Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Senior Moment Slip Up

Episode Date: May 25, 2026

One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! See omnystudio.com/listener for privacy information.

Hey guys, it's us The Jonas Brothers. I'm Joe. I'm Kevin. And I'm Nick. And guess what? We created our own podcast called, Hey Jonas. We invented a podcast?

Well, we didn't invent it. We just contributed to it. We're the first people to do podcasts. We get to ask other people questions because we're sick and tired of being asked questions. Well, sick and tired is a strong way to put it. But, you know, tired and sick. Listen to Hey Jonas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Just listen.

We don't care where you hear it. Another podcast from some. Some SNL late night comedy guy. Not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman, help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel,

help an Acapella band with their between songs banter. There's the worst singer in the group. The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard, uh, you only got in because your parents made a huge donation. The yard birds, right?

That's the name. The Harvard Yard, but they're open. Do you have a name suggestion? We're open. Since you guys are middle aged, one erection. Listen to humor me with Robert Smigel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcast. Humor me. I need some jokes to make me seem funny.

Your 20s can be so exciting. but they can also be really overwhelming, confusing, and honestly, just kind of lonely. May is Mental Health Awareness Month, and the psychology of your 20s is breaking down the science behind the biggest roadblocks we face. I was six years into my career, the 80-hour weeks, and just the first one in, the last one out, and I ended up burning out. There was a large chunk of my 20s that I, like, was just so wanting to, like, be out of that phase out of my skin, and I just, like, really regret not living in the present more.

You don't need to have everything figured out right now. You just need to understand yourself a little bit better. Listen to the psychology of your 20s on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Here's something that should not be as complicated as it is. Getting a racist statue removed. And here's something that should be a whole lot easier than it is. Getting a new one put up in its place. I'm Akila Hughes.

And Rebel Spirit, season two, is about both of those things. As I was watching these statues come down and I was thinking about, it meant that I grew up in a majority black city in which there were more homages to enslavers than there were to enslave people. Listen to Rebel Spirit Season 2 on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts.

Every family has its secrets. But what happens when you discover that your dad has been living a double life? That is not the look of an innocent man. Is everyone lying to me about who they are? I felt such desperation. I felt it was what I had to do.

Listen to Deep Cover the Family Man on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Brooke and Jeffrey in the morning. And you know, we get all the credit for all these second dates. Yeah. But really, it's our listeners

and their terrible dating decisions that we have to think. Yes. And the people who ghost people. Yes. Helping us out. Thank you. Your toxicity has made us so funny.

Yes. Yes. So thank you. Hey, don't forget, we do have 45 more minutes of this. We've got a full show over on the Brook and Jeffrey main feed. If you'd like it, follow that one as well. And let's get into your second date. Brooke and Jeffrey in the morning.

Second date update. 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? What? Hours? What? minutes. I feel like people typically talk like a week or two.

Hey, I'm at your window right now. Can you open it? I'll climb right in. I brought over some special juice for us to split. No, that sounds sketchy. I don't see any red flags. Jeff's at a weird app. Yeah, what app is that, Jeff? I'm not going to... Are you matching people on Google Maps? 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 because 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? Hi. How long did you wait before you met up with the guy from online? Yeah, I mean, we chatted on and off for like a month before we actually went out. Oh, my God. Slow game. Why a month?

I mean, is that, like, something you typically do? 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. Oh. And after you talk. for a month, is there a lot of anxiety going into that first meeting?

Because you've invested quite a bit of time at that point. Yeah, I mean, a little, but I was more excited. Yeah. That's what the special juice is for that I mentioned early. Keep you loose, relaxed. 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. I would be worried that I'd run out of things to say when I finally met him because I've already He covered everything. I mean, what do you talk about with a guy for a month? I don't know, like what we're doing, TV shows we're watching, stuff going on at work.

Yeah. Ooh, work drama. That's exciting. The weird thing, he kept, like, bringing up, he kept saying, like, oh, you seem so mature for your age. Huh? Like, he said it, like, three separate occasions. Is that a compliment or a diss? I don't know.

I mean. It depends on how old you are. Are you, like, 21 or like? I'm 25. Okay. Okay. So I can kind of see that. Yeah, I mean, 25, you could go either way for sure. Is he an older guy? Is that why? Yeah, what did he mean by that?

