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Marc Maron
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Jeff
Monday Sidekick the AI agent that knows you and your business thinks ahead and takes action.
Wendy
Ask it anything seriously.
Jeff
Monday Sidekick AI you'll love to start.
Monday.com Announcer
A free trial today on Monday.com.
Bert
The Burt show we call this the Burt Show's tough love advice. We ask guys only to be part of this. 404-741-1005 why guys only?
Jeff
Jeff well, sometimes women can't really give the bare bones, stripped down hardcore advice, especially to other women because those annoying feelings get in the way. So what will happen is you'll have a woman with a question like the one that Bert was talking about earlier. She thinks her boyfriend's cheating on her. And girls will be like, well, you know, maybe it's not. Maybe he's not. Like, you're always looking for that glimmer of hope, that pot of gold at the end of the rainbow, the ray of sunshine on a cloudy day. You're always like, well, maybe he's not. He is or he isn't. And guys will, you know what? It's going to hurt your feelings. It's going to be hard. But maybe he's just not that into you. And guys are going to cut right through that. No ray of sunshine on a cloudy day. If he's cheating on you, we're going to call it. If he's, you know, if he's a crappy guy, we're going to call it. If, if your friend has screwed you over, we're going to call it and just leave it at that.
Bert
We're a wily bunch, guys, and you don't have the, the, you don't have the playbook. But since we write it every single day, we can tell you guys what's really going on in your relationship if you give us all the facts. Good morning, Wendy. You were on Q100. How are you today?
Wendy
I'm doing great. How are you doing, guys?
Bert
We're doing okay. Just trying to get the voice disguiser a little bit adjusted for you. Nobody can recognize your voice, that's for sure.
Wendy
Thank you.
Bert
Alright, so give us some details about what's going on with your boyfriend. We got Hoss in here now. Also, we're gonna ask the guys that listen to the show to call up once they hear the details and give you real solid, solid, solid advice.
Wendy
I definitely want to know. I'm just. I'm kind of like getting completely crazy with this whole thing. I don't know. And you're right. I haven't talked to my girlfriends about it and it's gotten really. I just want to know if I'm being like paranoid or I'm being naive about this whole situation, but.
Bert
Hey, Wendy, hold on one sec. We're just trying to get the voice disguiser adjusted here. Somebody jacked with it over the weekend.
Wendy
Okay.
Bert
Okay, go ahead, start to tell us your story and we're just going to make the adjustments as you go along.
Wendy
I've been going out with a really great guide for almost, almost two years, about a year and a half. And he's really great. There's just a couple odd things that definitely send up like some red flags. And I just wanted to. I don't want to overreact because I don't want to mess up something that's really great. I don't want to accuse him of anything, but it's just like some little weird stuff. I haven't caught him in any of the, you know, classic, like, lies or no, you know, phone numbers from women or weird phone calls or anything. But there's just a couple little strange things that I just, I don't know, I just don't know if I'm being crazy or not.
Bert
Okay, give us some of these little red flags.
Wendy
Okay, here it is. Well, one weird thing, I don't know if it's even weird, but it's weird for me is he text messages all texts all the time, and then he deletes them. Like, my phone service is awful, so I'm always borrowing his phone, you know, and checking out. Well, I don't know if I'm not really checking out stuff, but I have noticed that he does delete every message he ever gets or anything like that.
Bert
Does he delete them as he responds to them or does he let them, like pile up a little bit and then just delete them all?
Wendy
No, I, of course I've never asked. My bad. No, they're. They're gone. They're. I mean, like almost any time, like the regular phone would just kind of delete them as they naturally happen. No, they're absolutely gone. And I know he's, you know, text messaging all the time, so.
Bert
And you know this because I had.
Wendy
Borrowed his phone and, you know, I don't know. All right, well, I looked. I mean, this, this kind of goes with some of the other things. So let me just let you know. I mean, I don't want to feel like I'm snooping around, but it's just something I've noticed.
Bert's Co-host
Okay.
Bert
All right, give us some of the others.
