Dating an Old Flame After Divorce




Jessica: Have you reconnected with any old flames since your separation or divorce? Maybe you found someone on Facebook and restarted conversations or more? We’re hearing about those situations all the time, and that’s exactly what we’re talking about in today’s episode of the Divorce etc… podcast. We’re the exEXPERTS, Jessica and T.H. We focus on helping you navigate your divorce and successfully moving on with your life. Please follow us on all social media at exEXPERTS, and check out for tons of free divorce related resources. Let’s bring in today’s guest.

T.H.: I mean it just makes sense if we’re talking about relationships and dating to have Jen Hurvitz here. She is the founder of Doing Relationships Right. She has a podcast, she is an author, she is a date coach extraordinaire. She is a no holds barred advice giver. We’ve talked about a lot of things with her that some we agree and some we don’t agree. But at exEXPERTS, we’re here to give you a lot of different perspectives, and you pick the lane that works best for you. We are so happy to have our friend Jen back on the show.

Jen: Yay, I’m so glad to be here.

Jessica: Hi Jen!

Jen: Hi guys. I’m so excited to be here. I love that you have different perspectives. I think that’s awesome.

T.H.: You have to. We don’t all think the same.

Jen: No.  

Jessica: And I love that we have different perspectives from you sometimes, like when we did that episode and you were like, ‘You can never merge families!’

T.H.: Blended families, oh my god.

Jen: Never blend them. Never.

T.H.: Oh my god, you guys have to hear that episode.

Jessica: But okay, so the whole reconnecting thing, we were literally even just talking about this before we started recording. But first, on the one hand, you’re like, that was my high school boyfriend. That was someone I knew in college, whatever. But explain to us the emotional mental reason why sometimes that’s where we go.

Jen: Well, I think it’s comfortable. Don’t you think so? Don’t you think it’s like a warm, fuzzy sweater that you just want to put on? You’re like, ‘God, it was great 25 years ago, so let’s just do it again.’ Right? You’re like, let’s just get on Facebook and go through my friend list and see who’s single today. You know what? What’s wrong with that? I think the apps are scary. I think that my clients come to me, I know they do, they come to me and they’re like, ‘I am scared out of my mind. I don’t know what I’m doing. I just got divorced. I’ve been married for blah, blah, blah years. I’m ready to date. But help me god, I don’t think I can do the apps. Where do I start?’ Do you know what? I go, ‘Get on LinkedIn.’ LinkedIn is the hottest dating site right now. It’s awesome.

Jessica: Come on!

Jen: I swear to you.

Jessica: What?

Jen: LinkedIn, Facebook—and I’m not talking about Facebook dating. I’m telling you

Jessica: Wait, stop, how do you even know on LinkedIn who is single?

T.H.: You’re checking credentials—

Jen: Because here’s why: you’re checking credentials—

T.H.: Are you working? Where have you worked?

Jen: Yes, T.H.

Jessica: Fine, but you have no idea if they’re married, if they have kids, what kind of relationship they’re in.

Jen: Well, do you kind of do, because here’s the thing, and this is a positive podcast right now, I’m not talking about looking at married couples. We’re not poaching. This is like for real, for fun.

Jessica: Right.

Jen: You have connections on Instagram. I mean, Instagram too, Facebook, you know your mutuals. You have mutual friends. You have mutual people. You have friends, you have all the blah, blah, blah, right? You also have a little bit of trust going on and honesty. You have everything in front of you in their credentials on LinkedIn, right? And you can do your due diligence without hiring a private investigator, without having to Google the person or do a reverse Google search. It’s all right in front of you. Let’s say that you find Steve so and so from ninth grade. Okay, and you’re looking at Steve so and so, and oh my gosh, you’re looking and you notice there’s no pictures of kids. Or there are pictures of kids, but there’s no wife.

Jessica: Pictures where? LinkedIn doesn’t have pictures of kids.

Jen: Okay, but LinkedIn definitely says—I mean you can look at your stuff on LinkedIn pretty deep.  

