Brooke and Jeffrey: Second Date Update - Awkward Thursday: Perfect Place For A Proposal

Episode Date: October 9, 2025

We’re doing a little something different today, it’s our first ever Awkward THURSDAY Phone Call!See omnystudio.com/listener for privacy information.

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until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County on the IHeart Radio app. Apple Podcasts, or wherever you get your podcasts. And to binge the entire season, ad-free, subscribe to Lava for Good Plus on Apple Podcasts. Samihante, it's Anna Ortiz.

And I'm Mark and Delicado. You might know us as Hilda and Justin from Ugly Betty. Welcome to our new podcast, Viva Betty. Yay! We're re-watching the series from start to finish and getting into all the fashions, the drama, And the behind-the-scenes moments that you've never heard before. But you were still bartending?

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World Mental Health Day is around the corner. And on my podcast, just here. With Dr. Jay, I dive into what it really means to care for your mind, body, and spirit. From breaking generational patterns to building emotional capacity. I'm going to walk away feeling like, yes, I'm going to continue my healing journey. Listen to Jess Hill with Dr. Jay from the Black Effect Podcast Network on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast. I'm the homeguard that knows a little bit about everything and everybody. You hear that exclusive?

Lauren came in high. I came in telling the truth. Every day, I'm bringing you the latest in entertainment, breaking down the headlines you can't stop talking about, and giving you my very unfiltered tape on the biggest stories in the industry. From exclusive news, and y'all know I got it, to us breaking down the interviews, because y'all are my co-host now.

I'm giving you the deep dives on some of the biggest moments in pop culture. Oh, my God. Listen to the latest with Lauren the Rosa weekdays on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Hey, it's Brooke and Jeffrey in the morning and we're trying something brand new today on your second date podcast but first we want to take a moment

and say thank you to all of our listeners who showed up for our YouTube live session yesterday. Yeah. We're trying to go live more often. So if you aren't following the show on all of the socials, it's at Brooke and Jeffrey. If you aren't already on YouTube, it's YouTube.com slash Brooke and Jeffrey.

Very creatively named handles. You can find this. Yeah. And then be disappointed with how we look. So there it is. Basically how it goes. Yeah. But today, today we heard you guys like the awkwardness of Tuesday. Yeah, you guys were commenting.

You want more of them. So here we go. You're getting what you ask for. Today is awkward Thursday. It's brand new. I don't know if we'll ever do awkward Thursday again. We'll see it. We'll see what type of response is solicit.

So it starts right now. Drama before a wedding? Ooh. Is it even possible? Yes, Jeff. Yes, it is. Very much. Sarcasm on this show?

What? How broke is it possible? No. In fact, one of our listeners is just weeks away from tying the knot, and she's come to us with a huge regret. Uh-oh. After something happened between her and a close guy friend while they were partying together. Uh-oh.

Let's not be what it is. It's not what you'd think, but it is probably worse. And she is desperate to reverse what's already been done. You're going to find. find out when we talk to her in a brand new awkward call coming up next it's awkward it's Thursday it's awkward Thursday phone call yeah what is happening we just paid for really professional imaging done it is nice to do a brand new segment every once in a while on this show with an exciting idea never done before on radio I mean never done since Tuesday you mean yeah with

extremely high production imaging made by the finest engineers and vocal artists on this planet. You know that there's no AI on this show. That's true. You're something like that. And it brings us to this, the first ever awkward Thursday phone call.

We're going to have a lot of listeners happy. We've been getting requests on the podcast feed to do it Monday, Tuesday, Wednesday, Thursday, and Friday. It makes sense. Things are just too awkward in the world right now and we had to add more awkward calls. A special one for this because one of our listeners reached out, seeking our help with her upcoming wedding.

Ooh, I love wedding help. So her name is Brittany. Brittany, first of all, how does it feel to know you're going to be making radio history with the first ever awkward Thursday phone call? No one will forget this moment. Wow, I got honored, I guess. Is that the right? I don't know why you're laughing, Brittany.

We're honored to have you. So apparently you've got a wedding coming up. They're usually such low effort, drama-free events. I'm not sure why in the world you would need our hands. But what's going on? Yeah, are you the bride? I am. Oh, congratulations.

