Podcast Summary: Holmberg's Morning Sickness – “WWBD – Sticky Exes, Age Gaps, and Roommate Revelations”

Date: September 8, 2025
Hosts: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Main Theme:
In this “What Would Brady Do?” edition, John Holmberg and the crew field awkward and raw listener dilemmas: Should you keep supporting your ex’s kids if you hate her? What to do when your teenage son is dating a 20-year-old woman? And should you make a move on a roommate who may secretly be gay? The team mixes humor, blunt assessments, and some unexpectedly sincere advice, staying true to their irreverent Arizona tone.

Key Discussion Points & Insights

1. Should a Listener Keep Supporting His Ex’s Kids?

[02:45 – 11:00]

• The Situation:
  Listener (accidentally outed as "Gary") has been the steady provider for his girlfriend’s kids—private school tuition and more—for eight years. Now he wants the girlfriend out of his life after discovering her snorting Adderall with a coworker in his bedroom. He cares about the kids, but doesn’t want further entanglement with the ex.

• Team’s Take:

  • Brady: “This is why you don't date a single mom...You gotta break up with the whole family.” [09:01]
  • Most agree: You have to cut ties after what’s already paid. Continuing to pay keeps you tethered to the ex and her drama.
  • Host: “I would just—because you’re always going to be attached to that broad.” [07:13]
  • Co-host: Suggests completing the semester or year for the kids, “so it’s not just a cold turkey cutoff,” but ultimately agrees with cutting support after that [07:37].

• Moral Dilemma Explored:

  • Sympathy for the kids in a bad spot, but the consensus is that continuing support drags out the pain and enables chaos, with potential for manipulation, especially given the mother's issues.
  • Notable quote:
    • Brady: “You're not going to help them out. You're just going to pay for a school so they can start snorting Adderall and getting pregnant when they’re 17, too. When does it end, is the question.” [07:25]

• Practical Advice: Let them finish what’s already paid for (semester/year), but after that, “run and cut your losses.”

  • “You have to do that thing…where you tell the thing you love to leave, and it doesn’t understand but it’s for the best. You have to do that to those kids.” [10:08]

2. My 16-Year-Old Son Is Dating a 20-Year-Old Woman – Should I Step In?

[12:21 – 16:16]

• The Situation:
  Listener “Doug” writes in: His son, nearly 17, is dating a 20-year-old. He’s torn between pride and concern about the age gap and legal/ethical implications.

• Team’s Take:

  • Brady: Admits it’s “touchy either way” but highlights that a 20-year-old woman dating a 16-year-old boy is odd, generally “something’s wrong with her” [14:01].
  • Cultural take: It’s more “expected” for a 16-year-old girl to date a 20-year-old male than the reverse. The team riffs on the perceived strangeness and how it’s generally not a “status symbol” for college-aged women to date high-school boys.
  • Host’s dad insight (with humor): “My dad met her, he’s like, ‘Something’s wrong with her. She shouldn't want to hang out with you.'” [15:21]
  • The crew jokes about parental reactions, referencing their own experiences with older girlfriends and parental skepticism.

• Practical (& Sarcastic) Advice:

  • Brady: “I think I’d get to know the girl and find out what’s wrong with her. Something’s wrong with her.” [15:07]
  • Generally: Monitor, maybe try to understand, but don’t panic unless red flags escalate.
  • “If you were 16 and had a 20-year-old girlfriend, Torfen Bunny would have stepped in. Something’s wrong with her.” [15:31]

3. Roommate Accidentally Outs Himself – Should Listener Make a Move?

[16:39 – 19:44]

• The Situation:
  “Shauna” accidentally sees a suggestive message pop up via Apple TV mirroring, implying her male roommate is romantically involved with their friend Jimmy. She has feelings for the roommate and wonders if she should make a move.

• Team’s Take:

  • Jokingly, Brady suggests Shauna “should go in there immediately and try to blow that guy” to keep him from “turning to the dark side” (reference to bisexuality/gayness), playing with their usual irreverent tone [18:11].
  • Warns of the typical roommate risks, “Boning your roommate can always go bad.” [18:11]
  • The team mocks the situation as a lost cause: “If he goes blazes, then you’ll know he loves Jimmy.” [18:53]
  • Advice is highly tongue-in-cheek and intentionally over the top—a hallmark of the show’s style.

• Underlying Message:

  • Don’t count on “turning” someone who may not be interested. Proceed with extreme caution around roommate relationships.

Notable Quotes & Memorable Moments

• Brady: “You have to dump the whole family, break your own heart. And then stop dating people with kids you gotta pay for. That's a disaster.” [10:46]
• Host: “I would just—because you’re always going to be attached to that broad.” [07:13]
• Brady: “You’re not going to help them out. You’re just going to pay for a school so they can start snorting Adderall and getting pregnant when they're 17, too.” [07:25]
• Brady: “A 16-year-old boy dating a 20-year-old girl says there’s something wrong with that 20-year-old girl.” [14:01]
• Brady (on Shauna): “Don't C-block him, Shauna. You should go in there immediately and try to blow that guy.” [18:11]
• Host (re: ex’s Adderall-snorting): “If I'd walked in on that, I'd be in jail. That guy's head would've come off.” [08:17]
• Co-host (re: ending support): “Like in those movies when a kid tries to like E.T. at the end of E.T.... It’s for the best. You have to do that to those kids.” [10:08]

Timestamps for Key Segments

• [02:45] – Start of “What Would Brady Do?” and first dilemma (supporting ex’s kids)
• [07:37] – Debate on whether to let kids finish school year/semester, consensus to stop after that
• [09:01] – “You gotta break up with the whole family”
• [12:21] – Teen son dating 20-year-old, parental concern
• [14:01] – “Something’s wrong with that 20-year-old girl”
• [15:21] – Host’s dad’s reaction story
• [16:39] – The roomate/Jimmy/Apple TV message love triangle
• [18:11] – “Go in there immediately and try to blow that guy”
• [19:44] – Wrap-up of WWBD segment

Tone & Style

Throughout the show, the tone is raw, comedic, and sometimes intentionally harsh, but sprinkled with genuine life advice. The team is unafraid to provoke or ridicule, all while sharing their takes with a sense of Arizona-realism that fans expect.

Summary Takeaway

If you want wisdom sugar-coated, this isn’t the show for you. “Holmberg’s Morning Sickness” listeners get straight talk:

• Cut drama loose—even if it’s sad for the kids, you have to protect yourself.
• Question strange age-gap relationships—and trust your parental instincts.
• And don’t expect to win over a possibly-gay roommate, but, if you try, be prepared for awkwardness.

If you need more harsh love, brutal honesty, or a bit of cathartic laughter at life’s messes, tune in for more “What Would Brady Do?”