Vault: He's Going for His Friend's Mom and She Is Mortified

Summary

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Podcast Summary

The Bert Show – "Vault: He’s Going for His Friend’s Mom and She Is Mortified"

Date: April 3, 2026
Hosts: Bert Show Cast (Ellie, Beth, Jason, Jen, etc.)
Main Theme:
A caller faces a tricky dilemma: her close friend wants to date their college buddy’s mom, who is newly single. The hosts and listeners discuss whether intervening is appropriate, explore the boundaries of friendship, jealousy, and debate the awkwardness (and potential) of such relationships.

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Key Discussion Points & Insights

1. The Dilemma Presented

• Caller’s Story:

  • A friend is infatuated with his college buddy’s mom, who is single.
  • The mom has flirted back, and the friend is considering asking her out.
  • The caller is torn: should she intervene or stay out of it?
  • Underlying possible jealousy since the caller used to date the guy.

• Notable quote (Caller):

  • "I just, I feel like my friend's flushing it all down the toilet and I don't know what to do. I... do I keep my mouth shut and look the other way, or do I say something?" (02:18)

2. Hosts’ Initial Reactions

• Beth, Ellie, Jason, Jen:

  • Generally advise not to insert herself in the situation.
  • Suggests, at most, encouraging friend to be honest with his buddy before acting.
  • Rationalizes that while awkward, it could lead to a positive relationship.

• Notable quote (Beth):

  • "I don't think you need to be in the middle of it really. I mean, you could encourage him to talk to his guy friend before he asks out the mom... But what if he says no? Then he could be missing out on a really great relationship." (03:00)

3. Is the Caller Jealous or Over-involved?

• Host Questions:

  • Are you personally attached to this guy? Do you still have feelings?
  • Do you just want to be part of the drama?

• Caller admits:

  • She and the guy used to date, so her concern is partly personal.
  • "It's not that I like him like him. It's that I really care about him." (04:00)
  • "It's just a train wreck about to happen." (05:05)

4. Potential for Ruined Friendships

• Hosts emphasize:

  • Could damage the guy’s friendship with his buddy if handled poorly.
  • Even so, it’s their business to navigate, not the caller’s.

• Debate over whether to tell the buddy first:

  • "Did you check with your buddy before he asked his mom out? I mean, that is kind of bold to do that." (05:41) – Jason
  • "If one of my friends asked out my mom, we're fist fighting right there." (10:14) – Chris (caller)

5. Listener Call-Ins and Real-Life Examples

• Happy's Call (07:25):

  • Shares her story of dating her friend’s father; they remained friends and everyone is happy now.
  • "He and I hit it off. We dated for six years... Her husband and kids play with my kids. Everything worked out wonderful." (07:36–07:53)
  • Hosts admit, while rare, positive outcomes are possible.

• Chris’ Perspective:

  • Urges the original caller not to interfere unless she admits her own feelings.
  • “If she’s so concerned for him, she needs to just, you know, lay it on the line. Profess her love for him and take her stand now. But to try to get involved, oh gosh... no reason to get involved.” (08:53–09:14)

6. Final Consensus

• Majority View:

  • Caller should not get involved; her concerns are driven by residual feelings and perhaps a penchant for drama or jealousy.
  • The only person who “needs to know” is the friend whose mother may be asked out; he deserves the courtesy to hear it first.

• Memorable moment:

  • Final remarks highlight the discomfort:
    • “Oh, my God. Somebody put their tongue in your mom’s mouth.” (10:42) – Jason
  • Laughter erupts at the frankness and absurdity, but the tone remains understanding and real.

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Timestamps for Major Segments

| Segment | Content | Timestamp | |---------|---------|-----------| | Dilemma Introduced | Caller explains the situation | 01:12–02:21 | | Hosts’ Initial Reactions | Should caller intervene? | 02:21–03:57 | | Exploring Motivation | Jealousy and personal stakes | 03:57–05:22 | | Friendship Risks | Is it worth ruining friendships? | 05:22–06:37 | | Perspectives from Listeners | Real-life story, advice | 06:37–09:14 | | Final Consensus & Call-ins | Should the caller intervene? | 09:14–10:49 |

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Tone & Language

The conversation was refreshingly candid, light-hearted with sharp moments of humor, but also earnest reflection. The Bert Show cast kept it real, playful (“the coug!”), and ultimately compassionate toward all parties involved.

