Why You Keep Dating Jerks

Dr. Lisa Marie Bobby: On today’s show, we are exploring a question. I know many of you have been asking yourselves at some point or another, which is, “Why do I keep dating jerks?” I know that this has been on your mind because I’ve had a lot of you reach out to me through our website — growingself.com, through Instagram. With these situations, you’re like, “You know what? I did it again. Why do I keep getting myself in these relationships, in these situationships, wind up not being a good fit for me? I don’t like it, I don’t want to do it anymore, but I also don’t know how to stop.” And that’s valid. 

Today, we are devoting a whole episode into unpeeling this onion and answering some of these questions for you. I have something exciting planned for us today. I am going to be doing a couple of things. I am an information person, as you probably figured out now if you’ve listened to the show before. I am going to be providing information and insight — just things that I have learned over the years in my role as a therapist, a dating coach, a counselor here at Growing Self. 

Then, I also am going to be speaking with one of my listeners, one of your compadres, one of our community has raised her hand. We actually put a call out on Instagram recently around, “Have you had a pattern of dating jerks? Do you want to talk about it with Dr. Lisa?” Our friend, Sarah, raised her hand and said that she has been working on this for a long time, and she also had this pattern and has some very special and hard-won insights to share with you about her process in this area. Lots of fun stuff in store for us today.

If this is your first time listening — hello, welcome. I’ll make this quick. Dr. Lisa Marie Bobby — founder and clinical director of Growing Self Counseling and Coaching. I’m a Marriage and Family Therapist, I’m a psychologist, I’m a life coach. This show is all about love, happiness, and success, and your love, happiness, and success specifically. If you have questions, or topics you would like me to talk about on the show, if you have a question for me and would like to discuss it with me on the show, I hope you raise your hand and get in touch. hello@growingself.com is how you can email. You can also get in touch on Instagram, @drlisamariebobby. 

A Harmful Dating Pattern

First of all, let’s just talk about this pattern, which is so common. I know that many people who come to our practice, Growing Self, we do a number of different things here. We do couples counseling, we do career stuff — even our individual clients that we work with, the work that we do is often very relational in nature. I’ve done a lot of research and writing on the topic of breakup recovery, and I think is an extension of that when people heal and grow. It can turn into dating coaching, which is wonderful. 

That can also be a difficult experience for people, particularly if they haven’t done a lot of this deeper work around patterns and subconscious motivations. Without that insight, without that self-awareness, dating can often be extremely discouraging and disappointing, I should say. The hope of this podcast today is to arm you with some new ideas to help make it more positive and productive for you. Again, as with all these podcasts, this is information. Information is not the same thing as having a growth experience. But hopefully, you’ll hear some things today that you can put to use in your own life that would be helpful for you. 

You deserve to have help with this because it’s an awful experience of feeling like you try to have relationships with these people. Just over and over again, you’re getting involved with people who treat you badly or they’re untrustworthy — maybe they’ve cheated on you, maybe they weren’t emotionally available, or maybe you just leave this experience feeling like they’re not valued, and that is terrible.

It’s hurtful to experience, but also, if we don’t figure out ways to break these patterns, it can be traumatizing and can really hold you back in some ways from trying again, daring to trust again, and put yourself out there again, and finding the real, healthy love that you want and deserve. I am here to tell you — the good news is that these patterns are 100% within your power to change, and it is your power to change it. Meaning, that it is also ultimately your responsibility to change it.

Tip number one: one of the biggest things I found that can be a huge barrier for people on this path of growth is this idea that, “I just haven’t met the right person yet. When I do, this will be completely different. I’m just going to keep doing what I’m doing, I’m talking to all these different people, and sooner or later, I will meet the right person, and then I will have a different experience, and this will all be better.” I am here to tell you that certainly, meeting the right person can be glorious and leads all good things. 

Unless you’ve done deeper levels of growth work, you will have a really hard time meeting that person. Here’s the fun part: if you do meet that person, you will reject them. There’s a lot to unpack here today. The first thing that I would like to request, as we do this work together today, is that you release that old narrative of I just haven’t found the right person, and I’m just going to put it over here next to me while we’re talking. I will hand it back to you the end of today’s broadcast. 

But in the meantime, just clear the decks for some new ideas that will have more impact on your life ultimately because it’s not luck, it’s not chance — it’s you. It’s you learning, and growing, and gaining self-awareness and clarity, and being able to understand your patterns so that you can ultimately find freedom from them.

Jerks And Attachment Styles

One of the reasons that people have jerks in their life — a string of jerks going back for decades, different shapes and sizes, but jerk-wise nonetheless, and this one is hard to wrap your arms around. 

If this is true for you, it is likely that you will need some professional support in order to work through this. But if you emerged from childhood as many people have with damaging experiences in your very early primary relationships with one or both of your parents, it may have left you with what we call “attachment issues”. 

You may be on either side of the spectrum, you may have a tendency towards anxious attachment where you never quite feel safe or secure in relationships, and you need a lot of validation and people telling you that they love you, and showing you that they love you, or you start to feel really anxious, and that can lead to controlling behaviors in relationships sometimes that makes it difficult to have the kind of relationship that you want. 

You may also have come out of that with what we call an “avoidant attachment style”, which is that you, from a very early age, became heavily defended and even are now subconsciously really protecting yourself from getting too close to other people, which in practice typically looks like being extremely perfectionistic and critical of the people that you date and get to know. 

You can start to get to know somebody, and it seems good so far. Then sooner or later, they’re not perfect anymore, you have all these reasons why they’re not your person, and you will withdraw from relationships — even if you don’t want to. I’ve talked to so many people, and it’s like a physical — like they feel grossed out by a person almost, it’s like on a physiological level

It is very common for people who have anxious attachment styles and avoidant attachment styles to come together in a non-blissful union, and essentially torture each other for several months before breaking up, and then oftentimes repeating that with a different person with a same kind of complementary attachment style. 

