09-08-25 - WWBD - Should He Continue To Help The Kids Of The Ex He Hates - His Son Is Dating A 20yo Should He Break Them Up

Summary

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?”

Transcript

[Host]

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[Mo]

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[Brady]

What would Brady do? Hmm. Yes, that's right. It's time for the world's most moral single kidneyed man to solve your problems. He's doing it despite him not being at 100%. But when was he ever really truly Brad? But he'll still look at your life and judge it. You people are making a mockery of yourselves. Couple of good ones today too, Brady. And it's brought to you by our friends at Mo Money Pond, 12th street and Indian School. MMP guns right inside Mo Money Pond will take care of you. If you have any needs for weaponry, they've got it. Guns. They've got ammo. They've got vests. They've got tack gear. They've got everything you could ever imagine. If they don't have it, they can get it for you lickety split. You got something that's hard to find, they'll find it. And they can work it Right there. Not to mention you walk through the beautiful showroom of Mo Money Pond while you're heading back to MMP Guns, which is right there in the store. Momoney pawn.com. 12th street and Indian School. And check out M&P guns.com as well. Brady Brady. To solve their issues.

[Co-host]

Ready?

[Brady]

I got two good ones. I don't have a third. One was stinky and I didn't really search out more. Here we go. And everybody's very nice in the beginning too. This guy says, dear Brady, first off, happy to hear you're doing okay. It's something to survive that C word. Think of that. Brady survived the C word. I'm happy for you. You're in my prayers.

[Co-host]

Nice. I still have that little category. If they're a miracle on my left kidney, John.

[Brady]

Why?

[Co-host]

I don't know. It's out there.

[Brady]

No, it's not a thing. You rely on medical science, my friend. If you were looking for miracles, why'd you go through the first half of this? Right?

[Co-host]

I didn't have time to stick around. I got a little time on this. I got a little more time.

[Brady]

So you're looking for miracles. As long as it's convenient. Yeah. I see. Convenience of miracles.

[Co-host]

There are. I'm putting conditions on it.

[Brady]

And I would have been.

[Co-host]

Probably shouldn't.

[Brady]

You didn't have in the first place. But let's just go with the doctors on this one and not I did.

[Co-host]

I could have rolled the dice and like you guys don't know what you're talking.

[Brady]

I'm waiting for a miracle. I'd prefer a doctor than wizardry. That's beside the point.

[Co-host]

Yes.

[Brady]

This one says should I still pay for my soon to be horrible ex girlfriend's son and daughter and their private school? I don't hate them. I just hate their miserable mom. We've lived together and I have been the only steady presence in everyone's life for the last eight years. Especially the kids. The dad killed himself with prescription pills. Not really. But it would have been better off if he had because he's just a disaster. I'm a successful person and at one point I was in love with this woman. But over the last couple years, she's been different. It's just gotten worse and worse. All I care about now are those kids. But I want her out of my life so bad. I don't know if I should just abandon the entire group. Should I pull the money for the school? I'm trying to be a decent person, but this is an awful situation. By the way I caught her snorting Adderall with her, quote, friend from work who had the nerve to look at me when I walked in and said, get out of here, man. It was my bedroom. I didn't pummel the dude because I didn't want to go to jail, but, man, did I want to. I just got rid of the shady bitch. Please don't use my name, Gary. Oops. So don't sign it.

[Co-host]

What is the real. I mean, you know, so pulling the money from the kids.

[Brady]

They can't go to the school.

[Co-host]

I know they can't go to the school. So what? How does that fix it for you?

[Brady]

I think what he's asking is, I dumped her. I want her out of my life. This is why I always say never date a single mom.

[Co-host]

Yeah.

[Brady]

And now I love the kids. They're in a bad situation. I've been paying their way to this nice school. I'm paying their way for this, that and the other. Do I just cut it all off or do I try to hang on to the kids and let them have a decent life or at least continue what they consider.

[Co-host]

I'm sticking with the kids.

[Brady]

Kids. You are?

[Co-host]

Yeah. I, I mean, because beast with the mom, not the kids.

[Brady]

But you don't want her in your life anymore.

[Co-host]

Now if the.

[Brady]

What if she starts getting some other.

[Co-host]

Dudes haven't done anything to you.

[Brady]

This is why you don't date a single mom.

[Co-host]

Because originally he agreed to do that. What is the only reason he did that?

[Brady]

As long as he's around when the fan.