Thank you. I'm super excited. And it's three weeks away. Oh, my gosh. Yeah, it's coming up. And it's crazy. I haven't had any drama. I know you were saying that as a joke,

but until one of my guy friends, like this happened with a guy friend, which I was surprised about. Oh, interesting. That's not who I would pin the drama on. Yeah. Yeah, a guy friend who's in your wedding. party or who is this friend?

Just a friend of my, like he's, you know, I've known since college, so he's just in my group of friends. Okay. And I guess this is like a month ago, we all kind of went out for, not really like a bachelor's, but kind of like an unofficial bachelorette celebration, you know,

just to kind of celebrate my wedding. Okay. Like a big group of your friends? Would your fiancee there too? No, it was just my friends. It was just all of us from like back in the day. And you know we're having a good time and drinking and whatever and at the end of the night well it's not what you think it's just so weird he kind of pitched me an idea

what kind of idea he said he wants to propose to his girlfriend at my wedding reception oh no you can't be that clueless he can't be that drunk to think that's a good idea even. Oh, man. What's even crazier is that, like, I was so excited that he was going to propose. I just, like, screamed and hugged him right away.

Oh, no. So you said yes? You kind of did. And I feel like he took that as a yes. Yeah. I would. How can you be mad at him for being like, oh, my God, I'm so excited for you.

And, like, he read that as, like, a positive reaction. I don't think that she's mad. I think now she just probably feel. like she's in a, she put herself into a bad situation is what it sounds like. Well, and what's even crazier is like, he was so, like, touched by that he was like, imagine like our weddings will be linked forever. Oh, man. That's kind of cute.

Anyone who's ever thought about proposing, that's what you think, right? You're like, look, it's like connection with the bride and groom. Yeah. And all your friends are already there to witness so you're ready to party and celebrate together. Here's the thing, though. The officiant, you can. just get it done. Yes.

Knock it round out. I get it. I think talking, I mean, I don't know if you want to talk him out of it, but I think even talking him out of it would save his fiance, because who wants to be proposed too? Oh, I didn't think you're hurry.

At somebody else's wedding. Like, every woman on the world knows that that's a huge faux pot. Clearly, we have a lot of opinions in this room, Brittany, but where are you on? What's going on with you and Dirk now? I have to, like, say something, but I just don't

know how to approach it. I just think he's going to be crushed. Okay. So you don't want it to happen. You don't want him to propose at your wedding. I don't think it's a good idea, no. And, like, my family hates it, of course. So, like, I was on the fence before, but because they were so strongly, you know, feel so strongly,

I was like, I have to really do something here. Okay. Because they're like, we're footing the bill, not for his engagement party. That's a good point. Maybe he should pay, like, for the bar. And then it would be okay for him to propose. What's the least important part of a wedding? Like, is there an area we can fit him in?

The groom is the least important part of the wedding. Honestly, we haven't even talked about him. Have you told your fiancé about this? No, because I didn't, I don't know. The groom would probably be all for it, too. He'd be like, yeah, sure, let him propose. I mean, I have to talk less. Yeah, it's my family who's the most, like, oh, no, this is not happening.

Yeah, that makes sense. You can see that, too. Have you talked to your friend again about, like, his proposal plans? No, but like we were at some birthday party or whatever, and he was kind of like, give me the look like, we know it's going to be extra awkward because he's under the impression that you're 100% supportive of his plan to pop the question at your wedding. Yeah. So how do we politely help her deliver the news that she is rescinding her blessing for his proposal? Oh, man, I forgot we got to give advice. Yeah.

Even on a Thursday, Jose, our job never ends, you know? That's right. Right, Brittany. That's who we're calling here. Yeah. Oh, God. I can hear your nerves already. I think it'll be fine.

I think he'll understand. Whenever Brooke says that, you know it's the kiss of death. So best of luck to all of us as we take a break for a quick second to think of some good advice to give you before you call your friend and tell him, I'm sorry. Even though I told you yes, now you cannot propose. at my wedding reception. That's a sound, it's got a lot of weight. I know, my heart broke just saying it. We're going to do it with your awkward Thursday phone call.