I also want to say that any of us in a certain type of relational system can exhibit an attachment style on one side of the spectrum or the other. If you are in a relation with somebody, for example, if you have a secure attachment style fundamentally, and if you are in a relationship with an avoidant person, you will become anxious and you will start looking like an anxiously attached person in that relationship. 

If you are a securely attached person, and you start dating somebody who has an anxious attachment style, you will very predictably move into this avoidant relational style with them because of their kind of way of showing up in the relationship. One way to dig into this and to see if it’s deeper attachment things going on at a much deeper level is to ask yourself, and it could be with the help of a therapist or you unpack this, “Did I essentially grow up, from the ages of zero to five, in a highly emotionally unsafe or physically unsafe environment?” 

Not that you needed to have perfect parents. Everybody’s parent is a weirdo in one way or the other. This is not parent-bashing, but patently unsafe. It was bad, you are suspect that it was left with traumas, left with scars, and it has persisted and been in these kinds of stable patterns in every relationship over time. But that would be a sign that there’s some deeper work to do. 

I just wanted to say that first because I think what these kinds of questions like, “Why do I date jerks?” We think that there’s some simple answer, and if you’ve lived through awful things in your early childhood, I want to be a better friend to you than that by suggesting that there’s some simple amp answer and do these three things, and it will be better. There is a longer road ahead, and it’s okay, and it can be healed, and it’s going to be an intentional process, and it’s also difficult to do alone. 

But until you do that, it’s going to be hard to break out of those patterns because not only do you have your own attachment style that will interfere with healthy relationships anyway, but it’s almost like your antenna is a little bit bent. You’re going to be fundamentally more attracted to people who are going to be nothing but trouble for you. 

Herr Freud, back in the day, noticed this in some of his patients, and it would show up in different places, but he termed it “repetition compulsion”, and observed the fact that people who had very traumatic experiences, particularly with their parents, particularly in early childhood, would try to heal it, close the gap, have a healing experience with a person in their adult life who was very similar to one of those abusive parents like, “I couldn’t get the love and care that I needed from my abusive father, so I’m going to find this guy who’s very similar to my abusive father, actually, and try to do this with him. In that way, have that healing experience”, and it doesn’t work, and it is also highly subconscious. People don’t even realize that they’re doing it. 

If any of this is ringing a bell for you, you can just stop listening to the “How to Not Date Jerks” podcast, and just make an appointment with a good therapist who has an attachment-based orientation to help you dig through some of this, and do a deeper level of more meaningful work. Just invest in it, and trust that through this deeper work, you will be ready to heal, and grow, and find a wonderful person. But until you do the work, that time that you spend dating will not be helpful to you. That’s my first piece of advice, for better or for worse.

Jerks Are Attractive

Another reason that I often see why people have a pattern of dating jerks when we unpack this is because jerks are often incredibly attractive humans — they really are. When we think about the stereotypical jerk, they don’t say terrible things, and act in horrific and shocking ways when you first meet them. No — they are often superficially charming. They are smooth talkers. They look good, they smell good, they often have admirable careers, and they can be really fun to talk to. 

They’ll sweep you off your feet, an experience that I think a lot of people are craving. They are subconsciously, when they’re going out and thinking about who they’re attracted to — or feeling attracted to, I should say, is people with a lot of sex appeal who have established good careers and these kind of admirable lives, and who are again, good talkers. Sometimes, there are certainly wonderful humans in the world that can be all of those things — they’re talented, they’re fun, they’re smart, they’re charming, they’re accomplished, and they’re also kind. That happens, it’s a thing. 

But oftentimes people who are not all that kind, who may actually have narcissistic or sociopathic personality traits, or who have highly avoidant attachment style, which is can be associated with sociopathic or narcissistic personality traits, often present as all that and a bag of chips when you first meet them. That is actually something that I have — part of my spidey sense that I’ve developed with other humans over the years is if somebody seems too good to be true, and is flattering you, and love bombing you, and talking about all these amazing things, wants to fly you somewhere on their private plane, that makes my narcissist alarm start flaring. 

Just pay attention to that and think about who you are attracted to, what those patterns are, and whether or not you might have a proclivity to sexy-hot chicks or the suave-debonair guys because again, there can be a pattern there. I think if you are prioritizing that charming experience, that butterfly experience, that exciting experience, that super sexy experience with people that you’re just getting to know. 

If that is what you’re looking for, and that’s what you’re vibing in the direction of when you are seeking partners — if you’re looking through online dating apps, or starting to text with people, or go first dates, you are going to be, by definition, rejecting people who are non-jerks, because most of the time, very nice, kind, decent, securely attached people are not that flashy. They’re not trying to impress you, they’re not trying to lovebomb you — they are just going about their life and looking for somebody nice to connect with, and go and do fun things with, and develop a real relationship with which often feels like developing a friendship with somebody.

Not Everyone Is A Jerk

A secure, emotionally healthy person is going to want to get to know you over a period of time, and it’s going to feel relatively calm and peaceful. They don’t want to have a 72-hour first date with you, so they often have healthy boundaries, they’re being appropriate. If you have a pattern of being attracted to the feeling, if you’re looking for that feeling, you’re going to encounter non-jerks and think, “Hmm, they’re boring”, or, “This doesn’t feel like it should”, because there isn’t that sizzle sort of feeling. 

Sometimes I’m sorry to say, people can even take this a step further. They have criteria that very nice, decent potential partners might not meet in terms of career aspirations, how much money they make, how much they weigh, how tall they are. If you are looking for superficial characteristics to guide your dating life, and not paying a lot of attention to things like values, and character, and who this person fundamentally is — you have a much higher likelihood of connecting with a superficial person because that’s the energy that you’re coming into this with. 

I’m not saying that to be critical towards you, but just to bring it into your consciousness because this is a mistake that a lot of people are making and not even realizing that they’re doing it. Again, knowledge is power, self-awareness is power, and if this is something that could be true for you, it’s really important to get clear and reflective around this so that you can break the pattern and do something different. 

