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Dana
Did I talk too much? Can't I just let it go?
Noah
I was thinking so much.
BetterHelp Narrator
Take a breath.
Caller/Commentator
You're not alone.
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Let's talk about what's going on. Counseling helps you sort through the noise with qualified professionals, and online therapy makes it convenient. See if it's for you. Visit betterhelp.com randompodcast for 10% off your first month of online therapy. And let life feel free, better.
Raj
Hey, it's Raj and Noah.
And we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with. Whether it's making new friends as an adult, managing our emotions, or even dreaming.
Noah
We'll be talking to experts in their fields who are definitely doing things right. So the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're gonna have full video episodes on YouTube. Because as long as there are things to get wrong, we're gonna be right here to help you do em better.
Raj
Love y'.
BetterHelp Narrator
All.
Host/Interviewer
Hey, the bird show we started with Dana a long time ago. 27 years old, had never been out on a date before. Her parents set her up with a 58 year old guy. All of a sudden, this relationship, like, I mean, accelerates so fast. She falls in love with this guy, he's talking about having kids with this guy, talking about moving in with this guy. Well, the last time we check in with Dana, she goes on vacation with the old guy and he's up in his hotel room, probably sleeping or whatever, or eating something that he put in a blender. Either way, she's down at the pool just hanging out, and she meets a guy her own age. And this is the first time she's ever gotten any kind of attention from anybody. So she's all smitten by the guy. Here's about 90 seconds of the last conversation we had with Dana.
Dana
The trip was great. It was beautiful there and he got an amazing room for us. You know what's funny though, is that actually one day, whenever he was gambling and stuff, I was hanging out by the pool. And I started talking to this guy. And the reason why we started talking is because I heard his accent, you know, and I was like, oh, are you from the South? And he said, yeah, I'm from Atlanta.
Raj
And.
Dana
And I was like, that's where I'm from, too. And so we just started talking, and he's really, really attractive, like, really cute guy. He's like 30 years old. And so we just started talking about stuff about Atlanta that we loved and what we were doing in the Bahamas, what we like to do while we were there, and, you know, just stuff like that. And so we exchanged phone numbers and emails, but he was really, really cute. So. And it was just funny. I was like, I can't believe I'm talking to this cute guy, because if this would have happened, like, seven months ago, this. I mean, I just felt like this wouldn't have happened seven months ago. But here I dating Carl, and now this cute guy wants to talk to me. It was just really bizarre.
Host/Interviewer
What do you think you're going to do with this whole situation? You think you'll start returning the emails? You think you're going to talk to Matlock?
Dana
I feel like I kind of do want to just go out with him just once, just to make sure and just to see. And I really think that Carl, like I said, he's such a gentleman. He's so great to me. And I think that if I'm honest with him, you know, I don't think you'd have a problem with me just making sure since we've talked about commitment and, you know, I feel like he would want me to, you know, do whatever I need to do to make sure first.
Host/Interviewer
All right, Dana, well, let's check back in with you again next week.
Dana
Okay.
Host/Interviewer
That was a couple of weeks ago. And let's try to make predictions here on what we think is going to happen with Dana here. Hey, Tiffany, why don't you start it?
Raj
Hi. I either think that she is dating.
Dana
The guy she met at the pool.
Raj
Or she married Matlock.
Host/Interviewer
Well, I mean, she what?
Caller/Commentator
Married Matlock?
Host/Interviewer
Married Matlock.
Caller/Commentator
One or the other polar opposites.
Host/Interviewer
So she's either married to the old guy or she completely dumped him and started seeing the younger guy.
Raj
Yeah, it could happen. I married my first boyfriend.
Host/Interviewer
Okay. 404-741-1005 I think that she talked to.
Caller/Commentator
Him about dating other people. He said it was fine, but probably had that, you know, something in his voice making it sound like he was threatened and that she, because she is Such a nurturer for him and wants to take care of him. And she's into this so heavily that I think they're engaged.
Host/Interviewer
Engaged?
Caller/Commentator
Oh, wow.
Host/Interviewer
All right.
