Latest / Divorce Coaches Academy / When Dating After Divorce Isn’t a Fresh Start, It May be a New Conflict Environment
Transcript
- Tracy Callahan: Thank you for listening to the Divorce Coaches Academy podcast. For more insights and training, visit divorcecoachesacademy.com. Welcome back to the Divorce Coaches Academy podcast. So at DCA, we talk about the idea that divorce is not just a legal process. It's a conflict process. And more importantly, it's a process that does not end when the paperwork is signed. Because what we consistently see in this work is that clients do not leave conflict behind. They carry patterns, their assumptions, and their ways of engaging forward into Welcome to Divorce Coaches Academy podcast, where we explore the role of divorce coaching in conflict resolution, decision making, and navigating divorce with clarity and intention. whatever comes next. And one of the most overlooked places this shows up is in dating. There's a common narrative that dating after divorce is a fresh start, a clean slate, a new chapter. But what if it's not? What if it's actually a new environment where some of the same internal conflicts, the same decision-making patterns, and the same relational dynamics begin to surface again? just with a different person. And if that's true, then the role of the divorce coach doesn't end once an agreement is reached. It extends into how clients prepare to reengage in relationships altogether. So today, we're exploring that intersection. And I am so honored to be joined by a dear colleague, Wendy Kesser. Wendy is the founder of, I love this, Get With Wendy. is certified divorce coach and professional matchmaker working with clients all the way from Los Angeles to Long Island. Wendy brings a unique lens to this conversation having extended her work beyond divorce coaching into partner selection while remaining deeply grounded in supporting clients through transition. In addition to her coaching and matchmaking work, Wendy teaches faith, based coaching practices through the Specialty Coach Training Institute. She previously served as COO of the non-for-profit Divorce and Discovery, where she co-led healing retreats and educational workshops for clergy supporting individuals through divorce. She's also a graduate of Brown University and, and, because she's not doing enough, will soon be continuing her academic work at UC Law San Francisco. And Wendy, we're gonna have a whole separate conversation on that, okay. Wendy's work sits at a really interesting intersection where we can begin to see how the internal work of divorce either translates into different decision-making or quietly repeats itself. And that's exactly what we're going to unpack today. So welcome, Wendy. Wendy Kesser: Thank you, Tracy. That was such a generous introduction. I am a fan of yours, a frequent listener of this podcast. I never leave it without learning something new. And I thank you for this invitation. Tracy Callahan: Well, I am so glad to finally get you on here. So you're a certified divorce coach, a professional matchmaker, and yet you refer to yourself as a rematchmaker. So I'd love to start there. What is rematchmaking, right? And how did that evolve from the divorce coaching space for you? Wendy Kesser: Haha! I gave myself that name. I trademarked it as could. I only work with divorced and widowed men and women. I have a particular fondness for this demographic. It's a very special niche for me. And my matchmaking work began when, from my earliest days, those first clients years ago came back to me for dating coaching. And the referrals I made to existing matchmakers didn't pan out. So I trained to become one myself. And I have to thank Rachel Greenwald who continues to be a mentor. She is ⁓ the OG matchmaker. But my niche is specifically for what I say, if it's not your first rodeo, I can't help you with first love, but if it's your second, I'm your man. Tracy Callahan: ⁓ Awesome. I love that. I think more people should be doing it, right? So we often say that people don't just leave a marriage, right? They carry forward how sometimes they functioned inside that. And that's a lot of the work that we do in sort of that awareness space. So do you see dating after divorce as a new chapter, as a continuation of how someone participates in relational conflict? What does that look like as they're sort of moving forward? Wendy Kesser: It's actually both. It's a new chapter in that dating after divorce or after ⁓ the death of a spouse is the most inherently hopeful thing that you can do. am irrepressibly optimistic about this. think in those situations, dating and companionship can be life-giving. And so I think it's a new chapter in that way. How many times in life do we actually get a second bite at the apple. It's not, ⁓ plate and I, and we'll talk about that distinction I'm sure later, but ⁓ it's a, it's a second go at it. It's also a continuation. And this is why I love, love my tribe because I'm only working with divorced and widowed folks. There's a data set there. There is a history, a ⁓ history of relational dynamics. Tracy Callahan: Mm-hmm. Wendy Kesser: that when I learn about, that informs the prospects I'm looking for for my clients. And I can identify what are behaviors that we would want them to repeat and what are behaviors we would want them to renounce. And so that makes my job in many ways very much more easy. Tracy Callahan: I love that, right? And