One of Us Never Married. One of Us Married Three Times. Lessons After 60

Have you ever looked back on your life and realized it didn't turn out the way you thought it would?

Recorded live at our nephew's wedding, this episode became an unexpected conversation about marriage, life lessons, mistakes, second chances, and the wisdom that only comes with experience.

Randy has been married three times. Sheri never married.

As we watched the next generation begin their journey, Randy shared what three marriages taught him about relationships, communication, forgiveness, and the things that truly matter. Along the way, we reflected on family, growing older, and how life often takes us down roads we never planned to travel.

In this episode:
💍 What Randy learned from three marriages
💍 The relationship advice he'd give newlyweds
💍 The mistakes that taught the biggest lessons
💍 Why listening matters more than most people realize
💍 Family, forgiveness, and second chances
💍 Looking back on the lives we never expected

This isn't advice from experts. It's a real conversation between a brother and sister who have taken very different paths through life and aren't afraid to talk honestly about what they've learned along the way.

If you're interested in life after 60, relationships, marriage, divorce, family dynamics, personal growth, retirement, or learning from life's experiences, we think you'll enjoy this conversation.

🎙️ Sherapy with Sheri & Randy is a podcast about life after 50, family, grief, reinvention, resilience, and finding meaning in the unexpected.

#MarriageAdvice #Relationships #LifeAfter60 #Retirement #Divorce #Family #PersonalGrowth #MarriageLessons #Over60 #LifeLessons #Sherapy #SecondChances #GrowingOlder #SiblingPodcast #RetirementLifestyle

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Theme music by: Sheri Todd and MakeBestMusic

Written & hosted by: Sheri Todd

 Recorded somewhere between healing and humor.

Transcript

SPEAKER_00 0:02

Where are we, Randy? I'm lost.

SPEAKER_01 0:04

We're in Redlands.

SPEAKER_00 0:05

Is that where we're at?

SPEAKER_01 0:06

We're in Redlands.

SPEAKER_00 0:08

Redlands Marketplace. We're at Redlands Marketplace. And we're here for our nephew's wedding. Our nephew Jeremy is getting married, and Randy and I are here. Um and we're going to talk about marriage. And believe it or not, I don't know how it's going to work out. Randy's been married three times. I've never been married, and we're going to offer some advice to our nephew. How's that going to work out?

SPEAKER_01 0:35

Take the keys and run.

SPEAKER_00 0:38

I'm sure all your wives said that.

SPEAKER_01 0:41

After a while.

SPEAKER_00 0:42

Yeah, after a while. And it's, I mean, it's kind of interesting, you know, watching Jeremy get married. And he was just, he was just so trusting and loving. And I and I remember once I went to the house, he must have been at five, and I went to pick up a shovel because I was gonna do some shoveling, make some, do some, uh, plant some flowers. So Jeremy comes out and he goes, What are you doing now, Sherry? And I go, Oh, um, I gotta go bury grandpa. He goes, What? I go, you know, grandma, she got fed up with grandpa and killed him, so I have to go bury him. And Jeremy looked at me and went, Can I come help? He was just such a sweet little boy. Of course, I, you know, and I know people are saying, what the hell are you telling a five-year-old that? I did tell him that killing people was wrong, and I was joking. So and then Jeremy did end up going to jail for murder later. No, I'm just kidding, that's not true. That's not true. It kind of makes you think of marriage when you see somebody starting a whole new life together. Burying them. Huh?

SPEAKER_01 1:45

Burying them. No, it kind of makes me think of marriage.

SPEAKER_00 1:49

Well, some people maybe. But no, it reminds you of kind of like I would think for you, like, brings back memories of one of your marriages.

SPEAKER_01 2:01

Back to get in burying them. Um no, I guess there's, you know. My first marriage, yes, my second marriage.

SPEAKER_00 2:09

Did you think you'd be married three times?

SPEAKER_01 2:11

No. Obviously not. No. No, I didn't. After Rose, I didn't think I'd be married again. Because I was in my late 40s.