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Notable Quotes

• Caller:

  • "I just, I feel like my friend's flushing it all down the toilet..." (02:18)
  • "It's not that I like him like him. It's that I really care about him." (04:00)

• Beth:

  • "Don't be in the middle... encourage him to talk to his guy friend before he asks out the mom." (03:00)

• Jason:

  • "Did you check with your buddy before he asked his mom out? That is kind of bold..." (05:41)
  • "Somebody put their tongue in your mom's mouth!" (10:42)

• Happy (Listener):

  • "We dated for six years... Everything worked out wonderful. So I think this lady should just butt out." (07:36–07:54)

• Chris (Listener):

  • "If one of my friends asked out my mom, we're fist fighting right there." (10:14)

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Takeaway

The cast agrees: Life’s complicated, especially when it comes to matters of the heart and friendship. The best course is for the caller to step back, let the people involved make their decisions, and only intervene if she’s willing to be totally honest about her own feelings. Things may be “weird,” but sometimes, as one caller’s story shows, unconventional relationships can work out — and at least they’ll make for a memorable story.

Transcript

[Caller (Concerned Friend)]

Oh, no.

[Beth]

My coffee.

[Caller (Concerned Friend)]

Bronnie. Here.

[Ellie]

New Brawny three Ply is now more absorbent.

[Beth]

Wow.

[Jason]

Got a clean shirt.

[Ellie]

Do you wear plaid? Summon the strongest.

[Jerry (Advertisement Voice)]

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[Ellie]

The Bird Show. Hey, Ellie. Welcome to the Bird Show.

[Caller (Concerned Friend)]

Hey, how are you?

[Jason]

Oh, good.

[Ellie]

How are you?

[Caller (Concerned Friend)]

How are you? Yes, it's early,

[Ellie]

relatively.

[Beth]

Remember who you're talking to.

[Ellie]

Yep. We have currently been up for four hours, but that's cool. Early for you. So tell us about your friend or this guy that you know.

[Caller (Concerned Friend)]

Yeah, so this friend of mine, we've been friends forever, and, you know, we went to different schools, but we're both graduating and saw him the other night, and he was telling me about this woman that he met, and he's crazy about her and stuff, and he was being really shy about how he met her. So I'm like, who is this person? Like, where did you meet her? And he finally found out that one of his friends from school. It's his mom.

[Jason]

Hmm.

[Beth]

So it's his college buddy's mom that he is infatuated with or Totally.

[Ellie]

And she's single and available to have a.

[Caller (Concerned Friend)]

Single and available. But that doesn't make it right. I just. I don't know what to do. Of course, he hasn't told his friend that he's crazy about his mom. He's totally flirted with the mom. The mom's flirted back a little because she's newly single, and he's thinking of asking her out. And I don't know what. It's like a train wreck about to happen. I don't know what to do.

[Ellie]

I don't think you need to do anything right.

[Jen]

Well, how long have they been friends?

[Caller (Concerned Friend)]

Throughout college. They're both graduating. I think he graduated a semester early. His friend's graduating in the fall. He's having to go to summer school, and that's why he's not here. So it's like a friendship that. That's gone on for, you know, what, three or Four years and I just. I feel like my friend's flushing it all down the toilet and I don't know what to do. I. I don't know, it's like, do I keep my mouth shut and look the other way or do I say something? You know, it's one of those awkward things. I just.

[Beth]

Well, we all have a friend like you in our groups that likes to be in the midst of everything. It sounds like you just want to be in the midst of everything because this is a kind of potentially scandalous whatever, but I don't think you need to be in the middle of it really. I mean, you could encourage him to talk to his guy friend before he asks out the mom or get his blessing or permission or whatever. But what if he says no? Then he could be missing out on a really great relationship with this woman.

[Caller (Concerned Friend)]

Really?