Wendy
The other thing is I am a completely trusting person. And he does go out a lot with his guy friends, which I think is really healthy. And I love it because I have a lot of girlfriends and I love going out with them too. And he has a regular Tuesday night. They play cards and have fun and go out and, you know, whatever. I think it's great. But sometimes it can be to like, you know, midnight, one in the morning, that kind of thing. And I have a couple girlfriends who just think that's a little weird. But I have no problem with it. Except I would think in the last. He has changed a position at the work he's had since he's gone out. He has kind of brought his own clothes. You know, he's brought his clothes so that he could go directly to work, so he could shower there because they have a gym and everything. And he get ready and go to work just from when he's gone out. And it is a little weird, but when he goes out to one of his friends house, it is closer to where he works. So it's not that unusual. But it's kind of compounded because of these other sort of things.
Jeff
Do you know what kind of clothes he's bringing? Like, is it something that he would wear out if he was going out with you to like a nicer dinner, or is it just like jeans and a polo shirt?
Wendy
It seems like stuff he would wear to work. I mean, because sometimes I'll see him after work and I mean, I don't know, it looks like he's just going to work after he goes out.
Bert's Co-host
So he goes out with his friends and then tells you he's gonna spend the night at his buddy's house, change for work and then go to work the next day?
Wendy
Yeah, or else he can just work.
Jeff
Closes oh, so he. I thought he was changing after work.
Bert
And then other way around. So he's going out?
Jeff
Oh, yeah, he's doing someone else.
Bert
Now, this is like in the middle of the week, right? So he's out to 2, 3 in the morning, crashing.
Wendy
Usually a Tuesday night.
Jeff
Tuesday night, adult guys don't have sleepovers.
Bert
Wait, now this is something important here. Is this every Tuesday night, or does this happen, like, a lot during the week?
Wendy
Does he stay over? But every Tuesday night he has a night, A guy's night out, usually. Okay, we have something like it's our anniversary or something. You know, that kind of a thing.
Bert
All right, so we've got staying out, he's got clothes. He's doing a sleepover at his dude's house. You got the deleted text messages. What else you have?
Wendy
Well, the only thing really kind of weird is this weekend where he's visiting relatives, like his supposed cousins. I shouldn't even be saying this, but his cousins who I've never met, and be honest with you, I've never even heard of him talking about. But now he has, like, you know, these cousins who live in South Georgia, and he's gonna go visit them, and that is fine. He's just not one of those, like, he is a good family person, like on holidays, but he usually, like. It just doesn't seem like a time like, I'm gonna go visit my cousins for some odd reason.
Bert
Have you met other relatives?
Wendy
Oh, yeah.
Bert
You've met them.
Wendy
Great. And they love me, and I love them. And that's the thing is I just don't want to overreact and mess something up. And, you know, the minute you accuse somebody or even ask, it just. I think puts just something into the relationship where then there's questioning and. And I don't know. I kind of feel like you should trust somebody until they do something that messes up with that trust. But it's not like I've caught him in lies.
Bert
Hold on a second. Have you. Have you called him over the last couple of days while he was in South Georgia? Has he picked up the phone, been available?
Wendy
Actually, he's going this weekend.
Bert
Oh, he's going this weekend?
Wendy
Yeah.
Bert
Coming weekend, just for a spontaneous weekend with the cousins.
Jeff
And why aren't you going with him?
Wendy
That's a good question. I don't know. I mentioned that, you know, I definitely could get away. I work a lot at home, and I could definitely get away. But he was like, oh, no, I never see him. And, you know, I just think it's good, you know, we'll see him at Christmas, blah, blah.
Bert
You know, hold on a sec. Hoss is already laughing at you. What do you got, Hoss?
Hoss
Yeah. He's cheating on you.
Bert
You think so?