SPEAKER_00 2:20

Rose was your second marriage.

SPEAKER_01 2:22

Yeah. Yeah. Now, Michelle, after that marriage, I thought, well, yeah, I might get married again.

SPEAKER_00 2:27

You know, after that, I didn't know, but which marriage turned out better than expected?

SPEAKER_01 2:32

Connie.

SPEAKER_00 2:32

Connie. The longest one.

SPEAKER_01 2:34

25 years. 25 years. She made my life better, made me better.

SPEAKER_00 2:38

Yeah.

SPEAKER_01 2:38

You know. Michelle and me were so young. Well, she was young actually, younger than I five, six years younger than me. So come through. We're on a podcast, so we have your permission to come. Okay. Okay. So um, yeah, so Michelle and me were so young that um I, you know, we were What surprised you most about marriage? The commitment.

SPEAKER_00 3:03

When it comes to, well, look, I I mean, I don't want to focus on your first marriage, but your first marriage always you have all these dreams, you have all these hopes. Then you start having children, and you know, did it turn out the way you wanted to, raising the kids, how you wanted to raise them with with Michelle? No. Even though you guys split up.

SPEAKER_01 3:21

No.

SPEAKER_00 3:22

Because I made a lot of mistakes, even after we weren't married, you know.

SPEAKER_01 3:26

I would I made a lot of mistakes with my kids, you know.

SPEAKER_00 3:30

Um, which a lot of people do, but what would you change differently?

SPEAKER_01 3:34

Well, I would have been more involved with my kids. I wouldn't have been taken off like I did a couple times. Um, different women all the time, kind of messing with their heads, instead of if I wasn't. Why you were married? Well, I did make a boo-boo when I was married my first time. Not my second time.

SPEAKER_00 3:51

During your first marriage, you you cheated.

SPEAKER_01 3:52

Yeah, I cheated on my first marriage, yeah. And like I said, I was a womanizer. So I never took any.

SPEAKER_00 3:59

This is why I never got married.

SPEAKER_01 4:00

Yeah. But I think we've all been kind of caught up in that. If you're a guy, you know, I think we all make the mistake, hopefully not, but I'd say 80% of us do. You know? So, can I learn from it? Yeah. I've been with Connie 25 years. I've never been with anybody. You know, not even close. And I've had opportunities, but I never did.

SPEAKER_00 4:25

That's good.

SPEAKER_01 4:25

Because I believe in karma.

SPEAKER_00 4:27

Yeah.

SPEAKER_01 4:28

You know, and I didn't believe it when I was young, but I sure believe it now when I'm older. And um, if you do something like that, I think it comes back to you. What way? I don't know. But it comes back and bites you in the ass, I'll tell you that.

SPEAKER_00 4:38

Do you think your kids are the same way? Like I said, I'm never gonna have a marriage like my parents, I'm never gonna raise my kids like we were raised. Do you think they feel the same way?

SPEAKER_01 4:48

Oh yeah, without a doubt. Yeah. Without a doubt. Yeah. My kids, uh, like my brand son, my Brandon, um, he's become uh has become like a million times better than me as a man and a father. And uh Candace is doing very well. And um, and Ashley's doing fine in her own way. She's struggling, but she's doing good.

SPEAKER_00 5:10

She's fine.

SPEAKER_01 5:10

You know, but she's fine. So I'm proud of my kids. You know, you know how our family's family. We're bugs. We're whacked out and weird or whatever, but we're we are not the traditional Brady Bunch. But we're close family. In our own way, we're all close. You know, on and off.

SPEAKER_00 5:27

Yeah, on and off.

SPEAKER_01 5:28

We're on and off. You know, it's the way it is.

SPEAKER_00 5:30

If you look back on all of your marriages, what do you think they taught you?

SPEAKER_01 5:37

Um patience, um, understanding, a whole lot of patience, faithfulness, and uh I think true love. What it is, what it means.