I agree with you. How many times in life do you get this sort of opportunity? And I think as human beings, we so innately like to be with others, right? And I also believe that in all human relationships that we have this need to be in relationships with other people. Wendy Kesser: Hmm. Tracy Callahan: We also know that all human relationships present in, engage in levels of conflict. So I think that there is this great connection there, if you will, this intersection when we talk about this, right? This ability to be able to create this next space to do something and to be able to look at how I wanna do it differently or what was it about that past relationship that then I want to maybe change for myself. not for somebody else. And, you know, I think this goes a lot to sort of identity and identity disruption after divorce, right, which does affect someone's ability to sort of make intentional decisions. I hear it as a divorce coach all the time. Right. And so how how do we help clients move from sort of that lack of clarity of maybe not being unsure or or Am I ready to moving towards a grounded decision-making process and doing this with intention? Wendy Kesser: When you've had a spouse for 10, 15, 20 years, you don't just lose the marriage. You lose a role. You lose a position. So I see those who are suffering from role loss, they're dating for replacement, not for alignment. They are wanting to put it all back together again. And as I say, they'll summon all the king's horses and all the king's men. but it ⁓ doesn't work that way. ⁓ And so that identity, when it's relational in a very specific way, of course, needs to be redefined. And what I do for my new divorce coaching clients is the same thing I do for my matchmaking ones, and that is a values audit. When I'm a divorce coach, I'm asking, what's enough? And when I'm... When I'm using that exercise with my matchmaking clients, my question is, what matters? And when you call just this huge list of values with words that have just shades of difference, then you really get to a well-defined ⁓ set of principles that we use as a touchstone throughout both processes. We go back to them whenever my divorce clients get triggered or whenever my ⁓ matchmaking clients are disappointed or frustrated, these are defining for them and it's how they like to show up in the world and feel best about themselves. Tracy Callahan: Yeah, I think that's so significant, Because it's not something, right? As people don't know how to get divorced, right? And we learn, right? And I always say this, unless you've been divorced before, how are you supposed to know how to divorce now? I think a lot of it is dating, you know, this whole fear of, I haven't done this in so long. how and why am I doing this? And I think that values are grounding in that values is so significant to help people again, make these intentional decisions, not just something that is either expected or they're supposed to fall into or that was just the assumption, right? Wendy Kesser: And also I do want to leave space. I say as a matchmaker, I have clients with different horizon lines. Companionship is as much a worthy goal as emotional intimacy. And when someone's right out of a marriage, there is an exuberance around physical intimacy because often that dried up a long time ago. just, it didn't end just when the marriage did. It has, there's been a drought for a while. And so there is a, Tracy Callahan: Mm. Wendy Kesser: a period of time when I think folks should be scratching things off there between the sheets of bucket list. And I think ⁓ that's just human. So it's not that I think there is an order to things that right out of one marriage, you're gonna start looking for the next serious one. There's also ⁓ some other, I'd say, ⁓ boxes to check perhaps. Tracy Callahan: Yeah, I like to say it's kind of like an exploration rate and I'm going to go even further than just say the emotional intimacy rate for a lot of people coming off marriages and divorce. There's been also a lack of physical intimacy and that connection. Wendy Kesser: Right, right. Tracy Callahan: Yeah. Wendy Kesser: I send all of my clients back to their physicians to have the talk as if they were 12 again, because ⁓ it has been a long time since a lot of my clients have been out there and it's a brave new world. So ⁓ they do go in educated and with safe behaviors. Tracy Callahan: Hmm. Yeah, all right. So I want to bring a little research in here, right? So we know from our work, I am a huge fan of our world famous marital researchers, John and Julie Gottman, right? That relationship outcomes are often driven more by interaction patterns than by partner traits. So as a matchmaker, right, from your perspective, And when we're looking at sort of these unresolved internal conflict patterns and how they show up in decisions people make when choosing a partner or entering a new relationship, where do you see that? Right? You know, it takes two to tango in any conflict dynamic, right? And I think often people are kind of like, well, I just need somebody who's the complete opposite of blah, blah, blah. Wendy Kesser: Yeah. So, Tracy Callahan: Yet, yet we know it's not necessarily the traits, it's the roles that the parties play in those, in those conflict dynamics. Wendy Kesser: 100%. I call that an overt correction, but I think it's ⁓ no more an unsuccessful strategy as ⁓ when clients come to me and more than one