Slightly Unsupervised

Reconnecting After Years Apart: How We Rebuilt Our Friendship

Jennifer Hobbs & Jackie Schroeder Season 1 Episode 46

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We Found Our Way Back: Rebuilding a Friendship After 15 Years Apart 

What happens when a friendship you thought was gone forever… finds its way back? 

In this deeply personal episode of Slightly Unsupervised, Jennifer and Jackie share the real story of how they reconnected after 15 years apart—and why rebuilding a friendship later in life is rarely instant, but always worth it. 

From high school best friends to years of silence, life changes, and separate paths… this episode walks you through the exact moments that brought them back together. It wasn’t one big conversation or a dramatic reunion—it was small steps, uncomfortable reaches, and choosing to show up again and again. 

They open up about: 

  •  The first awkward reconnection (and why it matters) 
  •  How vulnerability and courage rebuild trust 
  •  Why consistency—not intensity—is what brings friendships back to life 
  •  The emotional reality of reconnecting after divorce, distance, and time 
  •  What it really takes to feel safe, seen, and connected again 
  •  How to know if a friendship is worth trying again 


Plus, their Bestie Rapid Questions get real, emotional, and honest—covering what they wish they had said, what they’ve learned, and why losing each other actually made their bond stronger.
 
If you’ve ever lost a friendship, wondered if you should reach out, or hoped for a second chance… this episode is your reminder that some connections don’t disappear—they just need time, space, and a little courage to come back. 

Because the best friendships aren’t always the easiest… but they might just be the ones worth rebuilding.
 

This episode of Slightly Unsupervised was brought to you by the creators of Bestiemony®—the original friendship ceremony that proves soulmates don’t always come with a marriage license. Hosted by Jennifer and Jackie: best friends, business partners, and co-founders of the movement celebrating real, ride-or-die love.

💍 Book a Bestiemony: rhinestoneweddingchapel.com/bestiemony
📱 Follow us on Instagram at @Bestiemonies
📩 Got a bestie story to share or a subject request? Email us at ChickologyPodcasts@gmail.com

Jennifer

Hey there, I'm Jennifer.

Jackie

And I'm Jackie.

Jennifer

And welcome to Slightly Unsupervised, where best friends, business partners, and the chaos behind Testimony, a ceremony we created to celebrate the kind of soulmates who don't come with a marriage license.

Jackie

This podcast is all about that friendship energy: the deep stuff, the messy stuff, and the laugh still till you snort stuff.

Jennifer

So whether you're driving, folding laundry, or hiding in your car for some peace and quiet.

Jackie

You're in good company. Let's get slightly unsupervised. Today's episode is all about how we found our way back after 15 years. I don't think either of us knew if we'd ever be friends again. What do you think, Jen?

Jennifer

I think that's true. I think that, um, and I think this is this is where we should insert the way we did return, because I think it's important for people to really if we're gonna give you hope, we're gonna give you hope on how it you can reconnect. And it was not overnight and it did not happen. One day we were, I wouldn't say we were enemies, but one day we were blah, and the next day we were besties. We had to build back into that. And we've talked about it before. We have many podcasts out there. I'm gonna assume that you've known some of it, but maybe not all of it. So let me go over what happened, how we found our way back, because I want to give you connection. So Jackie and I uh went to the same high school, and we um we had a friend that was our class president, both of our friends, and she generally would put these things back together. And she um not sure what happened, but she I think had some kids at the time and she was out. She wasn't gonna help us with it. And we're a s clut we're a school that's very close to each other even now, just because we grew up in a tiny school, so everybody knows everybody. I mean, it's it's a pretty connected community. So having a reunion was going to have to happen, and somebody was going to have to take over. And I'm pretty sure that she told Jackie, you're gonna have to do it, right, Jack? And sent you money and said, Here's the money that was left over from the last one. Good luck.

Jackie

She did ask me. She did ask me.

Jennifer

So she turned it over to her. And so Jackie was now in charge of a reunion. Was it our 30th? 20th.