Hoss
Oh, yeah. I mean, dude, when you said the, the text message thing, I could kind of understand that guy might just, you know, it's kind of like, you know, emails. You want to delete them, you want to keep your. Your, you know, little text message box clean. I understand that. But then you say that, that he's talking about cousins that you've never met before, that he's never talked about before. If that was. If it was that close of family, he would have already mentioned them. He would already seen them. You had already been introduced to him. So now he's going to go see people that you never even seen or talked to, don't even know exist. Now he's staying the night. Yeah. Just like Jeff said, no guys have adult guy sleepovers. That's just. No, guys do.
Jeff
Now, in defense of some guys, I'm sure there are situations where guys go out to a buddy's house and they end up getting so, you know, hammered that they just crash on the couch.
Hoss
Yeah, but that's not premeditated, right?
Jeff
That's not bring a change of clothes. And that's not like on a Tuesday night when you got to work the next day. Like, that's like, you know, Friday night we started playing cards and then, you know, we just started drinking. And then next thing you know, it's 1:30 in the morning and they're ordering pizzas. And then it's 2:30 and it's like, you know what? I'm just gonna sleep here. I'll drive home tomorrow. And he rolls in the next day, obviously wearing the clothes he slept in, stinking like the pizza and beer that they drank the night before. And that'll happen. I mean, occasionally. Occasionally it's not gonna happen every Tuesday where he brings us. Brings his work clothes in.
Bert
Wendy, how old the guy is this dude?
Wendy
He's 31.
Bert
31. Okay, hold on one second for me.
Bert's Co-host
Now, we did not know that Jeff had brothers, stepbrothers, until like three years into the relationship. So I just want to point that out.
Bert
That's true.
Bert's Co-host
Three years into our relationship with you, we found out it was kind of the same with Bert, too.
Tony
What's that?
Bert's Co-host
I said I didn't know that you had Hayden brother. No son until yesterday. No. That you have half brothers, right? Yeah, I don't have brothers.
Jeff
And they're. But we're not dating. Like, I Think there's a difference.
Bert
I think the point that they're making here is that guys just don't readily share their relationships with other relatives.
Bert's Co-host
Yeah, I'm not making an excuse for him. I just feel like I need to point that out.
Jeff
If he's making up cousins, like, it's not like I think there's a significant difference between dating and co workers. Like you guys didn't know about my half brother or Bert's half brother because it never comes up in conversation. But if we were dating, if we were dating and all of a sudden I said, oh, yeah, I'm going up to North Carolina to visit my half brother, you should be pretty damn suspicious.
Bert
The voice disguise. All right, so we're only getting guys advice here. 404-741-1005. Tony, what do you think?
Chad
Hey, I think this is real easy. Is this one of the situations where she can call anytime she wants and she calls him up on Tuesday night and hears music in the background, the guy's laughing, playing pool things. Or is this one that's, oh, well, baby, I don't think you should call me on Tuesday nights and disturb me and so doesn't know what's going on. I think it'd be easy to call and find out what's going on.
Jeff
Or is the phone off? I think that's hugely telling if the phone is off or, you know, going. You can always tell when a cell phone's off because it goes. Right. Doesn't even ring before it goes to voicemail.
Chad
Voice disguiser, please.
Wendy
I've been able to get in touch with him. That's what one of the weirdest things is. No, I can. Or sometimes one of his friends pick up. So I know that. I mean, I don't call him every Tuesday because I want to be some kind of a, you know, a crazy girlfriend. But, you know, I have called him over there to like, have to make plans for stuff, but I'm not going to like check up on him or anything. It just sounds so weird when you.
Bert
Have called him, though, on those Tuesdays.
Wendy
He is other guys, you know, I mean, I'm friends with some of those guys, too. And that's the other thing. I really think they would tell me if something was going on.
Jeff
I'm sure they would.
Bert
I don't know. I don't know. Guys protect each other pretty well, so I wouldn't count on them.
Jeff
You know what guys say, Hoes before bros.
Bert
I'm just saying if he's. I think what you're Hearing here is if there's some accessibility there. If you call up and he's out with the guys, then you can take some comfort in that fact.
Wendy
I definitely can. The only thing, it's. I guess it's compounded with this other stuff, you know, like, I wonder, like, is he. Is he seeing her? You know, if there was somebody afterwards or something like that.
