01-19-26 - WWBD - MIX - Should He Take Trucking Job - His HS Nemesis Is Now Banging His Mom - Dec 2021/2024-BO

Summary

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Holmberg's Morning Sickness – 01-19-26: Should He Take Trucking Job? | High School Nemesis Now Dating His Mom

Podcast: Holmberg's Morning Sickness (98KUPD, Arizona)
Date: January 19, 2026
Hosts: John Holmberg, Brady Bogen, Brett Vesely, Dick Toledo

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Episode Overview

This episode’s "What Would Brady Do?" (WWBD) segment dives into two listener dilemmas:

1. Should a dad leave his low-paying job for a better-paying but family-disruptive trucking gig?
2. What should a man do when his former high school nemesis is now dating (and possibly sleeping with) his 64-year-old mother?

The hosts bring their trademark raunchy humor, irreverence, and surprising flashes of empathy as they weigh the pros and cons, heckle each other, and riff off-the-cuff on generational romance, truck stop shenanigans, and awkward family holidays.

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Key Discussion Points & Insights

1. Listener Dilemma: Trucking Job vs. Family Time

Listener Letter (Tyler):
Should he leave his $14-an-hour job and get his CDL for a better-paying cross-country trucking job, knowing it could mean weeks away from his kids and that his wife might have to quit her job?

Discussion & Advice

• Encouragement to Take the Leap:

  • Hosts generally agreed the career switch is a worthwhile risk.
  • "Try It." (02:04)
  • "They are signing big bonuses, like hundred thousand dollar bonuses to go up to get." (Co-host, 02:08)
  • "It's a better job. Always upgrade. Where's the problem?" – Brady (02:15)

• Family Sacrifice vs. Opportunity:

  • Brett jokes, "You get away from them kids." (02:22)
  • Brady riffs, "That's what they sell vacation homes for. You get away from the kids. I mean that's the whole goal of having kids is to get away from them. Becomes a giant hide and seek with the earth." (02:25)

• Practical Considerations:

  • Weighing upgrade of life versus time lost with children.
  • Suggestion: Try it—if it doesn’t work out, move on to another option.
  • "The only way you find out is going into that job and you all sudden you really like it. That's good. If you don't, you can find something else." (Co-host, 02:39)

• Cultural and Movie References:

  • Riffing on BJ and the Bear (TV trucker + monkey):
    • "Get a chimpanzee and go on the road." (Co-host, 03:47)
    • The humor devolves to imagining truck stop hijinks with a monkey and prostitutes.

Notable Quote

• "Kids—take this trucking job." (Co-host, 03:33)

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2. Listener Dilemma: His High School Jock Nemesis Now Dating His Mom

Listener Letter (Kenny):
His 64-year-old mom is now dating a guy who graduated two years ahead of him, who also once took Kenny's girlfriend to the Sadie Hawkins dance. The new boyfriend is, quote, “now boning my mother.”

Discussion & Advice

• Shock, Humor, and Awkwardness:

  • The hosts tease and riff at length, imagining humiliating scenarios for Kenny and epic holiday discomfort.
  • "How do you Get Mom? You gotta go to the holidays now with Derek Zellner. And he's just pushing your mom's osteoporosis hips all the way through the bed." – Brady (08:59)

• On the Age Gap:

  • They discuss precedents for relationships with wide age gaps and note it's unusual for women to date much younger men, but not unheard of.
  • Brady relates a personal story: "My aunt was 25 years older than the guy she ended up being with…her son was two years older than him…He stuck. That relationship stuck." (06:47)

• Empathy & Advice:

  • Suggestion to be honest with the mom about how weird it is:
    • "You tell your mom how you feel. Oh, it's just kind of weird for me, Mom." (Co-host, 06:39)
    • "I'm not telling her to stop necessarily, but I'm telling her, you got to understand how weird this is." (Co-host, 10:36)

• Comic Escalation & Dark Humor:

  • Imagining the new boyfriend brashly addressing his conquests:
    • "Tonight, I'm gonna enter your mother. Do I have your permission?... I'm gonna your mom tonight. Pass the gravy…She wants to experience north and South Korea. You know what I'm talking about." – Brady (12:43)
    • "You know what my favorite smell is? Ammonia based urine and baby powder from the diaper your mother has to wear because I've knocked the bottom off." – Brady (13:39)

• On Resignation:

  • "Just keeping my eye on you, Chet." – Co-host, 11:58
  • "You're gonna eventually see him boning your mom. It's gonna be weird when you...He's slapping down your mom's potatoes for Thanksgiving." – Brady (12:00)

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Notable Quotes & Memorable Moments

• On the Value of Upgrading Careers:

  • "Get your CDL license. It's a better job. Always upgrade. Where's the problem?" – Brady (02:15)
  • "The only way you find out is going into that job… If you don't, you can find something else." (Co-host, 02:39)

• Classic HMS Escalation:

  • "If you had a road monkey and you had hookers at truck stops, you'd see what the hookers up. You'd try it once. Why don't you please my friend here?" – Brady (04:09)

• Personal Anecdote on May-December Romance:

  • "My aunt was 25 years older than the guy she ended up being with… ended up getting along pretty well later. He stuck. That relationship stuck." – Brady (06:47)

• Unfiltered Family Holiday Nightmares:

  • "You gotta go to the holidays now with Derek Zellner. And he's just pushing your mom's osteoporosis hips all the way through the bed." – Brady (08:59)
  • "You're gonna eventually see him boning your mom. It's gonna be weird when you...He's slapping down your mom's potatoes for Thanksgiving." – Brady (12:00)

• On Awkward Family Talks:

  • "Tonight, I'm gonna enter your mother. Do I have your permission?" – Brady, comic roleplay (12:43)

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Timestamps for Important Segments

• 01:40–04:00: Listener trucking job question, hosts’ advice, and comedy riff on trucker life
• 04:51–07:50: Listener email about mom dating his high school nemesis, hosts discuss age-gap relationships
• 07:50–10:25: Comparing to other age-gap romances; the weirdness of family holidays
• 10:25–14:09: Further escalation of family awkwardness, comedic roleplay, and letting go

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Tone & Style Highlights

• Humorous, Raw, and Unfiltered: True to form, the hosts use dark, over-the-top humor, wild hypotheticals, and pop-culture riffs.
• Brief Moments of Sincerity: Genuine advice is given amid the sarcasm.
• Fast-Paced, Bantery: Lots of quick asides, inside jokes, and seamless return to the core dilemma.

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Summary

This HMS episode delivers classic, irreverent morning show comedy built around seriously awkward real-life situations. While never long on earnestness, the hosts offer real advice: seize career upgrades even with risks, and communicate—however uncomfortable—when family dynamics go weird. Above all, they remind listeners: sometimes, the only way through an uncomfortable mess is to laugh about it.

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Transcript

[Brett Vesely]

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[Byron]

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[Brett Vesely]

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[Brett Vesely]

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[Brady]

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[Brett Vesely]

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[Brady]

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[Brett Vesely]

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[Brady]

I have an opportunity to join a family member in a cross country trucking job. Should I leave my $14 an hour job to get my CDL and start a new chapter in life? The pay is better, but I would be away from my younger kids for weeks at a time. My lady could quit her job and be home 24 7. If I do this and she doesn't like her job anyway, that would just make it tight again. Tyler.

[Co-host or Guest]

Try It.

[Brady]

What would you do?

[Co-host or Guest]

They are signing big bonuses like hundred thousand dollar bonuses to go up to get.

[Brady]

Yeah. I don't know if that's what he's getting left. Getting a lot of dough. Get your CDL license. It's a better job. Always upgrade. Where's the problem?

[Brett Vesely]

You get away from them kids.

[Brady]

Yeah. Weeks at a time.

[Commercial Announcer]

I'm in.

[Brady]

That's. That's what they sell vacation homes for. You get away from the kids. I mean that's the whole goal of having kids is to get away from them. Becomes a giant H and seek with the earth.

[Co-host or Guest]

And if the missus is fine with it.

[Brady]

Yeah.

