My First Post-Divorce Date

What happens when you haven’t dated for thirty years and suddenly find yourself navigating modern romance at 54? After ending my 26-year marriage and spending nearly three years focused on healing, I finally took the plunge back into dating—and discovered something unexpected about my heart along the way.

The dating landscape has completely transformed since I last participated in it. Gone are the days of meeting through mutual friends or chance encounters; now we swipe through dating apps filled with bathroom selfies and decades-old profile pictures. As a betrayal recovery coach, I approached this milestone with both trepidation and curiosity—would my nervous system be triggered? Would I feel like I was betraying my ex-husband despite being divorced? The answers surprised me.

Unlike many who rush into new relationships post-divorce, I deliberately gave myself time to heal. This patience allowed me to approach dating with clarity about my boundaries and desires. I know exactly what I want (no camping enthusiasts, please) and what I don’t want (raising young children again). This self-awareness represents tremendous growth from who I was thirty years ago.

The most profound revelation came after my date ended. Sitting in my car, I realized that my heart—which I had consciously locked up “in a million chains” for protection—had begun to open. The possibility that genuine, trustworthy connections exist suddenly felt real. This emotional shift represents the essence of post-betrayal growth: not just healing enough to function, but healing enough to consider trusting again.

Whether you’re contemplating dating after betrayal or simply navigating your healing journey, remember that your timeline belongs to you alone. Stepping outside our comfort zones often reveals that we’re stronger and more healed than we realized. Want to create your own “happily even after”? Connect with me through my email or social media and let’s work together to make it happen.

Please follow me on instagram and facebook @happilyevenaftercoach and if you want to see what coaching is all about I offer a free 45 min. clarity call via zoom.

Email me: hello@lifecoachjen.com for any comments or questions.

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My website is www.lifecoachjen.com

Transcript

Welcome to my podcast Happily, even After. I’m life coach, jen, I’m passionate about helping people recover from betrayal. I rode the intense emotional roller coaster and felt stuck and traumatized for years. It’s the reason I became a trauma-informed certified life coach who helps people like you navigate their post-betrayal world. I have the tools, processes and knowledge to help you not only heal from the betrayal but create a healthy future. Today we begin to help you live happily even after. Hey friends, welcome to today’s podcast. Today I am recording at my home, which I usually do when I have a guest, but today the guest is me.

I was just thinking that I wanted to share this with you, but if you’ve been following me, you know that I’ve been divorced now for almost three years. Then I was married before that for 26 years. So I haven’t been on a date for 30 years. So the last time I dated was when I was 24 and I just recently turned 54. So imagine yourself in my situation and I’m sure many of you listening have been divorced or maybe are considering it right, especially if betrayals happened in your marriage. And I’m just going to say betrayal is hard Like it is so hard and divorce is hard right, but sometimes divorce is a better option and, in my opinion, for myself, divorce really has been such a relief for me. It’s given me the space I needed to heal, which I didn’t necessarily know that until it happened, which I didn’t necessarily know that until it happened, I had a lot of fear about getting divorced and I even had more fear about the thought of dating someone else, right. And so I just want to share some of my thoughts about dating when I was in my 20s to dating now in my 50s. So a few months ago I decided in 2025, I would make a goal to go on one date, and I know one date sounds kind of silly, but when I had gotten divorced, originally, my therapist had said Jennifer, you make it a goal to go on one date in the first year after your divorce because many people he has seen they kind of get stuck and the fear gets bigger, which I totally understand. And so I think right after I got divorced, I joined a couple dating apps and I matched with a few men and just talked to them.

But I realized quickly that, oh, my body was not ready to date. I could feel my nervous system reacting and I just knew I hadn’t healed enough for myself. And that’s really important to me because what I’ve seen with many clients, friends, people I know they get divorced and almost it’s like this freedom and like, oh my gosh, here my spouse has been cheating on me and so now I have permission to go on a date right To date anyone I want, do anything I want, and a lot of people tend to go wild and date a lot of people and sometimes and usually this happens they hop into a new relationship. They haven’t healed from their past relationship and, even though the person is different, they brought their brain with them and they sometimes end up with the exact same thing that they just left because that’s what they felt comfortable with. That person felt safe, even though they weren’t safe. They were lying to them and cheating on them. So it happens all the time and I just wasn’t willing to let that happen to me and I knew I still had healing.

So fast forward. Now I’m almost at the three-year mark, 2025. I feel like I’m in such a better headspace, I feel very good about where I’m at. So I decided I’m going to make this goal and things I’ve noticed dating in your 20s well, first of all, we didn’t have the internet. We didn’t have Facebook, any social media. So how you dated? You probably dated someone that you went to school with. In college, I met people in my classes. I met my former spouse at a bank where I was the customer and he was the employee which should have been a red flag for me, but it wasn’t and that’s how we met, and so you would meet through acquaintances or friends or a blind date. Anyways, that was how you dated right, and now it feels like maybe it would be easier now, but I think it’s so much harder.

