Intentional Living with Tanya Hale

Episode 293

Dating in Midlife




Hey there, welcome to Intentional Living with Tanya Hale. This is episode number 293, "Dating in Midlife." Welcome to your place for finding greater happiness through intentional growth, because we don't just fall into the life of our dreams...we choose to create it. This is Tanya Hale and I'm your host for Intentional Living. 


Hey there, welcome back to the podcast. So glad to have you here today. Thank you for spending your valuable time here with me. I know that it takes time and effort to show up here and I feel so grateful to have you here and I hope that this information continues to bless your life and continues to help you see things and understand things about how we can heal our relationships. You know that I love this midlife gig so much. I love that we have the experience and the wisdom at this age to really have things start making sense. To me, it almost feels like we have been collecting puzzle pieces all of our lives and occasionally been putting pieces together. But it feels like in middle age, all of a sudden we're like, "oh, this piece and this piece and this piece and they go here and I'm starting to see a picture and starting to see things." And I don't think I'm alone in the fact that it's taking me a long time to make some connections in life, but it doesn't take other people so long to make. And I think that's probably why you're here, because you're in many ways similar to me and that some of this just did not make sense for so many years and now that it does. I feel compelled to share it with you, for the life that it's been creating for me, and the life that I know that it can create for you, and the life that I see it creating for so many of my clients. Just really grateful to have you here, so thank you for investing your time here. 


Really quickly, just wanted to remind you if you are interested in the discussion group that I'm going to be starting in March, having to do with physical and emotional intimacy, please go to my website,, go to the "contact me" button, scroll down just a little bit, sign up for my "weekend win," so that you are on my email list and when the information comes out for that, you will get first dibs on what's happening. It will be there before it will even be here on the podcast. And I think it's just going to be so fabulous. It's going to be a, rather than a class, it's going to be a place where everybody goes out, collects information, brings it back, and we talk about what you're finding. Because I know that a lot of you have some great tools and resources to share. I'm planning on doing a Facebook group as well so that it makes it a really easy way to share all of the resources that we find. And I think it's just going to be an amazing place for all of us to get more clarity on what it takes to create emotional intimacy and physical intimacy, and why both of those are so important in our relationships. So go to, sign up for my "weekend win" so that you don't miss out on that. 


And that being said, let's go ahead and get started today. We are talking about dating in midlife. So I've had this topic on my list for so long, probably like, I don't know, I got married almost two years ago. And I feel like I figured out some pretty amazing things with how to date and how to find a person who was a good fit for me. And so it's been on my radar for a while, but it just kind of came back to me, as I've been doing the last two podcasts about divorce. And I was like, "okay, I gotta share this. I gotta share some information because I know that dating in midlife is really tricky." As I talk to a lot of people who are single in middle age, and regardless of the reason that they're single, there's just a lot of negative stuff about how horrible dating is and how miserable it is. And I just don't think it has to be that way. It was not for me. I think when we are really clear on who we are and on what we want, I think that dating can actually be a really incredible experience. And did I have a couple of tricky experiences? I did. I had one that was super, super tricky. And that was before I actually really started doing the work that I do now. And so I feel like the work that I do now really helped me to have a different experience with dating. And I'm hoping to share some of that with you today. And if you're not single and not dating, there might be some fun stuff here for you as well to incorporate into the relationship that you are currently in. 


So I do want to preface this by saying that I'm going to be sharing some really great information, things that were super helpful to me when I was dating after my divorce. And if you're in a position to be dating in middle age, whether you're divorced or whether you're widowed or whether you've never been married or whatever your situation, all of this may not apply to you. So what I want you to do is I want you to listen. I want you to identify the nuggets of wisdom and then check it with what feels good to you. Because all of this may not feel true to you, but I want you to see there's probably going to be some things here that you're going to go, "oh, I haven't thought about that before. This might be important." 