has, they say, ⁓ well, I definitely know what I don't want. And when I hear that, I think, ⁓ the past is still doing the choosing. when everything is relative to the former spouse, the marriage, Tracy Callahan: Mm. Wendy Kesser: then there's a capacity for new relationships that's not quite there yet. And so ⁓ I feel like my work as a divorce coach gets pressure tested by my matchmaking because anything, any internal conflict that isn't resolved will show up. I mean, you can sort the people who processed what happened from the people who just moved on from it. Tracy Callahan: Hmm. Wendy Kesser: The more successful strategy will always be to do that work first, because as you said, it is relational. It's not a trait, it's a dynamic. And so to get yourself solid, ready for ⁓ the next engagement will be crucial to having successful relationships. Tracy Callahan: Yeah. Yeah. Is that what people do? I mean, I'm just so curious, right? And in your matchmaking work, do people come in and say, you know, I'm looking specifically for this in a part? I'm just curious. never done it. I mean, I'm not asking you to, you know, disclose the matchmakers behind the door secrets, but how do people usually come in in that? Wendy Kesser: Okay, so I... you So how much time have we got? I could regale you for hours. I'm always the most interesting person at a cocktail party. ⁓ They come in with a shopping list, of course. They went tall, high achieving, well educated, check, check, check, check, check. ⁓ There's an expression that realtors use and ⁓ car salesmen use. It's called liars are buyers. They'll tell you one thing. You go and source. Tracy Callahan: I bet. Hmm? Wendy Kesser: the exact house, that exact car, or, you know, a profile with all those qualities. And then they'll be like, no, but what I meant was, so ⁓ I usually hear ⁓ that list of qualities that new clients come to me with the way Charlie Brown hears his teacher, like just, you know, mouth move, no words, because really chemistry is the X factor and Tracy Callahan: Yeah. Nah. Wendy Kesser: A lot of my clients are with folks they never thought they would be. Tracy Callahan: Hmm. Mmm, I love that right? It's you don't really know what you want. Do you I don't know? Wendy Kesser: ever. I mean, I have seen it over and over again. It's actually what's most exciting. ⁓ And to surprise yourself in that way can be thrilling. Tracy Callahan: Yeah, yeah. So we've spoken about sort of this readiness and capacity. You've mentioned it a couple of times, right? And I know you talk about shifting from this ideal of am I ready or this question of am I ready to ready for what, right? So what does ready actually look like in terms of someone's ability to engage in dating, not just their Wendy Kesser: ⁓ Right. Tracy Callahan: quote unquote desire to. Wendy Kesser: Readiness isn't a feeling, it's a capacity, as I said. Can you tolerate uncertainty? Are you emotionally available? Can you communicate with honesty? Can you show up with confidence and clarity? I think that these are the tells of someone who is ready or not. And when I said, are you ready? And then I think what ready for what? It may be that they are just ready for a short term, a three monther, as I like to say. ⁓ good on them because there's just all kinds of variety of needs. And as I said, you don't need to dive right back in immediately because there is some training ground to cover. ⁓ Although I think that the hazard, and I've seen this over and over again and it makes me sad the kind of disappointment ⁓ Tracy Callahan: you Wendy Kesser: and how unexpected this is for folks. The relationship that you have just out of your marriage, when that ends can be more biting than the divorce itself. Because you've really put everything into it. You really did think, I've put it back together. I have a newer model, a better version. And that sometimes, that second relationship, the first relationship after the marriage sometimes carries all of the disappointment. Tracy Callahan: Good. Wendy Kesser: of the marriage. Tracy Callahan: Yeah, yeah, interesting. Kind of like a, ⁓ and then does it shred along the way? Wendy Kesser: Mm. No, so then you develop little scar tissue, which I think is really helpful. That's another capacity for readiness. can you, do you have a thick enough skin? Because there are treasures out there, but you really have to know how to approach it. I always say the problem is not the pool. The problem is the filter. How are we sorting our prospects? Tracy Callahan: love that. The problem's not the pool. I used that one day and just so you know. All right, so let's talk a little bit about sort of pattern recognitions, right? Statistically, unfortunately, we know that second and third marriages fail at higher rates. They just don't. But the research suggests it's not simply just about choosing the wrong partner again, right? It's how people carry themselves forward. Wendy Kesser: All you. Tracy Callahan: and these same patterns, decision-making. You just talked about values and engagement. So as we're kind of talking to divorce coaches and they may be sitting there going, what is my role here? How do we play? I talked a little bit about in the introduction, the work that we do in helping bringing awareness to some of these conflict dynamics. For many people, I often say that divorce is a gift and they're like, Wendy Kesser: Mmm. Tracy Callahan: What, what the hell, there's nothing