Caller/Commentator
I think that she just wimped out of going out with the younger guy because she didn't want to risk losing the relationship with the older guy. So I think she's still dating Matlock. I don't think that they're like that much further along, but I don't think she went out with the younger guy, Jeff.
I think that she is married to the older guy and they have adopted two children from China.
Noah
Hmm.
Host/Interviewer
Damn, you stole mine. I think the old guy turned this into a little his and his and hers. That's what I think happened there in the Bahamas.
Raj
Really?
Host/Interviewer
Yeah, that's what I think. I think it was some serious, serious, crazy sex.
Caller/Commentator
If he was a 58 year old playboy, that might be the one thing he's never done.
Host/Interviewer
Hey, CJ, you're on all the Hits Q100. Hi.
Raj
Hey, guys. How are y'?
Caller/Commentator
All?
Host/Interviewer
Good, man. Make a prediction here. We got Dana on hold. She's ready to go.
Caller/Commentator
Go.
Host/Interviewer
All right.
Raj
I think that their last day down in the Bahamas, she probably walked in and caught Matlock giving himself a vegetable enema and has now decided to move in with the young guy.
Host/Interviewer
A vegetable enema? Yeah. Yeah, yeah, yeah. All right. That was going to be my second thing.
Caller/Commentator
I thought that could be a part.
Of the threesome though, like washing yourself out with potatoes. Like how does that.
Host/Interviewer
I don't know. I don't know.
Caller/Commentator
Hmm.
The wild world of colonics.
Host/Interviewer
Maybe we just go right to Dana. Hey, Dana.
Dana
Hey.
Host/Interviewer
Good morning.
Raj
Good morning.
Host/Interviewer
You're not gonna tell us anything that has to do with a vegetable animal, are you?
Raj
No.
Host/Interviewer
Okay, good. Alright. So the last time we talked to you, you're in the Bahamas, the old dude is up sleeping. You're down at the pool. You start hanging out with, luckily, some dude from Atlanta. Young guy giving you some attention, and you're really starting to have some questions now. Should I start dating somebody my own age? If so, how am I gonna handle this? Or should I just go with Carl and forget about the temptation of a young guy? Where we at?
Dana
Well, I told Carl, you know, that I met this guy from Atlanta by the pool and he. I don't know, he just. He didn't really have the response I.
BetterHelp Narrator
Thought he would have.
Dana
I think he kind of felt sort of sad about it or something. So I just didn't, you know, I didn't Go out with the other guy. I just told him that he, you know, talked to me and that, you know, we got along really well and stuff like that. So I just. Just by his reaction, I didn't go out with the other guy.
Host/Interviewer
So you didn't want to lose Carl?
Dana
Yeah.
Host/Interviewer
And you could tell that he was upset, so you didn't want to tempt that at all.
Dana
Yeah, I didn't. I just didn't even go any further with it. But I just. I told him, you know, that we talked and stuff, but I just didn't go any further with it.
Host/Interviewer
Now, I'm just curious. Since you made that decision and you decided not to call the young dude, have you been thinking about him more? Because sometimes when you pass something like that up and you don't get a chance to explore it, it starts to consume you a little bit.
Dana
Yeah, I mean, I kind of have. I kind of have been thinking about it, just wondering if, you know, I made the right decision, if I should have gone out with them, you know. So, yeah, I have thought about it. It's not consuming me or anything, but, I mean, I just. I have thought about it.
Caller/Commentator
Now, what if Carl turns around eventually and he wants to come to you and says, you know what, Maybe you're all right earlier. Maybe we should start seeing other people. Would you be bitter about the fact that you made the sacrifice for him?
BetterHelp Narrator
Um.
Dana
No, I don't guess I would be bitter about it. I mean, I don't know.
Raj
Then I would probably.
Dana
I don't know. I wouldn't say bitter, but I might be like, oh, man, I should have, you know, I should have done that. But I don't think I'd be bitter about it.
Host/Interviewer
So have things progressed at all? Good God, have they progressed? How can they progress with Clark?