SPEAKER_00 5:54

What's the one thing um that you would start doing sooner?

SPEAKER_01 6:01

Um probably patience. I've always been real short on that. So I work on that every day. Being patient. Be honest with you, like with people walking by us right now. It's bugging the crap out of me.

SPEAKER_00 6:15

No, Granny, I'm glad I'm glad you have patience.

SPEAKER_01 6:20

Well, I'm just saying, I'm still working with that. You've been doing this from the years ago, I've been screaming at somebody. But, you know, I'm just saying, it's just things you can do.

SPEAKER_00 6:27

You've been doing the podcast from the back of my police officer's car.

SPEAKER_01 6:30

So, um, I think I think I learned more now in my life than I did ever when I was younger.

SPEAKER_00 6:36

What advice would you give Jeremy?

SPEAKER_01 6:40

Listen. Really listen. Really listen.

SPEAKER_00 6:42

Do you think you do that in your marriage currently?

SPEAKER_01 6:45

I do. I could listen better.

SPEAKER_00 6:48

Not according to your wife, but okay.

SPEAKER_01 6:50

Yeah, I do, but I need to do better at it still. But I think that's the biggest thing for both of them is to listen. And try to understand.

SPEAKER_00 6:58

Yeah, to me, I think I would tell them that marriage, to me, you have to look at it like a business. And I don't mean that in a like a bad way, but it's about two people who love each other, and the marriage part is a business that you're growing together, that you want it to succeed, and you're gonna do whatever you can to make this business work.

SPEAKER_01 7:19

Yeah, but you don't want to get robotic either in your marriage either.

SPEAKER_00 7:22

What?

SPEAKER_01 7:22

Robotic.

SPEAKER_00 7:23

No, but just like with any business, you you there's gonna be mistakes that you're gonna learn from, and there's gonna be successes and whatever. But you've got to look at it. You can't just give up because it's something that you love so much that you're gonna work at it no matter what, because it's your business, it's your life, it's your livelihood, and you're together as a partners, and that's how it should be.

SPEAKER_01 7:45

That's where you listen. You have to listen to each other.

SPEAKER_00 7:49

Definitely, yes. You know, and you have to trust each other.

SPEAKER_01 7:51

When you listen to when both of you are listening, listening to each other, you can break it down and come to a conclusion.

SPEAKER_00 7:56

Okay, so what do you do? I'm always because I'm not not married, so I don't know. But what would you do when you are animate, like you definitely want to do something, and the other's like, no, I don't want to do it? How do you compromise that? How do you does one have to give up? Do you compromise?

SPEAKER_01 8:17

Well, bottom line, you're gonna have arguments, you're gonna have disagreements all the time. It's not gonna, that's never gonna go away. Um, I think with something like that, you just break it all down to what which would be better for you both of you to do? What's what's what's financially best? I think those are the main things. You gotta break everything down. Because people don't break things down, they just go you get mad or they just both go their own ways, what about it, or whatever. You gotta sit down and talk about and break it down and see what's best for both of you. Not for one, but for both of you.

SPEAKER_00 8:48

So, what do you think a successful marriage looks like? I mean, obviously, you think you feel, and it probably is, you're probably right, that your marriage to Connie is successful. What would you say made it successful?

SPEAKER_01 9:06

I don't know, listening's a big thing through marriage. I think listening and uh um doing things out of the norm for somebody like Connie. Maybe buy her flowers, no reason to buy her flowers, but buy her flowers, or maybe you heard her say something she wants, maybe go buy it for her, stuff like that, keep it alive, go out on date nights, stuff like that. Um and always hold hands if you can, which me and Connie have been trying to do a little bit more, like we go to a movie or something, we'll hold hands going up. Just keeping it, you know, kind of together like that.

SPEAKER_00 9:37

Yeah, I mean after 25 years, yeah. You gotta just step them forward.

SPEAKER_01 9:40

You know, fresh. Because you're so used to each other and and everything. Um, but I think that's important to keep that fire going, you know. And there's ways of doing it.

