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Jeffrey
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Brooke
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Jeffrey
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Jonathan
Mm, yeah, but I'm not itching to
Jeffrey
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Brooke
Visit your nearby Lowes
Jeffrey
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Brooke
and Jeffrey in the morning. And you know we get all the credit for all these second dates.
Jeffrey
Yeah.
Brooke
But really, it's our listeners and their terrible dating decisions that we have to think. Yes. And the people who ghost people. Yes, they're helping us out.
Jeffrey
Yeah. Your toxicity has made us so funny.
Gail
Yes.
Brooke
So thank you. Hey, don't forget, we do have 45 more minutes of this. We've got a full show over on the Brooke and Jeffrey main feed. If you like it. Follow that one as well. And let's get into your second date. Brooke and Jeffrey in the morning. Second date update.
Jeffrey
I feel like this gets brought up a lot. After you match with someone online. How long should you wait before meeting up with them? Two to three hours. Two to three minutes.
Brooke
I feel like people typically talk like a week or two.
Jeffrey
Hey, I'm your window right now. Can you open it? I'll climb right in. I brought over some special juice for us to split.
Brooke
No, no, sounds sketchy. I don't see any red flags. Chef's had a weird app.
Jeffrey
Yeah, what app is that?
Brooke
Chef?
Jeffrey
I'm not going to. Are you matching people? Don't make me the weird one here. I'm just saying, the woman on the phone apparently isn't quite as eager as some of us. Cuz she waited much, much longer than two hours to meet up with her guy. Her name is Gail. Gail. Welcome to the show, Gail. Three hours.
Gail
Hi.
Jeffrey
How long did you wait before you met up with the guy from online?
Gail
Yeah, I mean, we chatted on and off for like a month before we actually went out.
Brooke
Why a month? I mean, is that like something you typically do?
Gail
I guess. I mean, we didn't like chat every day and I had like some work stuff going on and I feel like it took them a while to ask me out.
Brooke
Oh, and after you talk for a month, is there a lot of anxiety going into that first meeting because you've. You've invested quite a bit of time at that point?
Gail
Yeah, I mean, a little, but I was more excited.
Jeffrey
Yeah, that's what the special juice is for. That I mentioned earlier.
Brooke
Keep you loose, relaxed.
Jeffrey
I think a lot of people know what you mean because also the longer you talk, the more you have gotten to know each other and form chemistry. So it's kind of both.
Brooke
I would be worried that I'd run out of things to say when I finally met him because I've already covered everything.
Jeffrey
I mean, what do you talk about with a guy for a month?
Gail
I don't know, like what we're doing TV shows, we're watching stuff going on at work.
Brooke
Yeah.
Jeffrey
Ooh, work drama.
Gail
The weird thing he kept like bringing up, he kept saying, like, oh my, you seem so mature for your age.
Jonathan
Huh?
Gail
Like, he said it like three separate occasions.
Jeffrey
Is that a compliment or a diss?
Gail
I don't know.
Jeffrey
I mean, it depends on how old you are. Are you like 21 or.
Gail
I'm 25.
Brooke
Okay.
Jeffrey
Okay. So I could kind of see that.
Brooke
Yeah, I mean, 25. You could go either way for sure. Is he an older gu. Is that why?
Jeffrey
Yeah. What did he mean by that?
Gail
No, he's, like, a couple years older. I mean, I don't know. Maybe it's the way I talk or, like, I use correct grammar. I don't know. I don't like.
Jeffrey
Or maybe the fact your name is Gail.
Gail
There's that, too.
Brooke
Okay, so it sounds to me like he meant it as a compliment.
Gail
I mean, I guess. And then at one point, he asked me how old I really was with, like, a smiley face, like, as if I was lying on my profile or something. I don't know. I thought it was kind of rude.
Jeffrey
Oh, weird. A joke, though, where, you know, tell me the real age. Make you laugh.
Brooke
I don't know. Yeah, because he's looking at your pictures like. I mean, it's all based on photos. Like, I'd be like, thank you.
Gail
No.
Jeffrey
Well, no. They'd been talking a few weeks, though, so they have that familiarity. What did you say to him?
Gail
I said, you'll have to meet me to find out.
Jeffrey
That's playful.
Brooke
Yeah. Was it right after, like, the conversation about your high cholesterol? Is that why I thought that you were old?
Jeffrey
So what did you end up doing for your date?
Gail
So, yeah, we made plans to get dinner, and because I'm hilarious, I decided to show up in an old lady costume.
Brooke
Wait, what?
