves. Well, how didn't I see it coming? How didn't I know? And then, often when I have conversations with people, and we we look back a little bit at what it was like in the run-up to the affair, once they've discovered their partner's been unfaithful, they notice some of the behavioural changes that they felt on like a more instinctive, more intuition, more gut sort of level, that they haven't really paid attention to.

 

Maybe they'd actually actively chosen to ignore them. But these can now form part of your new boundaries. Not for shutting people out, but for creating a space that allows healthy relationships to flourish.

 

So let's talk about these red flags. Obviously they can vary from person to person, depending on your experience and your comfort levels. Some common ones include straightforward dishonesty, lack of communication, or outwardly manipulative behaviour.

 

Others might be subtler, like when your partner respects your boundaries in words, but not in actions. Pay attention to your instincts in these moments. They're your early warning system.

 

And don't dismiss minor red flags, because often they are the precursors to bigger issues. However, spotting red flags is only half of the equation. Setting boundaries is the other.

 

Boundaries are not a sign of distrust. They're a manifestation of self-respect. Explicitly stating your boundaries provides a roadmap to success for any future relationship.

 

Think of it as setting the terminal conditions for the kind of love you're willing to accept. And once you've set these boundaries, be consistent in upholding them, even when it feels uncomfortable. That said, boundaries aren't static.

 

They're dynamic. They are constructed by you, and they evolve with you. As you grow, your boundaries may shift.

 

The key is to maintain open communication with your partner about these changes. Relationships are not a set-it-and-forget-it type activity. They're living entities that grow, adapt, and sometimes, yes, they even hurt.

 

By understanding your red flags and actively maintaining your boundaries, you equip yourself with a toolkit that can navigate the complexities of love without losing yourself in the process. And remember, this was something I remember learning. I was always fascinated by body language, facial expressions, trying to tell if somebody was lying, you know, these tips that people often share with, like, oh, if somebody's looking up to the left, they're thinking.

 

If they're looking down to the right, they're lying. Or, I can't remember exactly which it is, but whatever they are. Overall, they aren't very reliable markers of somebody's honesty, because everybody has a different baseline of what is normal for them.

 

And using these one-size-fits-all rules about what is a red flag is often not a reliable way of being able to judge somebody's trustworthiness or their honesty. However, when you start to spot multiple things that could be considered red flags, then that's worth paying attention to. Of course, as the betrayed, we're always going to have a heightened sense of what somebody is doing that might display a potential for dishonesty or give us some reason not to trust.

 

But these individual things on their own aren't enough, unless it's something really blatantly obvious, of course. But generally speaking, they're not enough. It's only when we have a collection of these things that then we can say, oh actually, there's enough going on here.

 

There's enough red flags, enough red lights. Maybe I should implement my boundary. I should follow through on my boundary, and I should protect myself in that nature.

 

And for more information on boundaries, I highly recommend you go back and listen to episode number 13, Know Your Boundaries, which explores this concept in much more detail. One element I will just readdress is that when it comes to boundaries, particularly when we're meeting new people and dating, we don't go out and actively list out all of our boundaries, all of the things, you know, we don't offer like a terms and conditions sheet that our potential date needs to sign before we get into any kind of engagement or communication. No, that's not the case at all.

 

What we're doing is, if somebody acts in a way that violates one of your boundaries, then you are going to do two things. First of all, you're going to make a request that actually, you know, that doesn't make me feel comfortable. If that continues, then I'm probably just going to remove myself from the situation.

 

And of course that can be, you know, customised to the individual scenario and setting, and I can always welcome to help people with boundaries. If you've got any queries about boundaries that you're wanting to set in your own relationships, then reach out, send me a message, and I'll more than happily help you formulate that in a way that feels in line with your values and isn't being used as a weapon against the other person through the form of threat or ultimatum. A boundary is always about protecting you and your emotional needs.

 

And remember, the act of setting a boundary is also an act of trust. It's trusting your partner to respect your needs and trusting yourself to enforce them. And this dual trust is a real foundation on which resilient, lasting relationships are built.

 

So as you venture back into the dating world, carry this newfound wisdom with you. It's your compass for navigating the often challenging landscape of love after betrayal. So what core underlying lesson can we draw from these different elements of dating after betrayal? If there's one key insight I'd like you to take away, it's that the relationship you have with yourself truly sets the tone for every other relationship in your life.

 

You can't control others, but you have full authority over yourself. Self-respect begets respect from others. Self-love attracts love.

 

If you're rooted firmly in your own identity, grounded by your values, and that's secured by your own self-confidence, you are far less likely to be shaken by somebody else's actions. That's why it's crucial to invest the time and the energy into truly understanding yourself, your triggers, your boundaries, and what you're truly seeking in a relationship. Don't let the past betrayal define your future.

 

You are not the same person you were before. You're wiser, you're stronger, and you're far more capable of creating the relationship you deserve. And if things don't go as planned, well, you'll know how to pick up the pieces, because you've done it before.

 

By taking this approach, you not only make it easier for you to find a partner who resonates with your life goals and your values, but it also makes it far less likely that you'll ever be a victim of betrayal again. Your self-worth doesn't rely on external validation, but a relationship can become a beautiful addition to an already fulfilling life. In this episode, I've really tried to explore the emotionally charged but immensely rewarding journey that is discussing the intricacies of dating after betrayal.