T.H.: Mine does not tell my personal.

Jessica: Me neither.

T.H.: But I do like the idea of looking on LinkedIn—

Jen: Mine doesn’t either.

T.H.: —for employment, and they’re not like a deadbeat.

Jen: Right. So you could go to Facebook first and then jump over to LinkedIn, right?

Jessica: Now they’ve seen that you’re looking at their profile on LinkedIn. They can tell—

Jen: Okay, only if they have a premium package. I’m not premium.

Jessica: Okay, so you can’t tell anyone who’s looked.

T.H.: Right. You can only see that people have searched you, but you can’t see exactly who they are.

Jen: Yes. Yes.

T.H.: So I’m going to tell a quick story. When I separated, I was not interested in dating because my ex was with somebody already, who was now in my kids’ lives. I was thrilled to be out of my marriage, but I was overwhelmed by everything. Dating was the last thing on my mind. Facebook was new back then. Everybody, we’re not super old, but we’re a little older. This guy reached out to me who I’d had a total crush on, and he had a crush on me in college. He goes, ‘Can you believe I just found you?’ I was like, ‘Oh my god, Michigan man.’ And he was hot. I was like, oh my god, this is perfect. This is going to be my second first date. It’s going to be with Michigan man. We knew the affection was there, but it’s so interesting because he could have been a murderer since the last time I saw him. He could have committed fraud. But I was like, ‘Oh!’ I go right back to college. I’m like, ‘Michigan man, that’s a great idea.’ We went out on a date.

Jen: Okay.

T.H.: And it wasn’t really a date in his mind. For me, it was like a first going out with a guy.

Jen: Sure.

T.H.: Nothing romantic happened, but I sat and we talked for hours.

Jen: Oh my god, I love that.

T.H.: And I was like, ‘Well, that was good.’ Then I got into a crazy crush in my head on him. Then I had to back myself off. But there was definitely a trust and a comfort, which could be very misleading, which I want you to share with everyone. Be careful. Just because they were a certain way back in the day, doesn’t mean they are now.  

Jen: Oh my gosh, that’s so true. Also, you’re vulnerable when you first get out of your first—

Jessica: Yes.

T.H.: You’re needy—

Jen: You’re anxious.

T.H.: You’re naïve.

Jen: Yeah, your first one out of the gate is always a little bit—you know how I feel about that—a little bit iffy. You got to be careful.

Jessica: I literally had forgotten about this, but now it’s all coming back to me.

Jen: Yeah, remember?

Jessica: When I was newly separated the first time, because this was before even Boston, and I actually know that I wasn’t the one that reached out, because I just wasn’t even in that headspace, I reconnected with sort of my first love from my Teen Tour in high school.

T.H.: She was 15, everybody.

Jessica: It wasn’t in Israel. That was after.

Jen: Okay, a different—oh, it’s like your Teen Tour.

Jessica: Trails West—

Jen: Yes, Trails West!

Jessica: Trails West. And I mean, whatever, he was kind of my first love. We never had sex or anything. We were so young back then, kind of my first love. I don’t remember how he reconnected with me on Facebook, but he had. You know what, it just so happened that he was also separated from his wife and working towards divorce. We got together a few times

Jen: And?

Jessica: —and it never went anywhere. I think we made out. Ultimately, I was like, he may still be like a great person, but lifestyle-wise—and he lived all the way out in Long Island and whatever—it really wasn’t going to work.

Jen: It’s kind of practice, right?

Jessica: A little bit, like totally, the familiarity. I cannot believe that I had forgotten about that.

T.H.: But you’re talking about somebody talking you were close with when you were 16. 

Jessica: It was 20 years later. For everybody listening, think to yourself, have you had at least one kind of rekindling of someone in your prior life before marriage that felt comfortable to you? I never thought that that was going to go anywhere with him, so it was fine. But I actually wonder how many people think like, ‘Okay, now this is our chance,’ and they think there’s going to actually be something now.