Now, another reason why you may feel like you are dating jerks and have a pattern of taking jerks — you might not actually be dating jerky people, you might be dating people that, over time, you come to realize are fundamentally incompatible with you. It’s not a good fit, and it doesn’t necessarily mean that they’re a bad person. 

But if you are feeling angry, or disappointed, or let down by them because they are not who you wanted to be, that would be a good sign that one of the reasons why you feel like you’re dating jerks is that you are getting involved with people on a more intimate level too quickly that if you had given yourself the time to slow down and get to know them a little bit better over time, you would have come to the realization that is not a good fit just in terms of who you are, what you want, personalities, the way that you communicate, values. It takes time to do that.

If you find yourself being really disappointed or surprised that people aren’t who you thought they were, it’s a good sign that you’re probably moving too fast — and a fix for this would be to slow it down, and really understand dating as a process of getting to know someone. You’re evaluating each other, “Is this somebody that I can have a nice long-term relationship with?” It is normal and expected that you would be getting to know people sometimes and saying, “Actually, no. Now that I’ve gotten to know you a little bit better, I’m not sure that this does feel like a good fit — not sure how much I like you anymore.” Totally fine. 

It doesn’t mean that person is a jerk, it means that you’ve done a good job and you’re both free to go. Now, there’s also a corollary to this. You could be, again, not dating jerks, but dating people who are not that interested in having a relationship with you. When you are trying to have an attachment and you’re all excited about somebody, and they’re not that into you, you are not their person, you are not what they’re looking for — you’re going to feel that, and it’s going to show up in the way that they’re behaving towards you. 

They won’t be committed to you, they may not be thoughtful about you, they may not be saying nice things, they might not be working that hard to try to make you feel good because this isn’t a relationship that feels like something they want to build with you. In these cases, I think it can be easy to look at these patterns of behavior and think, “Oh, that is a bad person because they’re not treating me kindly”, or “they’re not being respectful”, or “they’re not following through”, when in reality, maybe they’re not like a fundamentally horrible human being, they’re not a monster — they’re communicating that this isn’t a good relationship for you to be in with them. They don’t want to do this with you. 

What is also horrible, but it is true and it is common is that many people don’t like to be alone, and they will happily date a good enough person that can get strung along and can be like a placeholder in their life while they’re waiting for the right person to come along. If you’re with somebody who has a pattern of being checked out, or isn’t working that hard to be with you, there is a possibility that you might be occupying that space in somebody else’s life. It is so crappy and horrible to think about this — it really is. 

I feel like you deserve to know the truth so that you can make informed decisions on your own behalf into not try to make somebody treat you better or feel differently about you, that it’s okay to just be done — and it doesn’t mean anything about you either. I think we can all reflect, scrolling back through our minds about people that we connected with for a little while. For whatever reason, they weren’t bad people. They were fine, They were attractive, they were nice in their own way, but they just weren’t our person. I think we’ve all been in those brief relationships.

Dating People Who Are Not Jerks

I think that can help manage some of the self-esteem, “Oh, if I had done something different or better or whatever, then they would have liked me more.” Let’s just not do that and accept the fact that there are people that you’re not compatible with, and they’re not compatible with you, and that can just be okay. They’re not a jerk, you’re not a jerk, and we can all move on. There’s no need to demonize people in that space. 

Then, the other situation that we do need to talk about — there are two pieces of this. There are situations where you can get into a pattern of dating people who are not jerks. If you are bringing unresolved stuff into a relationship with you — like going back to exhibit A when we were talking about attachment issues. If you have work to do in those areas, and you haven’t, and you are dating people anyway, and you are engaging with them in some of those either avoidant or anxious attachment styles, people will begin to feel an act and be jerky-er than they were when you first met them. 

Because relationships are systems, and I think it’s important for all of us to be aware of how we are engaging with other people and the impact that is having on them. It might not even be due to attachment styles. If you haven’t done work around like emotional intelligence, and maybe communication skills are not something that you’ve taken time to develop in yourself, and maybe if you haven’t had a lot of relationships and haven’t done some work around, “How do I be a good partner for someone else?” 

Even simple things like learning how to be emotionally validating, being intentional about showing love and respect to other people — these are learned skills. If you are showing up in relationships, and you don’t know how to do these things, and other people are having not-so-great experiences with you as a result, they’re going to pull away from you, and they’re going to decide — like what we talked about — that you’re not their person, and they’re going to be less responsive to you, they’re going to be less interested in making you happy, and it’s going to start feeling to you like they’re being mean to you, they’re being a jerk. 

When in reality, they’re having reactions to the things that maybe you’re bringing to the relationship. Again, I am not saying these things to be harsh, or mean, or scary — but I think that there’s a lot of somewhat questionable dating advice around social media and other platforms. What I’m here to do on this podcast is to help you gain insight and awareness into yourself. I think it can be very difficult to identify some of these things. 

It is much easier to demonize others, to blame them for the experiences that we’re having in relationships. It’s difficult emotionally to look into the mirror and be like, “Okay, what am I doing to create these outcomes? What are the patterns that I’m bringing in? And what are the things that may be difficult to look at, but that I really need to look at because I want something better for myself?” 

The path of growth is often one of reality-based, authentic, sometimes darkness. We need to grapple with things that are real and true and sometimes challenging on the path of growth. I just wanted to mention these things because I’ve seen them come up so often in my clients and with other people, and I wouldn’t be doing you any favors if I weren’t honest with you. For what it’s worth, those are some of the reasons why you may feel like you are dating jerks. 

Very lastly, and then we will shift gears, another thing that I have seen in addition to all of the above is, I think of what I’ve shared probably the most easily solvable of problems if you will, which is not that there’s an attraction issue or rejection of good partners, or a way of showing up in relationships that’s not ideal. But rather, that you haven’t yet put the time and effort into getting really clear about who you are, your values — like the things that are most important to you to getting clarity about how you want a relationship to feel, the kind of partnership and life that you’d like to have with another person. 

