Same Friendship, Different Rules: Why Generations Don’t Get Each Other

Same Friendship, Different Rules: Why Generations Don’t Get Each Other 

Ever feel like you and someone you care about are speaking completely different emotional languages?

You’re not imagining it… it might be generational.

In this episode of Slightly Unsupervised, Jennifer and Jackie dive into why friendships across different generations can feel confusing, frustrating, and sometimes even hurtful—even when both people genuinely care.

From communication styles and emotional expression to boundaries, loyalty, and expectations, every generation was shaped differently… and those differences don’t just disappear in friendships.

Jennifer and Jackie get real about:

•  Why generational clashes happen (and why it’s not always personal) 
•  The biggest friction points between Gen X, Millennials, and Gen Z 
•  How the way you were raised shapes how you show up as a friend 
•  Real-life examples of generational misunderstandings in families and friendships 
•  Why some people want to talk everything out… and others just want you to move on 
•  How to navigate friendships when you see the world completely differently 

They also share honest stories about family dynamics, different perspectives, and the challenge of trying to connect when your emotional wiring doesn’t match.

Because sometimes…
 👉 it’s not the friendship that’s broken

…it’s the framework you’re both using.

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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.

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Transcript

Jennifer 0:00

Hey there, I'm Jennifer, and I'm Jackie. And welcome to Slightly Unsupervised. We're 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 0:11

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

Jennifer 0:16

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

Jackie 0:20

Let's get slightly unsupervised. Today we are talking about why generations class clash and what it does to friendships. Ever feel like you and your friend are speaking completely different emotional languages? You're not imagining it. It might might be generational. In this episode, Jennifer and I break down why friendships across generations can feel confusing, frustrating, and sometimes even hurtful, even when both people genuinely care about each other. From communication styles and emotional expression to boundaries and expectations. Each generation was shaped differently. And those differences don't just appear when we become friends. Jennifer and I get real about why generational clashes happen and why they're not personal. The biggest friction points between Gen X, Millennials, and Gen Z how different generations define loyalty, communication, and boundaries, and when generational differences strengthen friendships and when they break them, and how to navigate friendships with people who see the world completely different. Because the problem isn't always the friendship. Sometimes it's the framework you're both using.

Jennifer 1:21

Yeah. Have you ever thought, why is this bothering you so much? And what are they, why are they acting like this? Like it's no big deal. So, you know, I am a sister of a sister who is of a different generation. I have a sister 11 years younger than me. And it's one of those things that I find it often when I'm chatting with her or something about how um views the world differently than I do. It's, you know, the things that she gets kind of bent out of shape with, not something we generally get bent out of shape with, and probably vice versa. So the things that I get bent out of shape with, she's like, what are we talking about? Like there is a generational gap, and it's time to, you know, definitely at least acknowledge it and try to understand it. You know, it it happens that we're not always disagreeing. We're just different people. And sometimes when we're we need to go back to how we were raised. I was raised differently than my sister. And in a different household with a different mother, we're half sister, so we have d different stuff. And I'm constantly having to kind of adjust the way I converse with her about things because I now know that certain things she doesn't care about talking about because it doesn't matter to her. And it matters to me, but it doesn't matter to her. I've got to go to my friends for that. And then there's some things that my sister likes to talk about that I could care less about. It matters to her. I try to be a good sister and listen, but you know, she really should turn to other people for what she needs from them to get because although I try, it may not be what she needs. She's used to a different, different kind of perspective. And you know, there is a generational gap. I mean, I I don't know how else to explain this. There it just is. And it's more apparent as we get older that generations are different than us. So, you know, each generation was shaped by different stuff, you know, how they were parented. My mother my sister was parented kind of the same, but maybe a little differently than I was. So, you know, I was a parent of I was a child of a divorced parents out of the house. My sister was raised in a house. Her mom worked. There's no doubt about it. My dad was around too, and he was around more so for her than probably was when I was a child because he was there more. So she has a different perspective. Even my dad. I'm gonna tell you right now, the perspective on my dad is different from my sister to myself. And that's siblings is that way, I'm sure. But who he was as a person is different because we didn't I didn't have the access to my dad the way she had access to my dad, and how she looks at him versus her mother, how I look at my dad versus my mother. There's a generational difference there. And you would think that we would have more similarities on how we feel because he was the same man. I mean, I don't think my dad my dad didn't love one child more than the other. I never got that from my dad, but the difference perspective of it of how they were raised. Do you do you have any like any examples, Jackie? Of people that were, you know, you have, I know you have a couple of daughters that are in different generations about their perspective. Well, here's a good one. You do have two daughters that were raised differently, even though they were in the same sort of household, right? One has a different perspective probably than the other one because it would change by the time that one got a little bit older, the younger one got older versus the younger one that had more of the different perspective, you know.