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. Maybe the fact your name is Gail. Well, there's that too. Okay, so it sounds to me like he meant it as a compliment. I mean, I guess. And then at one point, he asked me how old I really was with like a smiley. face. Oh. Like, as if I was lying on my profile or something, I don't know.

I thought it was kind of rude. Oh, weird. That could be a joke, though, where it's, you know, tell me the real age, make you laugh. I don't know, man. Yeah, because he's looking at your pictures. Like, I mean, it's all based on photos. Like, I'd be like, thank you. No.

Well, no, they'd been talking a few weeks, though, so they have that familiarity. What did you say to him? I said you'll have to meet me to find out. That's playful. Was it right after like the conversation about your high cholesterol? Is that why I thought that you were old? So what did you end up doing for your date? So yeah, we made plans to get dinner and because I'm hilarious,

I decided to show up in an old lady costume. What? I love you, Gail. Just to troll him for asking how old you were? You went in full costume? The whole thing, I got a white wig. I wore this like flowery dress. She got a walker?

or something? I had a cane. A cane. Okay. No way. That is hilarious. What did Jonathan think when you showed up looking like that? 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 committed to the bed and I was like, oh, hello Jonathan. This is Gale. What was his reaction? I mean, he freaked out and then I like immediately like took off the wig and was like, He was like, this is a joke. I'm just kidding. I don't to, like, poke fun at you. Turns out, I'm a little older than I said all right.

That's really funny, actually. Did he laugh so much? Once he, 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 funny. Oh, you just kept it going. Can I get a prune back?

I think that was kind of funny at first. You don't want to over-commit to being the old lady, though. They have, like, a regular outfit. outfit on underneath. I was going to say it's not very hot. Yeah, I had like a cute dress on. Yeah. Okay, okay, good.

And they were at the pancake house at 4 o'clock. It's really going in on it. I mean, other than that, was there anything weird or awkward that happened while you were at the restaurant? I mean, conversation was good. I did kind of slip up a couple times. And I accidentally called him my ex's name. Yikes. Oh.

What's your ex's name? Jared. Oh, that's, I could see that. Two Jays. Yeah, yeah. My ex name is Yonathan. No, 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. Oh, that was, that's a good cover, though. You didn't delve into, oh, I keep calling you my ex. Still, I'm getting someone's name wrong multiple times. That's so rude. And it makes, 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. Yeah, but isn't that, like, competition for guys? Like, oh, a lot of people want her. Maybe some guys. 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?

I mean, we had a good date. There was a little kiss. Oh, cute. Did you take your teeth out before the kiss? I don't know. We've been, like, talking, but it's more, like, friendly. And he hasn't asked me out again. Okay.

So I don't know how he's feeling. I mean. Well, we can find out exactly how he's feeling. Oh, that's a good point. Yep, by using this old-timey landline that we have in studio. Dial the numbers, Jeffrey. We're going to do the rotodial on this one. Yeah, that's right.

And we're going to get your second date update right after this. Thank you. We said right after this. Don't fall asleep. Coming up next. Broken Jeffrey in the morning. Second date update. We got to 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 Wapner's going to give it to him this time. That'll teach you to Jaywalk. And throw him in the slammer. Okay. Oh, man. Alan, sit down.

It is 8 a.m. about, so we've got to get out of here. Oh, it's almost nap time. Bring it up because 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 still shared a cute kiss at the end. I didn't hear cute kiss. I just heard kiss. I don't know. What was it, Gail? What was the kiss? It was a little kiss.

A little. A little. Okay. Everything little to me is cute. Like a little, yeah. Yeah, like as tightly puckered lips as you can get. Okay, maybe that's not sexy.

Maybe that's more grandma style. Okay. That's the problem. Maybe you leaned a little bit too hard into the grandma thing and it kind of turned him off. Yeah, you're going to have to go with pigtails next time in a school girl outfit. I mean, what do you think, Gail? I really have no idea why. And I just, if it is, like, if he, like, snooped around and, like, found out that my

ex is Jared, I just would want a chance to explain myself and apologize. Oh, because you didn't tell him that it was your ex's name. No, but, you know, I really don't know. That would make you feel like you're not over. Not a good luck. 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.