Bert
Most guys are saying there's nothing to be scared about here. Don't.
Wendy
Really.
Bert
Yeah, most are saying that. Don't worry about it. Good morning, Chad, you're on Q100. What's going on?
Chad
Yeah, I was say that I really don't think it's an affair.
Bert's Co-host
Why? I mean, I. I mean, what. What do you think it is? Just. She's just being. Thinking. Yeah. Monday after Thanksgiving. What I'm trying to say is, why do you think that he's taking the clothes over? Do you think that the premeditated spend the night is normal?
Chad
I do it on occasion.
Bert's Co-host
Okay.
Bert
I'd say I'm with Chad. I don't think he's screwing around yet. Or at least I'd say you still have to give him the benefit of the doubt. It is.
Jeff
It is changed a little bit when she said that his buddies would answer the phone. Or like, if she calls over there. Like, the fact that there is a group of guys around, that helps, but still, like the cut. Like, if it was just that if the only thing she called up with was that I would start out by saying he's cheating, and then when the buddies answered the phone, it would be gone. But the random cousin visiting and the text messages, I also think I'm like csi, man. I look at all over the place. I'm pulling hair follicles off the car seat. I'm putting the whole thing together.
Bert's Co-host
Well, the text message thing, I think what Bert asked is so important. She didn't have the answer because text message memory in your phone is not unlimited. So I delete all the incoming and outgoing text messages every so often, but.
Bert
Not as they come in or out.
Bert's Co-host
But not as they come in or out. So, I mean, there's one moment you could be looking through my cell phone and there's nothing. And then others, there's 48 messages in my box.
Bert
You know, the thing that the one detail I still need, The one detail we. Is the. Is the distance between work and his house. Like, how far is it from work for him?
Wendy
If it's like rush, it could take like, probably like a little over an hour. You know, when he's at his friend. Especially if it's that gym. As he's over his house, it's more like 10 minutes. So it is a lot easier for him to go to work. I understand that. And I really didn't have a problem with it until I started talking, you know, to some of my friends about it. And then it was like, well, you're just being crazy. And, you know, why aren't you, you know, calling him on it and everything. And I just. My main thing is you're not messing up something that's really good because he's a good guy and I just don't want to mess it up.
Bert
Has he ever cheated on you before?
Wendy
Oh, no.
Bert
Never done anything? Never given you any indication at all anything's up?
Wendy
No, not at all.
Bert
I still think you got to give the benefit of the doubt.
Jeff
Yeah. Now that there's a commute issue where it's an hour if he goes home, but only 10 minutes.
Marc Maron
Damn it.
Hoss
H. Yeah, that's what. Yeah. Now that she said that. You should have told us that in the beginning. I wouldn't have felt so dumb by saying this.
Bert
I think you're okay at this point.
Wendy
I just been talking. I guess I need some help from you guys. And I really appreciate it. I really feel good about it. And definitely, I don't know, I think that's the way to go.
Jeff
It's just. Just.
Wendy
Let's just.
Hoss
You know what?
Jeff
Keep looking though. You'll find some reason.
Bert
Keep digging and digging and digging. Screw it up, girl. Screw it up somehow.
Wendy
Stop it.
Bert
See you later.
Jeff
That would be great.
Wendy
Thank you.
Jeff
I would start checking his email. If you could somehow get one of those spy bot things or something up on his computer and you could check his email, that would help your relationship. I think just to solidify the.
Marc Maron
Nothing.
Bert's Co-host
What if she just followed him this weekend? A couple car links behind all the way to.
Monday.com Announcer
You know.
Jeff
Here's what you need to do is go over to his buddy's house Tuesday night for the big sleepover.
Bert
Oh, that'll go over well for the.
Jeff
Big poker night slash slumber party.
Bert
I love how she says. The last thing she says is, hey, you guys did great. Thanks so much. Which means, hey, you guys said exactly what I wanted to hear.
Hoss
Thank you.
Bert
The Birch Show.
Jeff
G'.
Wendy
Day.
Tony
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Bert
It's a lot, yeah.