[Co-host or Guest]

And it depends on the. You know, if he's like, you know how involved on the kids. Like he was coaching little league or something like that. You could still probably work things out. I mean the only way you find out is going into that job and you all sudden you really like it. That's good. If you don't, you can find something else.

[Brady]

This is super accommodating Brady. Today everything's going to work. You're coaching little League. I don't know where that came in.

[Co-host or Guest]

Because of the osteen talk. He's got to feel right think.

[Brady]

I think it's cuz he's got to get Kirby a dog today to finish her punishment.

[Co-host or Guest]

Is there a Mr. Worldwide?

[Brady]

There you go.

[Co-host or Guest]

Is the job that he has.

[Brady]

Yeah. Fourteen dollars and a half.

[Co-host or Guest]

Does that have room to move up?

[Brady]

But okay. That said, that's time and amazing.

[Co-host or Guest]

It is time.

[Brady]

This is a thing where he can do the CDL license and guaranteed move himself.

[Co-host or Guest]

Right.

[Brady]

But it comes with work and getting out of the house.

[Co-host or Guest]

I don't know how you're doing at 14 an hour.

[Brady]

I don't either.

[Co-host or Guest]

Kids take this trucking job.

[Brady]

Yeah, I agree. And should nuts.

[Co-host or Guest]

Then if you can get, you know in a year or two you can buy your own private rig.

[Brady]

That's right.

[Co-host or Guest]

Get a chimpanzee and go on the road.

[Brett Vesely]

Oh man.

[Brady]

BJ and the bear reference. Bj. BJ from the bear is what I like to say. You got that road simian that's gonna be trained to do some things the hookers can't. Probably gonna pay a hooker to do it with the bear at least once. Right. If you had a road monkey and you had hookers at truck stops, you'd see what the hookers up. You'd try it once. Why don't you please my friend here.

[Co-host or Guest]

For a little bit.

[Brady]

And then the stories you could tell for ages. Dress em up not even dress them up. Just let them be full monkey. And then just have the hookers at the truck stops who'll do anything for 50 bucks. He ain't gonna believe what I had to do. You know that monkey I have? Huh? They had interspecies relations. I want to see Glowing bear.

[Co-host or Guest]

I want to see.

[Brady]

I want to see. I would. You'd watch that if you're a trucker here, that's. You're at Rip Griffins and the guy's like, you got a monkey in a car now? One of them hookers. Let me see. I know it's on the ring cam that cross country.

[Co-host or Guest]

Imagine all the Buc EE's you can stop at.

[Brady]

Oh, man. And get all those. Those lot lizards up in there. Oh, bang. Your monkey shower up. Because they're not human, the hookers at the truck stops. That's why all the truckers are serial killers. They get rid of them. Dear Brady, my mother has a new boyfriend. He graduated high school in 1996, two years before I did. She's 64 goddamn years old. This is awful. Here's what's worse. This dude took my girlfriend to Sadie Hawkins when we were in high school together. Now he's boning my mother. Oh, we weren't friends in high school because he was a stud jock and I was a nerd in the math department. Somehow or another, he still makes more money than me. He started his own company. I need a way to prank this prick and end this violently. I can't do the holidays like this. And yes, he can still kick my ass if he needs to. Kenny. Oh, Zellner and Marcy Kelly. Oh, wow. Hey, Zellner's a good catch. Shoot. You should be so lucky, homebird. Maybe they could get together, make a new version of her good son. What that would look like. Not this big nose, Cuckoo Stern wannabe. Shoot, DZ puts a baby in your mom, if he thinks about it. Doesn't even need to date her or see her or even meet her.

[Co-host or Guest]

Look who's got mistletoe over.

[Brady]

How many rings you got? I make DZ wear a tinfoil over his head in case some of those thoughts of him having sex with your wives and impregnating them gets out. Second that hits the ether, your wife has a baby in full. She gonna stop menstruating if she's in the same room with that man? Hey, dz. But yeah, DZ graduated two years ahead of me. It would be the same. Oh, and I read.

[Co-host or Guest]

Yeah, you'd have to talk To. I mean, you tell your mom how you feel. Oh, it's just kind of weird for me, Mom.