[Co-host]

That's what I'm saying is the original reason that he did that was because the mom, like, yeah, I'm. I'm winning her over.

[Brady]

Gonna. Dad not even winning her over. It's just like we're playing family, we're playing house. We're not married. But I'm taking care of everybody here because that's what I do. I need to put them in a better situation.

[Co-host]

I don't think it's. I mean, like, if you decide I'm not going to do it anymore, that's fine. I would say give them enough time because there are ways. You know, there's those programs that you can get the tax, you know, to private schools.

[Brady]

Yeah. Up to a certain amount.

[Co-host]

No, you can get the full amount. Not, not the esa. There's a separate one where people you can write up to. It's a 2100.

[Brady]

You're looking for that write off.

[Co-host]

Well, it would cause the kids to have to go around.

[Brady]

Yeah.

[Co-host]

And raise some cash and ask people.

[Brady]

But then you got to stay in contact with her to tell the kids how this. I'm cutting it off, man.

[Co-host]

That's what I'm saying. At least give them. I mean, and maybe not. You're cutting it just cold turkey.

[Host]

I would just. Because you're always going to be attached.

[Brady]

To that broad, then college for the kids.

[Host]

I'm sorry, but you know.

[Co-host]

And I understand. I'm just saying I'd probably give them.

[Brady]

Say it again, Fred. You're right.

[Host]

I'm sorry. But your mom's an Adderall. Snorting.

[Brady]

Yeah, they're already screwed up. You're not going to help them out. You're just going to pay for a school so they can start doing. Snorting Adderall and getting pregnant when they're 17, too. And then you're going to pay for that. When does it end, is the question.

[Co-host]

Two or three months.

[Brady]

Like, just finish this year.

[Co-host]

How about the semester? That's fair.

[Brady]

I mean, you already paid for it now. Yeah, I think that's it. But you don't keep paying for that after.

[Co-host]

Yeah, unless he paid it all up front.

[Brady]

Tell.

[Co-host]

I don't.

[Brady]

Get out of here, man. To pay for their school because that's who. She. She didn't resp. Like, that's bad. And the drugs thing is wor. And he didn't. He didn't even mention, like, if there was, like, a sex thing going on. But more than likely, if she's in your bedroom with some guy from work snorting at her, all there's.

[Host]

Get out of here.

[Brady]

Not where it ends. Yeah, and he had the nerve. Get out of here, man.

[Host]

I'd be in jail.

[Brady]

Oh, my God. I would be in jail. Yeah, that guy's head would have come off. That would have been bad. And probably, you know, I've seen a lot of Dateline specials where everybody in that room gets chopped up. OJ probably had that happen. He's kind of lost it. That's a tough one.

[Host]

Like Brady said, if they. He's already paid for it. Okay, fine. Let it roll. But after that, cut it.

[Brady]

Whatever you've paid for is the last you're paying.

[Co-host]

Yeah.

[Brady]

And then Gary, whose name we won't use. Run. Yeah, that's probably the best.

[Co-host]

The kids also would have to understand accent. I mean, if I was in. If I was.

[Brady]

Well, it doesn't matter if the kids, you know, but that.

[Co-host]

It doesn't matter. Has nothing to do with this guy anymore.

[Brady]

But if your kids understand or not, it doesn't matter. It's just whether or not you want to. Like, he's in love with the kids, too. Like, that's why you can't date a mom with kids. Oh, you can't date a mom with kids because you got to break up with the whole family. And most of the time the kids didn't do anything. And if they did, you know, sometimes the kids will wreck it for a good relationship. This is the other way around. Yeah. You gotta dump the whole family. It's gonna cost you a few bucks. But you were playing house. You paid for the kids.

[Co-host]

If you can't afford it, that's.

[Brady]

I don't think that's an issue.

[Co-host]

That's an easy.

[Brady]

I don't think that's an issue.

[Host]

It doesn't sound like it.

[Brady]

He basically was saying, should I keep doing it or not? And you were. You know, this is an easy out. Had you been married, you'd have been paying for all this, and you'd have had to keep paying for it. And you had to pay her an Adderall. Snorting friend. Spousal maintenance is the best thing for you. They just. I think one of the finished for me.

[Co-host]

There'd be one other caveat.

[Brady]

What's that?

[Co-host]

If it was like their senior year.

[Brady]

Well, that's easy. But then college comes around.

[Co-host]

But I'm saying I would. I would let them finish the senior year out rather than changing schools midway through.

