All Episodes

May 20, 2025 17 mins

One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hey, you found it the Second Date podcast. Thank you
so much for being here, hey, and for everybody that subscribes,
we truly appreciate it. I know that it may not
feel like that makes a difference, but it really does
make a difference.

Speaker 2 (00:10):
I go through our subscription list every day and I
kiss you all on the forehold good night every single night.

Speaker 1 (00:17):
That is so pressure, every single one to be so pressure.

Speaker 2 (00:19):
By the way, the guy users zero one four four
four heads a little salty, Thank you.

Speaker 1 (00:28):
And subscribe. We got a brand new Awkward Tuesday folks
all for you today. And I know this one struck
a chord with Jeffrey because it has to do with
an overbearing mother. Oh my god, there is no mother
more overbearing than Yeah. But before we get to that,
let's see some comments here. What do you gotta lot? Yeah,
Hallie Cruz said, Hey, guys, I'm a dog groomer and
I listen to you guys every day. It helps me

(00:49):
stay calm when I have a crazy dog on the table.

Speaker 3 (00:51):
You.

Speaker 2 (00:53):
Oh my goodness, does our show calm the dogs down
or make them like Nippy? I don't know.

Speaker 1 (00:58):
I'm scared of she has a reaction us talking and
accidentally hoop. She's the dog, you know, she just gotta.

Speaker 2 (01:04):
Do the whole thing.

Speaker 1 (01:05):
Yeah, yeah, we go, all right, let's get this second. Nope,
Awkward Tuesday, that's what we're doing. It starts right now.

Speaker 2 (01:14):
Some mothers can be a little overbearing. Oh yeah, like
maybe when you turn twenty one, they set up a
secret j date profile to find you a nice Jewish
wife without telling you about it, And next thing you know,
suddenly you're getting DMS from some yenta. It's the synagogue
trying to send you unsolicited mondol bread and a ziplock

(01:37):
of her homemade rugela when you never asked for help
in the first place. Yeah, yeah, that's traffic.

Speaker 4 (01:46):
Is good.

Speaker 2 (01:47):
Oh okay, he took it anyway. One of our listeners
came across a mother that was just like that, and
what was said to her is either going to be
the biggest misunderstanding ever or the most awkward roommate conversation
of all time. Oh no, you're gonna hear it in
your brand new awkward Tuesday phone call right after this.

(02:10):
It's awkward. It's awkward Tuesday phone call. There's certain events
that always seem to create drama. Yeah, where guaranteed by
the end, somebody is probably going to be crying in
a bathroom or fistfighting out in the parking lot. We're
talking bachelor bachelorette parties, Thanksgiving dinners, and of course brooks

(02:35):
out of wedlock baby showers. Wait, what always somebody's crying
at the end of those people Yeah, sure, but you
don't normally expect to find drama while attending your parents
work event.

Speaker 4 (02:50):
WHOA, I don't know.

Speaker 2 (02:52):
Yeah, apparently not, because that's what happened to one of
our listeners, Kayla, and now she needs our help with
an awkward Tuesday phone call. Kayla, Welcome to the show.

Speaker 5 (03:04):
Hi, thanks for having me.

Speaker 1 (03:06):
Oh my gosh, I can't wait to hear if you're
the starter of the drama, if it's somebody else's why
did you go in the first place? A question?

Speaker 2 (03:13):
That's true. The fact that you even still talk to
your parents, that's just impressive. But tell us what is
this work event that you wound up that somehow?

Speaker 5 (03:22):
Okay, so recently I went to a work event that
my dad's company was throwing.

Speaker 1 (03:27):
Wait, did your dad own the company? Sorry, maybe I'm
reading that wrong.

Speaker 5 (03:31):
Yeah, yeah, my dad owns the company.

Speaker 1 (03:33):
Okay, okay, yes, and you can't be part of it
and have nepotism if you're not.

Speaker 5 (03:37):
There, I'm expected to go. So they have this big,
like family day picnic for the whole company.

Speaker 2 (03:45):
Okay, I mean it's cute, cute.

Speaker 4 (03:50):
Yeah.