Jeffrey
I love you, too. Just to troll him for asking how old you were.
Brooke
You went in full costume, the whole thing?
Gail
I got a white wig. I wore this, like, flowery dress.
Jeffrey
Did you get a Whopper or something?
Gail
I had a cane.
Jeffrey
A cane? No way. That is hilarious. What did Jonathan think when you showed up looking like that?
Gail
He was, like, finishing a conversation on the phone, and he, like, looked confused as to why. Like, I was approaching him, and I was, you know, I. I committed to the bed, and I was like, oh, hello, Jonathan, this is Gail.
Jeffrey
That's amazing. I absolutely love it.
Brooke
What was his reaction?
Gail
I mean, he freaked out, and then I, like, immediately, like, took off the wig and was laughing. Was like, this is a joke. I'm just kidding. I poke fun at you.
Jeffrey
Turns out I'm a little older than I said online. That's really funny, actually.
Brooke
Did he laugh so much once he,
Gail
like, figured out it was actually me? He was like, okay, this is funny. And we joked about it. I, like, ordered a prune juice to be fun.
Brooke
Oh, you just kept it going.
Jeffrey
Can I get a prune bag? I think that was kind of funny at first. That you don't want to over commit to being the old lady. They have, like a regular outfit on underneath.
Brooke
I was gonna say it's not very hot.
Gail
Yeah, I had like a cute dress on.
Brooke
Yeah.
Jeffrey
Okay. Okay, good.
Brooke
And they were at the pancake house at 4:00'. Clock.
Jeffrey
Just really going in on it. I mean, other than that, was there anything weird or awkward that happened while you were at the restaurant?
Gail
I mean, conversation was good. I did kind of slip up a couple times and I accidentally called him my ex's name.
Brooke
Yikes. Oh, mine are still. What's your ex's name?
Gail
Jared.
Brooke
Oh, that's. I could see that.
Jeffrey
Two Js.
Jonathan
Yeah.
Gail
Yeah.
Jeffrey
My ex name is Jonathan.
Gail
You didn't know that that was my ex's name? He just like, corrected me and was like. No, it's Jonathan. I'm like, oh, I'm so sorry. I don't know why.
Brooke
Oh, that was. That's a good cover, though, that you didn't delve into. Oh, I keep calling my ex getting someone's name wrong multiple times. That's so rude.
Jeffrey
I think a lot of people would think, like, oh, she must be going on a lot of dates then. If I'm just like, which one are you? Yeah.
Brooke
Yeah, but isn't that, like, competition for guys? Like, oh, a lot of people want some guys.
Jeffrey
I would probably just cry. Guys, give her a break. She's a senior citizen. So how did you end things with Jonathan that night?
Gail
I mean, we had a good day. There was a little kiss.
Jeffrey
Did you take your teeth out before the kiss or.
Gail
I don't know. We've been, like, talking, but it's more like friendly. And he hasn't asked me out again, so I don't know how he's feeling.
Brooke
I mean.
Jeffrey
Well, we can find out exactly how he's feeling.
Brooke
Oh, that's a good point.
Jeffrey
Yep, by using this old timey landline that we have in studio.
Brooke
Dial the numbers, Jeffrey.
Jeffrey
We're gonna do the rotodial on this one. And we're gonna get your second date update right after this.
Gail
Thank you.
Jeffrey
We said right after this. Don't fall asleep now. Coming up next, Brooke and Jeffrey in the morning.
Brooke
Second date update.
Jeffrey
We gotta knock out this second date quick so we can make it over to the community room and watch People's Court. Oh, I've seen this episode before. Judge. Judge Wobner's gonna give it to him.
Brooke
This time.
Jeffrey
We're going old school. That'll teach it at jaywalk. And throw him in the slammer.
Brooke
Okay, Gewold, man. Alan, sit down.
Jeffrey
It is 8am about. So we gotta get out of here. Oh, it's almost nap time. Bring it up. Cause our listener Gail, who is 25 years old, by the way, decided to prank her date Jonathan by showing up to dinner dressed as a little old granny. Why did she do that? Because he kept saying she seemed so mature during their online chats and even asked, how old are you really? And so decided to prank him with the old lady costume. And the date went really well, minus the part where she called him her ex's name a couple times, but they
Brooke
still shared a cute kiss at the end.
Jeffrey
I didn't hear cute kiss. I just heard kiss. I don't know.
Brooke
What was it, Gail, what was the kiss?
Gail
It was a little kiss.
Brooke
A little.
Jonathan
A little?
Brooke
Okay, everything labeled me as cute.