[Brady]

You have to do that thing like in those movies when a kid tries to like E.T. at the end of E.T. when Elliot told him, go, get out of here, like it was breaking his heart. What's the other's like movies with dogs.

[Co-host]

Go.

[Brady]

Leave. Yeah, Shane. One of the great movies from the fish. Shane. He's screaming for him. You tell the thing you love to leave, and it doesn't understand why you do it, but it's for the best. You have to do that to those kids. You have to make it so they hate you, because otherwise they'll start calling you and hitting you up for cash on the side, knowing that you've got a soft spot for them. Mom's in the bedroom with that Adderall guy again, and we don't have any money for food.

[Co-host]

Short another 1500.

[Brady]

Yeah.

[Co-host]

On rent.

[Brady]

You gotta dump the whole family, break your own heart. And then stop dating people with kids you gotta pay for. That's a disaster. Stop dating people with kids. Morning sickness. Medicate.

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[Brady]

Did she go somewhere?

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[Host]

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[Brady]

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[Co-host]

Just tells me the thing not to be the. Is that if you really love the kids or like I love them, that's why I'm doing it. Yeah, then you'd continue doing it. But if you're questioning it.

[Brady]

Would you though?

[Co-host]

Because you can't. I mean, because then like there's people. That scholarship, you can do that if you want students to begin with, like.

[Brady]

Don'T let them know it.

[Co-host]

Hear about the kid. Like, you know what? I'm going to pay for his college.

[Brady]

That's great. But if mom finds out and she's going to start using them as ways to get money for her. She's a drug addict.

[Co-host]

That's. That's the ugly part of it, which I think is get out of there. Get out.

[Brady]

Dear Brady, I just found out my 16, 17 and 4 month old son, or 4 year old, he's not 16 months old. That changes the story completely. He'll be 17 in 4 months. My son's girlfriend is 20. On one hand, super duper proud of him, but on the other hand, I'm worried if he found himself a Britney Zamora. Should I put an end to this or let it go? He's got 16 months before he's an adult and none of this will matter. Doug, he's 16, she's 20.

[Co-host]

I'd be okay with it to an extent.

[Brady]

With the girl being 20 and the guy being 16.

[Co-host]

It all depends on what kind of, you know, I'd just be monitoring it pretty close.

[Brady]

I think I'd be more concerned if it was the guy who was 20 switched around.

[Co-host]

No, no, no, I, like I'm saying.

[Brady]

I wouldn't be as concerned if it was the, the girl who was 16 and the guy was 20. Like that's for some reason. Like that's touchy, but that's about right.

[Co-host]

It's close.

[Host]

That's Benny Mardona's.

[Brady]

You know girls who are 20 dating guys in high school, Something's wrong with them. Guys who are 20. Dating 16 year old girls is about the age gap you shoot for in life. Three, four years, right?

[Co-host]

I don't know, it's touchy either way. Four years, I, I could see it.

[Brady]

But how many girls, how many girls in high school are like, oh, my boyfriend's in college and she's 16 and he's nice. That's normal.

[Co-host]

There's definitely more girls.

[Brady]

That's normal.

[Co-host]

Older and older.

[Brady]

A 16 year old boy dating a 20 year old girl says there's something wrong with that 20 year old girl because they very rarely want to go back. So she's probably one of those.

[Co-host]

But there's always one or two.

[Brady]

Yeah, but she's probably. Yeah, but there's something wrong with them. They probably wanted to be the high school cheerleader life again. And colleges. She's not getting the attention she used to get when she was in high school. And so she's. Something's wrong with her. 20 year old girls don't want 16 year old boys. That's not a status symbol for a sophomore in college to be dating a sophomore in high school.

[Co-host]

They always go up. Unless she's not up.

[Brady]

They always go up. Yeah.

[Co-host]

If she's not, you know, you say sophomore, college, is she in college?

[Brady]

I don't know, I'm just throwing numbers.

[Co-host]

If she is, then there'll be.

[Brady]

Well, even if she isn't. I'm just saying the age of someone, 20 year olds with 16 year old boyfriends for girls, that's not looked on as normal. No 20 year old guy with a 16 year old girl is like, ah, cutting it close, don't you think?

[Co-host]

How long have they been dating too? Like was he senior? Freshman?

[Brady]

That's a tough one. I think I'd get to know the girl and find out what's wrong with her. Something's wrong with her. What would Kurt have done? You're 16, you got a 20 year old girlfriend coming around the house.