Jen: I have friends, that I can tell you right now, that thought they were going to marry the person.

T.H.: Because it’s so easy and so gentle.

Jessica: You have no idea what they’re like.

Jen: No, well, let me tell you something else that’s really crazy. I have a story for you. I have a girlfriend that went to camp with this guy, right? He was her love at camp, whatever. He reached out. They kept in touch. They were always friends. They always liked to touch base on their birthdays and blah, blah, blah. It was all this little hidden like, one day we’ll be together, even though they were both married. They both had kids. They just had this little friendship bracelet thing with like, one day I’ll see you at the buffet at a bar mitzvah kind of thing, right? They ended up both getting separated. They heard through the grapevine that they were separating and blah, blah, blah, and dee, dee, dee, and they got together. They were together for X amount of months. We all for sure thought that they were—

Jessica: Going to get married.

Jen: —going to get married. And he got back together with his wife.

T.H.: Jen, do you know the statistic—so I’m putting on the spot—or an idea of when you go back and rekindle an old love? I do know people who were sweethearts in high school, had their lives, and now they’re together.

Jen: Yes.

T.H.: And so I do have some of those stories. But does it work more than not? Does it not work more than it does?

Jen: You know what, I’ll look it up after and I’ll send it to you and we’ll put in the link.

Jessica: I feel like it can’t work more often than not, because we’d be hearing it much more often. Do you know what I mean?

T.H.: But everybody talks about the bad stuff. Nobody really talks about the good stuff.

Jen: I think this is good stuff. I really do. I think that if there’s just this, like I said, this cozy, warm, fuzzy—

T.H.: Blanket. Yeah.

Jen:—like this blanket. Even though the time is lost in between, and you go your separate ways, and you do your separate thing, for whatever reason, when you come back together, I don’t know why I’m getting emotional, but you come back together and it’s that same feeling.

Jessica: Yes. You pick up kind of where you left off.

T.H.: Like no time’s—

Jessica: I’ll tell you this, though, thinking about the Teen Tour guy, yes, it’s the warm, cozy feeling and all of that. But I’ll say this, I think for me too, it wasn’t like we had ever dated back in the day and had any kind of a bad break up. We lived very far apart. We met towards the end of high school or whatever. It just wasn’t going to work. We went our separate ways and hadn’t stayed in touch. In both of our minds, I’m sure it was still the idyllic situation, because there had never been any kind of negativity. But I will say, for everyone listening, and I wonder if this is how you feel, it was the idea of not having to go through your entire back history and learning someone all new from scratch.

T.H.: Right.

Jessica: Even if you missed 15 years or more, you already had some kind of a foundation prior to that—

T.H.: You already have a connection.

Jessica: —where you came from, your siblings, your parents, whatever you have to catch up. It’s someone who, regardless of how long before it was, found you attractive, who thought you were wonderful—

Jen: It’s safety. It’s a safety thing.

Jessica: It’s safety, but it’s also like, fuck my newly recent ex. I am still worth something. This guy, all these years later, still thinks that I’m hot and that I’m nice. 

T.H.: The bomb.

Jessica: No, but do you know what I mean? For me, that was part of it. It’s been all of this time, and he still—

Jen: Still wants you.

Jessica: —thought I was this great person that I had been 20 years earlier, which of course I was.

Jen: Of course you were.

Jessica: Of course I was.

T.H.: Maybe that’s why we go back because we need to be reminded.

Jessica: That’s what I think.


T.H.: Also, that was like a happy, innocent place for us, far away from the chaos of your marriage and your divorce and your conflicts. That was fairytale land back in the day on a Teen Tour, high school and college.

Jen: Well, because you didn’t have all this stuff you have now, right? You don’t have the mishegoss and the crap that you have with your—

T.H.: Right. It was simple.

Jessica: It was like escapism also.

T.H.: Yeah.

Jessica: Just able to reminisce and then have that attraction that was still there from years prior. And like you said, I mean, not for me and Teen Tour guy, but it is probably a good place to start re-experimenting.