So I really love a lot of the things that we've talked about the last two weeks because I feel that they are concepts and ideas that, when applied, will help you get to a healthier place, so you are prepared to enter into a healthy relationship. One thing that I find incredibly problematic in so many of our relationships after a divorce is that we think that our previous relationship was the biggest problem, that the relationship was the problem. And though our previous relationships did have a lot of problems, that wasn't necessarily the biggest issue. Because of that, a lot of us think that "if I just get a new partner, a new person, everything will be different." And yes, things are different because they are a different person. And your brain is caught up in the fact that it's a new person. It's a new situation. And so it finds a lot of comfort in the new situation for a short time. 


However, what we often don't understand is that we are taking the same person, which is us, with our same brain and our same patterns of thinking and behavior into the new relationship. So though our brain may find some novelty in the new relationship for three or four months, after that the old brain engages and we start showing up with the same patterns of behavior when we come upon similar situations. Shocker, right? It's a shocker that we are actually the biggest part of the problem. So it's really important that we do the work to see our previous contributions to the demise of our marriage and that we clean that up so that we are entering into a new relationship as to our destructive patterns of behavior and having created new patterns as well. Okay? So as a reminder, a new situation or changing the circumstance is not going to solve the problems long term. We have to go to the cause or the source of the problem, which is the patterns in our brain that are going to show up again. And I promise you they will show up again because that is what your brain knows to do to engage with similar situations. 


So as we talked about the last two weeks, learning how to clean up our own stuff before we get into another relationship is going to set us up for a much healthier and a much stronger relationship in the future. I see a lot of people who think that after they get divorced, what they need to be happy and to heal is another partner. And I struggle with this idea because I feel that we need to do the work on ourselves, that we need to get to a place where we accept and love ourselves and we don't need the acceptance and love of another person to feel as though we are whole and worthy. Now it's not to say that we don't desire connection, because that is that is a part of who we are being human, but we have to recognize and embrace our own wholeness and worthiness as a person first. That's not anybody else's job and I believe that when we can 100% be whole and healthy within ourselves first, then we can start to create a whole and healthy relationship. But until I feel complete and whole myself, I cannot bring a complete and whole person into the relationship circle to create a healthy relationship. 


I know that for me after I got divorced I didn't have much of a desire at all to date or have a relationship. I didn't go on my first date until two years after the divorce and during that date I found myself spending a lot of time talking about a current situation with my ex-husband that had me really upset. And that was an indication to me that I was not healed and that I was not ready to move into another relationship. So if you are hung up on being a victim and telling stories about how your previous spouse was or is the villain, you may not be prepared to create a healthy relationship yet. And the same is going to hold true for the person that you date. If while on the date, all they want to talk about is their ex-spouse and how they were treated wrongly and all the things that their previous spouse did, it doesn't seem to me that they have done the work necessary to own their own dysfunctional behaviors in the previous marriage and that they are not quite ready to engage in a new relationship in a healthier way. That's not someone that you would want to be engaging in a relationship with. 


OK, but that's not to say that you can't talk about your ex-spouses. The difference would be noting patterns of behavior or identifying characteristics. The difference will be whether the discussion tends toward victim mentality or whether it tends toward, "here are some details about my previous marriage situation." So we will most likely have a lot of healing taking place for several years. So we're not looking to be entirely healed before we date because we may never be right. There are some wounds that are really deep. There are patterns of behavior. There are traumas that we are having to work through and a lot of those will not be able to be worked through until we are in another relationship. OK. But at the same time, we want to do as much of that healing as we can. So we're looking at how far we have come along the healing path and what  direction we are headed. Alright. We want to be having been on the healing path for a bit. And this path will be very different for every person, but it really needs to be walked. I was single for about five years before I really felt I had healed and moved forward enough and was ready to engage in a relationship. 