good to like about this. But yet, for many people, if they have the appropriate professionals in place, it is a wonderful opportunity to start developing some of these conflict skills or relational conflict skills that they may not have had previously. A lot of my clients say to me, Tracy, if I actually was able to know some of this stuff, I think that I might have. engaged differently in my marriage. don't know if I necessarily would be here. And that's, not everybody. There's lots of reasons why people find themselves moving forward and separating or ending their marriages. But as divorce coaches, we grounded in dispute resolution are always supporting clients and looking at that thinking and feeling and their role that they've played in these conflict interactions. So when we're talking about this now and looking at this next stage, this next place where clients are going, how do you see divorce coaches sort of help clients in looking at some of these patterns? You talked a little bit about these different sort of phases, ready for what, moving through these different experiences, but. As they're beginning to explore new relationships, where do you see divorce coaches sort of sitting with us or supporting this? Wendy Kesser: Divorce coaches have a very sacred place in the lives of their clients as clients have that face ⁓ in the heart of divorce coaches. So already there is an opportunity that I don't think divorce coaches leverage sufficiently to be honest. I think there is a wonderful continuation of the work. If we think of divorce coaches as helping our clients consciously author their next chapter rather than unconsciously be a reactor to the last one, then we are already teed up for their next, for that next adventure, for their new next. So having that trust is, you know, we're already ahead of the starting line. I think another role that divorce coaches Tracy Callahan: Yeah. Wendy Kesser: can play and I think they ⁓ can play in matchmaking or at least in preparing their clients for dating is to manage expectations, ⁓ to really ⁓ help clients ⁓ to show kindness and self-compassion. And again, until they get that little bit of scar tissue, which is different than the scar tissue of a divorce actually. ⁓ the divorce coach as confidant and ally will continue to be valuable. As long as we are insisting our clients be informed by what they learned in the marriage and the divorce, then neither were for naught. And just being really ⁓ vigilant with our clients about extracting those lessons and holding them. ⁓ And then the final thing I would say, and this is just, Tracy Callahan: Yeah. Wendy Kesser: to best practices generally, and I think it's the responsibility of divorce coaches generally, is to know the appropriate pathways for referrals. mean, so referral pathways, and that is have a ⁓ contact list of ⁓ therapists, also grief counselors, maybe dating coaches, matchmakers, if that's appropriate. But I do think that, ⁓ telling our clients that there are resources out there beyond just us is a comfort. Tracy Callahan: Yeah, I love that. Deciding, you know, we talk a lot about informed intentional decision making, right? What am I choosing to do versus what am I responding to? Or I had to do because somebody X, Y, and Z, right? Which is a lot of the decisions that are often made or engaged in and divorce. Well, I have to do this because, and as we're sort of moving to this stage of autonomy, you know, I can't help but again circle back. to our David Rock's domains and our SCARF assessment, right? And when we look at these internal threats, either to status, certainty, autonomy, relatedness and fairness, how does that look as they're moving through this process, making these sort of intentional decisions and doing it with our eyes wide open, other than an expectation. Because I think the other thing that I'm hearing you say without you really saying this with the, and I'm gonna probably just be more direct on this is dating can be hard. it doesn't always just go out and it's unicorns, ⁓ rainbows and heartfelt everywhere, right? I mean, it can also, have its own feelings of sadness or questioning or disappointment. Wendy Kesser: Absolutely, as does everything actually and a lot of it is mindset. So that's ⁓ another important feature that divorce coaches can remind clients. I find dating after divorce intoxicating. think we're back in our own bodies where we're connecting with either the person that we had lost during the marriage or we're constructing a new identity. But either way, it is so optimistic. It is just sunny days ahead to me. I do think, so I appreciate that. I mean, I think I'm sure more than one of your listeners fell off their chair when I said that dating after divorce is the best, but ⁓ I do think that ⁓ it can be. Tracy Callahan: Well, I think that fired outcome, right? The thought is yes. I do think most people when they're ending their marriage envision themselves in another fulfilling relationship or one that is more fulfilling or meets needs at this stage of their lives that might've been different than when they got married 20 years ago when they were looking just to procreate and. and do, right? There's different things that we look for in our lives even in these different stages. Wendy Kesser: I'm so glad you said that because one of the great observations I've made in this demographic is that my clients for their first marriage, when they were in their