Jeffrey
Like a little. Yeah, like as tightly puckered lips as you can get.
Brooke
Okay, maybe that's not sexy. Maybe that's more grandma style.
Jeffrey
Okay, that's a problem. Maybe you leaned a little bit too hard into the grandma thing and it kind of turned him off.
Brooke
Yeah, you're gonna have to go with pigtails next time in a schoolgirl outfit.
Jeffrey
I mean, what do you think? Gail?
Gail
I really have no idea why. And I just. If it is, like, if you, like, snooped around and, like, found out that my ex was Jared, I just would want a chance to explain myself and apologize.
Brooke
Because you didn't tell him that it was your ex's name?
Gail
Yeah, no, but, you know, I. I really don't know.
Jeffrey
That would make me feel like you're not over.
Brooke
Not a good look.
Jeffrey
Well, let's ask him what the real deal was. I'm going to call his number right now and we're going to do it. That's how I say it on the radio. That's rated professional talk. Jeff, let's do this. Donna's number right now.
Jonathan
Hello?
Jeffrey
Hey, is this Jonathan?
Jonathan
Uh, yeah, who is this?
Jeffrey
I don't believe you that you're Jonathan now.
Brooke
I can't believe you didn't go in with the old man voice. I thought for sure that we were gonna hear Alan Winterbottom.
Jonathan
What old man? What? What? What's up? Actually, who's this Jonathan?
Jeffrey
Huh? What did you say?
Brooke
There it is. It's not overplayed. I still love it.
Jeffrey
You happy now, Brooke?
Gail
I am.
Jeffrey
Anyway.
Brooke
How you doing, Jonathan?
Jonathan
I'm a little confused, but I'm good.
Jeffrey
Me too. No, we're doing something with you right now. Jonathan, you're on Brooke and Jeffrey in the morning on a second date update.
Jonathan
I don't. Those words mean nothing to me. I don't know what you're talking. What you're talking about.
Jeffrey
Honestly, I don't really know what I'm talking about either. But a radio show, and we're on a task, right?
Jonathan
I'm on the radio right now.
Jeffrey
Yeah.
Brooke
Cool.
Jeffrey
Say hello to the six listeners we have.
Jonathan
Hey.
Jeffrey
They say hi back. Trust me. Anyway, we're trying to get some help for one of our listeners named Gail, who you went out on a date with recently.
Jonathan
Yeah, yeah, I remember Gayle.
Jeffrey
Okay.
Brooke
She sounds pretty funny. Did you think she was fun?
Jonathan
Yeah, you know, it was. It was a cute date. You know? I mean. Yeah, I like her. She's. She's cool.
Brooke
Oh, that's good.
Jeffrey
Good. We did hear about your date. Cause she told us that you went to a restaurant and she was dressed up as an old grandma.
Jonathan
She told you that?
Brooke
Yeah, it was funny. We all laughed.
Jonathan
Yeah, it was. It was definitely interesting.
Brooke
Oh, you didn't. You didn't like the joke?
Jonathan
Um, it's not that I didn't like it. I kind of don't know how to tell her. This is gonna. I'm just gonna come out. This is gonna sound weird.
Jeffrey
I think she understands that something odd is going on, because she told us you guys haven't really reconnected very much after the date happened.
Brooke
Right? Like, it's more. It felt like it moved into the friend zone, she said.
Jeffrey
And so she's ready to hear whatever the reason is for that, but she'd just like to get a little closure
Brooke
or maybe fix it.
Jonathan
I can definitely offer closure.
Brooke
Okay.
Jonathan
But after the date, something changed.
Brooke
What do you mean?
Jonathan
Well, I. Okay, I got in my car and I was driving home, and all of a sudden, I couldn't help but realize that I was more attracted to her as the grandma.
Brooke
Wait, when she was dressed up?
Jonathan
Yeah. And I didn't know how. I didn't know how to feel about it. Yeah, it just. It just did something for me.
Jeffrey
Okay, what. What about it was more attractive to you?
Jonathan
I don't know. I don't know. It just. It unlocks something, I guess. I think it was. There's something about the way her voice. I don't know.
Brooke
Fake grandma voice.
Jonathan
I liked the maturity. I liked the prune juice. I don't know. It was. It just seemed like. It just seemed like she knew what she was doing. And I found that really hot.
Jeffrey
I've heard of Big D energy, but not Big G energy. Big Grandma Energy. You're into that?
Jonathan
It's not so much the grandma thing, it's just like the older woman stuff.
Brooke
I mean, like a woman in charge. A woman who just makes decisions.
