Brooke and Jeffrey: Second Date Update - Second Date Update: Glad You Didn't Die

Episode Date: April 27, 2026

Charles’ date ended with Maggie telling him “I’m glad you didn’t die.” It was a close call but he’s here with us for a Second Date Update!See omnystudio.com/listener for privacy information.

A win is a win. A win is a win. I don't care what I'm saying. Yep, that's me. Clivert Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media.

Well, now I'm bringing all of that excitement to my brand new podcast, The Clifers Show. This is a place for raw, unfills of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to The Clivert Show on the I-Hard Radio app,

Apple Podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok. When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands. I vowed. I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends.

Listen to the girlfriends. Trust me, babe. On the IHart Radio app, Apple Podcasts, all. or wherever you get your podcast. I got you. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins. But the pregnancy appeared to be a hoax. You doctored this particular test twice in so much, correct?

I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing. Greg Alesspian. My mind was blown. I'm Stephanie Young. This is love track. Laura, Scottsdale Police.

As the season continues, Laura Owens finally faces consequences. Listen to Love Trapped podcast on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, everyone? I'm Ago Vodom. My next guest, it's Will Ferrell. Woo, woo, woo, woo, woo, woo. My dad gave me the best advice ever. He goes, just give it a shot. But if you ever reach a point where you're banging your head against the wall and it doesn't feel fun anymore,

it's okay to quit. If you saw it written down, it would not be an inspiration. It would not be on a calendar of, you know, the cat. Just hang in there. Yeah, it would not be. Right, it wouldn't be that. There's a lot of luck. Listen to thanks dad on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.

American soccer is about to explode. The World Cup is coming. I'm Tav Ramos. I'm Tom Boko. On our podcast, Inside American Soccer, you'll get the real storylines, the biggest decisions, and the truth about the U.S. national team. It wouldn't be a huge surprise if our team ends up in the quarterfinals or potentially a great run into the semifinals. Listen, Inside American Soccer with Tom Bogart and Tab Ramos on the IHeart Radio app, Apple Podcasts, wherever you get your podcast. Hey, we got a brand new episode for you today on your second day podcast.

Thanks for being here. We do need to reflect on our podcast last week, the episode. What was it called? Love at First height? Yeah, the two tall people. Yeah. Where, what, 6-6 wasn't tall enough for her something? Basically, yeah.

It's funny to hear. Dude, it's just wild. Where is she choosing these? I don't know. Finding them. What a niche thing. You have to date basketball players. Not even NBA, just around the world. Yes. True.

And what are people saying in the comments? Joe said inflation getting so bad. Six-six is a new six-foot. We're cooked. That's pretty funny. Sorry, I can't imagine this mindset because my type is actually shorter guys that are around my height. That's right. Oh, you're getting an applause from Ashton.

I've always been a medium guy, so. Shorter guys. I'm with her. Yeah. Imagine the coffin size they need to be buried. Oh, God, that was dark. Why would you say that? Where was your head at?

Okay, anyways. We're talking about it. Do you have to buy two blocks? No, done on comments. Done on comments. Okay, here we go. Let's get to your brand new episode. It starts right now.

Brooke and Jeffrey in the morning. Second date update. A little behind the scenes secret here. When we do these second date updates, it's Brooke and Jeffrey in the morning. Our producer takes a lot of time to coordinate these calls with the listeners. Is that a secret?

Because I'm pretty sure anyone that meets him, he complains about it. He's very, very stressed out. Yes. Because he's trying to help these people. Yes. You don't know how much work this is. Totally.

Today's caller, his name is Charles, has been booked six different times to do this over the past two weeks. Dang. Has not answered the phone for five of them. Okay. Well, we call from a weird number. He requested this. Yeah.

He scheduled these calls and he wasn't answering. Cold feet? Maybe we know why he's not getting this second date. Yeah. Maybe. Maybe. I don't know to answer my phone. Girls try to call me, but.

But he's finally on the phone with us on the sixth try. Wow. At least he was. Hopefully he hasn't hung up all. already. Charles, are you still there? Yeah. I've just had second thoughts about doing this more than once, but today I just felt like I've finally had the courage to go through with it.