[Brady]

Now, My aunt was 25 years older than the guy she ended up being with. Is that right? Maybe 20, something like that. But she. Her son was two years older than him. Something like that. He was 25, and she might have been like 48. So maybe 23, 24 years, which is weird for a woman to a man, but when you have an older son and the son was like. They ended up getting along pretty well later. He stuck. That relationship stuck. And by the way, my aunt's still alive and this guy's dead. He died in his 50s. She's like 80 now.

[Co-host or Guest]

It's like. Though the. Somebody described to me the Belichick thing. He's dating a 24 year old. So when he was.

[Brady]

When he just got Tom Brady.

[Brett Vesely]

Yeah, she was one.

[Brady]

Did you see him meet her parents?

[Commercial Announcer]

No.

[Brady]

It's on. He. They're 48 and 49 years old. Yeah. And Belichick's 74.

[Co-host or Guest]

I saw him. Belichick, at a gala. Yeah, she looked great. Of course she did.

[Brady]

By the way, about her.

[Co-host or Guest]

Looks great.

[Brady]

He looks great. He's never seen him happier. And Bill is. Bill's on the McAfee Show. He does Inside the NFL. He's. He's phenomenal. He's everything you want Bill Belichick to be. Outside of, like, those. They just realized he's been snowing us for 30 years with those press conferences.

[Co-host or Guest]

Of hate just because he hates the.

[Brady]

Media and the evil empire. He was playing a game and they realized how funny that is, that he's Andy Kaufman. That was 30 years of him just going, I'm not gonna answer your questions. We're on to Indianapolis. Watch him on McAfee. And on Halloween when he dressed his young concubine up as a mermaid and acted like he was fishing. Pat's like, saw you fishing there. Bill saw fish and you're doing right. He goes, yeah, I caught a big one. And it's like, oh, that was. He's good. But. Yeah. And that Caliento used to tell me all the time, the only thing he ever heard about Belichick was, he's hilarious. Like, that was the. Like, this dude's funny. So it's different, though, when your mom. Oh, if your mom started to smash.

[Co-host or Guest]

Graham Carpenter, two years old. Right.

[Brady]

Start smashing Clubba. Like, that's probably about the same. It's pretty close.

[Co-host or Guest]

Well, I was putting it on the athlete side. Like, superstar basketball player.

[Brady]

How do you Get Mom. You gotta go to the holidays now with Derek Zellner. And he's just pushing your mom's osteoporosis hips all the way through the bed.

[Co-host or Guest]

But he makes me happy.

[Brady]

She has got osteoarthritis and he is just putting. What is this guy? He graduated in 96, which puts him around 40 something. 41 2. I don't know if he can put.

[Brett Vesely]

His weight on her, Jon.

[Brady]

Oh, he's not even 40. Am I doing that right? Yeah, he is.

[Co-host or Guest]

Yeah.

[Brady]

96 puts you there because you'd be 20 and 98 and that was. Yeah, so he's. He's in his mid-40s and he's just smashing mom. Smashing her. He's 46, she's 64.

[Co-host or Guest]

I'm saying something to my mom.

[Brady]

Is that right? I'm doing something wrong there. Either way. What do you say to her? Well, stop phoning my high school friend.

[Co-host or Guest]

How weird it is.

[Brady]

Do you know that guy used to pick on me? He was a badass in high school and I was a nerd. He took my date to Sadie Hawkins. Hey, wait, Sadie Hawkins? She asked him?

[Co-host or Guest]

Yeah, that's the other way around here.

[Brady]

They took him to Sadie Hawkins. Ah, it gets worse. That's terrible. Wow. So you go to your mom and you say, have you. By the way, somebody just sent me this too. This is Mark Davis, the Dutch boy, the owner of the Raiders. Have you seen his girlfriend?

[Co-host or Guest]

Yes.

[Brady]

Oh, billionaires win.

[Co-host or Guest]

Are they still together?

[Brady]

I don't know.

[Brett Vesely]

She.

[Brady]

She claims.

[Co-host or Guest]

Moving on to the next.