Let's do it, Jeff. Let's do this. I'm down his number right now. Hello? Hey, is this Jonathan? Yeah, who is this? I don't believe you that you're Jonathan now I can't believe you didn't go in with the old man voice

I thought for sure that we were going to hear Alan Winterbottom What old man? What's up actually? What is Jonathan? Huh? What did you say? There it is. It's not overplayed.

I still love it. You happy now, Brooke? I am. Anyway. How you doing, Jonathan? I'm a little confused, but. I'm good. Yeah, 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. I don't, those words mean nothing to me. I don't know what you're talking about. Honestly, I don't really know what I'm talking about either. We're a radio show, and we're on a task right now. I'm on the radio right now. Yeah.

Cool. Say hello to the six listeners we have. Hey. Hey. 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. Yeah, yeah, I remember Gail. Okay. She said it's pretty funny. Did you think she was fun? Yeah, you know, it was a cute date, you know. I mean, yeah, I like her. She's cool. Oh, that's good.

Good. We did hear about your date because she told us that you went to a restaurant and she was dressed up as an old grandma. She told you that? Yeah. It was funny. We all laughed. Yeah, it was definitely interesting. Oh, you didn't like the joke?

It's not that I didn't like it. I kind of don't know how to tell her. I'm just going to come out. This is going to sound weird. 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. Right. Like it's more, it felt like it moved into the friend zone, she said. And so she's ready to hear whatever the reason is for that, but she'd just like to get a little closure.

Or maybe fix it. I can definitely offer closure. Oh, okay. But after the date, something changed. What do you mean? Well, 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. Wait, when she was dressed up? Yeah.

And I didn't know how, I didn't know how to feel about it. Yeah, it just did something for me. Uh, okay. Oh, wait. What about it was more attractive to you? I don't know. I don't know. It just, it unlocks something, I guess.

I think it was something about the way her voice. I don't know. You like the fake grandma 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.

I've heard of Big D energy. but not Big G energy. Big Grandma energy? You're into that? It's not so much the grandma thing. It's just like the older woman stuff. I mean. Like a woman in charge, a woman who just makes decisions.

Yeah, makes decisions, tells me what to do, you know. So hearing Brooke talk to you right now. You should see the thing. Don't tell you what to do. That's true. That's kind of a grandma's better, isn't it? It is definitely hand-stick. Cropped, okay?

Is that a gray hair bro? I don't have gray hair, Alexis. I don't know. It makes me feel taken care of. Okay. Okay. Well, she sounds like a confident woman. It doesn't sound like you should shut the door on it.

Yeah, but there's more. After the date, I went back online and I've been talking to more mature women. Oh, you change the age filter. I bumped it up a little. Oh, God. I mean, no judgment, but I'm just, I'm trying to think of how Gail must feel hearing all of this right now. Well, I was hoping you all would tell, wait. Oh.

What do you mean? Yeah. Yeah, what do I mean? I mean, Gail's actually on the other line right now listening. Oh. Oh. Gail? Yeah.

Uh, hey. Hi Jonathan See how it sounds like you guys have a lot to talk about here Look I mean you're cool and all But I'm there's something that date It just made me realize I want someone older I'm just confused and Kind of shocked

I don't really have to say Like you want someone like 50 years older than you Like is that why you kept I didn't say 50 oh exactly 50 would be great Wait, 50 years older or exactly 50 years old? Exactly 50 years old. Okay. That's the sweet spot for him.

I mean, it is a good age for women. I'm not there. It is a good age for women. Some of the people I'm talking to online are amazing. Wow. What about the woman you're talking to on the phone line right now? Gail, you're great. It's not like I don't.

It's not like I don't like you. It's just I don't see us in a relationship. He wants to be with someone who can't have pregnancy scares. Some women get pregnant at 50 as possible. It's true. Gail? He knows his facts. I'd love to hear what you're thinking right now.

I mean, I guess I guess I'm kind of like offended that you thought I was more attractive when I had a wig on. and glasses. It's not that I'm not attracted to you, Gail. It's just like, you're too young for me. He's like two years older than her. Never heard that ever on the show. Oh, my gosh. I guess I'm glad I could assist in you figuring out your stuff.

Yeah, there you go. That was a very mature thing of you to say. A 25-year-old. Yeah, I am mature. I'm excited to see you turn into the mature woman. I'm going to stop her to stop her right there before it goes any farther.