twenties, they were chasing status. My clients now who are in their fifties, sixties and seventies, well read, well traveled, sophisticated, they don't yet realize that they're the ones that confer status. Now they're the poor kids. And there have been articles recently about why younger men like older women. And this is one of the reasons. So I feel like, you know, if you're not having fun dating after divorce, like come see me. Tracy Callahan: Come go see Wendy. You need. I think everybody does need that though because I do I I you know I don't really dance in this space much with the work that I do with clients ⁓ sort of the post divorce but it's certainly something that we explore in interest right part of the work that we do in dispute resolution is what is that desired outcome what is the goal what am I working towards. And that very much does incorporate a vision of them with somebody that they are happy with and compatible with and sharing experiences. And yes, that threat, I love that you use that example of status because when we know that there is in these internal dynamics within those dimensions, they're based on a threat reward. So yeah, at 50 something years old, I am comfortable in my status. I have accomplished where I wanna be successfully and all those things. But yet, right, there might be a different threat for perhaps financial security or wondering what my older years are gonna look like financially. So I think it really, really significant in playing into this process. Wendy Kesser: I see it when clients don't date, they audition. ⁓ They're not engaging. They're just constantly asking, do they like me? Am I saying the right thing? How do I come across? ⁓ Those clients are not building the skill of recognizing healthy partners. They're just getting better at being liked. So I think that we are, as ⁓ coaches, always encouraging our clients to optimize for choosing rather than being chosen. Tracy Callahan: Yes. Okay. So now we're saying that, right? As we sort of wrap, if you were to leave divorce coaches with two or three things to be most mindful of when supporting clients moving into date, what would those be to ensure clients are really approaching it with kind of what we talked about? Intention, greater awareness, understanding those relational conflict dynamics that they may want to look at. differently as they're moving forward with that. Wendy Kesser: I think it's, we're going to sort of in this context give with one hand and take away with the other. I think we're going to give a sense of ⁓ confidence and achievement that our client just came through a crucible moment. It is probably going to be the hardest thing they've ever done. And so there is, I hope, a level of ⁓ pride. ⁓ If it was done with integrity, if it was done well, then ⁓ there is something to look back on and be proud of, and that should be taken forward. So as a divorce coach, to leave a few ⁓ tips for them, I think they have had this front row seat to the worst moments of our clients' lives and to remind them still that they've got it going, that better days are ahead, that the work continues, that it is a continuum. ⁓ But I also think that, ⁓ but to remember that all of these things that we're talking about are not qualities, they're functions. ⁓ So I think that the work goes on to bring forward the next chapter with the lessons of the last one. Tracy Callahan: Yeah. Yeah, absolutely. Thank you, Wendy, so much. I really think what sort of highlights today's conversation is really something that we also really, really recognize at DCA is that clients don't need just help moving forward, right? Often they need support and sort of engaging differently in what comes next, doing it with intention, doing it with. capacity, doing it with awareness and understanding because dating after divorce isn't simply just a new beginning, right? It's a totally new environment where lots of our old assumptions or expectations can resurface, right? Where familiar roles can reemerge and unresolved internal conflicts show up and influence our decision making. Yet we also know that with support and intention, it can be intoxicating. as Wendy says, right? And that again, our shift with clients and helping them bring that awareness is not in telling them what to do, but helping them develop that clarity and capacity to do this and do it. That's the work, right? Not preparing clients necessarily to find the, I'm air quoting right partner, but helping them prepare. to engage in relationships that reflect their values, their awareness, their intention. And I think when divorce coaching is sort of grounded in that, it extends well beyond the divorce itself, right? Even when that agreement is done. So Wendy, I can't thank you enough for bringing your perspective to this conversation and for helping us expand how we think about this next stage for our clients. For all of you listening, you can learn more about Wendy and her work is the best at GetWithWendy.com Wendy. Wendy Kesser: It is, thank you. Tracy Callahan: Yeah, and we'll put it in the show notes. And to those listening, if you are a divorce coach or a professional working in this space, this is where our work continues, not after conflict is over, but as clients step back into a new form. So I wanna thank you all. Thank you, Wendy, and we really appreciate all of your listening. And until next time. Wendy Kesser: Tracy, thank you. Tracy Callahan: Thanks.