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

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.

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)

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)

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)

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

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.

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.