But I am going to ask kind of a weird question. Would you be interested in going out with Gail one more time if she dressed up as the old lady again? I don't know that Gail has volunteered for that. Just the voice would be good.

Oh, wow. Gail, how about you give them a little flavor right now? I don't think it's going to Look out. Wow. Kind of did it for me, too. Is it getting hot in here or what? Okay, so you're feeling what I'm feeling about.

Just being sarcastic. I'm getting hot flashes. Oh, you're man's draught. Yes, I am. Brooke and Jeffrey in the morning. Hey, Ontario. Come on down to Bed MGM Casino and check out our newest exclusive. The Price is Right Fortune Pick.

Don't miss out. Play exciting casino games based on the iconic game show. Only at BedMGM. Access to the Price is Right Fortune Pick. is only available at BedMGM Casino. BetMGM and GameSense remind you to play responsibly. 19 plus to wager, Ontario only. Please play responsibly.

If you have questions or concerns about your gambling or someone close to you, please contact Connix Ontario at 1866-531-2,600, to speak to an advisor free of charge. BetMGM operates pursuant to an operating agreement with Eye Gaming Ontario. The newest tracks. Let's go. New music. And the next big thing. Always on the new music first.

Your first place to hear it home. now. Iheart new music. Your digital station for brand new drops, fresh vines, and tomorrow's bangers. Powered by North by Northeast Music Festival, taking place June 10th to 14th across Toronto. Iheart new music. Stream now online on your smart speaker and preset on the free Iheart radio app. Well, if this is a trend, I think it bodes very well for somebody in this room.

Who? Alexis. Ah. What's me? Because now your mom will be hit on by more of your boyfriends. Yeah. Please, don't think my mom is 25. We should have hooked Jonathan up with Alexis's mom.

It would have been perfect. 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 know, waited out. Invented a time machine and aged herself by 30 years and then gone back. Like opposite of Botox.

Inject yourself with wrinkles. I'll call it Mottox. But, yeah, really no chance for her in that one. Nothing she could have done. No, but a big self-discovery for him. 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. Yes. What's the podcast, you know? Is that a new fancy fishing rod technique there? Broadcast. Yeah. Okay.

Hey guys, it's us. The Jonas Brothers. I'm Joe. I'm Kevin. And I'm Nick. And guess what? We created our own podcast called, Hey Jonas.

We invented a podcast? Well, we didn't invent it. We just contributed to it. We're the first people to do podcasts. We get to ask other people questions because we're sick and tired of being asked questions. Well, sick and tired is a strong way to put it. But, you know, tired and sick. Tired and sick.

Listen to Hey, Jonas, on the IHeart Radio app, Apple Podcasts, or wherever you. you get your podcast. Just listen. We don't care where you hear it. Another podcast from some SNL late night comedy guy. Not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman, help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel, help an a cappella band with their between songs banter. The worst singer in the group? The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard.

You only got in because your parents made a huge donation. The group. The yard birds, right? That's the name. The Harvard Yardt. They're open.

Do you have a name suggestion? We're open. Since you guys are middle-aged. One erection. Listen to humor me with Robert Smigel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcast. You know me.

I did. Some jokes to make me seem funny. Hey, I'm Dr. Maya Shunker, a cognitive scientist and hosts of the podcast, a slight change of plans, a show about who we are and who we become when life makes other plans. I wish that I hadn't resisted for so long the need to change. We have to be willing to live with a kind of uncertainty that none of us likes. You can have opinions. You can have like a strong stance. and then there's your body having its own program.

Listen to a slight change of plans on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Here's something that should not be as complicated as it is, getting a racist statue removed. And here's something that should be a whole lot easier than it is, getting a new one put up in its place. I'm Akila Hughes, and Rebel Spirit Season 2 is about both of those things. As I was watching these statues come down, I was thinking about what it meant. that I grew up in a majority black city in which there were more homages to enslavers than there were to enslave people.

Listen to Rebel Spirit Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Every family has its secrets. But what happens when you discover that your dad has been living a double life? That is not the look of an innocent man. Is everyone lying to me about who they are?

I felt such desperation. I felt it was what I had to do. Listen to Deep Cover the Family Man on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.