Jackie 4:32

Like they probably Right, but I wouldn't know how what the perspectives are. You know what I mean? Like I wouldn't, yeah, I wouldn't know how to say what their perspectives were. That would they would have to say that.

Jennifer 4:43

But I'm just saying, like, it changes, right? They're they raised in the same household, but there's a little bit of a different perspective there.

Jackie 4:49

Well, it's different because when the oldest was was raised, the mom and dad were still together. And then so by the time they broke up, she was going to college where the the youngest was only going into junior high school. Right. So she was going when you know, when you're hitting puberty and stuff, your parents are splitting up. So you have a dad who's by himself and moving on, and then moms who's moving on and getting married. So yeah, her perspectives will be different. But like how she uh like they don't talk to me about that, so I wouldn't know what their difference is. But of course, yeah, it's gonna be way different.

Jennifer 5:22

Yeah, but I mean it's just like the perspective of like my m sister and even though we're born in the same, it's the same thing. Like by the time my sister came, her her perspective is different because her life was different in that situation, and my perspective is different for that. So it's it's a generational thing too. What is the age difference between the girls?

Jackie 5:40

Five.

Jennifer 5:40

Five years.

Jackie 5:41

Five years. Yeah. Well, no, I think it's five, five or six, something like that. I can't think right now. Sorry. No, it's okay.

Jennifer 5:48

No, it's okay. They weren't they weren't in the same six.

Jackie 5:52

Let's see.

Jennifer 5:52

They weren't in the same.

Jackie 5:54

I'll have it by the end of this podcast. I will have it figured out.

Jennifer 5:57

Well, I can tell you because you said that one was like junior high and the other was in high college already. There's a big gap there. There's at least four years of high school they weren't in there together, and the others, you know, so it's probably five or six years. Yeah, so it's probably five or six years between us. Yeah. But they're they're, you know, are they in different different generations or is one of them a Gen Z and one of them uh or one a millennial and one a Gen X?

Jackie 6:25

I don't know or Gen Z to figure it out. Now I feel like I don't even know my own children, but I gotta think it out. Like I told you, people oh no, that was on my last podcast. We do two podcasts a day.

Jennifer 6:35

But um yeah, I'm working on two two nights of grandchildren one night and another night I But it's a good example because uh the reason I brought them up, not to talk about them because we're not talking about it, but that they are in the same perspective is that they have a mind that's different, raised differently in a different way than the other one because of the just the life had happened differently between them. And that is how it is for my sister and I, too. So for her and I, when we have a same conversation about the same person, we would think we'd have the same perspective. We do not, because there's different parenting that happened there. So it's all about timing, it's all about where you are in life and how you are as a generation and how you see the life of you know, the perspective of things.

Jackie 7:16

So this thing's six years. I think it's six. I think I'm still thinking about it. I'm good. It's six. I'm pretty sure it's six.