Special Thursday. Play the sound effect. We'll do it right after this. Hold on. It's awkward. It's Thursday. It's awkward. Thursday.

Phone call. What is it about brides and grooms that makes them think their wedding day should be all about them? Oh. That's on you. Don't get it, but of course we have a bride to be on the phone named Brittany who says I don't want my friend to propose at my wedding Even though I kind of already gave him permission to do so earlier Classic bride But you know what sure we'll help her crush a young man's romantic dreams

That's the way you're framing it is awful That's the truth am I saying anything that's not true? It's just your tone. You're right. I'm the evil one. Thank you Brooke you've been a bride before Or what's your advice to a fellow bride? Well, I think what you need to do, Brittany, is you need to use the toddler method on this one. Yeah, you know, like when toddlers are having a tantrum and they're really emotional, you don't try to fix the behavior. You distract. So what you need to do is you need to come up with better, more awesome proposal ideas for him.

So he just even stops thinking about your wedding as an option. Oh, yeah, that is a good idea. I didn't believe her tone You sound a lot like me When I'm talking about brides I just defended you As a guy If you make us think we have a good idea

That could work Thank you Jose Okay So that's some advice Normally we go to Jose for more But since this is a bridal thing We should probably ask another female I should stay far away from this

So we're going over to Alexis Any hot tips you got for Brittany I'm about a hot tip But you don't want to ruin your friendship So I think you should deflect the blame. Well, you're going to blame somebody else? Yes, of course. Like, specifically, your mother-in-law.

There we go. Mother-in-laws are easy. My mother-in-law doesn't want this to happen. It's like, if you're going to blame it on anybody, blame it on the person, you're probably not going to get along with. That's one thing I've learned from Brooke. Yeah. That should have been Brooks' advice. So, there we go. You have a little bit to work with. You could choose to use it

or not, but we're going to dial your friend Dylan here and let you make your awkward Tuesday phone call to rescind rescind permission for him to propose. Okay. Yikes. This should be fun. All right.

I'm going to dial it right now. Let's see how it goes. Hello? Jill. Is that my pickle? Hey, Brittany. Britty, brit, britt, britt. Hey.

What's up? What are you doing? Oh, man, I'm good. I'm great. How are you? How's your boo? Oh, good. It's good. We're getting so excited. I am super pumped. Not only just for me, but for you, your wedding. And then, ah, you already know. I'm just so excited about you being my bestie and

allow me to do what I'm so nervous to do, but I'm so excited to do. Yeah, you know what, Jill? I wanted to talk to you actually about that specifically because, you know how, like, we were going to take that trip to Cabo. I was thinking, like, that would be a really, like, instead of the wedding, like, maybe, maybe, like, you could propose when we go to Cabo and, like, everyone will be there, but it won't be, like, stressful and, like. Wait, hold on. Where is that coming from?

We already got things in motion about proposing at your wedding, right? So, you know, oh, my God. You know, Tommy's, like, mom is, like, so uptight and, like, so crazy. Yeah, I do. Like, so insane. Like, I was talking about it, and she, like, blew her lid, like, was, like... And, you know, I have to live with this woman for, like, the rest of ever. Okay, okay.

Okay, bread, britty, bread, okay, best friend, I got to stop you there because I don't like where... I don't like where this is going. I don't like the vibe. But it's not you, I hear you, it's mom-in-law, soon-to-be, I get it, however. I mean, you know, I love you. I love you. I support you, like, 100% of super stoked about this. I think it's such a great thing for you. It is great.

It is great because I told Michelle's parents that I was going to do it at your wedding, and they were going to be there. So I don't think Cabo is going to work, you know what I mean? I don't have, we don't, that's like not, we didn't plan for that for like our guests with some stuff. Like, you know, no, no, no, no, no, no, no, no, Brit, Brit, Brit, just close your eyes and picture. Reception. Everything's going great. Woo, yay.

Everyone's getting married. And then I propose to Michelle. It goes great. She says, yes, everyone's happy. We walk outside of the reception, not to take away from you, but just me and her walk outside the reception. And her family is going to be there. to, you know, take that in and be super excited for us, you know what I mean?

Oh, my God. I am crazy. What? Hello. Did you say awkward? You said that was awkward? No. A lot of people did.