SPEAKER_00 9:50

Well, I I definitely wish Jeremy, my nephew, a lot of luck in his marriage. He's i i it's his first marriage, and he's taken on a lot. He's he's he's got he's already have two children, and he's gonna be a stepdad to two other children. So he's got it on his lot on his plate, but I think him and Ashley, if they work it out and stick it together and and and it will it will be successful for them, but it's not gonna be easy, and I think they already know that, but it's not gonna be easy, but I wish them all the love and luck in the world.

SPEAKER_01 10:24

It's gonna be a hard road ahead for them.

SPEAKER_00 10:26

But it's I think the key to it is like every day say to each other I love you. Well, yeah, but also say one thing you're grateful for. Like what's what what are you grateful for today?

SPEAKER_01 10:40

I'm just grateful I wake up every morning.

SPEAKER_00 10:42

Okay, but today in particular.

SPEAKER_01 10:44

But today, waking up, I was hoping for a great day because uh Jeremy's getting married and we're gonna do stuff like we're doing.

SPEAKER_00 10:51

Round family.

SPEAKER_01 10:51

Round family. Um and that's what I said.

SPEAKER_00 10:54

I'm grateful for. I'm grateful for our family.

SPEAKER_01 10:56

Yeah, I'm really grateful our family.

SPEAKER_00 10:57

It's not perfect, but we do have a lot of fun, boy. We have a lot of fun.

SPEAKER_01 11:02

Well, after mom died, I think we've kept it together pretty good.

SPEAKER_00 11:06

And being at the age that we are now, we're all older, and um we're realizing that there's not a lot time left for all of us, and it's important to spend as much time as we can.

SPEAKER_01 11:18

Well, kind of like what we're doing right now, this what we do in the web our podcast and all of other stuff we do. It's because we both said it's something we want to do and have fun with, you know? It keeps the hook family together and stuff too, a little bit, you know, because they watch them and they have fun with them. So yeah, I mean it's it's great, you know.

SPEAKER_00 11:38

So subscribe if you're new here.

SPEAKER_01 11:40

Yeah.

SPEAKER_00 11:41

If you're not new here and you've been here before, go on and subscribe, you're gonna love it. And uh if you're listening on uh your favorite podcast app, follow us. Yeah, and it'd even better if you came over to YouTube and watch us do this live.

SPEAKER_01 11:57

Watch me come out and dance a little bit.

SPEAKER_00 12:01

He's becoming a celeb with his little dancing, yeah. His his Donald Trump dance.

SPEAKER_01 12:07

Yeah, it's a lot of fun. Please subscribe, we'd appreciate it. It means a lot to us if you do. We've got a lot more stuff coming to us coming this way.

SPEAKER_00 12:16

We're building a really great community, and we want you to be a part of it. So thank you for subscribing. Thank you for watching Cheropee with Sherry and Randy.

SPEAKER_01 12:26

Randy, and make sure you come to this marketplace, it's a lot of fun. Check it out.

SPEAKER_00 12:30

Redlands have a lot of places that you'll like it. Redlands Marketplace. Check it up on if you live in the area or near Redlands, you probably already know about it, but it's a big place with a lot of restaurants inside, couple bars, stuff like that. You can have them apparently can have a wedding in the back. Yeah, which is where it's it's actually very pretty.

SPEAKER_01 12:51

It is pretty cool, yeah.

SPEAKER_00 12:52

In fact, Randy did a dance video walking down the same aisle to have Jeremy and his wife.

SPEAKER_01 12:58

Check it out.

SPEAKER_00 12:59

So thank you for being with us, and we hope to see you soon. And whatever you do, always remember to embrace your voice.

SPEAKER_01 13:08

Take care, everybody.

SPEAKER_00 13:09

Hey, thanks for hanging out with us for a bit. If this felt like your kind of conversation, go ahead and subscribe and follow. We'd love to have you back.