Jonathan
Yeah, makes decisions, tells me what to do, you know?
Jeffrey
So hearing Brooke talk to you right now must be really a trip. You should see the picture.
Brooke
She'll tell you what to do. That's kind of a grandma's sweater.
Jeffrey
It is definitely hand stitched.
Brooke
Okay. Is that a gray hair bra? I don't have gray hair, Alexis.
Jonathan
I don't know. It makes me feel taken care of.
Jeffrey
Oh, okay.
Brooke
Okay. Well, she sounds like a confident woman. It doesn't sound like you should shut the door on it.
Jonathan
Yeah, but there's more. After the date, I went back online and I've been talking to more mature women.
Jeffrey
Oh, you changed the age filter.
Jonathan
I bumped it up a little.
Jeffrey
Oh, God. I mean, no judgment, but I'm just. I'm trying to think of how Gale must feel hearing all of this right now.
Jonathan
Well, I was hoping you all would tell. Wait, oh, what do you mean?
Jeffrey
Yeah, yeah, what do I mean? I mean, Gail's actually on the other line right now listening.
Jonathan
Oh,
Jeffrey
Gayle.
Gail
Yeah.
Jonathan
Hey.
Gail
Hi, Jonathan.
Jeffrey
Yeah, it sounds like you guys have a lot to talk about here.
Brooke
Yeah.
Jonathan
Look, I mean, you're cool and all, but I'm. There's something that date just made me realize I want someone older.
Gail
I'm just confused and kind of shocked. I don't really have to say, like, you want. You want someone, like, 50 years older than you? Like, is that why you kept.
Jonathan
Oh, exactly. 50 would be great.
Brooke
Wait, 50 years older or exactly 50 years old?
Jonathan
Exactly 50 years old.
Jeffrey
Okay. That's the sweet spot for him.
Brooke
I mean, again, it is a good age for women. I'm not there.
Jonathan
It is a good age for women. Some of the people I'm talking to online are amazing.
Jeffrey
What about. What about the woman you're talking to on the phone line right now?
Jonathan
Gail, you're. Oh, Gail, you're great. It's not like I don't. It's not like I don't like you. It's just I'm. I don't see us in a. In a relationship.
Brooke
He wants to be with someone who can't have pregnancy scares.
Jonathan
Some women get pregnant at 50. It's possible.
Brooke
True, Gail, he knows his facts.
Jeffrey
I'd love to hear what you're thinking right now.
Gail
I mean, I guess I'm kind of, like, offended that you thought I was more attractive when I had a wig. On and glasses.
Jonathan
It's not that I'm not attracted to you, Gail. It's just like you're too young for me.
Jeffrey
He's like two years older than her. Never heard that ever on the show. Oh, my gosh.
Gail
I guess I'm glad I could assist in you figuring out your stuff.
Brooke
Yeah, There you go.
Jeffrey
That was a very mature thing of
Brooke
you to say, 25 year old.
Gail
I am mature.
Jonathan
I'm excited to see you turn into the mature woman.
Jeffrey
Before it goes any farther, but I am going to ask kind of a weird question. Would you be interested in going out with Gale one more time if she dressed up as the old lady again?
Brooke
I don't know that Gale has volunteered for that.
Jonathan
Just the voice would be good.
Jeffrey
How about you give him a little flavor? Right now
Gail
I don't think it's going to work out.
Jeffrey
Kind of did it for me, too. Is it getting hot in here or what?
Jonathan
Okay, so you're feeling what I'm feeling back now.
Brooke
Just being sarcastic.
Jeffrey
I'm getting hot flashes premenopausal over here. Yes, I am.
Gail
Brooke and Jeffrey in the morning.
Jeffrey
And now for a bit of breaking news. Between your breaking news with me, the Geico Gecko, here are some things you ought to know today. People who switch their car insurance to geico save about $900 a year. Experts are calling that Nice to know. Also, plants can hear when bees buzz. My ficus just heard that. And finally, animal experts have confirmed that goats have regional accents. I'm getting a hint of Irish there. It feels good to get good news. It feels good to Gecko.
Brooke
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Jeffrey
if this is a trend, I think it bodes very well for somebody in this room.
Brooke
Who?
Jeffrey
Alexis.
Brooke
Ah,
Jeffrey
now your mom will be hit on by more of your boyfriends.
Brooke
Please, they'll think my mom is 25.
Jeffrey
We should have hooked Jonathan up with Alexis's mom.
Brooke
It would have been perfect.
Jeffrey
Match made in heaven.