It was a sound effect that we played on our radio show called Brooke and Jeffrey in the morning because you're on it right now, bro. What are you talking about? I'm on a radio show. Yeah. This is our show. You've actually been on it this.

entire time. We're doing something called an awkward Tuesday phone call. Sorry, awkward Thursday. Yeah, yeah. Oh, no, I blew it. It's an inaugural version, so you should be honest. So, I don't know any of you, so Brittany, what the hell is happening right now? Right, yeah, Brittany, maybe you need to

come clean. I'm just, okay, I am so sorry. When we were out celebrating the wedding or whatever, and then you pitch this idea to me, I was just focused on, like, being so excited for you and Michelle that I would, like, flip. But I think you misread that as me saying, yes, you can do it at the wedding.

Okay. No, I definitely thought that was, yes, I can do it at the wedding. And that's understandable. Yeah, we all right. Yeah, yeah, yeah. Congratulations. Those are all good things. Okay, all right.

If I can be completely just kind of open and transparent, all right, so things kind of aren't going the best between Michelle and I right now. Why are you... Your girlfriend, your girlfriend's, Michelle, are we understanding that right? Yes, yes, yes. And you want to propose to her? Just hear me out, please. Yes, I still do, but we're kind of not staying together right now.

So I thought the best thing to just kind of reinvigorate what we have is to propose at your wedding. Oh, bro. So you're going to get denied in front of everyone at her wedding. Hi. Brother, everybody knows you just get. I have a baby. Dylan. Yeah.

It sounds like you need to work on some things with Michelle before you move on to marriage proposal. Yeah. Well, this should be like a sure thing. It is a sure thing. It is a sure thing. Are you hearing Brittany, though, and what Britney's concerns are, right? No, not really. Okay.

Okay. That's a little selfish. So that being said, are we all good now, Brittany? You feel like you're in a better place? No, no. What even happened? No. It's like, now it's like, what?

Is this going to be some sort of reality show in the parking lot of my wedding? Spectacle. Cobbo sounds like such a good idea, Dylan. It sounds like just so there. But then he has to buy plane tickets for her parents to Cabo, and that's going to be a lot of money. I don't know that the parents need to be there. In the end, this is really, it's Britney's wedding day. It's going to be Britney's decision on whether or not Dylan can pop the question there or not.

So, Brittany, really, it's your choice. I'm saying no. At this point, I'm just going to say no. No, you already said yes. Like, I invited her family, but I feel like I don't need your permission. And I just might pop the question at during the wedding. During the wedding. Without her approval? She already said yes. No, she's saying no, Dylan.

I love to be at this wedding. Watch this happen. Dylan, you're going to get yourself uninvited to your best friend's wedding. Okay, so hear me out Maybe, just maybe I'm a tad bit emotional right now And I'm just in a vulnerable place right now That's okay, that makes sense

Yeah I bet Brittany would be a great person To get other ideas from on how to propose First you get some ideas from me About how to talk to Michelle And get her on the good side Yeah, I mean that That could be a good idea

And I should have told you earlier But yes, she's not talking to me And she's staying out of parents And I... Oh, no. Okay. Well... So when you told the parents, they were like, yeah.

Yeah. Nobody was going to be in the parking lot. Yeah. Michelle wasn't going to be at the wedding, it sounds like, but... Okay. Dude, I know you want to get married, but you really have to get used to the idea of women saying yes, but meaning no. Ah, I see what you're going to have. Yeah.

Okay. Brooke, you're on board with that, right? I didn't really fully understand your statement. That's a yes. I'm reading between what she's saying. She is 100% agreeing with me. Anyway, that's your awkward Thursday phone call. Brittany, stay in touch and let us know how your wedding goes, okay?

I will, guys. Thanks for your help. Brooke and Jeffrey in the morning. All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky. went unsolved, until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy Kilder, we know.