Jennifer 7:24

I've gone on and she's over there calculating right enough. So, anyways, well, we want to talk about the generational clash between the ports because of the friendship bases that you know we generally, I generally have friends that are close to my age, and like because I get along with them, and because we're not trying to recreate how we are, because it's all pretty much the same. And I'm sure that most generations do that too. But at some point you are gonna cross generations and have a friend that is in a different generation than you, and it can definitely cause some concern when you are looking at things from a different perspective, and um, you know, you have to you have to kind of do some studying on their generational stuff that they should, you know, it's not necessarily like I said, my sister and I are raised by the same man, we look at him differently, is because life had happened differently. And I have to go into my sister's mind sometimes and try to think about how she was raised and why her perspective is different than mine, rather than just accepting um that we just see it differently. It's it's her generation's a little different than mine. So I'm constantly having to do that. Do you have any friends, Jackie in a different generation than you? Do you have any ones that are like younger? You have a lot of people around you. Yeah.

Jackie 8:44

Mm-hmm. Do you have any I'm just gonna go, I just make a lot of sarcastic remarks. You know me. I'm really good with just being a little passive aggressive. So I'll make it. You are very good at passive aggressive. Yeah, I am, and I can I can get along because usually ones are they're not usually close friends. You know what I mean? They're usually acquaintances or just friends, but not ones that I'm worried about if I say something or I have to like know exactly their feelings on something. You know what I mean? Like we don't talk enough about what they're so basically you are you show up as you.

Jennifer 9:20

You don't really worry about it. You're like, didn't land, it didn't land, moving on.

Jackie 9:24

Like pretty much, yeah. Because I mean, like some of them we've even like spent weekends at the river or something with, you know, and I'll just be like, oh well, you know, we're older if I say something wrong, or you know, if they don't agree with it, or I'll be like, uh, you know, in my time, you know.

Jennifer 9:39

Right. In my days in my day, this is how we did it. But do you remember that your parents or your grandbrothers kind of did that too? I think it's funny. Do you did you think I have this because the generational gap, and I was just telling you about this at my last podcast that Tony Robbins, who does extensive studying on human subjects, told us that generations go back and forth, but I always find that I got along better with my grandmother, which is a different generation than my mother. Um and could easily communicate with her, and she understood me more. That's how I felt. Do you have that maybe with your grandmother?

Jackie 10:17

Oh, yeah, you know I did. I was really close to my grandmother. Definitely. I still am. I mean, as she's getting older, she's getting harder, but that's because she's getting kind of like the dementia, um, all that kind of stuff. And you know, the Alzheimer's the sundowners, she gets really angry. So things are a little bit different now. But when yeah, when she was all there more.

Jennifer 10:35

Yeah. Definitely. When you were a kid, like when you were a kid, did you feel like way way more understood by your grandmother than your mother?

Jackie 10:41

Oh, yeah. Definitely.

Jennifer 10:42

Yeah, that's how I felt too.

Jackie 10:44

I don't know. I could tell her anything, and she didn't have a problem with anything. She kind of tell me stuff. She'd tell stuff about my mother because my mom always tried to act like she was just Miss Perfect. And my grandma would make sure that no, that's not how it was. Your mother did this. Oh, she had me at the top uh just up angry all the time. She would do this and that, and right.

Jennifer 11:08

And she's like, No, that's not what happened.

Jackie 11:10

No. Interesting.

Jennifer 11:11

But they do say that.

Jackie 11:12

Grandma would just tell me I'm just being a teenager, I'm just doing what everybody else did. Thank you, grandma. Thank you.

Jennifer 11:18

Thank you for understanding me. That's how I felt with my grandmother too. So maybe skipping generations is the key. Maybe you don't you don't find the generation right next to you, you go to the one beyond it. Maybe that's why grandparents, grandparents or get along with their grandchildren so well, because one, they've already raised their children, so they've already got a perspective on that, and they realize that's a big job and they don't want to do it, so they get to enjoy more. So maybe that's the key in this too. But in the friendship world, you're going to have to do some studying. I hate to tell you it, but you ought to, you know, if you have chat GPT, just put your perspective, be like, my perspective on this is this, and this my friend is on different millennials or different age group, and how did why are they acting that way? Sometimes I do that with my sister. I'm like, Chat GPT, what is going on with my sister? Like, I don't see this at all like this. And my sister sees it this way, and then it explains it to me. I'm like, oh, okay, I got you. It's like therapy, but free. Well, kinda. It's chat GPT.