So now what you do is get on an app and post like five or six pictures of yourself. They ask you questions, the basic things like right, like, are you married? Well, hopefully you’re not married on the dating app, but there are lots of people married on the dating app, like divorced, widowed. What’s your job? You know you answer these questions and you scroll through them and you swipe down if you’re not interested and you swipe up if you’re not interested and you swipe up if you are interested and you pick your age range and you see pictures and for me, I paid the extra whatever amount of money. There’s free websites, free apps, but then you pay extra so you don’t get the ads and you can see people from just not where you live directly. You Like, you can see people from other states and even other countries, and I just wanted to get my pool a little larger, and so that’s what I did.

What I have found interesting that men, many men, they really enjoy posting pictures of the animal that they killed, hunting or these really daring things that they like to do. I don’t know if they’re showing off, if they think that’s cool For me immediate no. If you tell me your favorite thing to do is camping absolutely not You’re a no for me. So I think, as a woman and a man, you need to get clear of really what you’re looking for, and, of course, they ask you lots of questions to make sure you’re finding someone that matches with you, but you only have a few choices, so you really aren’t sharing your whole personality, anyways. So I just find it so funny. Men love to take selfies in the bathroom and I’m like did you notice the toilet seat was up? Because I did, and that’s an immediate no. So I just it’s hysterical.

I love I screenshot and send them to my friends and my daughter because we think it’s hysterical that someone thought that that was the picture to put on their dating app. Like this is the presentation here. Hey, world, this is who I am, and they can pick some of the worst pictures. It is quite humorous. If you want a good laugh, find your friend that’s divorced and swipe on her dating app, because it’s hysterical. Anyways, so this is how we have to date in 2025. And, of course, I have sweet neighbors and people that have sent me their brother or their friend, that have sent me their brother or their friend, and so far that has not been how.

I haven’t gone on a date with anyone of those people. But it’s a lot different. So just fair warning, if you’re like, oh, it’s going to be so easy to date and meet people, no, it’s not. And then you’re just meeting a picture, right, you don’t even know their personality, you don’t even know their last name and what. I also have found and heard that people will post a picture but that was like 20 years ago or 10 years ago, or they lie about their age. They lie about their height. My daughter is like mom. They lie about their age. They lie about their height. My daughter is like mom. Any man that says whatever height they are, just deduct two inches, which I find hysterical. That men like to lie about their height, but women we lie about our weight, right? I mean, they don’t ask you what you weigh, but it’s just interesting. It’s a very good social experiment, anyways.

So this year I decided, okay, I’m going to get on the dating app again. Matched with several people. The other thing I found that you match with people you think, oh, this is our time to communicate. Oh, no, dead silence, right, like, are you on the app for a reason? Did you forget you were on the app? Why aren’t we communicating? And don’t ask me, ask me an open-ended question. If I ask you an open-ended question, you should respond with an open-ended question with me, as opposed to no. Yeah, I mean, we are in, am on this experiment, right, can I get a date? Can I get a date in the year of 2025? Okay.

The other thing if you are dating, like, really get clear on what you’re looking for, because for me, I am looking for someone to add to my life, because I already have an amazing life. I don’t want someone that it would be a burden or Anyways. And I’ve decided I’ve already been a mom. I love being a mom. I have four amazing kids, but I don’t want to raise your kids. I don’t want to be a stepmom. I don’t want to raise your kids, right. I don’t want to be a stepmom, I don’t want to be a bonus mom, I want to be a friend to your adult children.

And so a lot of 50-year-olds, people in their 50s, have younger kids, which is, I guess, valid, right? They got married later or for whatever reason, they have a four-year-old and a 10-year-old and so that’s immediate no for me. I’m sure you’re a great guy, but I don’t want to deal with your ex-wife. I don’t want to deal with raising teenagers again. I did that and it was hard and I love my kids and I’m sure I could like yours and probably love yours Little ones. I just don’t want to be a parent of them.

So I have a few like absolute no’s, okay, and for me, women in general right, like it’s a risk. There are some women that really need to find companionship because they do have little kids. If I would have divorced my husband years ago, I’m sure I would have been in a different mindset around dating and finding a companion again, but my mindset now is no, I love my life, I love my freedom, I want a companion, I think. But it’s going to look different. So really get clear on what you want. And if you find yourself jumping in when you’re not ready, that means you’re just not healed yet and that’s okay. Dating obviously will give you triggers, especially if you’ve been betrayed, but it is a way to really learn lessons about yourself and to have huge growth opportunities, I think. Okay.