Okay. And is this... Awesome. That's awesome. I'm guessing this has been the same person all six times we've tried to call you, right? Oh, that's a good question. It's the same girl. Okay. My name's Maggie. And at this point, how long ago did you meet her? It's been probably three weeks. weeks. Oh, okay.

I was with a buddy who was getting a tattoo and she was the tattoo artist. Oh. Interesting. See, there is something real sexy about tattoo artists. Yeah. So I was in the waiting area and I could see her do her work for like half an hour and she was so beautiful. Okay. Did you have any interaction with her or did you just stare at her?

Yeah. With your mouth open? Just. No? No. interaction you talked to her oh sorry i was just thinking about maggie you sent him right back to that moment watching her work her magic on his arm okay yeah so after they were done i'm i'm kind of a shy person yeah but i asked her out by writing my phone

number on the back of my buddy's receipt with a message that said i think you're cute but i spelled your you are. Oh. I thought it was kind of because he's hip like that. Dude. Yeah. You curfite it was you and not your friend.

That was a strong move. Oh, that's a good point, Alexis, because it was on your friend's receipt. Oh, that could actually, that's, yeah, that could be confusing. Oh, yeah. I didn't think about that. Yeah, but I gave it to her,

so I was hoping she knew it was for me. Okay. Okay. It's a little better. Did she contact you? Yeah, she texted me, and she agreed to get dinner together. Okay.

Wow. Good. Okay. So she saw something she liked, too. Yeah, that you are. That turned on. I meant him. Oh, whatever it was, good work.

I mean, what were you feeling going into this date? I was excited. I was a little nervous, and I picked a restaurant that was close to her apartment to make her feel like I was thinking about her. That's good. Did she tell you where her apartment was? Thank you, Jose. How did you know where she lived? Yeah, it was by the tattoo shop, and she said she kind of lived.

close to there. Oh, okay. Okay, that's good. That's good. That's good. Okay. So what was it like? You meet her and what happens?

Yeah, so I picked her up and I think there was a miscommunication about the time. So I ended up being a little late by like, I don't know, 15 minutes, but it was fine. 15 minutes late? Okay. It's not a big. It's not a word. It's probably already anyways. Yeah.

She would have made you wait that long. All right. She comes out and we walked to the restaurant together. and you know how there's like really loud restaurants with everybody talking yeah well this was just not that it was really quiet so people could hear a lot oh no the opposite i hate that yeah did that make were you like Alexis did that make you uncomfortable it kind of did because she was just even prettier than the first time i saw her and there were times where i just caught myself just staring at her and then there was a silence

and then I was only a couple feet away, and I just had to snap out of it. Yeah, it sounds like you go into that trance mode often. Okay. Yeah, let's start calling her now, because I feel like there's going to be a lot more positive. I think we need to do, like, an alarm sound to get his attention back, so.

Sorry, sorry, I muted myself. You're right, Charles. So, okay, so there are times you're in the restaurant. You were so enamored by her stunning beauty that you didn't even have words, you were just staring at her. Yeah, so I don't know if I may have come across as a boring person, which sucks, but maybe that's why she hasn't answered. And I mean, I'm sure she meets a lot of cool guys that come into the tattoo shop.

Yeah, but I bet you're right. I bet she gets asked out a lot, but I bet she doesn't say yes very often. Yeah, those are, like tattooed musley guys aren't writing you are on their receipts like you do, bro. That's cute. On their friends' receipts, not their own. He didn't know. Exactly. You're unique, and I bet she appreciates that.

So tell us how the date ended. Well, the most embarrassing part was the walk back to her apartment. Why? I was kind of looking at her, and I almost got hit by a car. What? Oh, what? They honked really loud. They honked so loud.

Yeah, they were able to eat you. They're trying to startle you to get out of the way. You didn't get hit. No, no. Well, the last thing she said to me. It was, I'm glad you didn't die, which I thought was kind of sweet. Oh. Well, yeah.

It's better than I wish you had died. Yeah. So it's better than that. Dang it, that car missed. So maybe it's not the way that you wanted the date to go when you envisioned it in your head, but there's a chance we can save this. Yeah, and you're probably not a boring guy, right? You got lots of cool stuff going on in your life. Yeah, you got quirks.