Dana
I mean, we. What I wanted to do was I wanted to take him to New york over the 4th of July just as a thank you, you know, for taking me to the Bahamas. And, you know, so we are, you know, we're supposed to talk about going, but I kind of. The way I've been feeling lately is I kind of. I don't know, I don't want to go to the, you know, to the 4th of July weekend in New York. I kind of just want to hang out with my girlfriends because everybody's going to Linux and. I don't know, I just. I'm sort of. Sometimes I kind of think right now I just want a little bit more space because Carl's kind of getting sometimes a little bit Boring to me. You know what I mean? Like, not. I don't feel that way completely, but I just. I kind of want to hang out with my girlfriends, but I already talked to him about going to New York, so I don't know. I'm just sort of thinking right now if I should stay home with my girlfriends or go with him. You know, like, if this. I don't know. I'm kind of wondering if I'm just going through a phase. But I don't know, because it's my first relationship, so I don't know if people kind of feel like they want to cool off sometimes. I don't know. I just don't know if it's a phase or not.
Host/Interviewer
You almost heard the dramatic dun, dun, dun, dun.
Caller/Commentator
Did you talk to Carl about this yet?
No.
Dana
No, I. You know, after I told him about the guy and stuff, I just don't want to worry him because I just. I don't know if it's a phase I'm going through, so I just don't want to talk to him about it.
Caller/Commentator
What do your girlfriends think you should do?
Dana
Well, they.
Raj
They just.
Dana
They still don't like me going out with him, so I really. Sometimes I don't talk to them about it because I know what they're going to say, so. And they, of course, want me to stay with them and go to Lenox, so I already know what they're gonna say.
Caller/Commentator
What are some of the things that, you know they're gonna say?
Dana
Well, I mean, I know they're gonna be like, well, you know, of course he's boring, because, you know, you're younger and you should be having fun and. And I do have fun with them. I just, you know, I don't know, I'm just kind of feeling a little bit bored. But I do have fun with them. It's just a different kind of fun.
Host/Interviewer
Are you starting to question now? I mean, because you guys haven't really been going out that long. Although things have progressed, right, really, really quickly. I mean, a couple of weeks ago, you were talking about marrying this guy and having kids with him, and now you're saying you're kind of bored by what's going on. Is that scaring you at all?
Dana
A little bit. I mean, because I just. I don't know, I kind of feel like I'm just going a little bit back and forth right now. I mean, because on the one hand, you know, I was okay with that, you know, with not going out with the young guy, because I do, you know, I still like Carl a lot, but on the other hand, like, I don't know, I just, I feel like I need to have a little bit of space and have a little bit of fun with my girlfriends and, you know, so I don't know, I'm just. I'm kind of going back and forth.
Host/Interviewer
Calls are starting to come in now. 404-741-1005. As they always do when you're on. Hey, Kelly.
Caller/Commentator
Hey, good morning.
Raj
Good.
Dana
How are you guys?
Host/Interviewer
Good, thank you. You're on with Dana.
Raj
Hey, Dana, I. How long have you guys been together? Oh, gosh, I can't remember from the.
Dana
It's not been that long. I mean, it's just been.
Raj
Yeah, see, that's my thing. I mean, the whole age thing concerned me to begin with because my mom was married to a man who was 13 years older than her, and the marriage didn't even last five years simply because of the different habits. But second of all, normally when you're in a relationship and you've only been together for a little while, it should stay new for a while. You shouldn't be bored that easily, and you shouldn't be getting tired of them so soon. And my thing is, I'm just wondering if, because you waited for so long to date somebody, it's usually a good idea before you start talking about being serious with somebody that you, you know, date around a little bit, figure out, you know, who you. What interest you might have because you may, you may not even know, you know, what you want out of a relationship right now. Excuse me.
Dana
Sorry.
Host/Interviewer
Yeah, it's so hard because you have no experience to fall back on. You know, like, you don't have anything to compare them to. You have no previous experience in dating whatsoever. So he's the only guy. And I think if I was you, the big red flag would be, I have no experience. I was by myself before. I was alone before. And this guy still born me to tears, you know?