Brooke
It's always good to hear though it's nothing you did. I mean, honestly, the only thing she could have done to fix it was just to wait. Wait till she got old or, you
Jeffrey
know, invented a time machine and aged herself by 30 years and then gone
Brooke
back like opposite of Botox. Inject yourself with wrinkles.
Jeffrey
Yeah, call it Mo tox.
Brooke
Yeah.
Jeffrey
But yeah, really no chance for her in that one nothing thing she could
Brooke
have done was but a big self discovery for him.
Jeffrey
Yeah, she helped him. Something good did come out of this. And if you ever want to get a second date update, you can always email the show. We'll help you out. And if you want to catch up on all of our second dates, they're up on our podcast. Wherever you get your podcast at. Brooke and Jeffrey.
Brooke
Yes.
Jeffrey
What? What's the podcast? Is that a new fancy fishing rod technique there? Broadcast. Okay, and now for a bit of breaking news. Between your breaking news with me, the Geico Gecko, here are some things you ought to know today. People who switch their car insurance to geico save about $900 a year. Experts are calling that. Nice to know. Also, plants can hear when bees buzz. My ficus just heard that. And finally, animal experts have confirmed that goats have regional accents. I'm getting a hint of Irish there. It feels good to get good news. It feels good to Geico. Ryan Reynolds here from Mint Mobile with a message for everyone paying big wireless way too much. Please, for the love of everything good in this world, stop with Mint. You can get premium wireless for just $15 a month. Of course, if you enjoy overpaying. No judgments. But that's weird. Okay, one judgment anyway. Give it a try@mintmobile.com Switch upfront payment
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Jeffrey
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Jeffrey
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Date: May 25, 2026
Host: iHeartPodcasts – Brooke and Jeffrey
Episode Theme:
This episode follows the "Second Date Update" format, where a listener seeks help after being ghosted following a first date. The hosts call the person who didn’t reply—in this case, Jonathan—to uncover what happened. The episode is filled with comedic banter, uncomfortable honesty, and a bizarre twist about attraction and mistaken maturity.
The show centers on Gail, a 25-year-old listener, who went on a date with Jonathan after a month of chatting online. Despite a creative and humorous first date (involving Gail dressing as an elderly woman to poke fun at Jonathan’s comments on her maturity), Jonathan’s coolness in the aftermath left Gail confused. The hosts investigate: Is it the prank, the conversation missteps, or something stranger that’s put Gail in the 'friend zone'?
(04:33-05:14)
“He kept saying, like, oh my, you seem so mature for your age… Like, he said it like three separate occasions.” – Gail (04:36)
(06:00-07:17)
“I committed to the bit and I was like, 'Oh, hello, Jonathan, this is Gail.'” – Gail (06:44)
“That is hilarious. What did Jonathan think?” – Jeffrey (06:24)
(12:10–14:26)
“I couldn’t help but realize that I was more attracted to her as the grandma.” – Jonathan (14:15)
“It unlocks something, I guess. I think it was...there’s something about the way her voice...I liked the maturity. I liked the prune juice. I don’t know, it just seemed like she knew what she was doing. And I found that really hot.” – Jonathan (14:38)
(15:08-15:56 and 16:07)
“After the date, I went back online and I’ve been talking to more mature women.” – Jonathan (15:43) “You want someone, like, 50 years older than you?” – Gail (16:45) “Exactly 50 would be great.” – Jonathan (16:54)
“I guess I’m glad I could assist you in figuring out your stuff.” – Gail (18:09)
On being too mature:
“Or maybe the fact your name is Gail.” – Jeffrey (05:09)
On costumed dating:
“Did you take your teeth out before the kiss or…” – Jeffrey (08:40)
On Jonathan’s surprising attraction:
“I liked the maturity. I liked the prune juice… she knew what she was doing. And I found that really hot.” – Jonathan (14:42)
On Gail’s response to Jonathan’s honesty:
“I guess I’m glad I could assist you in figuring out your stuff.” – Gail (18:09)
On the overall situation:
“That was a very mature thing of you to say, 25 year old.” – Brooke (18:17)
The tone is classic “Brooke and Jeffrey”—sarcastic, lighthearted, occasionally risqué, and always leaning into awkward moments for laughs. The hosts gently roast both Gail and Jonathan, poking fun at the bizarre turn of events while still treating Gail’s feelings with some care. The twist—that Jonathan found the mature/grandma act so compelling it changed his entire dating strategy—is handled with astonished disbelief and plenty of jokes.
For more Second Date Updates, find the Brooke and Jeffrey podcast on Spotify, Apple, or iHeartRadio.