Yeah. Yeah. Period. I believe that. He's pausing to think about him. Let's call Maggie here in a minute and show her just how exciting and cool and awesome of a person you really are. Dude, boring people don't call radio stations. No. Only the cream of the crop. Yeah. The coolest people.

So we're going to come back, call Maggie, and try to get you your second date update right after this. Broken Jeffrey in the morning. Second date update. Quick recap, if you're just joining us. us because I don't want to lose Charles again, like we have multiple times in the past, is he met a tattoo artist named Maggie, asked her out to a restaurant, and picked her up at her apartment, a little bit late, but it was okay, according to him. Yeah, I have a theory that he's spaced out in traffic. He's spaced out a couple times in our car.

I didn't think about that, but that's probably why he almost got hit by a car. And he went through like four cycles before he finally decided to go on green. But the awkward part, he says, aside from the moments when he just caught himself staring at her, was when he almost got hit by a car on the walk home. Yeah, that's the one. And the last words that she told him before they went separate ways was, well, I'm glad you didn't die. Which is kind of sweet. I mean, endearing.

So it's been three weeks since that date. And that's because he hasn't answered our producer's call to come on this show. This call is two weeks in the making, and the longer we wait, the more. awkward this is going to be, so we better just make this call. Charles, are you still on the phone, first of all? Yeah, I just, I hope I didn't blow it. It's okay if you did. That's our job,

is to give you another shot. Yeah, I hope so. So let's do this. I'm going to dial the number right now. Here we go. Hello. Hey, Maggie. Is this Maggie? Yeah, who's this? Okay. It's really aggressive Jeff. Sorry. I realized Is this Maggie?

Sorry, I realized I was screaming. No, this is a radio show. We're called Brooke and Jeffrey in the morning. Hi, Maggie. Good morning. Okay. I'm sorry. Why are you calling me?

We've actually been waiting two weeks to make this call, believe it or not. It sounds worse. It's not your fault. No. It's from a listener that you went on a date with, a guy named Charles. Oh, oh, okay. I'm sorry. This is a little weird.

Yeah, we know. I get that. Do you remember Charles? Because you went out three weeks ago. It's been a minute. Yeah, I remember him. What is that, what does that have to do with you guys calling me? So what we're doing now is called a second date update, trying to help Charles figure out if there's a chance that maybe the two of you could see each other again?

Or if not, if there was something he did wrong on the date that made you lose interest. Okay, that's a good pivot because that was a weird pause. It wasn't like one thing It was just It was honestly It's kind of a weird date Okay Okay

Yeah Like for example He was supposed to pick me up From my apartment And like we agreed on a time And I was like waiting there It's like he's five minutes late He's 15 minutes late

I look outside my window And he's just like standing outside On the sidewalk What? Wait He's there the whole time I don't know how long he was there But it's like he was just waiting outside

Like he hadn't, like, texted or said, hey, I'm here or anything. So finally, I called him and I was like, hey, are you here? And he says, yeah. Oh, my gosh. Maybe you just looked outside, like, right when he got there. Yeah, maybe, yeah. Even when I was like, hey, you didn't tell me that you're here. And his response was, well, I was just hoping you'd see me.

Oh. Oh. Come on. It's kind of funny. Going up to doors is, like, answering phones. I hate it. Okay. It's like, it's like, someone's like.

Someone opened this for me. Yeah, honestly. Bottom line is you did eventually go outside and meet him and go out on the date. We know that happened. Yeah. I went down and, you know, we walked to the restaurant and he, you know, he was really polite. He asked me a question. I answered his question and then it was just like silence.

Oh. Yeah. And I was like, I literally was like, do I need to reboot this guy? What is going on? That was so well said. Or maybe it was something about the question and the answer that really threw him for a loop. He said, what color? are your eyes.

Oh, that's a quick answer. Oh. I was looking at you. It just was like an immediate conversation stopper. And it's like, I didn't want to be like, what color are yours because I looked at him. It's not flowing. You guys don't have any like conversation chemistry. But, you know, like it's a very beginning of the day.