But my healing journey didn't begin until probably about nine months after my divorce was final. My husband, Sione, on the other hand, had been divorced for less than a year when we got married. But he had started going to individual counseling about five years before his divorce to begin his journey of healing and understanding how he was contributing to the dysfunction of his marriage. So he had done a large part of his work before the divorce happened. But here's the deal. The work has to be done. We have to figure it out. When we jump into dating, before we have taken a good walk on the healing path, we may find ourselves dating to shore up our own insecurities of being alone or even dating to prove that we are capable of a relationship. I think the best place to begin dating is from a place that says, "I am great on my own and I'm happy being single." This doesn't mean that you would be a man-hater or that you would never want to get married again, but it comes from a place of saying being single is infinitely better than being in another dysfunctional, hurtful relationship. 


Now, I know that we're all different, but a degree of finding peace with where you are, I believe, is an essential element of being ready to be in relationship again. Before I started dating with real intent, I was in a really good place. I loved what I was learning, who I was becoming. I felt that I had grown into a much healthier version of myself and that I was understanding the dysfunctional patterns I had been complicit in creating in my previous marriage. And I was really happy. When I go back and listen to my podcast from that time period, I hear myself saying that I was in the best place I had ever been in my life. I honestly did not see how life could be much better than it was at that time. And during that time period, I had a conversation with my life coach about it and told her, "why would I want to mess up my life with a man?" And I honestly believed that getting married would mess up my life. All my mind could conceive of was that marriage was hard, that I would have to give up my freedom and my independence and have to compromise all the things to make somebody else happy, all in order to take care of a grown man who would need too much and take more than he gave. And my life coach reminded me that I got to choose the person I married. Basically, she just said, "Tanya, just choose a different kind of person." And I don't know what it was about that, but it helped me realize that not all men were the same, that I could find somebody different. And that it was very likely that someone out there wanted the same kind of equal partnership that I did. And I was very happy. 


After that call with my coach, I sat down and I wrote some ideas about what I wanted from marriage. And here are some of the things that I wrote: "I don't need a man, but I want to want a man. I want to learn how to create intimacy that I've never had. I want to learn to love cleanly without expectation. I want to learn to love someone I don't already have a bond with like I do with my children. I want to learn to show up authentically and vulnerably who I really am without hiding any parts of me. If I'm going to find the love of my life, I need to be the love of my life. I want a relationship that is easy. It will be easy to love him. I want to be self-aware, cognizant of how I'm showing up. I want to learn to address my wants and needs and his wants and needs and move into connection and intimacy rather than contention when conflict occurs. I want to learn to love like I've never loved before." 


So as I've gone back and looked at this list, I've been amazed at the insight that I had and that I didn't have a list of traits or qualities of what I wanted in a spouse. Rather, I had a list of characteristics of the type of relationship I wanted to create and what it would take for me to create it and the kind of person that I wanted to be in a relationship. So at the time, I was beginning to realize that I wasn't looking at a relationship so that I would have someone to love me, but rather I was looking at a relationship so that I could have someone to love so I could really learn to love and show up in a relationship like I never had before. I realized that my old patterns were going to create the same type of relationship and that I needed to learn how to show up very differently than I had in my previous marriage. I think we live in a society very often that says that we get married so that we have somebody to love us and I want to push back against that idea. I think that we get married so that we have someone to love, so that we can learn to love better, so we can become a person who can be more loving and accepting. 


So although in my happy single life, I realized that I had grown a lot as a person in the previous five years and that some of  my next greatest growth would come in the context of a healthy relationship, in applying the concepts that I was learning in relationship. And through this analysis of my current state of mental and emotional relationship health, I felt I was ready to date and practice relationships, although I wasn't sure I was ready to do that, to anticipate getting married yet. And I did see dating as practice, learning to do all the things I had previously decided I wanted in a relationship. So I started by approaching dating as practicing learning how to love cleanly. If you haven't checked out "Clean Love," my podcast called "Clean Love," go back and check that out. I think it's like 92 or 93. Okay? It's learning to love without expectation. This dating would be practice learning how to be accepting of another person's flaws and inconsistency while also being aware of my own. Dating would be practice learning how to show up as me having a voice, choosing to be seen and heard rather than just seeking to keep the peace like I had before. 