Jackie

Um, see, she was there for the 10th, so it was our 20th.

Jennifer

20th reunion. I think. Okay. Wasn't our 20th? I think it was the 20th. Yeah, it was, I think, our 20th. So so anyway, so at some point, somehow, we must you must have got a hold of me, or I got a hold of you, or something, or I don't remember the exact details about it, but I think I got a hold of you. Yeah, because you had to tell me about it. I need help. Yeah. You need to help. Yeah. So we said, okay, we'll help. You know, I lived, I lived pretty far away from you at that time. I was six or seven hours away, but I said, okay, we can help. We'll come down and, you know, you had to put together all the other stuff. You had to put it all together, but we would come down and help decorate and stuff. So I think that's how we kind of did it. So we stayed at a house and we live up in a mountain, and Jackie had her house, and I stayed at another house. And so we came over and we helped put the decorations up. And as soon as you start getting in that space, right? The same space we'd always been in, which is like in a mountain with all our friends and stuff, you just start, you know, having those sort of little connections, right? Little like, you know, we used to be, we used to do that, or this song came on, or whatever those things are that you're getting back into that sort of nostalgic reunions are nostalgic anyway. So it's back to being high school.

Jackie

So we kind of did that and we had a really good reunion. Somebody asked me how it felt, like asking all of you to help me. To help you, yeah. I'll tell you honestly, it it was like walking on eggshells. Was it? Yeah, it was all that. It was kind of hard because um I hadn't asked you like the 10-year. I didn't ask you guys all for that help. Um, I think you guys did help with a little decorating just because we you guys everybody had offered for that 10-year, but it was just everybody the tenure everybody does offer and do everything. Of course. Because it's just the fact that I took over for the 10 20 year and it just took over a whole nother situation. Right. That was really hard. Right.

Jennifer

Yeah.

Jackie

And to it was and I did make those notes about the situation. It was like walking on HL asking for the help.

Jennifer

Right.

Jackie

And it was I think that kind of brought us back together a lot on that one.

Jennifer

Yeah. Because somebody showed up, right? It was like, can you help me? And it's like, okay, I could come, you know, I'll I'll do it. I'll say that.

Jackie

And if you remember, I was going through a divorce. I had just gone through a divorce, and you guys really didn't know any of that. I had gone through a divorce, actually.

Jennifer

Yeah.

Jackie

I had already started dating someone else.

Jennifer

Yeah, you were dating your current husband, no. He was, yeah.

Jackie

And so nobody really knew what was going on. I really hadn't told many people. I was just going through my my my thing. Because I remember one girl asking me, yeah, when did that happen? Oh, how did you get him? And I was just like, I didn't get him. It just happened.

Jennifer

He got me, by the way. I mean, yeah, that's how we need to be looking at that. I am a prize position.

Jackie

I was just like looking at her going, is that a question you asked?

Jennifer

No, that's not. See, I just stomped on her. That's the friend I am. What do you mean? How did she get him? How did he get her? That's what I'm saying.

Jackie

So actually, it's one of the girls you just talked about before we got online. So really. And her name starts with a B. See?