Jackie 12:15

That's too much work for me.

Jennifer 12:17

I'm just like, whatever. My son, my son is very concerned that I get too much information off Chat GPT.

Jackie 12:24

I'm like, I'm worried about that too. You do like to go to Chat GPT Play.

Jennifer 12:28

And then like, I'm like, it's the only where, like, in our generation, we went to encyclopedias, right? That's where we got information from.

Jackie 12:35

If we wanted to learn about you could not go to the encyclopedia to ask why your sister was thinking this.

Jennifer 12:42

This is true. But now that we have, this is my point, is that we were very limited in what we could go back and look for. We had to like, I don't even know where we got our information from. Somebody knew somebody did something. You know, like hairdressers, hairdressers are really good for information because they sit and talk to people all day long. And then you go talk to them, and they'll be like, well, so-and-so did such and such, and that's how they solved it. You're like, well, that's how I'm gonna solve my problem then, because the hairdresser told me that. That's kind of how our generation went. So now I have Chat GBT, and I'm like, look, I think my sister might be strange. Nope, no, ma'am, she's not strange. She thinks differently. And I'm like, nope, I think something's wrong. Like something is definitely wrong here. Nope. Ma'am, it's you too. You have a different way of thinking at it, and so does she. So, you know, your sister's not all, she's all there, but maybe she's, you know, got a different perspective. So even though we don't know if ChatGPT is always right, I do know that it has helped me deal with my sister more. And I invite you, if you're having issues, go to ChatGPT and ask their perspective because they will give you a new perspective and you'll be like, hadn't thought of it that way.

Jackie 13:45

I'm going to continue looking for my regular therapist. And that's just what I'm going to go with. But you know, if you all want to follow Jen with the Chat GPT, there you go. Go ready.

Jennifer 13:54

ChatGBT or find a therapist. ChatGPT is $21.95 a month. It's not a good thing.

Jackie 13:59

Follow what you want as Jackie, if you want to follow Jackie, therapists are just fine, also. Just for it, yes.

Jennifer 14:06

And you know what? Therapists have their way because therapists have a way of looking at it from a different perspective because they studied it where we don't have that.

Jackie 14:13

And I enjoy seeing a face and a person.

Jennifer 14:16

Can I invite you to maybe talk to your hairdresser? Because your hairdresser has quite a few things to talk about.

Jackie 14:22

Mine's too busy telling me about how her husband's buying a new car and all this stuff. So you're just I was just talking about the extensions of this girl that was just there. Yes. They're all a little bougie at my place, so uh I don't talk much to them.

Jennifer 14:35

You know why? They're millennials, and they're probably like, eh, I want to talk about that, or Gen Z or something. So, anyways, these are just they're just giving you some perspective on it. You know, I'm coming up with my sister because I have a close relationship with my sister most of the time. Um, and we we have most of the time, I mean, I'm gonna be honest, most of the time we're close, sometimes we're not. Um, and we come back around, but sure her perspective is different than mine, and my perspective is different. And my kids are in her perspective too, but I don't have quite the generational gap with them because my kids were maybe raised with me and think more along the lines, I think, or they're boys and they don't require as much maintenance. Is that a good word?

Jackie 15:17

Sure.

Jennifer 15:18

Like check-in, like emotional maintenance.

Jackie 15:21

Or they grew up with you and they didn't they know to disagree with you. Yes, mom, but then when they go away from you, they're like, Can you believe that?

Jennifer 15:30

I'm on to you, boys. You can tell when you give side eye. I know how to give side eye too. Dear Lord, what's mom talking about? All I know is that my boys don't have a problem with my boys, but I get it. They, you know, have their own perspectives too.

Jackie 15:45

So yeah, and that's what we want. We want them to be live their lives.

Jennifer 15:49

Yes. They can't agree with my generation and grow up like me. So I get that. So, anyways, just leave some room in your life for these generational gaps and try to find somewhere to find some reflection, some honest reflection about it. I vote chat GPT, Jackie votes a therapist, so either one would be good. Or just somebody that, you know, can understand that might have perspective, and maybe you have a couple people that you know just you just go along and maybe be friends with them and be passive aggressive and be fair, make friendships.