So now on to what I want to share with you. So here I am talking with a few different men, and there is one from out of state, and so he mentioned he was going to come to where I live. And I’m like, cool, one day. He’s like hey, do you want to go to dinner? And unfortunately it was at three and I already did have plans, and so I said no, but what about? Maybe tomorrow or another day we could go to lunch. So he agreed and that happened late at night, 10 o’clock at night. I’m like, oh my gosh, my first date is going to be tomorrow. Oh my gosh, my first date is going to be tomorrow.

And I decided also in my dating, like I’m going to be very transparent with my kids. I’m going to let them know, hey, I’m going to go on a date because we have a lot of history of secrets and lying in our family, sadly, and I’m just not doing that anymore. I have nothing to hide and I’m not covering for that anymore. I have nothing to hide and I’m not covering for myself. There’s no need, right? I’m very pro. We do not lie in my house and if we do, it’s a problem. But so far, so good, as far as I know, right.

But my kids were pretty close and pretty honest, so I just wanted to tell them and I just have to give a big shout out to my kids were pretty close and pretty honest, so I just wanted to tell them and I just have to give a big shout out to my kids how sweet and kind and excited they were for me, which means a lot. I know they want their mom to be happy and honestly I’m so happy. But I think a little part of them thinks like okay, cool, my mom’s going on a date, like wow, this is exciting, anyways. So my daughter she of course we. Okay, cool, my mom’s going on a date, like wow, this is exciting, anyways. So my daughter she of course we go to my closet. What am I going to wear? I’m like, okay, let me decide on my pants and then pick out a few tops and tomorrow I’ll try them on and see what is feeling good, right? So I had an appointment and luckily it was a hair appointment. I didn’t tell him that because I was like, okay, I just have an appointment, so we need to go after my appointment.

So I set the time and attempted to go to sleep and I found myself so nervous I felt like I was like a teenager again. I was like, oh my gosh, I can’t believe. After all, this time like it’s been a long time I’m going to go to dinner with, or actually lunch, I’m going to lunch with another man that’s not my spouse and is a stranger that I met on the internet. I mean, that feels scary, right and so, but this is the way, this is how you do it. My kids are like mom, you meet him there, you pay for your own lunch. And if my daughter’s like, if you’re having a hard time, like if it’s awkward or weird, tell him you have to go to the bathroom, text me, I will call you and you can just tell him you need to go because your kids need you. So I was like, okay, this is our plan, right, this is my way out, in case something. You know, he’s a creep or weird or whatever.

So I really struggled sleeping and I woke up and I started getting ready. I actually made a video so you can go watch it on my Instagram stories, or not Instagram stories on my reel. I made a reel. So get ready for the day. Go get my hair done which was great, because you always feel better when you have your hair done by someone else than yourself and I drive to the location.

Well, originally he said hey, do you want to meet at this restaurant? That was in the city that I live in. And when I saw that, I was like, no, I do not want to meet there. But past me, I think would have just said sure, because I didn’t want to. What if I told him I didn’t want to go there? And I think I just wasn’t as confident. But I said, actually, I’d prefer to go to this restaurant in this city. I said, actually, I’d prefer to go to this restaurant in this city. Are you okay with that? So I’m really proud of me because I am really getting good at speaking what I want and need, and he didn’t care, right, clearly, because he was like perfect. And then the other thing is I was thinking, oh, I’m going to, probably I might be running late, so I just wanted to tell him and my kids laugh at me because they’re like you didn’t need to tell him that I’m like well, when you’re in your 50s, you tell people. That’s the kind thing to do in my opinion. This is who I am, so I get, when you’re in your 20s, you date differently, but I think people in their 50s, hopefully, are a little bit more mature and kinder.

Anyways, so, if you guys know, I have a group of friends that I go walking with and I haven’t even told them that this was happening, because I didn’t know it was happening Thursday, when I went on a walk with them, it happened that night and so I decided to send them a video and they went crazy. They couldn’t believe it. So I show up at the restaurant five minutes early and he’s not there and I got this pit in my stomach and I thought, oh, what if he’s not coming? Okay, well, that’s okay, I can have lunch and it will be fine. It didn’t mean anything about me and it’s okay if he’s not coming.

I learned a lot getting ready for this and feeling like, am I ready for this? So I text them. He’s not here. They’re like it’s okay, just wait, he’s going to show up. He’s going to show up, which I really appreciated. They’re giving me that boost and sure enough he walks in the door. And sure enough he walks in the door.

And I laughed because I think I shook his hand, which, of course, weird, right. But he looked at me and he said, oh, thank goodness, you look like your pictures, I’m not getting catfished. And I said, oh, is that a common thing? He said it happens a lot, and I just think that’s so sad, right? People are presenting themselves in a way and they’re not that person, and I’ve heard from many other people that I’ve told this story to that they’re like oh my gosh, that has happened to me so many times. And so if you are dating, put your real picture out there. You don’t want to show up and have the random person or put a recent picture, not from 10 years ago. Okay, we change and we have to just embrace what we look like right today, right?