[Brady]

She said, I didn't know he was a billionaire. I just loved his hair. Right. So you go to your mom and you say, please stop or I'm not. I. I would cancel Christmas.

[Co-host or Guest]

I'm not telling her to stop necessarily, but I'm telling her, you got to understand how weird this is.

[Brady]

I'm not coming to Christmas if Chet's there's why I love Chet. I'm not coming. Let me repeat. I'm not coming to Christmas if Chet's there. Why don't you want me to love. You can just not Chet.

[Co-host or Guest]

And all of a sudden I'm just not. You know, it's hard not to trust Chet.

[Brady]

Why? You think he sent it to get you?

[Co-host or Guest]

Not necessarily get me or just. You've had a hang up on Chet.

[Brady]

For a long time.

[Co-host or Guest]

You're not. I'm like, this is something not right here.

[Brady]

I remember.

[Co-host or Guest]

I'm not buying into this.

[Brady]

I remember you, Chet. You think Chet is pulling a fast one over the whole Family or just getting this guy again? You don't think he really loves your mother?

[Co-host or Guest]

Yeah, I don't know.

[Brady]

I'll tell you this. My Aunt Joan and Uncle Bob, vastly different in age. It lasted like. That was real love. Yeah, it really was. When you saw them together. He's a little dopey.

[Co-host or Guest]

And what's the.

[Brady]

What are we talking about here?

[Co-host or Guest]

He's mid-40s and she's in 64.

[Brady]

64 something.

[Co-host or Guest]

So it's 20 years, I guess. It's not that big.

[Brady]

It's not a huge gap as far as like, oh, my God. But still, he's older than your son by two years. That's something. That's something. And we don't know.

[Co-host or Guest]

Just keeping my eye on you, Chet.

[Brady]

Yeah, well, you can keep your eye on him all you want. You're gonna eventually see him boning your mom. It's gonna be weird when you. He's slapping down your mom's potatoes for Thanksgiving.

[Co-host or Guest]

And then you're talking food this time, right?

[Brady]

Her pureed tacos. Or I guess it would be turkey pureed. All that food he's got to put in a blender for your mom before he smashes that ass. You know, your mother and I have a very active sex life there, Kenny. Oh, yeah. The only thing that gets in the way is her colostomy bag. But you know what? That smells like love to me now. You know what, Chet? I'm gonna leave Christmas for a little while. That's right. Cause I was about to bone your mother.

[Co-host or Guest]

If I hear that.

[Brady]

Be nice if you weren't here when that happened. Hey, Kenny, come here for a second, son. Don't call me son, Chet. Hey, tonight I just wanted to let you know. I wanted to ask permission. I don't think I was ever a gentleman about this. I've entered your home, I've entered your family. And tonight, I'm gonna enter your mother. Do I have your permission? What? Yeah, I'm gonna your mom tonight. Pass the gravy. That's what your mother says. Pass the gravy. She wants to experience north and South Korea. You know what I'm talking about. You heard it earlier this morning. I'm going over the dmz. Watch out for the border. It's guarded. Yeah, by the pen's panty liner.

[Co-host or Guest]

Yuck. What if he was talking like that the whole time? And then you just. You record it.

[Brady]

Mom, you know what my favorite smell is? Ammonia based urine and baby powder from the diaper your mother has to wear because I've knocked the bottom off. She doesn't control it anymore.

[Co-host or Guest]

She's not that old.

[Brady]

She is though now, Brady, because I've put her through the paces now that I've knocked a silly. Did you know your mom was a squirter? I do. She's not that old, but it feels like.

[Co-host or Guest]

Before you come over, can you pick up the medication over there at Walgreens? Your mom still has the uti.

[Brady]

She's itchy real bad. My bad. Why do you still wear the face shield from COVID chat? Your mother's a waterworks. It's amazing. Just in case. Sometimes she just looks at me and sprays. It's like summer in New York. We're playing stickball and we open up the fire hydrants and when I say stickball, what I mean? I heard you. Arizona's most powerful rocket station. It's out of control now. 98k u PD if you're looking at.

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[Brady]

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