I’m not talking about like that extremely specific, “Okay, she needs to be 5’8”, and she needs to have sandy blonde hair.” Those kinds of things are not what I’m talking about. But it’s more around, “I really want to be with an emotionally safe person that I can talk to about real things. I want to feel valued by this person, I want to feel fundamentally respected by this person, I want to feel like we’re going on in the same direction in life. By the way, what is that direction that I want to go in? I have to get clear about that before I can figure out if somebody is going in the same direction as me or not.” 

Doing that kind of self-exploration work can build the foundation of clarity. Then, when you do start dating again, you can be looking for people who are much more than just attractive or fun to talk to. It’s more around, “What kind of experience would I have with this person as a long-term partner?” 

Off the bat getting to know people for who they are, and deciding as you’re dating whether or not this feels good for you, this feels compatible, “Am I experiencing greenlights with this person, and I want to keep getting to know them and getting deeper into the pool of a relationship?” Or, “Am I having experiences that don’t feel really good for me, or making me worry that we’re not that compatible?” And, “Am I overriding my own good judgment here because I’m excited about this person because they feel attractive to me. I feel butterflies — they’re sexy.” 

Remembering that they’re very different parts of our mind, and that the part of your mind that feels, the part of your mind that experiences, excitement, and attraction is not the same part of your mind that has the ability to think critically and make good decisions, and that’s really the part of your mind that you need to stay engaged with when you’re dating. Okay, so this was a quick crash course in things to think about when you’re dating. 

If you are interested in more on the subject, there’s a lot more on this on previous podcasts. You can scroll back through, or certainly, hop over to the blog at growingself.com, and check out some of our good dating advice over there. We do also have a little dating coaching program. If you want to dig into some of this work, there are activities and worksheets, and things that you can do to gain insight. But I tell you, there’s not, I think, a substitute for, in some ways, talking to somebody about this because that’s where you really get help in uncovering those blind spots and developing the kind of self-awareness that we all need to make different choices and to get different outcomes. 

This concludes the informational part of our broadcasts. Now, though, I really wanted to do something to make this more — not like real, but I’m a big believer in understanding, gaining wisdom, and understanding the depth of awareness by not just reflecting on our own experiences and taking in information, but really hearing about the stories of others. 

For this reason, I have invited Sarah to join us on the show. Sarah is actually a listener of the podcast, and we began doing a new thing recently where we thought it would be fun instead of just talking abstractly and from a distance about your questions and the topics that were most important to you guys, “Hey, let’s start bringing people on the show and actually having real conversations that I’m sure you’ll be able to relate to.” 

We put a little post out on Instagram who says, “Hey, who has had the experience of dating jerks?” Sarah was kind enough to raise her hand and share that — you’re intimately familiar with those. I thought it would be so fun just to, maybe if it’s okay with you, get some insight into your story, and the things that you learned along the way for the benefit of our community here on the podcast. So, thank you. 

We do not have to go into all the details, of course. But when I’m working with somebody in the capacity of a therapist, or a dating coach, one of the most important places that we will start is with your relationship history because that’s when we can start to see patterns. I think that when we’re living in the moment, it’s hard, sometimes, to know why we do what we’re doing. But I’m curious to know you’ve shared that you over time noticed a pattern of dating jerks. Would you give us the short version of your dating history to the degree that you’re comfortable? And when did you begin to notice that this was a pattern for you? 

Sarah: I have only really ever been in two long-term relationships that were actually established relationships where it wasn’t just talking or getting to know one another — those stages that are very popularized now. One of which I’m in right now, the other one was with a previous partner. We’ve been almost broken up for an entire year now, and my boyfriend and I currently have been together for — it’ll be six months in four days.

Lisa: Congratulations.

Sarah: Yes — and he is wonderful. He’s definitely not a jerk. Definitely not any of the things that I’ve experienced with previous parties. But out of everyone who wasn’t in either of these two relationships with me who I did, myself, being attracted to and attracting, the qualities that I noticed, it was initially — I was expecting a spark. Dating coaches will say certain things like that — and it depends on the dating coach and their expertise, of course. 

But the way that so many things are mainstream nowadays, it felt like I was supposed to be, “Okay, I know I have a chance with someone like this. Or maybe I feel like, “I feel a connection there. I feel like there could be something that can grow and transpire from this.” When really, I was giving my I was getting my own hopes up and give myself a way to easily, allowing myself to become vulnerably and emotionally attached and tethered to this person. 

Any of these people, very quickly — with how much time we would spend together, what we would talk about, how I felt like they might have been different quote-unquote, “from the last person”, and it’s kind of like whenever I noticed a pattern. That’s what I found myself doing most often.

Unrealistic Expectations of Dating

Lisa: That is so relatable. I see that so often in my clients. I’m hearing that they’re these two pieces of it. First of all, it’s one that is so common — it’s looking for this feeling and expecting to feel a certain way that ultimately wound up not being a reliable indicator that this was actually a good person in our relationship. But can we unpack this for a second? Because I think especially with women — sometimes with men, but like I see people do this so often. What was that feeling that you thought you should have? 

Sarah: I, now, can recognize it as an unsteady and unstable — dare I say like insecurity-ridden feeling, “Wow, this person will complete me. I’m only half of a person. I’m looking for someone to make me whole”, have nearly unrealistic expectations of how the relationship will pan out whenever you don’t even know them for that long, whenever you are unsure of one another’s moral compass — or if you guys want the same things, are they thinking of you the same way that you’re thinking of them. 

But that spark, that feeling is just butterflies — it’s the nervousness, newness of it all, the magic of meeting someone new. It can’t rely on a single spark. I know that I’m listing a bunch of different things aside from dating. 