A story that law enforcement used to convict six people, and that got the citizen investigator on national TV. Through sheer persistence and nerve, this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist. producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn or any of that other stuff that

you all said. They literally made me say that I took a match and struck and threw it on her. They made me say that I poured gas on her. From Lava for Good, this is Graves County, a show about just how far our legal system will go in order to find someone to blame. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

And to binge the entire season ad free, subscribe to Lava for Good Plus on Apple Podcasts. In early 1988, federal agents race to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. We had 30 agents ready to go with shotguns and rifles and you name it. But what they find is not what they expected. Basically, your stay-at-home moms were picking up these large amounts of heroin. They go, is this your daughter? I said yes. They go, oh, you may not see her for like 25 years. Caught between a federal investigation

and the violent gang who recruited them, the women must decide who they're willing to protect and who they dare to betray. Once I saw the gun, I tried to take his hand and I saw the flash of light. Listen to the Chinatown Stang on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. Safe to say the first awkward Thursday phone call did not disappoint.

It was awkward. It sure was. Why do I like to open to it better than the regular one? Honestly, yeah. It's really funny, but it feels like we have more luck on Tuesdays. How do you know? We've never tried this before. We have one time and it failed.

So it's a zero percent success rate. Awkward Tuesday's got at least a 1%. They're still friends. We made some progress there. That's the, okay. And just an observation. It is interesting that Brittany was talking a lot at the beginning of the call, but by the end, she was hardly saying anything.

Because it's like, what do you say when your friend basically is suggesting that his whole relationship basically hinges on him proposing at your wedding. Yeah, that made it so much worse. That always works well. Desperate wedding proposals are always successful. That's how your parents met, right? I get it. They're both in a tough position.

I just hope they get it resolved quickly because that's not something that should be. be on Brittany's mind in the lead up to her nuptials. No, not somebody else's wedding. No, what she should be thinking about is nacho bar. Hello. Huh? Yeah. Oh, you want to put a nacho bar at Britney's wedding? Yes, at a nacho bar.

Everybody's happy with nacho bar. The cheese fountain would be pretty fair. Yeah, the nacho cheese fountain. It's slaps. But in the spirit of weddings, I'm going to pop a little question to our listeners right now. I want to know, will you make us the happiest morning show on Earth and subscribe to our podcast? Aw, he's on his knee. That's sweet.

Are you saying yes? Are you waiting for them to... Hit that subscribe button. We love you. The murder of an 18-year-old girl in Graves County, Kentucky, went unsolved for years, until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns.

Listen to Graves County on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. And to binge the entire season ad free, subscribe to Lava for Good Plus on Apple Podcasts. Samihante, it's Anna Ortiz. And I'm Mark and Delicado. You might know us as Hilda. And Justin. From Ugly Betty. Welcome to our new podcast.

Viva Betty. We're re-watching the series from start to finish and getting into all the fashions, the drama, and the behind-the-scenes moments that you've never heard before. But you were still bartending? I didn't know that. The bar back is like, is that you? And it's a commercial for Betty.

And I was like, I quit. I quit. Listen to Viva Betty on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. I love that you created his system that revolves around you creating pockets of peace. World Mental Health Day is around the corner. And on my podcast, Jess Heal with Dr. Jay,

I dive into what it really means to care for your mind, body, and spirit. From breaking generational patterns to building emotional capacity. I'm going to walk away feeling like, yes, I'm going to continue my healing journey. Listen to Jess Hill with Dr. Jay from the Black Effect Podcast Network on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. guys. I'm the homeguard that knows a little bit about everything and everybody. Let me know. Lauren La Rosa. You hear that exclusive? Lauren came in. Hi. I came in telling the truth.

Every day, I'm bringing you the latest in entertainment, breaking down the headlines you can't stop talking about, and giving you my very unfiltered tape on the biggest stories in the industry. From exclusive news, and y'all know I got it, to us breaking down the interviews because y'all are my co-hosts now. I'm giving you the deep dives on some of the biggest moments in pop culture. Listen to the latest with Lauren the Rosa weekdays on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. Culture eats strategy for breakfast, right? On a recent episode of Culture Raises Us, I was joined by Valicia Butterfield, media founder, political strategist, and tech powerhouse for a powerful conversation on storytelling, impact, and the intersections of culture and leadership.

I am a free black woman. From the Obama White House to Google to the Grammys, Valicia's journey is a major. masterclass in shifting culture and using your voice to spark change. Listen to Culture raises us on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.