Jen: It is.

Jessica: Because the whole getting back into things is actually right.

Jen: Because it’s safe.

Jessica: Right.

T.H.: I think safe and comfort are the two big words here. I’m curious, anybody listening to this show, we want to hear from you, have you rekindled a relationship from someone in your past, from high school, or college, or Teen Tour, or your kindergarten love? I mean, who the hell knows. We really do want to hear from you on this because I think the conversation can go on and on. But we’re going to pause for a moment. Because we know it’s hard to get honest and reliable information about your divorce, dating, and life in general, so we’ve done the work for you with exEXPERTS and our Divorce etc… podcast. Jess and I had one another to ask all of the questions and figure out the answers. Now you have us too. We are your no bullshit, no nonsense girlfriends through divorce and beyond. Ask us anything about life and all that comes with it. Be sure to subscribe to our weekly newsletter to get exEXPERTS in your inbox and find out all the updates on the latest Divorce etc… podcasts and events. Don’t miss out on information and tips you really need going forward through your divorce. If you want some one on one time with us girls, you can sign up for a private session. We know that the work really begins when the divorce is over. You can connect with us and get all of this information at We’ve lived it, so we get it.

Jessica: Here’s where I want to go for the next question, Jen. We’re talking about these rekindling your relationships with someone where the fantasy was still there, and there wasn’t any bad blood. What about the idea of people wanting to go back and reconnect with someone where there was a break up for a specific reason? And even though—

Jen: Don’t do it.

Jessica: Well, I don’t know. Yeah, maybe, but yes, yes. People are thinking like, ‘Okay, but that was 15 years ago. And so maybe now?’

T.H.: What did I know?

Jessica: Right. So what do you think about all that? Share your story.

Jen: I mean, I’ll tell you. I was with my boyfriend for, god, six years. Last year, we broke up. We weren’t angry at each other. We weren’t mad. We just went our separate ways. It wasn’t working. For whatever reason, we wanted different things. Our paths went in different directions. And it was awful. It was awful for both of us. But we were saying goodbye, and that was it. I was definitely ready, and he was not. He wasn’t. I think he just definitely was not prepared. And I was already done. I was done. I was done in my head—

T.H.: Right, you already had it in your head.

Jen: I had it in my head. Like a lot of people do, I think when you break up with someone, either a separation or a divorce, one person sometimes is over before the other person.

Jessica: Yes.

T.H.: Yeah.

Jen: Very oftentimes. And so I was ready, and I was done. I broke up with him, and he was devastated. I moved on very quickly. I had met someone that I was friends with, a good friend of mine from home, from Detroit, and we were friends. Through my five year relationship, we remained friends. We never met. We never did anything that wasn’t—it was all aboveboard. But we were friendly and friends. Yeah, and I started talking to him afterwards very quickly. He came in hard and fast and realized I was single and just love bombing and blah, blah, blah. I moved into a relationship very quickly that definitely did not serve me in the end. But over the year, Jim blocked me. We did not speak. I mean, it was over, and I never thought I was getting back together with him. I never looked in his direction. It was done, and I was done. I had moved on. He had moved on. He had a girlfriend. We did a podcast yesterday where we explained everything. But over the year, he did a lot of work, and I did a ton of work. It was horrible my relationship. I was in therapy, he was in therapy, blah, blah, blah. I’m going fast. Two months ago, three months ago, we got back together. We just found our way back to each other. I don’t want to cry, but sometimes in life, you need to let go of something for lots of reasons, a) to realize what the hell you’re doing in your life. I needed to get my shit together. I didn’t know it at the time, but I did. I had to do some work on me. He had to do some work on him. I think my point is that sometimes breaking up is the best thing you can do. You just don’t know it.

T.H.: Right, because then you take a step away.

Jen: Yeah, I took a step away. But I had zero intentions of ever—both of us were done. When you say it like, is it okay to get—I never would tell my client that it’s okay to get back together with an ex. So, from a coaching perspective, I was like, ‘What Jennifer? What are you doing?’ But…

Jessica: But your relationship with him, like you said yourself, it had been six years. This was post divorce.