Tony
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Marc Maron
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Date: November 25, 2025
Host: Bert and The Bert Show Cast (Jeff, Chad, etc.)
Caller: Wendy
This episode is a classic “Tough Love” segment on The Bert Show, focusing on giving blunt, straightforward advice to listeners facing relationship dilemmas. The spotlight is on Wendy, a caller who's anxious about perceived “red flags” in her nearly two-year relationship. Instead of getting advice from her girlfriends, Wendy turns to the guys on the show—believing she'll get no-nonsense, unfiltered feedback.
“Sometimes women can't really give the bare bones stripped down hardcore advice... those Ann feelings get in the way... Guys are going to cut right through that. If he's cheating on you, we're gonna call it. If he's a crappy guy, we're gonna call it.”
(01:43)
"...since we write [the playbook] every single day, we can tell you guys what's really going on in your relationship if you give us all the facts."
(02:39)
“He text messages all the time, and then he deletes them... I have noticed that he does delete every message he ever gets...”
(04:21)
“He has a regular Tuesday night... play cards, have fun... sometimes it can be to like, midnight, 1:00 in the morning...”
(05:32)
“His supposed cousins... I've never met... never even heard of him talking about. But now he has, like, you know, these cousins who live in South Georgia...”
(07:39)
“Yeah. He's cheating on you.”
(09:08)
“Adult guys don't have sleepovers.”
(07:15) “That's not premeditated, right?... that's not, like, on a Tuesday night when you gotta work the next day.”
(10:01)
Chad brings up past family surprises:
“We did not know that Jeff had brothers, stepbrothers, until like three years into the relationship.”
(10:41)
Jeff (on what’s suspicious):
“If we were dating, and all of a sudden I said, ‘Oh yeah, I'm going up to North Carolina to visit my half brother,’ you should be pretty damn suspicious.”
(11:15)
Tony asks about communication:
“Is this one of the situations where she can call anytime she wants and hears music in the background, the guy’s laughing, playing pool... Or is this ‘don't call me Tuesday nights’?”
(11:45)
Wendy clarifies:
Bert:
“Guys protect each other pretty well, so I wouldn’t count on [the friends telling you].”
(12:46)
“Text message memory in your phone is not unlimited. So I delete all the incoming and outgoing text messages every so often...”
(14:25)
“It could take, like, probably a little over an hour... at his friend... it’s more like 10 minutes.”
(15:07)
“I think you’re okay at this point.”
(16:01)
“Just keep looking, though. You’ll find some reason to keep digging...”
(16:13)
“What if she just followed him this weekend a couple car lengths behind...”
(16:33)
“That would be great. Thank you.”
(16:22)
“I love how she says, ‘Hey, you guys did great. Thanks so much.’ Which means, hey, you guys said exactly what I wanted to hear.”
(16:45)
“Guys are going to cut right through that. No ray of sunshine on a cloudy day.” (01:49)
“Yeah, he’s cheating on you.” (09:08)
(later retracted after added context)
“Adult guys don’t have sleepovers.” (07:15)
“Start checking his email. If you could somehow get one of those spy bot things... that would help your relationship...” (16:23)
"Just follow him this weekend..." (16:33)
"That would be great. Thank you." (16:22)
The Bert Show crew maintains their famously candid, humorous, and slightly irreverent atmosphere throughout. They blend real empathy with teasing and comical exaggeration, keeping things light even while addressing sensitive insecurities. The “guys only” format results in a fast-paced, no-nonsense feel, but ultimately the advice is practical, not mean-spirited.
Wendy’s concerns about her boyfriend trigger a spirited “tough love” analysis from The Bert Show’s male panel. Though initial reactions are suspicious (“He’s cheating on you”), as more context is revealed (commute, frequent phone access, mutual friends), the panel softens, generally encouraging Wendy to trust her boyfriend unless real evidence emerges. The segment highlights common dating anxieties, the importance of context, and the tricky balance between trust and vigilance—served up with the humor, authenticity, and camaraderie that The Bert Show is known for.