Jennifer

I will attack when it provoked. So, but yeah, so that was kind of the the just the little clipping of it. Mm-hmm. We went, we did some, there were other activities that weekend. So we we kind of got back into the same space. And then I think from there we went back to our perspective. I went back home, and then we just we had opened the communicational line enough to say, I think even you were like, hey, do you want to come down and stay for a weekend with your son? Yeah, but do you want to come? So I'm like, see, now here's where it gets complicated. Two things have happened so far that I want to go over this because we're trying to help friends. First, Jackie asked if we could help. That's a reach, right? She was uncomfortable. She did it anyways. So at that moment, if we'd said no, I'm not helping, that would have killed it, right? So you have to be willing to do some things to get back in space. It wasn't necessarily comfortable for me either, but you do it, right? You say, okay, we'll take a baby step. And that's what it was. It was a baby step. Like, can we be in the same space? Is that safe? You asked, you put you extended something. I agreed to do it. We did it. So the second one, where you asked me to come down to your house for the weekend, that's what I remember was the house for the weekend to your house. Again, she extended something, which takes courage, and me accepting to come down again. So those are little tiny building blocks that happened the way that we found our way back to each other was that she extended, I came, I actually brought my son with me and we had a weekend. We had some friends over, some people that we both knew from the mountain, and they came over. We spent, but we had a good weekend, right? We had a we're we had a nice weekend. When I went back probably home Sunday morning and, you know, we spent probably Saturday. I don't remember what we did. I remember the one night we did. I don't remember what we did the next day. Probably went to the lake. We always go to the lake. And so, you know, just little baby steps, y'all. And baby steps that may not be the most comfortable, but you still do them, right? She had to extend and I had to come. So be keep that in mind when you are thinking about maybe returning to a friend about if they ask to be receptive to that and to extend. I had to drive seven hours to come see her, right? That's a big that's not like she lived down the street from me. I had to make a journey to go see her. So I think the next thing probably Jackie.

Jackie

And I want to admit, I had anxiety that weekend. Did you? Yeah. Yeah, I do. I still had some a little bit of a harder time because I was still a little anxious just about everything. Yeah. And I'll admit to that. I did have I wasn't the perfect uh hostess. What do you call it? Hostess. Hostess with the most because I I can be the perfect hostess. But I had a little anxiety. I was a little worried about everything. But I think it turned out good.

Jennifer

Yeah. And I came. And we, you know, slow connections, right? Slow connections. I think the next thing that we must have done after that was you came to my house. Do you remember that? You guys came up for your anniversary.

Jackie

Yes. Rick and I did. Yeah. And you did something really special for us.

Jennifer

Yeah. So the next connection is like, okay, I've come to your house. Now you make a seven-hour journey to come see me, right? And you did. You're like, okay, I'll come. So those are all just little things that happen between us that now we're spending a little more time together. We're in different environments. I'm in your environment, you're in my environment, you're at my house, I'm at your house. We start to just sort of slowly build back and forth between this. And yes, it was your anniversary. I'm pretty sure we sent you off to dinner. We had a friend that worked there. I think he did some fun things for you there. But just little things, right? Little connections.

Jackie

And then you had actually, didn't Chrissy come up?

Jennifer

Was it that time? No, she came later. That was a different time. I thought she was the first time. No, the first time you came, Chrissy came when it was a motorcycle weekend. Yeah. It was a different weekend. But she came. Yeah. We had another time with Chrissy with that. Um, anyway, so that was Kit. And then what else did we do that was really kind of slow but steady? Just back and forth, maybe a few times. And then I think we went to Vegas what time did we?

Jackie

Oh, we did a weekend where we all just went to the village. Right. Remember everybody was there, right? Was it like we did like a weekend?

Jennifer

Yeah, yeah. I brought Michelle up and I think the other girls were up there.

Jackie

Kind of girls there. Shane was there.

Jennifer

Oh, yeah, that's right. Yeah. You got mad at me about Shane.

Jackie

The other one was there.

Jennifer

Do you remember that when you got mad at me about Shane? Because I was like, oh, let me send boobs. Because she'd be out of a job. You're like, you can't be saying things like that. I'm like, oh my God, my sister had a boob job. They're not even attached to her anymore. They're just like for show. Let me see ya. Like, and you're like, you can't say things like that. So we got a little tiff. We got to get over it. We moved on. Yeah. Then we went to then we went to Vegas. We went to Vegas for a girls' weekend. That got a little wild too, but we had a good time. And just little things, right? There was a time in Vegas that that you needed me, I think. And I showed up for you. Mm-hmm. Hard. I was in my protective gen mode with you. You know, we had a little bit of whatever, and I got in the middle of that and took care of that and made sure you were okay and got you back safely where you needed to be. So again, little tidbits of things that happened between us that just slowly build into can I trust you? Am I safe with you? Are we still connected? All those things had to be reconnected. Like we're not like one little plug-in. It was like different things needed to be plugged in on different aspects. Like, can I trust you again? Am I safe in the space with you? Do we still have a connection? Do I still enjoy you? Are we still funny together? Are we still gonna have a like all those little things? You have these questions in your head about that of how are you going to be reconnecting to somebody and how that all flows? And is it a safe space? And it took time, y'all. It did not happen over yet.