He's a shy guy. You had to have gotten that vibe before you even said yes to him, right? So. Yeah. I got quiet. But again, I'm like giving him a chance. We get to the restaurant and, like, sit down. And the first thing he tells the waitress is, like, she comes to the table and he just immediately starts apologizing for, like, taking up space.

Oh, no. Oh, wow. What? I'm sorry. Like, I'm sorry we're here. Does the air cost money because I'll happily pay to breathe the same air? Or I'll just stop breathing. I can take a deep breath.

Yeah, yeah. And I don't mind shy, but it's like no confidence is a little hard for me. Yeah. That's right. Well, sometimes they say, like, the best relationships are when you can just sit in total silence and say nothing to each other. Yeah, the key word there is comfortable silent. I hear you. You don't want him to be silent, and we're not going to let him be silent anymore.

I really hope he says something. He has been quietly listening in on this phone call. I do need to let you know Maggie. Wait, what? Yeah. Yeah. Yeah, I am. Wow. Feeling a little set up here.

Sorry about that, but that's just how this works. Only a confident guy would do something like that. I don't apologize, Jeff. Yeah, Jeff, wait. No, I'm the shy boy. Charles. Yeah, Charles is the masculine guy. Go ahead, Charles.

Hi. Hi, Maggie. He's here. Hi, Charles. He answered. I'm really, I'm really sorry about this whole thing. I just couldn't do it myself. And so I will say I only apologize for the same.

space thing because we were two people taking up a four person table. Oh, that actually is something that I know is when we do too. They sat you there, but the restaurant was literally half empty. Oh, so yeah. Probably because they were looking in, they were like, oh, wow, that table that they're sitting at. That guy's got energy, he's going to need space.

Yeah, I can't go in there. I just thought it was a little weird, and then, like, you asked the waitress if they outsource their napkins. It felt like you were, like, not to talk to me. Are these from China? What?

I was just trying to make small talk and... And he's not very good at it. Yeah, that's the problem. But I think she's saying, if you're going to make small talk, maybe make small talk with the person you're on a date with, not with the waitress. Yeah.

I just, I felt like we're trying to, like, look at anything else with me or talk to anybody else with me. Yeah. Like, this is kind of what I'm talking. I've lost him. Dude, the reboot was such a good description. Oh, my God.

Just unplug and plug him back in. Charles. Yeah. I don't know. I think you're so beautiful that sometimes I just find myself staring. And earlier, when the radio people were asking me questions about you, I just kind of zoned out because I was thinking about you and your beauty and me being with you. And that's nice.

I mean, that's very sweet. I guess I think I'm just, I don't normally meet guys like you. That's not a bad thing. Thanks. You didn't have to say that. Aw. I feel like we've reached the point in this really riveting conversation for me to jump in real quick and ask if Maggie, you would be interested in going out on another date with Charles. And if you were, we would pay for it.

Look, I think, Charles, that you're very sweet, very nice. I don't really think our personalities are very aligned. Like, I just, I think we're really different. But I do think you're a nice guy, and I do have a younger sister who's single. She's very cute. She's way more introverted than me. You guys might be, like, a better match. That's a cute idea.

What do you think about that, Charles, going out with Maggie's younger cute sister? Yeah. But don't you think that would be awkward? It wouldn't. She just awkward. I don't think she thinks that. Not for me? I don't know.

How would it be awkward for you? Like, at Thanksgiving, I'm just staring at you all through dinner. Oh, my gosh. Oh, no. Charles, you're the one that's making it weird. Yeah. I stop staring. Well, she does look at it.

look like me. So hopefully you're staring at her. And Thanksgiving is a long ways away. So you know. She's giving you a lot of grace on this, Charles. Yeah. I should be very patient. Um, okay. Okay. Okay. So I think we're paying a date now for Charles to go out with Maggie's younger sister. Yes. More introverted sister. Good. Hopefully. Oh my God. Charles, I will do this for you, but this is like one chance, okay? And you can't wait three weeks to call her. Yeah, follow up, man. Okay.

I can do it. You can do it. Okay. Okay. And you're excited. I'm excited. All right. Not in a bad way, but does he kind of suck energy out of the room?

Not in a bad way, I said. There is no good way of that. I'm just thinking. I just think a lot. Yeah. Got it. That's my bad because I never think, so that's probably why. You were literally the opposite of Jose.