[Ellie]

Yeah.

[Jen]

Why are you so against it? Why are you so against the relationship

[Caller (Concerned Friend)]

with the, with the mom?

[Beth]

Is it the age difference that's bothering you or the friendship?

[Jason]

Is it the fact that he's the mom?

[Caller (Concerned Friend)]

I think it's. I'm not sure. I'm not. It just seems so out of the blue and I just, I'm just. I don't know how much of it is that he really likes her and how much of it is he really likes the idea of it. And I don't know, maybe I do need just keep my mouth shut.

[Ellie]

Do you like this guy by any chance?

[Caller (Concerned Friend)]

We used to go out, so yeah. I mean, it's not that I. It's not. Well, listen, it's not that I like him like him. It's that I really care about him. Uh huh.

[Jason]

Well, I think that, I mean, I

[Ellie]

think you, you just don't want to see him get hurt.

[Caller (Concerned Friend)]

Yeah, I really, you know, this person that the son of the woman is a really great friend of his and I just, you know, I feel like sometimes guys don't think about it as much as girls do. Like ruining a friendship over something like that.

[Ellie]

Is it. I mean, there are always. I think Jen touched on this and I think it's more often. But there are guys who do this too. But there are oftentimes girls who like to place themselves in situations that are dramatic so that they have something to do. Do you think that maybe that's what you're.

[Caller (Concerned Friend)]

I don't think. I'm not sure.

[Jason]

Well, if you're not sure, then you can't do anything about it. I mean, if you really, if you're really grossed out by him asking A friend's mom out, that's one thing. But if you have feelings for this dude, then, I mean, you can't. I mean.

[Caller (Concerned Friend)]

I mean, I guess you're biased. It's a little bit of everything, but. But really, really, really, for the most part, it's just. It's just a train wreck about to happen.

[Ellie]

And it's like, do you think it might not be.

[Jen]

It might not be. I mean, it might be a really cool relationship.

[Beth]

And if you've still got feelings for

[Jason]

him, that's the problem.

[Caller (Concerned Friend)]

I mean, I guess that's kind of why I called. It's like, do I just keep my mouth shut or say something?

[Jen]

So let's just say their relationship worked out. Would you still be friends with this guy?

[Caller (Concerned Friend)]

Oh, of course.

[Jen]

Would you support the relationship?

[Caller (Concerned Friend)]

Yes. Yes, I would. I really adore him. Yeah.

[Jason]

Well, I mean, yeah, I think that it is kind of funny that he's asking his friend's mom out. And I think in any situation, you're like, well, did you check with your buddy before he asked his mom out? I mean, that is kind of bold to do that. But, yeah, I mean, that's the furthest I'd go.

[Caller (Concerned Friend)]

Weird. On a lot of different levels. You know, we're just graduating from college, and so, yeah, life's a little different now.

[Beth]

So you said that the mom is newly single. Is the mom newly single from the dad?

[Caller (Concerned Friend)]

No, no, no, no.

[Beth]

So mom and dad have been broken up for a while, but mom was in a different relationship and then out of that one. Okay. Because I could see why he wouldn't want to approach his friend if he's like, hey, buddy, your dad just stepped

[Jason]

out of the picture.

[Beth]

Let me just jump.

[Jen]

I think it's different.

[Beth]

I mean, if she's been dating and, you know, and it's. It's not that. I don't think it would be as sensitive to the son in that situation.

[Ellie]

Hey, Beth. Welcome to the bird show.

[Happy]

Hey, good morning, guys.

[Ellie]

How are you?

[Happy]

I have a question for you guys. If put yourself back in college, you've been friends with your college friends for, you know, three, four years, and your friend came to you and said, hey, I want to ask your mom out, or, I want to ask your dad out, wouldn't you find that to be crazy? Wouldn't you freak out a little bit?

[Ellie]

It would be weird, but it doesn't mean it shouldn't happen. It would definitely be freaky.

[Jason]

I mean, yeah, it would freak me out, and I think it's a weird thing. But in the case of our listener. How much responsibility does she have in that?

[Ellie]

Zero.

