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

Episode Date: January 3, 2025

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

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

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on the Black Effect Podcast Network, the iHeartRadio app, Apple Podcasts, or wherever you go to find your podcast. 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? with them? Two to three hours? Two to three 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 got 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 why why a month i mean is that like something you typically do i guess i mean that 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 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 earlier

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 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. It depends on how old you are. Are you like 21? 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? 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. Or 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, you know, tell me the real age make you laugh. I don't know, man. Rick does not look like a laughing dog. Yeah, because he's looking at your pictures. Like, I mean, it's all based on photos. Like, I'd be like,

uh, thank you. No. Well, no, they've 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 good. That's playful. Was it 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. Wait, what? I love you, Gail. Just to troll him for asking how old you were?

That is amazing. You went in full costume? The whole thing. I got a white wig. I wore this, like, flowery dress. Did you get a walker or something? I had a cane. A cane.

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, you know, I committed to the bit, and I was like, oh, hello, Jonathan, this is Gail. Oh, my God.

That's amazing. I absolutely love it. What was his reaction? I mean, he freaked out. And then I like immediately like took off the wig and was laughing. He was like, this is a joke. I'm just kidding. I didn't want to like poke fun at you.

Turns out I'm a little older than I said online. 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. 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 overcommit to being the old lady. Do they have, like, a regular outfit on underneath? I was going to say, it's not very hot. Yeah, I had, like, a cute dress on. Okay, okay, good's not very hot yeah i had like a cute dress on and yeah okay okay and they were at the pancake house at four o'clock 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 J's. Yeah, yeah. My ex's name is Yonathan.

He didn't know that that was my ex's name. He just, like, corrected me and was like, no, it's Yonathan. I'm like, oh, I'm so sorry. I don't know why. Oh, 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.

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, 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. how did you end things with jonathan that night i mean we had a

good date there was a little kiss did you take your teeth out before the kiss or 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. Well, we can find out exactly how he's feeling. Oh, that's a good point. Yep, by using this old tiny landline that we have in studio. Dial the numbers,

Jeffrey! We're going to do the rotodial on this one. And we're going to get your second date update right after this. Thank you. We said right after this. Don't fall asleep now.

Coming up next. 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. Throw him in the slammer. Okay, old 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 kiss. A little kiss. Okay. Everything little to me is cute. Like a little mwah. 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 a 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 schoolgirl 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 him. Not a good look. 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 radio professional talk.

Let's do this. I'm dialing his number right now. Hello? Hey, is this Jonathan? Yeah. Who is this Jonathan? Uh, 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? Sorry, Jonathan. Huh? What did he say? No. It's not overplayed. I still love it. You happy now, Brooke? Sorry, Jonathan. Huh? What did he 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. 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, I remember Gail.

Okay. She sounds pretty funny. Did you think she was fun? Yeah, you know, it was a, um, it was a cute date, you know? I mean, yeah, I like her. She's, 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. It was hilarious. 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. Okay. But, um, after the date, something changed. What do you mean? 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. Oh. What?

Wait, when she was dressed up? Yeah, and I didn't know how to feel about it. Yeah, it just did something for me. Okay. Not expecting that. Yeah, what about it was more attractive to you? I don't know. It just, it unlocked something, I guess. I think it was something about the way her voice.

I don't know. You liked 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. Okay. 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 must be really true.

You should see the picture. She'll tell you what to do. That's true. That's kind of a grandma's sweater, isn't it? Oh, my God. It is definitely hand-stitched. It's cropped, okay? Is that a gray hair, Brooke?

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 changed the age filter. This is all going to be shocking. 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, what do you mean? Yeah. What do I mean? I mean, Gail's actually on the other line right now listening. Oh, oh, Gail. Yeah. Hey. Hi, Jonathan. 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, um, like you want, 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. I'm not close yet. It is a good age for women. Some of the there. I'm not close yet. It is a good age for women. Some of the people I'm talking to online are amazing. Wow. He doesn't need you to tell him. What about the woman you're talking to on the phone line right now, Gail? Gail, you're great.

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. It's possible. Gail, 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 you 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 work 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 right now. Just being sarcastic. I'm getting hot flashes premenopausal over here. Oh, you're man straight. Yes, I am. Brooke and Jeffrey in the morning.

Well, if this is a trend, I think it bodes very well for somebody in this room. Who? Alexis. What? It's me.

Because now your mom will be hit on by more of your boyfriends. 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 invented a time machine and aged herself by 30 years and then gone back. Like opposite of Botox.

Inject yourself with wrinkles. Call it Motox but uh 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. What's the podcast now?

Is that a new fancy fishing rod technique there? Rod cast, sure. Okay. Brooke and Jeffrey in the morning. Ugh. We're so done with New Year, New You.

This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and We love that for you. Someone else will, too. Be more you this year.

And find them on Bumble. Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

$1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm A.J. Stevens, Vice President of Client Strategy at Athletes First. Introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. You are cordially invited to the hottest party in professional sports. I'm Tisha Allen, former golf professional and the host of Welcome to the Party, your newest obsession about the wonderful world that is women's golf. Featuring interviews with top players on tour, tips to help improve your swing, and the craziest stories to come out of your friendly neighborhood country club. Welcome to the Party with Tisha Allen is an iHeartWomen sports production

in partnership with Deep Blue Sports and Entertainment. Listen to Welcome to the Party, that's P-A-R-T-E-E on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The OGs of uncensored motherhood are back

and badder than ever. I'm Erica. And I'm Mila. And we're the hosts of the Good Moms Bad Choices podcast, brought to you by the Black Effect Podcast Network every Wednesday. Yeah I'm Mila. And we're the hosts of the Good Moms Bad Choices podcast, brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms. But not your mommy. Historically, men talk too much. And women have quietly listened.

And all that stops here. If you like witty women, then this is your tribe. Listen to the Good Moms Bad Choices podcast every Wednesday on the Black Effect Podcast Network, the iHeartRadio app, Apple Podcasts, or wherever you go to find your podcasts.