Speaker 5 (03:50):
So I'm there with my parents and they're talking with
some of my dad's coworkers, and of course they do
it all old people do. They show each other of
their kids.

Speaker 1 (04:01):
I mean young parents do that too, but fine, Well, yeah,
once you reach a certain age, once you have kids,
do you want to show them off?

Speaker 2 (04:09):
Well, yeah, if you're proud of them. Sure not everybody is, Okay,
So they're showing pictures of kids.

Speaker 5 (04:16):
Yeah, And there was this one woman there and she's
showing me a picture of her son, and she's saying, Oh,
he's so cute, right, and he's your age and single
if you're interested.

Speaker 1 (04:27):
Oh yeah.

Speaker 5 (04:28):
Parents love to do that and always it took everything
in my power not to react because I recognized him. Yeah.
Well her son has been dating my roommate for over
a year now.

Speaker 1 (04:45):
Wait what yeah.

Speaker 4 (04:48):
About her? Yeah?

Speaker 1 (04:49):
Why is she trying to set him up? If he's
in a committed relationship.

Speaker 5 (04:52):
I don't know, so, like I kind of hinted to
her like, oh wow, like he's really handsome. It's hard
to imagine no girl has snatched him up.

Speaker 4 (05:00):
Uh huh.

Speaker 5 (05:00):
And the woman says to me, well, he was in
a relationship, but he broke up with her six months ago.
So what Like, clearly he's been telling his parents something,
but he's been lying to them. He's been telling them
something that's not true.

Speaker 1 (05:15):
And you're sure he's dating your roommate like he's been
over in the passage.

Speaker 2 (05:18):
Yeah, no, that's actually a good question.

Speaker 5 (05:20):
Absolutely, Okay, he's my roommate, Like I know what he
looks like.

Speaker 2 (05:25):
Any hold on, not to like defend this guy, but
I have overbearing parents, and I definitely don't tell them
everything about my.

Speaker 1 (05:34):
Personal can tell them anything. I don't tell my mom
if I'm dating someone till it's like years in Yeah. Yeah,
oh my god, I actually introduced him on the second date.

Speaker 2 (05:42):
Oh god. Yeah, especially not with my dating life. So
he will have a reason for keeping that information from
his parents.

Speaker 1 (05:51):
Yeah.

Speaker 5 (05:51):
I don't know.

Speaker 1 (05:52):
I mean, I think Jeff might be honot something because
it could also be what if the mom hated your
roommate and so he just lied and said, oh, we
broke up, so we didn't have to hear her complain anymore.

Speaker 2 (06:02):
Did she seem like a hateful woman when you were
talking to her?

Speaker 5 (06:05):
No, No, she seemed totally nice in her She's obviously
trying to set up her son.

Speaker 2 (06:10):
Yeah, that is the keystone mark of a hateful person
to love life Jeff issues speaking her personal experience here,
I'm just saying, yeah, maybe she hates her son.

Speaker 1 (06:23):
So wait, so did you tell your roommate about this?

Speaker 5 (06:26):
Not yet. I got his number from her phone, and
I feel like I need to talk to him first
and be like, why do your parents think that you're
single right now? Like what's going on?

Speaker 2 (06:38):
And you didn't bring it up to his mother?

Speaker 5 (06:40):
No, because like, again I don't know what's going on,
but I feel like everybody should be on the same page.
And I'm putting this really awkward position of knowing but
not knowing what to do.

Speaker 2 (06:52):
It is a weird position.

Speaker 1 (06:53):
And what's your relationship like with your roommate's boyfriend.

Speaker 5 (06:56):
I mean, like, we don't hang out a lot, but
he's at our place obviously, so I see him and
we've had some good times together, but obviously this is
just a really like sticky situation.

Speaker 2 (07:08):
Yeah. Yeah, And so the advice that you're looking to
get before you make your call to the boyfriend, it
sounds like, what what are you wanting to hear from us?

Speaker 5 (07:18):
I guess, like, how do I confront him being like,
your mom told me that you said you were single,
but I know you're dating my roommate.

Speaker 1 (07:28):
Yeah, I mean that does come across as a little
accusatory right off of that.