I started off just looking at dating as practice and it served me really well. I needed a lot of practice in order to figure out how to put the tools I had been learning into practice. So one of the first challenges I found was figuring out how to date from a place of abundance rather than a place of scarcity. This meant that I couldn't go on a date with someone just because they had asked me. If I wasn't interested, I had to learn to say "no." This took some practice to figure out that if I wasn't interested, it wasn't the best use of my time. Scarcity mindset in dating is a place that thinks there are not enough good men to go around and I'll probably have to settle for something or compromise on things that I really feel are important. I'm just going to go out with everybody. I'm going to give everybody an equal chance. Let's just get rid of those types of thoughts right now. Can we? I promise you, you are better off being single than settling. Scarcity mindset with dating will either have you choosing not to date at all or dating people who aren't a good fit because you're scared that they may be your best option, that there may not be anybody better than that person out there. 


So many single people I talked to are really honed in on this scarcity mindset. "There aren't any men who want emotional connection." "All the men only want sex." "They are only interested in super skinny, beautiful women." Those types of thoughts are scarcity mindset and they're not true. And these types of thoughts will keep you from dating in a way that will find someone who is a good match for you. Now, are there men like that? Of course there are, but focusing on the men who are isn't helpful. So let's look at how dating from scarcity plays out in the thought model. So let's put our thought as "there aren't any good men left." What feeling does that create when you think that thought? Maybe despair, maybe hopeless. And then what actions come from our hopelessness? We don't look very hard. We show up half-heartedly, we give up easily, we settle. 


From my experience dating and also coaching with men, there are a lot of single men who do want an emotional connection. This is just like so many women, the fact that they just don't know how to create it. Very few of us know how to create a safe space for each other and how to own our own and have difficult conversations without attacking or blaming. If you're dating someone who was previously in a very difficult marriage situation, chances are they have a very skewed idea, like most of us did getting out of a divorce, about what it takes to really have a healthy relationship. We don't have the skills that we talk about here in this podcast. So when we can learn these skills and then start to implement them, we create a safe space. for others to try them on, to practice them as well. That's one reason why the relationship tools that I teach here on this podcast are so important even when you're single. You can learn how to create the kind of relationship where you both feel safe to step into emotional intimacy. 


Okay, alright, so once you've gotten yourself to a healthy and a stable place, you've learned some amazing relationship tools to create something different. You've created an abundance mindset and decided to start dating, how do you do it? Okay, so I'm gonna share with you what I did that was incredibly effective for me. This may not be what works for you, but the basic concept of show up as yourself will hold true. I got on a few dating apps and I worked on my profile until I felt like I was showing up as genuinely me as possible and it was kind of a work in progress. I did my first couple of profiles and then went on some dates and then I changed them and went on some dates and changed them, right? It was a process of figuring out what was working and the kind of people that I was getting. But once I really got down to bringing it down to who I really was, then the kind of people that I started attracting and pulling in were very different. So showing up as genuinely as possible meant that I had pics of myself with makeup and without. I had close head shots, I had medium shots, I had body shots. Also, I was very honest about my likes and dislikes. I am not a pet person and I stated that directly on my profile because pets are a huge deal to people and especially to pet people, right? If someone was a huge pet person, he  and I would not be in good fit, right? Because I don't like to be bothered with all the things that pets entail. And a lot of people love all of that stuff. It's so worth it to them. Also, I am a weekly church attender and I stated that. And I said that that was who I was looking for. 


I also let it be known very clearly that I was looking for a deeply intimate emotional relationship. Okay, now those three things right there, there were other things in there, but I really tried to show up as me, right? And those are three of the biggies. Those three things immediately made some really great men swipe whatever direction said no. And that's good. The profile is a way of weeding out the people you wouldn't be interested in. It's not something to pull in as many as possible. Your profile needs to be a place to weed out all the people that would not be a good fit. Everything you can put in to narrow the pool of people who would be a good fit is important for you to put in. 