[Happy]

I think she needs to kind of stay out of it. I agree with you there, but I just. You guys seemed kind of blase about the whole thing, and I'm thinking that would freak me out. I'd be like, you're right.

[Beth]

No, you're right. Yeah, you're right. I think it's just putting ourselves back in that place.

[Jason]

Yeah. I think it's weird.

[Ellie]

Happy. Welcome to the bird show.

[Happy]

Hi. Hey. When I was in college, my best girlfriend's father was single. Came to visit. He and I hit it off. We dated for six years.

[Jason]

Whoa.

[Happy]

Split it up. We are still best friends today. I love his new wife. His daughter and I are still friends. Her husband and kids play with my kids. Everything worked out wonderful. So I think this lady should just butt out.

[Ellie]

So he came to visit. I just want to go back to the. When he came to visit your roommate.

[Happy]

Right, right.

[Ellie]

So how did you guys come to a point where you hit it off? Like, did he take you? Because usually when a parent comes to visit, they take out the. The kid. But then, like, every friend that can latch on and get a free meal because, you know.

[Happy]

Exactly. Exactly. He took me and her out because roommates. And he and I just hit it off and laughed, mind you. He had been widowed for four years, and I got her blessings. She was happy to see her dad. Happy.

[Ellie]

All right. Thanks for the call, Happy.

[Beth]

But I do think that's rare.

[Ellie]

Hey. Hey.

[Jason]

I don't think it's cool, but, I mean, it is kind of weird. I wouldn't want anybody to ask my parent out, but. But again, focusing back on our listener, is she responsible for, you know, trying to stop being involved?

[Ellie]

Hey, Jason, you think Ellie has to intervene here?

[Chris]

Oh, absolutely not. Girl's crazy. Crazy.

[Jason]

Why is she crazy?

[Caller (Concerned Friend)]

There's.

[Chris]

There's no reason for her to be involved.

[Caller (Concerned Friend)]

She's.

[Chris]

If she's so concerned for him, she needs to just, you know, lay it on the line. Professor love for him and. And take her stand now. But to try to get involved. Oh, gosh, yeah. No reason to. No reason to get involved.

[Ellie]

I'm sniffing out a lot of either jealousy or that the girl who's the friend who's always involved.

[Beth]

Personally, no, I think it's jealousy. I mean, she said they used to date Ellie. I mean, can you admit you still got feelings for this guy and that's why you don't want him to date the cougar.

[Chris]

The coug.

[Caller (Concerned Friend)]

It's just That I still worry about him. Yeah. You know, I guess maybe my feelings are there, is that I worry about him and, you know.

[Happy]

Okay.

[Caller (Concerned Friend)]

I mean, if it. I mean, listen, I didn't know if it was weird or not. That's why I called in. But if people think it's not weird, fine.

[Beth]

So you're not to be worried about your ex.

[Ellie]

So the majority of college.

[Beth]

Go have fun.

[Ellie]

The majority of people have said that you don't need to be involved, you don't need to do anything.

[Jason]

So I think it's two separate issues whether it's weird or not. But I think that you obviously are clouded in. In your feelings for him, so you just have to stay out, regardless of how dramatic it gets.

[Ellie]

Hey, Chris, you'll be the last call on the topic.

[Chris]

Yeah, it's that chick. Doesn't have anything to do with it. But the dude had to tell his friend because if one of my friends asked out my mom, we're fist fighting right there.

[Ellie]

Now, does he have to tell him before the first ask, or should they?

[Caller (Concerned Friend)]

Oh, yes.

[Chris]

Dude, if somebody. If one of your friends asked out your mom, are you not gonna be seriously PO'd?

[Jason]

We can't give intern Michelle a hard time for dating somebody 12 years older and having them having a child around her age and then you being cool with somebody asking your mom out.

[Ellie]

I'm not saying I'm cool or not cool with it. I'm just saying maybe it doesn't have to come up on the first date. Like, go out if there's chemistry.

[Jason]

Oh, my God. Somebody put their tongue in your mom's mouth.

[Jerry (Advertisement Voice)]

Oh, shut up.

[Ellie]

The Birch show.