Speaker 2 (07:32):
Right, Yeah, you kind of just want to put him
on the spot and see what he has to say,
how he defends himself.

Speaker 5 (07:37):
Well exactly.

Speaker 2 (07:38):
Sounded a little harsh. Yeah, yeah, but you know what
I mean, put him on a pedestal and we'll put
him somewhere.

Speaker 5 (07:47):
We're gonna do something.

Speaker 2 (07:48):
We're do something with it. Before first, we're going to
give you our advice though, right, if we come back
and let you make your awkward Tuesday phone call to
figure out what's really going on with your roommate's boyfriend
after this, hold on, it's awkward, it's Tuesday. It's awkward
Tuesday phone call. As a woman, I imagine it would

(08:10):
be the ultimate compliment when an older lady comes up
to you in public and says, Hey, you seem nice
and desperate enough to date my single son. How about it? No,
I feel like that happened to you all.

Speaker 1 (08:25):
The time, broke it, didn't.

Speaker 2 (08:28):
You didn't seem nice enough.

Speaker 1 (08:30):
No, I don't think I've ever been nice enough for
somebody's son. But I'll just tell you the only reason
I don't think it's a compliment is because everyone that
my mom has ever thought was cute was Yeah, it's unlike,
we don't need to lead with personality. Mom.

Speaker 2 (08:45):
Well that's the situation that one of our listeners, Kayla,
found herself in recently, and it would have been flattering,
except she knew the guy from the photo that the
lady was showing her. Yeah, it's a guy who's currently
dating her room mate and has been for over a year.

Speaker 1 (09:02):
Yeah, they're like in a real relationship.

Speaker 2 (09:04):
But just get smaller. The mom's told her, No, he's
single and he has been for months. Yeah, so that's
a giant red flag because obviously he's not. And she
never told the mom that day about it, never brought
it up to her roommate either. Instead, she's turned to
the most trusted source on the entire planet, a radio

(09:26):
show named Brooke and Jeffrey in the morning to help her.

Speaker 1 (09:29):
Can we just applaud her to for not blowing things
out of proportion before she gets an answer from the
boyfriend like that right now?

Speaker 2 (09:37):
Dude, what is that true?

Speaker 4 (09:39):
Thank you?

Speaker 2 (09:39):
Yeah, hopefully we have some decent advice for you. Brooke,
do you have anything to.

Speaker 1 (09:44):
Okay, listen, this is what you need to do. When
you call him. You be like, oh my god, I
have the funniest story to tell you. I ran into
your mom and she tried to set me up on
a date with you.

Speaker 4 (09:56):
Okay, you know what I'm saying. I don't know.

Speaker 5 (09:59):
I just feel so awkward, like and I've never really
talked to him on the phone before, so.

Speaker 1 (10:03):
I know you're like Alexis, phone calls are hard.

Speaker 2 (10:08):
But I think there's some merit to that. If you're
really nice to him, it'll make him put his guard down.

Speaker 5 (10:13):
I'm definitely gonna be nice. Okay.

Speaker 1 (10:15):
We don't even know that he's in the wrong.

Speaker 2 (10:17):
That I think he's in the wrong already, that's true.

Speaker 1 (10:20):
I think she's just scared of silence, like Alexis would be.
On the.

Speaker 2 (10:25):
You need the silence because then it forces him to
talk embrace the silence, and if all else fails, threatened
to release his nude photos.

Speaker 1 (10:34):
Against the laws.

Speaker 2 (10:35):
Last resort is what I'm saying. But I'm going to
dial this guy's number. Have we even learned his name yet?

Speaker 4 (10:40):
His name to Aaron?

Speaker 2 (10:41):
Okay, scumbag Aaron potentially scum back, yes, thank you, alleged.

Speaker 1 (10:48):
Potentially he's actually a good guy.

Speaker 2 (10:51):
We think all of them. Okay, here we go. I'm
going to dial it and we're going to step away.
Let you make your awkward Tuesday phone call. Will jump
in if you feel like you need a help. Okay, Kayla, Okay, okay, okay,
got this.

Speaker 5 (11:10):
Hello, Hey Aaron, this is Kayla. How are you.