So anyways, he of course, made a joke about me being a betrayal coach, which was sweet and kind and we ordered our food and I get my wallet out and he’s like absolutely not, I’m paying. He’s like I am paying for your lunch, which I really appreciated and I didn’t mind. I wouldn’t have thought anything if I would have paid, but it was really sweet that he wanted to pay for my lunch. So we go, sit down, have lunch and I was really focused on okay, how am I going to feel sitting at lunch with another man and is it going to feel awkward? Am I going to feel, am I going to get triggered? Am I going to feel like I am cheating? Right, because even though I’ve been divorced, I was so loyal to my husband to a fault, right, loyalty is a great quality I have, but it kind of kept me in an unhealthy marriage for a long time. So I just was curious, like, okay, how am I going to feel? And honestly, I felt nothing.

I wasn’t like feeling betrayed, like I was betraying someone. I felt very authentic, real, like this feels good and normal, which was such good information for me, right, like that’s why I think I’m so proud of myself for doing this, because it was stepping out of my comfort zone and kind of gauging like, okay, how healed am I? Right, all the work I’ve been doing, all the things I tell people, I coach people on every day and I’m implementing it too, and it’s working, and so I was just really happy about that. But, honestly, I couldn’t have asked for a better first date. He was golden, he was amazing.

We talked for two hours. I think we could have stayed there for even longer if he didn’t have somewhere to go and I mean it would have been awkward to stay at where we were for longer than that. But I just am so grateful that he wasn’t all the things I created in my mind that a first date could be, all the horror stories that I’ve heard about, or weird things or creepy. I didn’t feel unsafe, which is really important to me. Do I feel safe with you? That’s important. So I don’t know. So I don’t know.

I really like in that moment after well, okay, so after the two hours we left, we walked out together, we drove obviously separate cars, and he’s like can I give you a hug? And I’m like, sure, and I guess I went in for the side hug, which my kids have totally teased me. They’re like mom, you gave him a side hug. I’m like I don’t know. That’s just how it happened. So I’m still awkward, right, I’m still it, just I don’t know. That’s what happened.

So that is the story of my first date with this person, with this person. But what I learned is that I could see myself in that moment, after I sat in my car and I was like I have had my heart locked up in a million chains and locks and I’m like no way am I ever getting married again, no way am I ever opening my heart to someone, because it was shattered in a million pieces a million times over and over again. So I really just kind of have shoved that down, that thought and that feeling, and in that moment I realized like, oh, there are really good men out there, there are people that don’t cheat, right, that don’t have affairs Okay. The other side note is he has a similar story as me and I didn’t know how much that would resonate with me, how much that connected me with someone, but a hundred million percent I think whoever if I ever do choose to marry, they will have shared the betrayal experience. I could be wrong about that, but the fact that he felt the same pain that I have really felt very connective, very important to me. That is something like, oh, interesting, and so I didn’t know, because I haven’t ever dated anyone besides him and so his story was so similar to my story and I really appreciated that Anyways.

So as I was reflecting, I was like, oh, I could see myself maybe dating more or getting in a serious relationship. I know something about myself is that I’m not one to like want to date 10 men, five men, three men at the same time. Like I’m, I’m a more like I want to just be with you, right, like if I find someone, it’s like no, we’re going to just be together, like I don’t need to be dating around. I know that that’s not who I am, but you got to find that person right, find the match. So, anyways, it really opened my eyes up and it’s been really fun. It’s been really fun.

I just appreciate my kids, my friends, how supportive and they’re my cheerleaders. I don’t know why I’m getting emotional, but for a long time I felt alone in my pain, and now I know I have a whole group of women and my own children and my parents and my siblings cheering for me to be happy, and I am happy, but the possibility that there is a good man out there that can love me, for me and that isn’t lying to me and gaslighting me and criticizing me all the time and wanting me to be different. Anyways, it was just really beautiful. So I felt my heart kind of open, a little bit open to okay, maybe this could be a possibility, to okay, maybe this could be a possibility, maybe I could meet someone. Right, the fear kind of dissipated and I do have lots of other concerns and worries and anyways.

So I just want to shout out if you are where I am want, shout out if you are where I am. Doing hard things is a way to stretch and grow, and I just want you to know that you can find your happily even after. If you want to learn how to live happily even after, sign up for my email at hello at lifecoachjen with one n dot com. Follow me on Instagram and Facebook at happily even after. Coach, let’s work together to create your happily even after.

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A woman with blonde hair wearing a white turtleneck and plaid jacket smiles at the camera.

Hi, I’m Jennifer

I love helping women and men heal from betrayal. I originally started this podcast with my husband and since my divorce I have taken it solo. I love sharing and talking about the 50/50 of life and providing tools to help you along your path to healing.