Jackie

And it's definitely back to where, yeah, definitely a safe space. That's for sure.

Jennifer

Yeah. So all those things happened. Give that stuff some time and don't expect to be like the first time we hang out again, this is gonna be full blown. We're best friends again. We had to work back to that. We just did. It it's just part of the connection. And also our other friends that we're best friends with, they were, you know, all that kind of came together around the same time, right? Yeah. Like the connection for them and the connection with all of us to get into this like really tight knit space that is such a beautiful place to be with your with your friends and to know that we have each other's back and that we're gonna show up for each other. And we've had that, those things have been tested many times. And I think that we always come through for each other, don't you? I always feel that way for all of our friendships. Like I need you and I need you to do this and you need to do that, everybody steps in. And I that's a beautiful thing to have with your best friends. Yeah, it took time and it took some, it took some situations that you know, but eventually it can come back. And I don't think I think from the time that that reunion happened, probably three or four years in between there, don't you think? Aren't we like 38 when we had a reunion? The 48.

Jackie

Yeah, I would say so.

Jennifer

Around the 38, 39. Sometimes we do them a little later. So, you know, it didn't happen.

Jackie

And then we started doing combines after that. Yeah.

Jennifer

After that, yeah. So definitely reunions with other people. Because we start losing people and start to get harder to get people there. So all right, Jack, do let's go into the dusty rapid question. You go first.

Jackie

Okay. Do you ever think we'd actually find our way back? Yes. I definitely thought so.

Jennifer

Yeah.

Jackie

I'm glad we I didn't know how much time it would take, but I knew I always knew it would. I had a feeling.

Jennifer

Did you ever think, Jack, and the same question, did you ever think we'd be uh as close as we were before back to that?

Jackie

I didn't know if it would, but I always hoped it would.

Jennifer

Yeah, that's how I was too. I had hoped that you could come back to that. Yeah. But you don't know. You don't know because people change, right? We all grew up. So okay. What did you feel the first time that we reconnected? You said that. You were anxious, right?

Jackie

Anxious peace, love, and ah. Those are the other words I put.

Jennifer

Oh, that's awesome. Like, were you a little excited? Like, do you feel like like, okay, we're gonna do this? Like we're gonna hang out and do this and be.

Jackie

I think it goes with all of it. Yeah. It goes with all the definitely.

Jennifer

That's me too. That's how I would feel too. Okay, you're next.

Jackie

Did it feel like time passed or like we both picked up where we left off? Both, as far as I'm concerned. Yeah. Time and seeing the kids grown up, yeah, new husbands, etc.

Jennifer

Yeah.

Jackie

That's what makes it all different.

Jennifer

It did pick up, it did pass. Things were different, but the connection was the same, right? Once we got back to that connection, it wasn't a different thing.

Jackie

Like I said, just seeing the kids grown up, be having us both with new husbands, seeing our new lives, um, but being with each other, it just seemed like we're kids again. Right. Like our friendship was like where we were, like our husbands talking about how we talk, like we're like back when we were the young kids again. Right. Like we picked up right where we were. You know what I mean?

Jennifer

Yeah, we did. Like time hadn't passed, but time had passed. Like we were different, but we weren't different. It's confusing, but it it did work that way for sure. Okay. Um, what did you what do you understand about me now that you didn't back then?

Jackie

You just need to work on yourself and work on your goals.

Jennifer

That's what you thought about me.

Jackie

About you.

Jennifer

That I just needed to work on myself and my goals.