Jackie 16:19

It's all good. Whatever, whatever works, you know, have a friend.

Jennifer 16:24

Right. Find your place, whatever it is. Like whatever works for you, but just know we're not all the same. That's all we're gonna get to. All right, Jackie, let's go into thesty rapid fire questions. I'm gonna go first. Yeah. Do you think people today expect too much from friendships, Jackie? Expect too much from friendships? Yeah. So think about not your old friends, but think about new friends that you've made. Do you think that they are they asked too much? Like is it too much?

Jackie 16:53

I think it depends on your age.

Jennifer 16:55

Yeah. It's generations, right?

Jackie 16:56

Different generations. Generations. So that like what we're talking about. Yeah. Um maybe newer friendships actually. I think if it at my age, if you want if you're expecting me to be your best friend and um it's it's not gonna happen. I've got my best friends. If you just want a friendship to like hang out and do stuff, you know, like us moving to a neighbor new neighborhood. It's that we enjoy hanging out with the people that we've met here. But I don't think it's not gonna be.

Jennifer 17:18

Do you find that a relief sometimes? Like I'm not looking for a best friend. I've got my best friends. That's how I look like it.

Jackie 17:24

It's like it's nice to just go hang out with the the people. Like we have some, like we um have some friends down the street that they just bought a trailer and we're gonna go um to go take our new one to go just test it out. You know, you have to test out a new trailer, make sure go close by. And uh, they actually got their first one ever. And so we said, Oh, you should just bring it where we're going so you can test it out. And then my husband knows a lot about trailers, so he's this person's never used one before. So he's gonna kind of show him stuff on it so he can figure, you know, know how to use it and not mess it up. And uh, so we're like, yeah, just come where we're going. So they're actually going just so that my husband can show them things. But you know, it's not we're not gonna be best friends, but we're gonna hang out and like we're gonna be at the pool that's by the place that we're going, but you can pay money to go to the bigger pool where you can hang out with more people and do that. Well, we're like, Yeah, you can go do that during the day. We're gonna hang out at the other pool. And then we have our other friends coming, my best friends, like Michelle's coming and her husband to hang out with us at the pool that's smaller, right? And you know, more quaint for us with our best friends. Right. But we're gonna still hang out with these people, you know what I mean?

Jennifer 18:26

Right. So you're not in the big pool looking for new people to hang out with. You already have that kind of set. Uh-huh.

Jackie 18:32

But we but we're fine hanging out with these people, but they're not gonna be our best friends. But we'll hang out with you. Yeah, exactly.

Jennifer 18:39

But when you have a best friend, it does take a pressure off of any friendships that you start because you're like, Yeah, we can be totally cool. Like, you got a best friend? Cool. I got a best friend too. Like, we don't need to be each other's best friends. I think that helps sometimes in making friendships with people because it's very chill. Like, if we connect, we connect. If we don't, we don't. It's not like a forced, I don't need we don't gonna connect, we don't have to connect. It's not, I'm not looking for a friend to fill my life up with. So, anyways, okay, Jackie, how about have you ever thought this is not serious, but your friend disagreed 100% for me? Sure. Like, you're like, it's chill. Let me go back to my friend that I just called about something in my life that was like shaky, and she's like, it's fine. Like, and you're like, serious? No, it's not. Okay. Yep. So, yeah, different generations are gonna have emphasis. Same thing with my sister. Sometimes I'm like, this is not that serious, and she's like, This is completely serious. And you're like, I don't understand, but okay, let's talk about it. So I have that with her too. So all right, Jackie, you go. Do you believe loyalty should outweigh personal discomfort? Believe that loyalty should outweigh personal discomfort. Yeah, be loyal. Like, let me give you a perspective, Jack. If you were somebody was talking shit about me, we'll go there. And you're at a wedding, and it's not a real good place to really pipe up because it's a different environment. And the question is, should you still be loyal to me because it's gonna be a little uncomfortable for you in that situation? That's kind of what I'm reading into it. I'd expect you to still be loyal. You know what I mean? Yeah. Do you get what I'm saying? It's loyalty in an uncomfortable place, still being loyal. So, do you believe that it should outweigh personal discomfort? Is the question. Yes, I do think so. Do you think so? Yeah, you should still, whether the environment's good or not, you should still be a good friend. I think. Have you ever felt overwhelmed by someone else's emotional needs? Have I ever needed too much from you? And you're just like, shut up, Jen. Sure. Thanks, Jack. You're like, go away, girl. I don't need this right now. Move along, find somebody else.