Lisa: Oh no, it’s wonderful. I appreciate you unpacking all this perspective. I’m hearing that there’s that spark, that kind of chemistry feeling. Then, I think I’m hearing that it bloomed into a lot of fantasy. You talked about having a hope that you found the person that could “complete you” potentially. 

Can you say a little bit more about that? I know that you have a different perspective now because you’ve worked on yourself, obviously. But what can you take us back to that time of what would be some of the things that you would be imagining or telling yourself about one of these people who wound up not being a good partner for you? 

Sarah: One person I can think of in particular would be my ex. He immediately swept me off my feet. At first, I felt, “Wow, he has a good head on his shoulders. He seems like he knows what he wants in life.” He seems very sure of himself — and it wasn’t so much a confidence thing. It was more like, “Wow, he seems like sure about me”, at the very beginning. It made me feel wanted, and I deserve someone who’s very loving, and caring, and compassionate about me. 

But the way that someone appears to you at first is all you know of them. It doesn’t give you much time to really make a good educated guess on how the rest of the relationship will transpire. It is easy to fantasize. But a lot of times, I found that I was let down by the discussions that we’d have and where I thought, “He was everything I wasn’t”, or “He was super similar to me in certain ways.”

I thought that, “Oh, well — maybe he could very well complete me. Maybe, he could be that one piece of my jigsaw puzzle that has been missing and arrived for so long.” Struggling to figure out how to fit him in was where a lot of conflict arose. 

Lisa: No, I get that. Then, to understand, there’s so many people who are creative, and intelligent, and conscientious is that you used the word “fantasy”, but imagine these things, imagine qualities that you had and qualities that he had, especially in the early stages of the relationship where he was making you feel really good. He came on strong, he said all the things, you’re like, “Wow, I am loved! This is it! I’m having this experience.” 

But then, you’re saying that there were ideas about what should be happening, expectations that you wanted him to fit into, and then that is when it started feeling hard sometimes. Is that it? What would be an example of that? 

Sarah: An example would be, I think, whenever he was so chivalrous and charismatic at the very beginning, but then maybe there’ll be an instance where I found that, “Oh, he didn’t do that thing that he did once before. Why isn’t that happening anymore? Why am I not getting a good morning text? Was that just at the beginning? Should I keep on expecting that?” I dug myself into a deeper hole because I was not as communicative as I am proud to say that I am now. 

I was not as upfront in saying — just sitting down, having a one-on-one with him, and having a very intimate, serious discussion on, “Hey, I feel like these are some of my needs.” But then, there’ll be instances where that didn’t happen anymore, where it didn’t happen all over again. To make matters worse, there would also be some fights that came out of those things where we would have disagreements. It didn’t start off at the biggest problems, possibly. 

It would also be various things such as we had a huge difference of opinion on certain civil rights movements, or I was very proactive, and I want everyone to be with who they love and for all the reasons that they can provide. As long as you’re not hurting yourself or anyone or anything else around you, I think you’re living your life. That’s like my philosophy. He didn’t like that. 

He didn’t like that I didn’t have enough structure in my life. He didn’t like that I would try and be communicative, but then it felt like attacking and accusatory to him — even if I would try and phrase it as civilized, and as diplomatically, and as heartfelt as possible. Truthfully, sometimes it wouldn’t be enough to avoid the bigger confrontations and to try and see past the differences. I was a little bit more optimistic about our relationship. Honestly, I can admit now that I saw a lot of red flags, and I completely bypassed them. It was like — I saw a red light, ran it every time. 

Lisa: Get swept away by those big feelings in the beginning. What I think I’m hearing in your story is that there was that first kind of relational piece that just felt so good like, “This is the way it should be.” Then, I think I’m hearing that he has stopped saying or doing some of the things that had felt nice to you in the beginning, and you were trying to get him to do that again. Then, that was leading to tension. Maybe, that went the other way, as well. 

But I’m also hearing that as you two got to know each other better over time, that there were some fundamental differences and four defining values that started bumping up against each other. We never know what those are really until we get into the pool with somebody and have opportunity. That takes months, sometimes years, to really understand what those pieces are. Is that what I’m hearing? 

Sarah: 110% accurate. You’re right. If you were to go on a date and be like, “Okay, so what’s your stance on religion?”

Lisa: Holding a clipboard. Right. 

Sarah: I can be like, “Are you really a potential suitor?” I guess that’s one way to do it. You’d be a very forward person and much more ballsy than I am.

Lisa: It’s sort of like an assessment before the first date, “Here are 200 questions — true or false?”

Sarah: “We’ll get to you in a month.” Exactly. But it’s not always like that. Maybe what he really meant to say was this, maybe what he really meant to do was this over here, maybe he’s trying to show me that he loves me even though we had that disagreement that made me feel unheard and unseen — maybe there is hope for us. I would just keep on holding to that little bit of hope that I kept on trying to… 

Lisa: That’s also really common. As we’ve talked about on this podcast in the past — early-stage romantic love has a very intoxicating quality. It actually changes the way that people think, and part of what it does to our brains is idealize that other person. I think I’m hearing that there was that disconnect — that you were seeing things and observing things, and things like, “I don’t really like that.” 

But there was this other part of your brain that was in that space of hoping. But it sounded over time, you didn’t really like the person that you were getting to know. You wanted him to be different than what he was. Is that the right way of saying it? 

Sarah: Very true — it totally became that. I had fallen in love with a version of him that he was only going to be for so long — why not look past some of these things? 

Dating A Jerk Advice: Red Flags

Lisa: But the feelings are so powerful in the beginning. I think that we’re also trained by the culture to follow our feelings, and it’s like hard insight and life experience. That is not always really helpful. We need to not follow some feelings — but it’s so hard to do, especially when they feel so powerful, like in that early stage relationship. 

But a moment ago, you mentioned that, as things went on, you were noticing, what you described as “red flags”, and you were like, “Oh, maybe it will be better.” But what were the red flags? 