Speaker 4 (11:17):
Oh hey Caylen, What's what's up? What's going on?

Speaker 5 (11:25):
I just something kind of funny happened the other day,
and I just I just wanted to ask you about it.
If that's okay, Do you have a minute?

Speaker 4 (11:36):
Uh? Yeah? Is everything okay?

Speaker 6 (11:39):
I mean it's it's kind of odd for you to
call me out of the blue.

Speaker 5 (11:44):
Yeah, I know, I know. I normally just like to
see you, but I just I had to ask you something,
uh privately, So but yeah, if you just if you
have a minute, Can I just ask you something real fast?

Speaker 4 (11:57):
I mean, sure, what what's the what's up?

Speaker 5 (12:01):
Okay, So the other day, my dad's company had had
a party and I ended up seeing your mom there
and she showed me a photo of your and she's like, oh,
my son is single, which was just really weird because
I know you've been obviously with my roommate. So I

(12:22):
just wanted to like ask what was going on, Like
does your mom think that you're single? Or is that
just like a mistake or something.

Speaker 4 (12:32):
So this is really funny you even asked that. I mean,
my mom found out she was going to your parents' party, right,
And I was like, another daughter. She's really cute, and
my mom she's like, well you should date her. I
mean she's better than who you're dating.

Speaker 5 (12:47):
Okay, well obviously that's not true, but okay.

Speaker 4 (12:56):
Well I mean it is true. But anyways, I was like,
that would be weird. Yeah, and she so, you know,
well you've met my mom.

Speaker 6 (13:03):
She's like, let me try, let me try, let me
I'll talk to.

Speaker 4 (13:06):
Let me try. And I'm like it's not the worst idea, right,
So I was like, okay, yeah.

Speaker 5 (13:11):
Sure, wait, so hold on, I'm trying to wrap my
brain around this. You are with my roommates, but you
told your mom it was fine to tell me you
were single.

Speaker 4 (13:23):
Yeah, and my mom was. She's all about this. She's like,
oh yeah, a lot of ceols. And you know you've
met my mom.

Speaker 6 (13:29):
She's very yeah, so she Yeah.

Speaker 5 (13:34):
Sorry, I'm just I'm having trouble understanding.

Speaker 4 (13:39):
Why come on? I mean, is it really that crazy?

Speaker 5 (13:44):
What is what crazy?

Speaker 4 (13:46):
I mean, you and me?

Speaker 6 (13:47):
I mean, that's not so crazy, right, are you?

Speaker 4 (13:53):
Listen? Now that you serious?

Speaker 5 (13:55):
Right now? Yeah? I mean, what do you what do
you think?

Speaker 1 (13:59):
Oh? What do you mean?

Speaker 4 (14:00):
What do I think? You're with my roommates temporarily? I mean, listen,
it could be you and me. I mean, we we
get along and then and you're not as messy as her.

Speaker 6 (14:15):
And you know, listen, your your lease is up in
three months, and I figured, well, you could just move out,
get your own place, and then we can start dating
on the you know, on the down low.

Speaker 2 (14:27):
Wow, you have it all planned.

Speaker 1 (14:30):
Out so creepy.

Speaker 2 (14:32):
Sorry I hit the awkward before I heard her. I
should have given her a chance.

Speaker 4 (14:36):
What are you going on?

Speaker 2 (14:38):
Alexis You're right? He is a good He's a cheater.

Speaker 5 (14:41):
I didn't see that coming.

Speaker 1 (14:43):
I got a good feeling about Yeah, I was trying
to cheat.

Speaker 4 (14:48):
You're here? What is going on with.

Speaker 1 (14:53):
Us?

Speaker 2 (14:53):
Oops? So guescats out of the bag. You're on the
radio right now with a show called Brook and Jeffrey
in the morning. What no, no, no, no, no, yeah yeah, yeah,
no no you got you guys need no no, you
guys need to delete this really well.

Speaker 1 (15:08):
Delete it and send it to your girlfriend.

Speaker 2 (15:11):
Yeah, okay, why would you guys do this?

Speaker 1 (15:14):
Cam?

Speaker 4 (15:14):
Why would you do this?