Raj
Yeah.
Caller/Commentator
You know, I mean, in all fairness, because, I mean, I am concerned by the age difference, but in all fairness, most relationships, you have the honeymoon phase where you can't get enough of each other. You spend 24 7, you think about each other 24 7, you let the electricity. You forgot to pay the bill because you spend so much time, electricity goes out. You know, like, you forget together. I mean, like, you, you are so in love. And then, you know, there's a certain period of time that happens, and then you start, you know, kind of going back to your Friends. It's time to reconnect with your friends and stuff. So in dating, it's normal to have that intense phase that ends up kind of waning. But I don't know if the word boring comes into play when you kind of transition from the honeymoon into normal life again. Yeah. So, you know, it's probably a combination of both, but I. I feel like the age difference is a factor in this, you know.
Host/Interviewer
Hey, Andrea, you're on with Dana.
Raj
Hey, Dana, I just want to say, in about 10 years, your call guy is going to be dead. And don't ditch your girlfriend. If you ditch them, you're going to be left all alone.
Host/Interviewer
Oh, come on.
Caller/Commentator
I love how people think somebody's in their 50s is so elderly. He's not old. In 10 years, he's going to be dead.
Host/Interviewer
So don't pitch your girlfriend.
Caller/Commentator
Come on.
Noah
Hello.
Host/Interviewer
Hi, Stacey, you're on with Dana.
Dana
Hey, Dana.
Raj
I was married to a guy who's 20 years older than me, and we had three kids together. But after we. We divorced after seven years because interest just changed. It doesn't work. There's just. It just doesn't work. Go with a young guy and.
Host/Interviewer
Well, at this point, there really is no young guy. I mean.
Raj
Yeah, but there could be.
Host/Interviewer
So you say get a little bit more experience. Start dating people your own age.
Raj
Well, yeah. I mean, the age gap just does. It does not work.
Host/Interviewer
But she went all of these years. I mean, she's 27 now, 28 years old, and never had a date. So you're saying, you know what? Date guys your own age. But that wasn't.
Raj
Date guys younger. Don't date someone. I mean, it just. It doesn't work.
Caller/Commentator
Can we please take the age out of this and remember that Dana is dating her first person ever, regardless.
You don't think age is a factor in her.
I don't think it's relevant in this. I mean, boredom, whatever. That's not relevant. Even if she wasn't bored with him and he was one year older than her, I would still say it's your first. Her first date ever was with this guy. Age does not matter in this case. I mean, if. If it was a situation. You know what I mean? Like, if we want to discuss the age thing, whatever. We're going to get 50% of calls of people who are 20, 30 years apart and they're perfectly happy. The other 50% are people going to say, I did it, my sister did it, so was unhappy. Blah. That's not it. The point is, anybody who Went out on their first date, one date. And then decided that's the person they want to spend the rest of their life with is wrong. Like, don't do that. Don't. That's a bad idea.
Naive decision.
Yeah. Spend six months, date a couple other people, and then go back to that person if you want, but just don't. Because my thing is, the boredom is not going to have anything to do with, you know, the fact that their interest might be different because he's older. I think the boredom might come from the fact that five years from now, if they're married with a kid, she might go, God, what else is out there?
Raj
What if.
Caller/Commentator
Even if she was. Even if she was 21 and the guy was 22.
Host/Interviewer
Hey, Dana, at this point, do you have any idea what you're going to do for July 4th, day and night?
Dana
No, I. I still don't know. I mean, I'm listening to what everyone's saying, and I don't know. I still don't know because I just. I still really like Carl, you know, And I just don't. I'm not ready to say. Well, because I'm feeling a little bit bored, you know, that I want this to stop. I'm just. I'm not ready to do that yet. So I'm not sure.
Host/Interviewer
All right, well, let's do this. I mean, this will be perfect timing for us. And when we come back on the 5th, we'll talk to you to find out what you did the day before on the 4th.
Dana
Okay?
Host/Interviewer
Okay.
Dana
Okay.
Host/Interviewer
All right. Good luck.