Sarah: Red flags, they came in waves sometimes. Sometimes, it would be like we had a great day, and there was no fighting, there were virtually no disagreements whatsoever. Then, there’ll be other days where we had a ton of disagreements, red flags. He began to start to say some things that were borderline very questionable to my moral compass and the way that I view individuals on a worldwide global scale, saying things like, “Women don’t have an opinion on that.” 

Yes, I was flummoxed whenever he would say some of these things. I figured I really hope that we can come together and bridge the gaps because of our differences — not have to break up in spite of them. But certain things kept on rolling around. But anytime that we couldn’t talk it out, it would turn into him screaming at me, yelling at me that my opinions were inadequate, that I didn’t have the right to think certain ways. I wish I was making this up. I wish… 

Lisa: Wow. No, I don’t want to make you relive all of that on a public forum here. It got really nasty and really abusive. 

Sarah: These are the most tumultuous relationship of my life. 

Lisa: Definitely. Then, I think you’re also describing something, though, that is so common, which is the old idea of the frog in the pot of boiling water. Have you heard that? If you turn it up slowly, the frog doesn’t know when it’s hot enough to jump out? Like doing that with yourself, “Okay, I don’t like this — but can we work through this? Is it something that can be repaired?” And legitimately not knowing in some ways, which I think is really valid. 

Especially for a younger person, it can be hard to see this stuff come in — even in an abusive relationship. It’s not like somebody just punches you in the face on the second date. Any of us can be like, “I think…” at that point. But that’s not what happens. The heat goes up slowly, and then you’re emotionally entwined with somebody who is officially being really damaging and toxic. At what point were you finally, “I’m not doing this with you anymore, buddy.” 

Sarah: Even while I was still in the relationship, I wasn’t looking for better. I was trying to really stick with it no matter what. But to really put myself through so much turmoil, and emotional abuse and neglect, and everything else possible that could have gone wrong in the relationship, I kept on thinking to myself, “Maybe it’s best if we end this, and I hope you find who or what you’re looking for because I could never make you happy, I could never be enough for you in this.” 

Because even if I didn’t subconsciously or even verbalize it to myself, I wasn’t enough for myself in that moment because I didn’t choose myself right from the beginning. I didn’t verbalize the way what he was saying was making me feel. He didn’t take any of it into consideration to begin with. There was going to be no resolve ever that we were going to reach. Some people like that simply, as sad as it is, you cannot reach. 

Lisa: Oh, I absolutely hear you. I’m so glad that you arrived in that space, as painful as it must have been, to get out there, Sarah. But it just says so much about you, and just what a fundamentally healthy person you are. No, really! You’d be like, “Ah, this does not feel good”, “I had hoped it would be one way, but this is not good for me”, recognizing, “That isn’t good for me”, and also I think recognizing — this is the hard part for a lot of people, but there’s like a self-betrayal component in a lot of these. 

There was a lot of learning that happened through this experience, and not that anybody would have signed up for — but valuable, nonetheless, to be on the other side. Then, I’m curious to know, because you had mentioned that this was a significant relationship. But then there were other people that you sort of started to do this with is what I got the impression of, that same sort of pattern of that attraction and fantasizing, and then feeling really disappointed by people. 

Were there others after this relationship, or going through that one relationship where you’re like, “I don’t learn enough about what not to do again, but I’m done with you people.” 

Sarah: A really good question between my ex and my current significant other, there was nobody. I really took a lot of time to reflect on — I was wondering and questioning my worth for weeks, if not months on end, and it took a decent amount of soul searching for me to be able to say, “Even if there is no one out there for me, that is not the end-all-be-all of Sarah. That is not my composition.” 

Lisa: Totally. Really spent some time stopping, and really spending some time connecting with yourself, “Who am I? What are my values? What do I care about? What do I want in my life? How can I serve the world?”, and these anchors to bigger things. I’m so glad that you did that. I see, so often, people are just jumping right back into a very similar feeling situation. I just think that says so much about you that you really slowed down, and just got really clear and okay with like yourself — like rebuilding yourself. Is that the sense I hear? 

Sarah: Kind of what you were saying, this is another pattern that I noticed throughout my dating and up until the ex. I was not only attracting, but attracted to, and giving all my time, attention, effort, energy, even too emotionally unstable, if not entirely unavailable individuals. These were people who had — in more than one way and maybe not entirely verbally at that, they had said, “Hey, I’m not looking for anything long-term.” 

But maybe it was with their body language, with their actions — because actions really speak louder than words. Just the way that no one really ever cared about what I was needing and what was best for, not just themselves, but for myself as well in and out of the relationship until I was to be single, and to really reflect on everything that had happened, and how much turmoil I’d experienced and to reflect.

Attracting the Wrong People

Lisa: There was a recognition of this pattern over time that you had been attracted to, as you say, most emotionally unavailable or unstable people. Can I ask you the zillion-dollar question here? I’m hearing that once you became aware of that, “I can’t do that anymore”, that things change for you. But the zillion dollar question that I think so many people struggle with to define and articulate for themselves — can you say, “What if it was about those people in the beginning that was actually so attractive?” 

Sarah: This is going to be a bajillion, bazillion dollar answer for you because as we’re talking more about this, the more I’m able to be more specific. At first, I thought that they were very mysterious — and mysterious can always come off as attractive. But mysterious, in a dark, “I probably need help”, and I thought that I could help them kind of way. But first off, they did not act like men. They acted like children, and they most often had troubles and experienced something early on in their childhood with their parents, specifically their mother. 

I wanted to swoop in, and make them my build-a-boy project — that’s how I coined it. It’s very — oh my gosh, this is not build-a-bear, but this is like the revamping and the refurbishing of someone who has been broken before, or rather bent. In order to get them back into shape, I figured maybe I could help them with that. I didn’t think about the fact that, “I’m not a therapist.” 