Jackie

Because I felt like you, like I wanted you to just for some reason I felt like you just like you weren't being yourself. So like you needed to do, I guess you just need to be your like do what you needed to do.

Jennifer

Right.

Jackie

You know what I mean? I I don't know how to explain it, but living a life that wasn't like to me, you weren't being yourself. So it was like now it makes sense, like how you've just made yourself into this successful person. So that's what you needed to do. Right. Or I'm just like, what are you doing? Like, what are you doing? Like all the time. That's how I felt. Like, what are you doing? So now I know what you were doing. You're trying to figure out you needed to go do something.

Jennifer

Yeah. I need to get on the path that they're doing. That makes sense. Like that makes sense now. Yeah, like it does.

Jackie

You were just like, uh like even like the people you're hanging out with, like, what are you doing? Yeah. Now I understand. And you were always trying to help people, and you're always trying to do, you know what I mean?

Jennifer

Yeah.

Jackie

And sometimes it was like, no, you're supposed to be helping me, not anybody else. Like, I was just stupid.

Jennifer

Like you know, I call her down. I'm like, Jackie, listen to me. Listen to me because I need you to remind me of this. I have to turn this person off. I'm not helping them anymore. So remind me when I want to help them. And that's what I know. Yes. So exactly. She's right about that. Or sure. Okay, you go next, Jack.

Jackie

What do you appreciate about your friendship now that you didn't before?

Jennifer

The connection. I think that I appreciate the fact that we're so tightly connected and so easily able to be with each other that I don't know if we knew that before. Like I said, there's always that time you're like, well, I had it with her, but with everybody else. You know what I mean? Like you don't realize that those connections are pretty far and few between. So you don't get that with everybody.

Jackie

Mine is support, love, peace, laughter, trust, and vulnerability vulnerability. That word is hard.

Jennifer

We have to look up dictionary words, believe me. I like that.

Jackie

Vulnerability. I'm gonna learn how to say it again. Well, I needed to practice that like five times before we started this. Vulnerable.

Jennifer

We had to look up words, y'all, and we're gonna be able to do that.

Jackie

I knew the word I wanted to say. I made that word.

Jennifer

I know. We're at it. But you like this before we do this. So we're I think this would be perfect. Yeah. I think peace, laughter, trust. Yeah.

Jackie

That's everything about us.

Jennifer

Yeah. Laughter, especially. I mean, we do have we go down.

Jackie

I love the laughter.

Jennifer

Funny rabbit holes about we could just be, y'all, we could be in like Starbucks lying and just talking about the order we just made and we're dying laughing.

Jackie

And we'll just look at the person behind us or in front of us and we'll both start laughing and we know exactly what we're laughing at. Sorry, people. All right. Do you trust our friendship more now or less more? More. Yeah.

Jennifer

It's solid though, right? It was I I don't have to worry about there was always this other third person in our relationship before. There was always a problem with that. So now that we don't have that problem, it's for now it's we don't even put our our husbands in the third equation.

Jackie

It was weird. Yeah. When we're younger, for some reason, the men we put in our equation. Yeah. Where now that we're older, we're like, you're not in our equation anymore.

Jennifer

Yeah, yeah.

Jackie

Like we need to separate, like we love you. You're our best friends too, but you're not in our equation. Like we can we know how to separate it now.

Jennifer

Yeah, for sure.

Jackie

I wish I would have known that when I was younger. I wish I would have known how to separate that. Yeah, it would have made a big difference.

Jennifer

Okay, do you think losing each other made your friendship stronger?

Jackie

Yes.

Jennifer

100%. Yeah.

Jackie

I mean, I wish we would have figured it out younger, but it's definitely made it better now. But I wish we could have figured that out younger, but it doesn't work that way.

Jennifer

It doesn't. We had to some time apart, and that's okay. But yeah, our we're stronger now than we probably would have been. We would have probably, you know, you know.

Jackie

But I think maybe these younger people will be better at it.

Jennifer

You think?