Caller/Commentator
Thank you.
Host/Interviewer
All right. And again, thank you for letting us share in this whole thing.
Dana
Okay, thanks, guys.
Host/Interviewer
Appreciate it.
BetterHelp Narrator
Bye.
Noah
Bye.
Host/Interviewer
And I guess there's no real chance that he's going to listen in and say, okay, I don't want my life exposed here because he doesn't even know that there's an FM band yet.
Caller/Commentator
Come on.
But don't you notice more maturity in her voice since the first time we talked to her?
Well, less giddy excitement that time, I thought for sure. Like, I thought when we've, you know, every time we've talked to her about Carl, she's been like, you know, kind of giggly and giddy, and this time she's like, yeah, I'm not so sure.
I want to go to New York.
Host/Interviewer
You can hear that. You can hear that. All right, we'll check back in with her on the 5th when we get back from vacation, find out what she did over July 4th. Hey, the bird show.
Raj
Hey, it's Raj.
Noah
And Noah.
Raj
And we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with. Whether it's making new friends as an adult, managing our emotions, or even dreaming.
Noah
We'Ll be talking to experts in their fields who are definitely doing things right, so the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're going to have full video episodes on YouTube. Because as long as there are things to get wrong, we're going to be right here to help you do them better.
Raj
Love y'.
Caller/Commentator
All.
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Episode Title: Vault: She’s In Her 20s And NEVER Had Been On A Date!
Release Date: January 14, 2026
Host: The Bert Show Cast (Pionaire Podcasting)
This episode revisits the ongoing story of Dana, a 27-year-old woman who, until recently, had never been on a date. The episode explores her whirlwind entry into dating, beginning with her parents setting her up with a 58-year-old man, Carl, and the challenges she's faced as their relationship quickly accelerates. The show features reactions from the cast and callers as Dana navigates intense emotions, second thoughts, and the pressures of her first romantic relationship—all while grappling with issues of age difference, inexperience, and personal growth.
“I can’t believe I’m talking to this cute guy, because…this wouldn’t have happened seven months ago.” — Dana [02:59]
“She either married to the old guy or she completely dumped him and started seeing the younger guy.” — Host [04:07]
“I think that their last day down in the Bahamas, she probably walked in and caught Matlock giving himself a vegetable enema…” — Caller [05:30]
“I kind of have been thinking about it…just wondering if I made the right decision, if I should have gone out with him…” — Dana [07:26]
“I kind of want to hang out with my girlfriends…but I already talked to him about going to New York…I'm just sort of thinking right now if I should stay home with my girlfriends or go with him.” — Dana [08:20]
“It’s so hard because you have no experience to fall back on…this guy still bores me to tears, you know?” — Host [11:54]
“Anybody who went out on their first date, one date, and then decided that's the person they want to spend the rest of their life with is wrong. Like, don't do that…” — Caller [15:03]
“Can we please take the age out of this and remember that Dana is dating her first person ever…even if she was 21 and the guy was 22…” — Caller [14:13]
“I still really like Carl... I’m not ready to say, because I’m feeling a little bit bored, that I want this to stop.” — Dana [15:38]
“I thought when we've…talked to her about Carl, she’s been like…giggly and giddy, and this time she’s like, ‘Yeah, I’m not so sure.’” — Caller [16:29]
On sudden attention:
“I can’t believe I’m talking to this cute guy…if this would have happened, like, seven months ago…I just felt like this wouldn’t have happened.” — Dana [02:59]
On moving too fast:
“A couple of weeks ago, you were talking about marrying this guy and having kids with him, and now you’re saying you’re kind of bored…” — Host [10:07]
On her friends’ advice:
“They still don’t like me going out with him…sometimes I don’t talk to them about it because I know what they’re going to say…” — Dana [09:33]
On relationship firsts:
“Anybody who…decided that’s the person they want to spend the rest of their life with is wrong. Like, don’t do that. That’s a bad idea.” — Caller [15:03]
Next Update: The cast promises to check in with Dana after July 4th to see what she ultimately decided and how she's feeling about her relationship moving forward.