Jackie 20:50

I'm like, can we just go into Nashville and have some fun?

Jennifer 20:56

Jackie's coming to Nashville, y'all. In June, we can't go be together so we can podcast together. And I have promised to be more a host than a I don't know. We're gonna work too. It's we'll work, but we'll have more fun. So we're gonna go.

Jackie 21:13

Have you ever felt dismissed by someone who doesn't express emotions the same way?

Jennifer 21:18

Yes. A hundred percent. I think everybody has. Right? The generation before me, really, about how I needed something, and I got emotionally dismissed. Like, we don't talk about that. It's fine. Go, you know, like they don't have a she didn't have a package to unpack to be like, well, here's the problem is that you have, you know, you're this or you're that. My mom had no concept of that. Like, just don't talk about it, move on. Like, so yes, I think that I have definitely felt dismissed by somebody who didn't express emotions the same way. And I'm sure the generation millennials feel the same way by us because we are not as bad as our mothers, but we Are somewhere in between the two, so I'm sure that happens too. Okay, if you ever think it's easier or harder to maintain friendships across generations, harder is harder. I don't think it's easier because I think every other generation might be easier, but for the generations sandwichiness between us, the one before and the one after, it's definitely harder to maintain those because we're we don't think the same a lot of times.

Jackie 22:25

So next have you ever ended or distance from a friendship because your values didn't align to 100% on values.

Jennifer 22:33

If you don't have the same value, I don't know how you can be friends. Yeah, exactly. If you have a value of something that means nothing to me, or I think is shallow, or I think is incorrect, or whatever, you cannot. I'm not in a position where I can just like, well, that doesn't matter to me. Your values do matter to me to some degree. Like you have to be more aligned with me if we're gonna be friends. Otherwise, it doesn't work very well because I'm doing something I don't agree with, or if you agree with something I don't agree with, or something, you know, so that is okay, Jack. To be honest, are you open to understanding different friendship styles, or do you think yours is right? Oh, I'm open to understanding others. Okay, I think I'm right. Ours is right.

Jackie 23:15

Ours is right, but I think I'm understanding the different others.

Jennifer 23:18

Yeah, I can understand.

Jackie 23:20

Come on, I'm not gonna be like mine is right, and that's it. I mean, of course, maybe when we turn this off, I'll say that, but you know, ours is better.

Jennifer 23:28

I mean, get on with it.

Jackie 23:31

Obviously, it works.

Jennifer 23:32

We grew up that way, that's how we know. Friendship conflict is not all friendship conflict is about friendship. Sometimes it's about the land you're using. Different generations just don't think differently, they connect differently. And maybe the goal isn't to change each other, it's to understand each other enough to stay connected, anyways. Alright, if this episode hit you in the fields or made you laugh way too hard, we consider that a win.

Jackie 23:53

Be sure to subscribe, leave a review, and share it with your ride or die.

Jennifer 23:57

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

Jackie 24:01

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

Song 24:17

We stick together at 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 out of eye and heart to heart. The heartaches and ups and downs and this life you've stayed right next to me. I've outta make you laugh till you cry. Look at everything under the moon. The definition of a bit's friend. It's good. It's good. And we'll keep it to the race. Whatever connected same page we're writing a story, every day we'll keep on going every day. There's not enough words and it's right for you to make. The heart aches and bats and dance and this life don't stay right next to me. Uh bottom bake you laugh till you try it. The definition of trust is loyalty. You and me love trust that says loyalty, you and me.