Lisa: No, I totally get it. But how much insight? Because I think there’s like an archetype for that — the wounded bad boy who’s saying, “I’m not really emotionally available, I don’t want to be in a relationship.” This can happen with men, too. I’ve seen this happen all the time with men who have wonderful values around helping and service, and who really are fundamentally nurturing people. 

It’s almost like that becomes a way to express those values, and get to be this person that you want to be — like the helper, the empathetic, the compassionate person, like, “I can help you grow and heal in that space. That was that attractor factor, it sounds like. 

It’s very intoxicating, isn’t it? There’s power, there’s value — and I think all of us have been vulnerable to that. We can almost get trapped sometimes by our most noble virtues and gifts when they’re in directions that are ultimately not good for us. Does that sound familiar? 

Sarah: I couldn’t have phrased it any better. That sounds 100% accurate to me. 

Lisa: And everybody because there are a lot of people listening to this right now. I don’t want to suggest that everybody’s hook would be the same as the one that you’ve described. But I think the point is that you are able to do this marvelous reflection around, “What was it that was leading me to be attracted to that kind of person, and gain that insight and self-awareness?” 

Because when things are happening subconsciously and automatically, we don’t get a chance to do, “Oh yeah, there’s that thing again, I’m going to do a manual override because I know that is going to not take me in a good direction.” But you were able to do that, and I would like to encourage anybody listening to this — that’s how we break out of these patterns, is not being angry with yourself that, “Yes, I date these kinds of guys, and I need to stop doing that”, but really, with compassion, visiting with that question, “Yes, but why does this make sense?” And you did that. 

Sarah: I feel like a lot of this pattern that had developed for me in my romantic relationships, more specifically, had been something that was not always in place, but was the majority of my time as a young woman actually dating — not just stating my kindergarten crush or anything. 

To actually see people who had lived and experienced things, and to try and make sense of why they felt like they could treat me the way that they could, I felt like I’m such a giver. I so rarely in life feel like I want to actually take from people. I say that to totally not sound like self-centered, but I really do think that’s like… 

Lisa: Aware of your worth. 

Sarah: But it took a lot of learning for me to be able to say and realize, “Maybe I need to really look deeper and wonder, ‘Why am I going after these specific kinds of guys? What is it about them that makes them mysterious, toxic — I’m willing to overlook all of your red flags and your stop lights just to be with you? What is it about that makes me attracted and that I’m attracting them?’” 

Lisa: It’s marvelous. I think, again, such a common element of these situations is that I think we can look to the other person as like this seductive force. But I think that there’s less awareness that we are seducing ourselves in some ways by our own internal narratives and becoming intoxicated. Exactly. This is good stuff. 

I know our time together is limited, so I also want to pivot because you had all of these marvelous awarenesses. I’m sure that we could unpack so many other things with additional time together — I know there’s more to the story. But over time and after having a particularly bad experience, you’re like, “I do not want to do that again.” You spent some reflective time. It sounds like you became more deeply connected with yourself, and I’m guessing kind of your internal values. 

This is a question — did you find yourself being more intentional when you felt like maybe you were ready to try again? If so, how was that experience different in — not so much in terms of the person that you dated, but in terms of your process, like who you were attracted to? How you connected with them? What parts of your feelings were you listening to? And what parts of your feelings were like, “That’s actually not as important as I used to think it was?” How would you describe that? 

Sarah: I want to say, first and foremost, I love this question. It’s one that I don’t really think about — I think about, but I don’t think about it. I don’t think about how I’m going to answer it, but I’m very grateful for the way I’m dating after the really nasty breakup I experienced. I wanted to really take some time, after reflecting, to make a list of all the qualities in someone who I really do want to have. I want to share my time with someone who builds me up. 

I want to share my time, and my love, and my energy, my body even — everything — with someone who is willing to try to get to understand me. Not have just a one-line response to what I have to say, but to really try and understand where I’m coming from and to build a connection with me that goes beyond the physical appearance. That will fade one day — I will not look the same that I look right now. 

In 10 years, even much less 50, I feel like I’m so thankful for having the time to really reflect and be more intentional about dating. That way, I wasn’t just going to put myself right back out there and not know what I wanted. I wanted to make a list — not based on the physical appearance, but to make a list of the qualities that I want to work on finding in someone else, see for myself, not have to dig it out of them, and then really try and work on those same things on myself. Why would you ask of certain qualities and someone else, and not have them yourself? 

Lisa: Absolutely. “I want somebody who’s compassionate, and trustworthy, and fun”, but then you turn it into, “So how do I be compassionate, and trustworthy, and fun”, of whatever those things were. 

Sarah: Yes. There were all these — I was building a better version of myself, not for someone else to love, but for me. That way, I knew the most important relationship in my life is always going to be with myself. 

How to Date a Nice Guy After Dating Jerks

Lisa: Ironically, having a better relationship with yourself is also the pathway to being a better partner — they’re the same thing. I just wanted to mention that because I think when we hear people say, “Oh, focusing on me, my needs”,  I think that it’s easy to interpret that as being self-centered — and that is not how I took what you said, by the way. But it’s a very generous act because that is how you become a better partner, and that’s what you were doing. 

Sarah: Precisely. 

Lisa: How would you describe the difference in your process when you finally met the person that you’re dating now that you described it as being a really positive relationship? I’m curious to know — if it’s okay to say — did you feel the same kind of attractions with other people, or was it different for you? Were you looking for different things? How long did it take to get to that pool? 

Sarah: I love this question so much. I’m so thankful for him. I wanted to experiment with myself, if you will, and I put myself out there. But I would only ever swipe right on people who I thought had a nicer, kinder demeanor about them. Even if I felt like, “Oh, man, maybe we were two different people, but I want to not just jump to the assumption or the conclusion of that. But I want to actually make good conversation with them, and see how they interact with me in just trying to get to know me.” 

Lisa: You were prioritizing kindness — your perceptions of kindness over other things. 