Jen: Yes, post divorce.

Jessica: You were broken up for a year and got back together, which I feel like, I mean, I personally can understand. However, I’m talking about someone who you dated in college or in your twenties, and it ended for whatever reason, and then you like moved on and got married and were in another relationship for 10 years, 20 years, and now thinking, would that be a good idea? I know of a girl right now who is dating—I met her in college. She married another guy we went to college with. They were married for 20 years. Presumably, when she was kind of done in her marriage, she somehow reconnected on Facebook with her high school boyfriend. She and her husband got divorced. She moved here to be with the high school boyfriend. Now it’s been like, I don’t know, several years, like three years. They’re living together. She thinks like, this is her guy.

Jen: Okay.

Jessica: I’m like, interesting. I feel like you think this is your guy.

T.H.: Maybe he is her guy.

Jen: Maybe he is her guy.

Jessica: Maybe he is.

T.H.: It’s three years.

Jessica: Maybe he is. 

Jen: Why wouldn’t he be?

Jessica: I feel from the brief conversation we’d had about it, it just seemed like, I don’t know, it seemed too easy. I just was worried for her. You’re really going all in and investing in this.

Jen: Sometimes it’s easy.

Jessica: It’s easy to get sucked into the sense of comfort—

Jen: Okay, I totally get that.

Jessica: —and not be completely objective and not have a fully clear perspective because of wherever you’re coming from. 

Jen: Sure.

T.H.: But, Jen, so now we’re going to reverse it and we’re going to coach you. I think your situation is different for a few reasons. You were well done with your divorce.

Jen: Yes.

T.H.: You knew already what you didn’t want and what you did want. You needed this break up to get your shit together, which is exactly what you used this time for. So that when you decided to go back to him, or if you hadn’t decided to go back to him, you would be clear and you had finally arrived for yourself.

Jen: Yeah.

T.H.: And you hadn’t arrived yet. So you may have met him, but you hadn’t fully become where you needed to be. Now you are in a place where you can be together at the same level. I think that’s different.

Jessica: No, I agree. It’s 100% different. Also, Jen and her guy, I mean a year is a long time, but they were only not together for a year. I’m talking about you’ve dated someone, and 15 years later, you rekindle.

T.H.: Right, but she went back to a comfort. So we all go back to what’s comfortable for us, no matter what it is, like a guy, a girl, a habit, an addiction.

Jen: But also, Jim and I would not have gotten back together had he not gone to therapy.

T.H.: Right, because you were already up here and he was still here.

Jen: Right.

T.H.: You both had to have been—

Jen: Yes, do the work.

T.H.: —where you needed to be for each other.

Jen: I have a question. As far as the girl who got back together with her high school sweetheart, was she coming out of a divorce as well?

Jessica: I think she was unhappy in her marriage.

Jen: Okay.

Jessica: I think she deliberately reconnected with this guy on Facebook.

Jen: Also, that’s different. That’s what we need to have another episode about.

Jessica: Yeah. And then maybe he was already divorced, the high school guy, and it was her first boyfriend or something from high school. 

Jen: That’s a little different.

T.H.: But it’s so much easier.

Jen: So much easier.

T.H.: Because you got a guy. You don’t have to deal with dating apps. You don’t have to sit at a bar. You don’t have to be set up.

Jen: Yes, it’s more comfortable.

T.H.: I don’t discourage that. I feel like for your own good, to get your feet wet. Get a little skip in your step. Have a little boost of your confidence. What the hell, what do you have to lose, as long as you just keep your head on straight?

Jessica: Agreed. I think I’m more like, can it work?

T.H.: Look who it worked for?

Jessica: Not in her situation in particular. This is what I think. I think that a lot of people get out of their marriages and have reconnected with an old flame and feel like because they reconnected, however the reconnection happened, because somehow they reconnected, they’re like, it’s meant to be.

T.H.: Totally.