Yeah, you are, brother. Thank you so much. Welcome. Brooke and Jeffrey in the morning. Experience Megan Maroni live on her only Canadian tour date. June 20th in Toronto. Media wants to send you and a friend with travel from tripcentral.ca. The smart way to book travel.

Two nights hotel, $1,000 cash. Plus the new album on vinyl. Cloud 9, available now. Download the free Iheart radio app. Listen to Pure Country for 10 minutes. Win your way to Megan Maroney. World is hard on beautiful things. Every day you listen is another chance to win.

A win is a win. A win is a win. I don't care what you're saying. Yep, that's me, Cliver Taylor the 4th. You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger

than I ever imagined. And now I'm bringing all of that excitement to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated.

One week, I'll take you behind the scenes of the biggest moments in sports and entertainment. And the next, we'll talk about life, mental health, purpose, and even music. The Clifford Show isn't just a podcast. It's a space for honest conversations, stories that don't always get told, and for people who are chasing something

bigger. So if you've ever supported me or you're just chasing down a dream, this is right where you need to be. Listen to the Clifford show on the IHeart radio app, Apple Podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok.

You know what? That call was two weeks in the making. We went through a lot of ups and downs. Probably more downs than ups, if we're being honest. But at the end of the day, I think we should all be proud of Charles. Okay. It's It took him a lot to fester up the confidence just to call us.

This guy is getting a lot of dates, by the way. Yeah. He must be really cute. With attractive women. But he's clearly a guy who's not comfortable speaking to people one on one, let alone on a national radio show. But he took a risk. He put himself out there for this.

And what do you know, it paid off. He got a secondary date with the girl's sister. Yeah. Just put it out there. I don't know if I could go through that again if the second date with the sister doesn't work out. Oh, bro. Well, she's like him. Imagine both of them.

I know. Thank you, Jose. Right now I'm on your side. I am the opposite. I hope we do a second-day update with him in another three weeks to get back with Maggie's sister. Yes, and it's just the both of them saying nothing. Yeah. We're going to edit it down.

That is my dream. But you know what? If you're a good talker or a bad talker, however you talk. We're taking it. Yes, we're not picky. Email the show. We'll call that person who's not calling you back and go find all of our second day podcast up online. Wherever you get them at Brooke and Jeff.

A win is a win. A win is a win. I don't care what you're saying. Yep, that's me. Clifford Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media.

Well, now I'm bringing all of that excitement to my brand new podcast, The Clifers Show. This is a place for raw, unfills of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to the Clifford show on the I-Heart Radio app,

Apple Podcast, or wherever you get your podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok. When a group of women discover they've all dated the same prolific con artist. They take matters into their own hands.

I vowed. I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends. Trust me, babe.

On the IHart Radio app, Apple Podcasts, or wherever you get your podcasts. I got you. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins, but the pregnancy appeared to be a hoax. You doctored this particular test twice in so-ins, correct? I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern.

Two more men who'd been through the same thing. Greg Gillespie and Michael Mancini. My mind was blown. I'm Stephanie Young. This is Love Trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to Love Trapped podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

What's up, everyone? I'm Ego Wodham. My next guest, it's Will Ferrell. My dad gave me the best advice ever. He goes, just give it a shot. But if you ever reach a point where you're... banging your head against the wall, and it doesn't feel fun anymore. It's okay to quit.

If you saw it written down, it would not be an inspiration. It would not be on a calendar of, you know, the cat. Just hang in there. Yeah, it would not be. Right, it wouldn't be that. There's a lot of luck. Listen to Thanks, Dad, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. American soccer is about to explode.

The World Cup is coming. Ramers sending on the Army. I'm Tab Ramos. I'm Tom Boehner. On our podcast, Inside American Soccer, you'll get the real storylines, the biggest decisions, and the truth about the U.S. national team.

It wouldn't be a huge surprise if our team ends up in the quarterfinals or potentially a great run into the semifinals. Listen, Inside American Soccer with Tom Bogart and Tab Ramos on the iHeart radio app, Apple Podcast, wherever you get your podcast.