Sarah: Another big one is — I swiped right on my boyfriend specifically because I just thought that something about him was different. Then, when we started talking, he was very kind, very positive, optimistic, career-driven, and he was very slick too. A day or two into talking, he was like, “Wow, this is so great. I love your career interest. We can talk about it more on Friday or something.” I was like, “Ooh, slick.” 

Lisa: Just out of curiosity — do you think that you would have been attracted to him prior to having done all this work on yourself?

Sarah: No, because I wouldn’t have been attracted to who I am today. I wouldn’t have loved her first. I wouldn’t have gone through all the mess, all the heartbreak, the turmoil — everything. I needed the turbulence to be able to show me and appreciate what was good when I had it good. 

Lisa: What would you say was different about the way that early stages of your relationship unfolded compared to the experience you had in a relationship that wound up not being a good thing for you? 

Sarah: Wonderful question. I told him right from the start, “I do not feel comfortable with us making open-ended promises. It really makes me get my hopes up. If we don’t follow through, if no actions are done to set those parameters in place, I don’t feel comfortable following through on actions if I know that the other person isn’t. Blanket statement — please don’t make me any promises, and I won’t make you any promises. 

Lisa: That we’re just getting to know each other. Any promises made are incredibly premature — “I don’t know you yet.” 

Sarah: Exactly, “I can’t rely on you, I cannot trust you because I can’t trust myself in this just yet.” But we both talked about was that in our previous relationships, we did not verbalize. We both had breakups right around the same time — so ended up working out. But through everything we had gone through in our previous relationships, we came to the conclusion that, “Oh, a pattern that we’re noticing with one another is much more healthy than these previous relationships.” 

We want to keep up the good behavior and continue to have open discussions — just laying it all there out on the table. It’s not to say that we say ugly things to one another. That is not the way that we discuss things, but to allow for the conversation. For all cards on the table, it’s always up for discussion. If you set a boundary in place, and you’re thinking about maybe changing that boundary or revisiting it to say, “Hey, here’s what I’m now feeling comfortable with.” 

Anything that we can discuss, it’s not like we have to approach it with fear or an insecurity of, “Oh my God, my partner might leave me. What if I say this, and the whole world comes crashing, comes tumbling down?” 

Lisa: That’s so wise — let this sort of mutual commitment to being honest and authentic, and really talking about how you feel because that is, I think, always one of the most important things any of us could do to avoid getting into a relationship with a jerk. Because as soon as you do that with a jerk, you’ll know quickly that this person isn’t going to be a good partner for you. 

If you’re authentic and talk about how you feel, and it is met with hostility or defensiveness, or minimization and reset, you can be done. That’s what dating is for. I think that idea — let’s fail as quickly as possible by being authentic, and you guys did that from the beginning. You took those chances. You’re like, “How does he act when I say this about how I actually feel?” And it was a positive experience, which is a green light — we keep going. 

Sarah: I love the way that you phrase that beginning because we do have the most genuine, honest, and respectful relationship I’ve ever been in — will probably ever be in because of the way that we talk to one another, and the way that I feel so revered, and he will clarify with what I’ve said. Very similar to you actually, “I’m understanding what I’m hearing — the whole nine yards, right here. I’m like, “Yes…” 

Lisa: Emotional intelligence, communication skills. But you gave yourself the time to get to know that those things were true about him. I think what is very easy to do, and what I hope some of our listeners take away, is that we can have that flash — like exciting feeling, and skip over that whole getting to know who you actually are part, and develop a very serious attachment to somebody. 

Oftentimes, there’s like a sexual component, which not in a morality-based way, but because we have a physiological attachment to people with whom we’re sexually intimate and can get emotionally welded to people, and then start to find out that, “Oh, I can’t communicate with this person in a healthy way. We don’t have values that are in alignment”, “This person is not a good friend to me. I don’t actually like this person, but there’s this emotional thing that’s already happened that’s very difficult to get out of.” 

I think what I’m hearing you say is that it was a more gradual process, more akin to building a friendship where you are getting to know who he was as your emotional connection was beginning to build. Is that how you would describe it? 

Sarah: I would. There was a moment where I wasn’t too sure because he had asked me to be his girlfriend, and I was still newly out of my last relationship, and still trying to figure some things out even though I did really like him. I love his personality, and I liked his friends. He just asked me and I was like, “I don’t really know. Maybe we should just take a little bit slower than that.” But I remember specifically… 

Lisa: But how did he react to that? 

Sarah: He was like, “Okay, I don’t see how things could go wrong.” But I said myself, “I don’t want to mess this up. I really do want to take our time because there’s no due date on this. There’s no expiration date either. There’s nothing telling us that we cannot take as much time as we can. I feel like we should just get to know each other better.”

I got to know a decent amount of him, and the way that he follows through on his actions with the way that he would treat me in the first month or so like us even knowing each other — very appreciative of that. Before we even established what we even were, he wanted to hear about what my day was like, and wanted to try and see what the future could look like together. 

I love that we’ve taken the time to do some of the dirty work. I feel so much better with him. He doesn’t complete me, but he’s definitely something that complements my life, and I love that about him. 

Lisa: Well, that’s wonderful. Sarah. I’m so happy for you. Thank you so much for coming and just sharing your story with our community here today. I think it’s one thing to have somebody like me — they like, “Okay, here are things to think about, and tips”, or whatever. But I think there’s something so relatable in your story. I think so many people that have struggled with this just — I could imagine them nodding their heads and being like, “Yes!” 

But I think it can be difficult to identify things in ourselves because we have blind spots. It’s hard to see ourselves. But I think when we do hear other stories and insights of others, and we can resonate with them, it’s such a powerful experience because then you can say, “Yeah, me too”, and start connecting some of those dots. 

That is 90% of the work — is just bringing this stuff into awareness. I think that you helped a lot of people do that today. I heard you mentioned earlier that some of your core values were around kindness, and generosity, and helping others. I just want you to know that I think you probably helped a lot of people today. 
Sarah: Thank you.