Speaker 1 (15:16):
It's not it's not her fault. You know, your your words,
your actions.

Speaker 4 (15:21):
I was just asking the.

Speaker 5 (15:22):
Question, I mean, what are you talking about?

Speaker 4 (15:24):
This ridiculous on the radio like this?

Speaker 1 (15:28):
You are the most upset innocent person.

Speaker 2 (15:30):
I've ever That's a great stage. Clearly, Aaron, you're aware
that this breaks some social rules here. Otherwise you wouldn't
be as upset as you are right now.

Speaker 4 (15:41):
No, I mean, the cat's out on the bag.

Speaker 6 (15:44):
Sure, I can't it, but you can't blame a guy
for trying.

Speaker 1 (15:48):
And how Hilary you were about it, how like you
just thought she was going to go along with this.
Why would you ever think that.

Speaker 4 (15:55):
It wasn't my idea. It was my mom's ideas.

Speaker 6 (15:57):
Come on, Oh, I thought about it, and I thought, yeah,
that's great.

Speaker 2 (16:04):
Actually they do say mothers know best. Yeah, hey, honey,
you should cheat on your girlfriend if mom is telling
me to. Okay, But I don't know, Kayla, what are
you thinking now that you're hearing all this.

Speaker 5 (16:16):
I'm thinking that this is absolutely disgusting and I'm absolutely
gonna wait.

Speaker 1 (16:22):
So you never thought about you and him together?

Speaker 4 (16:27):
We get along great?

Speaker 1 (16:31):
I was a joke, Karin, dude.

Speaker 2 (16:33):
Even if she was attracted you in any way, I'm
sure her friendship means way more than some random dudes.
I know. If you're not happy with your current girlfriend,
that's okay, but don't bounce over to the roommate is
like twenty feet away.

Speaker 1 (16:45):
Especially before you've broken.

Speaker 2 (16:47):
I mean you could, but at least be single again.

Speaker 1 (16:51):
Listen.

Speaker 6 (16:52):
It wasn't my idea.

Speaker 4 (16:53):
My mom came up with this and I just went
with it.

Speaker 3 (16:56):
O man with I mean you understand that, right, yeah,
because what every girl wants is a guy who can't
think for himself and only has his mom to lit
them fill.

Speaker 2 (17:06):
Oh there's hope. Okay, Well, it was definitely an awkward call.
But the good news is at least the truth did
come out spicier.

Speaker 1 (17:17):
Than I thought. I did not think this. I thought
that mom. I mean, the mom is obviously a whack
could do. But like I thought, I.

Speaker 2 (17:28):
Don't know, take out in nineteen fifties and encyclopedia.

Speaker 5 (17:30):
I think it used to you know.

Speaker 1 (17:32):
What I'm saying.

Speaker 5 (17:33):
No, I'm just so thankful for you guys helping me out,
because otherwise I would have thought he was innocent too.

Speaker 2 (17:40):
It seemed like a misunderstanding.

Speaker 1 (17:41):
You need to go get a bottle of wine to
bring home to your roommate tonight.

Speaker 2 (17:46):
And have a good so that Karon and the roommate
can split it and have a nice evening just the
two of them.

Speaker 1 (17:55):
That's a party, brooking Jeffrey in the morning,
Advertise With Us

Hosts And Creators

Brooke Fox

Brooke Fox

Jeffrey "Young Jeffrey" Dubow

Jeffrey "Young Jeffrey" Dubow

Jose Bolanos

Jose Bolanos

Alexis Fuller

Alexis Fuller

Popular Podcasts

Boysober

Boysober

Have you ever wondered what life might be like if you stopped worrying about being wanted, and focused on understanding what you actually want? That was the question Hope Woodard asked herself after a string of situationships inspired her to take a break from sex and dating. She went "boysober," a personal concept that sparked a global movement among women looking to prioritize themselves over men. Now, Hope is looking to expand the ways we explore our relationship to relationships. Taking a bold, unfiltered look into modern love, romance, and self-discovery, Boysober will dive into messy stories about dating, sex, love, friendship, and breaking generational patterns—all with humor, vulnerability, and a fresh perspective.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.