Also, when I was looking at the app, I would swipe "no" on anyone who had a pic with an animal. Anyone who said weekly religious observance wasn't important to them. And often of those who said they just wanted somebody to have an adventure with. Now, I love a good adventure. Case in point, I'm in Samoa for a month with my husband, right? But I wanted so much more in a relationship than an adventure buddy, okay? And to be sure, I walked right past some great people with this being my strategy. But not every great person would be a great fit for me. Abundance thinking isn't afraid to say "no" to a bad fit because it knows that there are people out there who are an amazing fit. I just have to find them. But if I'm so hung up on bringing everybody into my circle, it makes it much more difficult to find the people that are a good fit because I have a lot more people to filter through, okay? 


So then when a match was made and we connected over text, I would jump right in. I had stated on my profile also that I'm pretty straightforward and I don't like to play games. So owning up to that, I would quickly, and Sione teases me all the time because he was like, "yeah, I think it was your second text message that you did this," and I thought it was my third, but here we go. Really quickly, I would say something like, "I'm not a game player, let's just jump right in. I'd love to hear what your three greatest successes and three greatest failures are and why." And then I would often send them mine even before they asked me to send mine and before they sent theirs. So this was very strategic for me. So here's what I was doing. I love to have deep, meaningful conversations. And so the person I ended up dating would need to want the same. I wanted someone who is self-reflective and can see their own crap and not be afraid of addressing it and who will have a growth mindset as far as learning from their crap, seeing it, learning from it, and moving past it. These things were non-negotiables for me, and asking this type of question helped me to learn if this person was the kind of person that I knew that I wanted. 


Many men immediately deleted me for good. Like, all of a sudden they were gone. I never heard from them again. Guess what? If that question turned them off, they are not my person. And then I had less people to sift through. Some men came back with something that was less deep than I was interested in. For example, one man said not making the high school football team was one of his greatest failures. That was great information for me. He probably isn't the kind of self-reflective person that I was looking for if he has to go back to high school to identify one of his greatest failures. Also, some men came back with something silly and avoidant. Again, Good data. They seem to be uncomfortable having serious conversations. Not my kind of person. 


So also the reason I would send them my three greatest successes and failures right away before they responded was to show them what my expectations were. And I sent some really vulnerable things. Okay, this was all very strategic for me. I was trying to weed out all the extras that were not a good fit. I was trying to narrow it down to people who would be a good fit. So some of the other questions that I would ask at the very beginning of speaking with someone were things like "what are your three greatest strengths and your three greatest weaknesses?" "How did you contribute to the demise of your marriage?" "What is one of the greatest lessons you've learned since your divorce?" Okay, so for me, these types of questions honed in on some of the things that I felt were really important. Self-reflection, being able to be vulnerable. Men who weren't comfortable or willing to go there probably weren't going to be a good fit for me. So it's super important that you are aware of what really matters most to you in a relationship and that you make sure that those things are addressed and that you stick to them. 


When a lot of people hear about my approach, they're shocked that I would jump in the deep end so quickly, but that's my personality. Right, that's who I am. I didn't want to play games and waste time. I was in my 50s. If the man I was chatting with wasn't my person, I wanted to know it as soon as possible. And for me, this was a huge abundance mindset for me to say, listen, I'm going to weed out all the people that aren't a good fit right away. I don't want to spend time on them. I want to find people who very possibly would be a good fit. And if he was uncomfortable with vulnerability, I wanted to know that. I was collecting good data to help me lead people out. 


So the other piece of this that I thought was super important was me showing up as me. I wasn't pretending to be somebody I wasn't in order to draw more men in. If they weren't going to like the real me right up front, they probably wouldn't ever like the real me. It was better for me to find out right away rather than spend three, six, eight months investing in a man who would never accept me for me and someone I always felt I needed to put on a show for. And then once I met up with someone, I focused on continuing to show up as me. I spoke up, I shared my opinions, I asked a lot of questions, I got vulnerable and continued to ask them to step into vulnerability as well. I worked to be as honest as possible, noticing patterns of when I was tempted not to be honest, as that was a good indicator of destructive patterns of behavior for my previous marriage. I used this time as an opportunity to see where am I struggling showing up. Where am I struggling trying to keep the peace? Right? Because I decided that never again would I keep quiet just to keep the peace. I would look for and expect an equal partner, someone who wanted emotional intimacy, someone who wanted physical intimacy, someone who truly saw me and accepted me even on my worst days. 