Jessica: It’s meant to be. We’ve gone 20 years without talking.

T.H.: And look us now. It’s our time.

Jessica: Somehow you found me. I found you. Through a friend, at someone’s funeral, at someone’s kids Bar Mitzvah, whatever the hell it is.

Jen: It’s bashert.

Jessica: That’s right.

T.H.: It’s meant to be.

Jessica: That’s I think really where more I’m trying to go.

Jen: I get you.

Jessica: I think that people think that just because they reconnected means it’s a sign.

T.H.: Right.

Jen: But they can’t stay together just because they think it’s a sign. It has to work.

T.H.: I know. But they’re living in la la land. There’s a girl I know who was recently divorced. It was amicable and everything. I’m like, ‘How are you doing?’ She goes, ‘I reconnected with the love of my life. It’s going to be great.’ In my head, I’m like, ‘God, I hope so. But I don’t think so.’ But I didn’t say that to her.

Jessica: Right. That’s what I’m thinking. But that’s what I’m thinking about the other girl.

T.H.: It’s almost like you need to go through this after your divorce to learn that there’s so much more to another relationship.

Jen: And you hope to god that they do. But the ones that don’t are stuck in this relationship—

T.H.: They’re going to have a rude awakening again, that’s all. That’s how you learn.

Jen: Yes.

T.H.: That’s how you learn.

Jessica: I agree with the idea that it is a nice way to re-enter the dating game because—

Jen: But don’t put all your hopes in one basket. Don’t put all your eggs in one basket, right? Don’t count on it to be something. Don’t go searching for this fairytale.

Jessica: Right.

T.H.: Right.

Jessica: Right. That’s what I think. Yeah. But do you feel the majority of people that you know, or the majority of your clients have at least rekindled at some point with someone prior to their marriage again? I’m not talking about having taken a break like you dated someone after. I’m talking about someone from way back when.

Jen: Usually, the first relationship out of the gate happens that way.

Jessica: Yeah, because you’re too scared to really get out there, get out there. 

T.H.: No, but it’s easy.

Jen: It’s easy. Or it’s someone who’s been your friend, or you’ve been talking, or you met playing tennis, or it’s your wife’s sister’s cousin’s brother, or it’s your friend you met at the dog park. Do you see what I’m saying? It’s that, ‘Oh, he found me on Facebook. He slid into my DMs. I heard you’re single from your cousin’s friend.’ It’s that one.

Jessica: Right, right.  

T.H.: What are the odds?

Jen: What are the odds? What are the chances?

Jessica: Yeah, exactly.

Jen: So you can Google it. ‘Oh, my god, it’s meant to be,’ but no.

Jessica: It’s so funny.

Jen: Just have fun.

Jessica: Yeah, and according to Jen, Doing Relationships Right, it’s alright to do that.

Jen: It’s alright. But just don’t put a ring on it.

T.H.: Don’t get too caught up. Just enjoy it for what it is.

Jen: Right, for now. Do your theory of dating for now, everybody. It’s in the book. Just date one day at a time.

Jessica: Totally. Totally. Alright, well, we’re going to do another episode about the other part of that topic that we talked about. But in the meantime, if you have actually rekindled with someone from your past, someone from college, someone from high school, someone from camp, let us know. We want to continue the conversation.

T.H.: And are you still with them?

Jen: Yeah, we want to know if it worked.

Jessica: Right. How long did you rekindle for?

T.H.: Right. We want to hear your story.

Jessica: And are you still together.  

Jen: And are you still together? Yeah.

Jessica: Totally. If you enjoyed this episode of the Divorce etc… podcast with the exEXPERTS today, then can you help us out? Please, subscribe, rate, and review the podcast to help us increase our reach and be able to help more people like you going through divorce and beyond. Check the show notes for more info on Jen, her books, her coaching packages, and her podcast: Doing Relationships Right. And of course, share this episode with anyone you know who can benefit from listening. Have a great day.

Leave a Comment

You must be logged in to post a comment.