 

Starting with how to rebuild trust without lugging the baggage of past relationships, we've spoken about the crucial timing aspects of dating after betrayal. You don't want to rush back into the dating pool. It's important to recognise when you're genuinely ready for a new relationship.

 

We also explored the necessity of identifying red flags and establishing clear boundaries for future partnerships. The linchpin of all of these discussions is the central insight that your relationship with yourself sets the precedent for every other relationship that you will have. Trusting again isn't about giving somebody else a chance.

 

It's about giving yourself the opportunity to experience love, trust and happiness in a new context. Your past may have shaped you, but it doesn't have to define you. Reclaim your narrative and prepare for a future filled with more authentic connections.

 

I want to thank you again for joining me on this amazing journey. We're 50 episodes in and I can't wait to carry on and get another 50 done. It's so much fun and hopefully with the insights that you've gained today and hopefully you can take some of those, use them as actionable steps to move forward in your life and in your relationships to really take back that power, take back that control that you feel like you've lost and ultimately find the love that you truly deserve.

 

And just to add, there's an element, although we've been talking about dating specifically today, everything that I've spoken about here is also true if you are rebuilding a relationship with your unfaithful spouse. If you have experienced betrayal within your primary relationship but you're choosing to stay, both of you are choosing to stay, then of course everything that we've spoken about today still applies. You're still dating.

 

You just might be dating your current partner. The same basics are there. Now I promised at the beginning that I would share a little bit about my own dating experience, which is something I did do, you know, a couple of years after getting divorced.

 

I went through many of the things that I've discussed today in terms of trying to judge when was the right time. I asked myself lots of questions. In fact, lots of what I've spoken about today has come from that period and the notes and the journals that I wrote at the time.

 

I did go on a variety of dates. I met lots of people online. In actuality, I met my wife originally online.

 

We met on a website in the UK called plentyoffish.com back in 2009, I think it was. And the dating world was a little bit different. The online dating scene was a little bit different then.

 

Of course, the advent of Tinder and 20 million other dating apps that there are now changed the face of it a little bit and there's definitely some new dynamics to consider. But all of that aside, one of the things that I found challenging, let's say, or most interesting, was the fact that I was dating as a, you know, divorced father. People make judgments.

 

They do. And there's only so much information that I wanted to put on my dating profile. I didn't want to give all of the ins and outs of exactly why I was divorced and single.

 

I didn't want to divulge all of my, you know, desires and wants and needs going forward. Although that is becoming more commonplace and arguably there's some utility in that. There are a combination of factors that are definitely different.

 

The whole concept of ghosting is, well, it was new to me at the time. But it's something that definitely happens and it's painful and it's unpleasant and I would rather it didn't happen. It brings up those feelings of rejection that I certainly felt when I was in my younger years, certainly my teen years through school, and I think can be quite common for many guys.

 

This feeling of rejection, the fear that you're not good enough and not wanted. So having that sort of brought back to the surface was, you know, an interesting if not somewhat challenging experience. But I did learn some things.

 

One was this now almost embedded belief that I have in myself and thought that I have is that I'm happy for people to be wrong about me. I as much as I had previously wanted to try and always portray the best possible image of me to other people, and I'm not just talking about dating here, I'm talking in general, I was bothered about what people thought. And I'm not saying that I no longer care about what people thought or think, sorry, but I'm absolutely okay if they misinterpret what my true intentions are or what it is that I'm trying to represent or what it is I'm trying to do in my business and who it is I'm trying to help.

 

I'm happy for people to be wrong about me. And having that psyche, that mentality in the dating world I think can be very very useful and really offer that element of protection in some ways. Because, you know, so what if somebody doesn't like you? So what if they don't get you? So what if you're not on the same wavelength? I mean there's eight billion of us on the planet.

 

The likelihood of us all being perfect fits is pretty remote. So it's it's not surprising that that's not always going to align. The other thing that I think I learned which has also helped me in building my business is the concept of not giving up.

 

I also believe, and this again this is a very personal opinion, that those who succeed are the ones that don't quit. And okay, your end goal might not look like exactly what you thought it was going to. But you only fail if you quit.

 

Another really useful life hack. It may sound so obvious but it's so easy. We get scared.

 

We don't like the negative emotions that come with rejection or hard work or challenge and this applies to all areas of life. When we do that we stop and we look for something else and then we've wasted it. So you can either learn or you can win.

 

And they seem to be like the best two options so I'll take them. And that for this week is a wrap. So until next time remember you are not alone on this journey and as you heal and you grow so does your capacity for love and happiness.

 

If you or anybody you know is struggling with any of the concepts, topics, ideas or experience that I've been discussing on this episode or any of the other episodes in this series, please reach out. I offer a variety of tools, support, one-to-one coaching that can help you move forward over and above that of the podcast. As always you can email me directly at luke at lifecoachluke.com or you can visit the website lifecoachluke.com and use one of the chat features and facilities there.

 

Contact form, whatsapp, instant chats and I'll always respond as quickly as I possibly can. I'll speak to you next week. Look forward to it.

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I am Luke Shillings, a Relationship and Infidelity Coach dedicated to guiding individuals through the complexities of infidelity. As a certified coach, I specialise in offering compassionate support and effective strategies for recovery.

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Luke Shillings Life Coaching

Waddington, Lincoln, UK

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