[Host]

Oh, he'd be like, nice kill kid.

[Brady]

That's what my dad would have been. Yeah. There was a girl named Sherry that I worked with at Tony roma's that was 19 when I was 16. And she started to hang out with me and my friend Mark and I think she liked Mark. But then I started making her laugh and stuff and then I think she started to like me. But my dad met her, he's like, something's wrong with her. Her like really goes, yeah, she shouldn't want to hang out with you. And my dad was basically C blocking me. He's like, why Is she like you? I'm like, I don't know. She's pretty. Yeah, I know, it's weird, right? He goes, yeah, it is. I don't like this at all. Something's wrong with her. Like she could do better than a boy. Yeah, something's wrong with this chick. You can't be 20. You can bone some kid like, oh my God, what have I just done? But you don't date him unless you're a mental basket case. If you were 16 and had a 20 year old girlfriend, Torfen Bunny would have stepped in. Something's wrong with her.

[Co-host]

16, 20.

[Brady]

Yeah, something's wrong with that girl. Now if you were 20 and had a.16, you had a. You were in college and didn't you go to a high school? You had a high school girlfriend, 22.

[Co-host]

And 19, I think.

[Brady]

Well, she's. When she was in high school.

[Co-host]

No, she was. No, she was a freshman in college.

[Brady]

That doesn't count. I'm talking like if you go back to. And I was 25, that's pretty good.

[Co-host]

25 and 19.

[Brady]

19, that's pretty good. That's a weird age, but that's for a guy that's normal. A little strange. This one says, dear Brady, much love player. Hope you're recovering well. I just had my TV flash an Apple code on the screen and then the screen switched to a screen mirror of my roommate's phone. And I stared at it like, what's going on? There was a quick flash of an email or a text or something that said, no one will know, but that was the best night of my life. I love you. And it was to our mutual friend Jimmy. I don't know if my roommate is gay. I don't know that that would even surprise me. But I've had feelings for him for a while and I'm wondering if I should make my move with this information. Should I still do it? Signed Shauna. So Shauna is watching tv, screen comes up as it will when you screen mirror and says, put this code in. Yeah, but if he doesn't have to do that and just flips through it, it'll just pop right up on whatever screen. If he's already pre done, she sees a message, then it goes away and it was to a dude. So it's two dudes saying they love each other. Jimmy and her roommate. And now she's like, oh, I'm gonna lose to a fella. Should I try to bone him before he gets a taste of the dark.

[Co-host]

Side, before he converts, by the way.

[Brady]

How old are you, Shauna? This is an awful lot of roommates going on.

[Co-host]

Well, read the title again then. Then prepare for looking for another roommate. You think the downside of it, if you don't hit it off and it backfires.

[Brady]

That's true. Boning your roommate can always go bad. Yeah, don't c block him, Shauna. You should go in there immediately and try to blow that guy. Don't even talk to him. Just get in there and start with your mouth open and just start pointing to it. Say that. Do it like the. Like the monsters from Mars attacks and point to the hole in your face and hope that he jumps in.

[Co-host]

She does have the. You know, they've been roommates for a while, it sounds like. Or a couple of months, so that's out of the way.

[Brady]

I'm just saying, like, there's no. They're roommates. Who knows?

[Co-host]

How long are they getting along as roommates?

[Brady]

Not as long. Not as well as they could, Brady. And if he goes blazes, then you'll know he loves Jimmy. Yeah, a good girl roommate will do that. They'll hop right in the room and just go. Are you dating anybody? Nope.

[Co-host]

It's so powerful. It can help rent.

[Brady]

I was gonna say, he's gonna pay your rent. Yeah. You're gonna have pockets full of cash, you know? Yeah, yeah. You keep that jaw dislodged, you're gonna be paid. Everything's free.

[Host]

American Express payments.

[Brady]

Oh, I'm having trouble with bills. Oh, yeah, I could help you with that. Run right into that room right now. If you're both at home, Shawna, and get to work. You're gonna lose him to Jimmy if you don't.

[Co-host]

If it sounds like Mars attacks, it's.

[Brady]

A good thing I gotcha. By the way, you got an email that says a 20 year old girl dating that 16 year old must be a big fat hog. Yeah, something ain't right there. Nobody thinks that's a normal deal. There you go, everybody. That is what Brady did. And he solved all the problems. Easily Arizona's most powerful rocket out of control now.