Jackie

I don't know. I listen to them. I don't think so. I don't know. They're all so weird. They're all so weird. I mean, I love y'all, but the way y'all talk to each other and the way you talk to us, I don't know. Don't listen to us.

Jennifer

I think they're too competitive with each other. Stop, y'all. You're not in competition. You need these women in your life. So stop. Just get over it. Relief.

Jackie

Is there anything you wish you had said to me back then? Probably been better with my words that I believed in you and thank you.

Jennifer

Aw, thank you. That's very sweet of you. Because now I'm gonna cry.

Jackie

I'll start crying.

Jennifer

I know. I'm gonna cry too. But we didn't have that.

Jackie

We really say things like that back then.

Jennifer

No, but we didn't even have that in like life. You know what I mean? Like someone to tell you that. So it does make me cry too. See, Jack? No, I'm crying. My eyes are all red. You can't see us, but okay. Um, is there anything you wish to have said? Yeah, the same thing. Oh man, Jack, I wish I would have said, you are so much better than this. Like you deserve so much better than uh, you know, what I thought you were getting. And you have so much to give, and you're such a great person. Like, I would have that's what I would have said. I've been like, man, is this really what you want to settle on? Because you have you're such a unique and beautiful person that somebody is gonna be so lucky to have you one day. And that's probably what I would have said, you know, like find your match, find someone that loves you the way that you deserve to be loved. And she definitely has it now, and I don't have that problem. And you know, but I am protective of her, y'all. Like, you know, I got one side up on my eye, like, what'd you say, Rick? Like, oh, okay, good. You said something nice, like, but that's just that's just best friends, right? He's a sweetheart. So okay, you're am I next or next? You're next. Okay. Do you think some friendships are meant to come back?

Jackie

Always.

Jennifer

Always, yeah.

Jackie

If they are real and true and for the right reason. Yeah. That's what I believe. Yeah.

Jennifer

There's some people that could walk back into our lives tomorrow, Jack, that we're friends with or we're friends before, and we'd be like, hey, welcome back. Like, because I think that, you know, when you love somebody, this love story is.

Jackie

My wrong hand. Sorry, Rudy. I'm doing this. They all make fun of me because I do the wrong hand signs.

Jennifer

Doing the hang loose instead of the rock and roll. It's all right.

Jackie

I had to do that so the tears will stop.

Jennifer

All right. It's last one's on you.

Jackie

What's what does our friendship mean to you now? I said everything, love, my life.

Jennifer

Yeah, it does. I complain, you know, when I want to complain, I call her. When I want to cry, I couldn't call her. When I'm a laugh, I'm gonna call her. Like it's just a it's just a unique connection and it's just everything. Like that's all I can say. It's just everything. So if you uh if you have a friendship, you get a second chance that you know, we are encouraging you to do it because it can really be life changing and such a so healing for so many reasons that you didn't even know you needed healing from can come from this. So we encourage you, please, if you have a friend that you don't know, try to test the water. If this episode hit you in the field or made you laugh way too hard, we consider that a win.

Jackie

Be sure to subscribe, leave a review, and share it with your writer dad.

Jennifer

And when you're ready to make your friendship official, book your testimony at rhinestoneweddingchapel.com.

Jackie

Because the le the best love stories don't always come with a ring.

Song

We stick together, ride or die to the moon, and no amount of space could ever come between us two. The reuniting's like we've never been apart, and every single time we're either eye and heart a heart. Through heartaches and ups and downs in this life, you've stayed right next to me. I've ought to make you laugh till you cry. Look up everything under the moon. The definition of a best friend It's good. And we'll keep painted through the race. But ever connected. Same page. We're writing a story. Everything will keep on going everyday. What you made a made. The heartaches and ups and dance and dislike. Don't stay right next to me. I thought I'll make you laugh till you cry. Don't come through the mole. The definition of a best friend. It's good. It's good. It's good. Trust. That says loyalty. You and me. Love trust. That says loyalty.