This is the thing about midlife dating that's so amazing: we are so much more clear about who we are and about what we want, about what our non-negotiables are. So let's capitalize on that and get a much better match, our second or third or fourth time around, getting married, right? So my mantra when I was dating was, "if he doesn't make my life significantly better, it's not worth it." Meaning, "if I get married and my life is about the same, so not worth my time." We are risking too much at this age to get in another tough and terrible marriage. If he makes my life just a little bit better, also was not worth it to me. By the time I bring in a home full of furniture and he does too, that we'd have to figure out what to do with, we'd have to combine all of our resources, we'd work through having children who may or may not be on board, someone needing to move, there was just too much at risk. So for me, if he didn't make my life significantly better, it wasn't worth it to me. And I can honestly say, Sione makes my life significantly better. Do not settle, my friends. Do not date from scarcity mindset. You will never have the relationship you truly want if you are willing to settle. That doesn't mean he has to be perfect, because you will never get that and you will never be that. But do not settle for someone who does not want what you ultimately want and who isn't willing to work for it. 


There are some things that are really important to look for. One: do you have intellectual compatibility? Intellectually, can you have conversations that match each other, where you can have stimulating conversations, where you push each other in what you're thinking? You also need to have some emotional compatibility, this ability to hold space for each other. You both want to grow and progress at the same levels, right? You're not always going to grow at the same times, but you both have to have the same kind of growth mindset. A lot of what we talk about here on the podcast is both of us wanting to grow, both of us wanting the same thing. And then we've got to have some, what Simon Sannick calls, "creative sexual compatibility." Right? And that has nothing to do with sex. It has more to do with understanding our sexuality, wanting to engage with our sexuality at about the same level. And that that's part of that creative side of us. Right? If one of you wants sex five times a week and the other one wants sex twice a month, that's not good compatibility. We get to talk about this stuff and we have to talk about this stuff and it has to all be on the table. It's part of having those honest, open communications. We really need to have these things to have great relationships and we get to choose. Do not settle. Do not settle. 


Okay. So that's going to do it for me. Next week though, I'm going to talk about my 90-Day dating process and show you how and why it worked for me. Now, it may not be something that you're interested in, but it will hopefully give you some ideas about how you can approach the actual dating. I will say that I have had other friends do the 90-Day process as well. A really good friend right now who just got engaged to her guy after three and a half months. Right? Like, so they were four and a half months. I think this process of stepping into the kind of relationship that I'm talking about doing the things that I've  talked about really helps you understand fairly quickly who they are, who you are, and if you're a good match. So you're going to want to tune in next week to do that. And the 90-Day dating process is also something that you could adjust and incorporate into already established relationships if you want. 


Okay. So that's going to do it for me. I hope this has been really, really helpful. I just think dating in middle age is not the misery that a lot of people are going to try and talk you into believing that it is. I loved it and I found some amazing men when I started dating this way and I really honestly believe that I'm not a unicorn here. I think we just really get to start implementing tools and concepts and some doggone honesty into our relationships. I think we can we can do this and find incredible matches out there. I think there are way more men and women out there who want a really serious intimate partnership, but nobody knows how to get there. That's what I'm here to help you do. Okay, hope that helps. Have an awesome awesome week and I'll see you next week talking about the 90-Day relationship. See ya! 


Thank you so much for joining me today. If you would love to receive some weekend motivation, be sure to sign up for my free "weekend win" Friday email: a short and quick message to help you have a better weekend and position yourself for a more productive week. Go to to sign up and learn more about life coaching and how it can help you get to your best self ever. See ya!