Brooke and Jeffrey: Second Date Update - Awkward Thursday UPDATE: He Saw What He Saw

Episode Date: November 6, 2025

The couple on the phone today came on our show just a few short months ago, and their story was so captivating, we brought them back today for the first ever Awkward THURSDAY (UPDATE)!See omnystudio.com/listener for privacy information.

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Strange accidents and brutal murders. In what seems to be, a plot ripped straight out of breaking bad. Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to paper ghosts, the Texas teen murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history.

And some of the worst people, horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Cal Penn, and on my new podcast, here we go again. We'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends, like Bill Nye, Lily Singh, and Pete Buttigieg, to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high?

Look, the world can seem pretty scary right now. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to Here We Go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day. My fellow Americans, this is Liberation Day. Stories that move markets. Chair Powell opened the door to this first interest rate cut. impact politics, change businesses.

This is a really stunning development for the AI world and how you think about your bottom line. Listen to the big take from Bloomberg News every weekday afternoon on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts. Today is like super special. Welcome to the podcast. It's Brooke and Jeffrey in your second day podcast because we have an awkward Thursday phone call. Yes. But we're getting the couple back on.

And I cannot believe these two are. back on. No, seriously. When you hear part one, you'll understand. Yes. Yes. So you need to listen to the whole thing. We're going to have the original play. And then part three will be when they're back on. Do not miss it. Yes. But first, comments, because we love them. Yes.

Kelvin said, I'm listening from Ghana while getting over a broken heart. Oh, yeah. It's all right, Calvin. I think this will make you feel better. When you hear what's going to happen next. Because it could be this bad. All right. It's all starting right now. One of the most memorable awkward Tuesdays of the year

where one of our listeners caught his girlfriend out at a bar wearing an engagement ring and it wasn't his. The truth shocked us all but maybe even crazier is we get them back on to give us an update. Like them? Both of them? Good or bad? You'll find out it's a special awkward Thursday phone call right after this. Everyone's been asking for this.

It's an update from an awkward Tuesday phone call. Right after it's done, we're going to have them back on the phone to find out where they are now. It's awkward. It's Thursday. What? It's awkward Thursday. Phone call. Is there any circumstance where you're out somewhere and you see a friend's significant other doing something that they shouldn't be doing?

And you decide to keep your mouth shut? Uh-oh. Because, I mean, you can rationalize it in your head. Like, you know what? It's not really any of my business. I don't want to jump to conclusions and stir up drama if that's not really what's going on. My eyesight really isn't that good anyway. That could have just been a mannequin and I'm totally seeing.

So you're not saying it's just like, you've got a meaty ice cream on a non-cheat day. Yeah. Is there any chance you do that? Or do you go tell your friend immediately what you saw? Well, it depends. It depends on the relationship with you are. Is someone grocery shopping with somebody I don't know? Or are they literally making out?

Why, did you guys see something? No, we didn't see anything. Why, why aren't you telling you? Why aren't you sure? I don't think I would tell you. Oh. No. Thanks, friend.

And I'd show you. I'd be like, this is how they kiss. See, this is exactly what happened to our listener, Jacob, who is left dealing with a very bizarre situation now, and he does not know how to proceed. Jacob, hey, man, are you holding up okay? Honestly, you guys, not really. Oh, no. Oh, my God. I'm dying.

Who, wet, wear, all of it. Okay, so I've been seeing this woman, her name is Shannon, for about a half a year now. We didn't live together or anything, but I'd say it's been going pretty good for the most part. I thought this was going to be about someone you saw that we had to call the friend. This is about you?

Yeah, yeah, this one's about me. Dang, okay. One night she was out with her friends, whatever. I got a weird call around like 11 from a friend of mine, my friend Omar and Omar was like, hey, are you home? Because I got to come over and tell you something and he was like really kind of on edge about it.

Come over too. Exactly what I was going to say. A friend says I need to tell you something to your face. I'll be like, friendship's over, dude. Sorry. I can't handle it. I don't like anything, sorry. That must be pretty serious if he's like demanding

to go see you. Yeah, no, I knew it was important. So I was like, all right, come over, whatever. He tells me that he saw Shannon out at this place called Crystal Lounge. Oh, sounds like a shady place. She was with a guy, and she was wearing an engagement ring. Huh? Oh, on her ring finger?

Are you sure that this guy's good at left and right? Because I have made that mistake before. And I have friends, I don't even know what that finger is. And he was pretty adamant, and that's why he had to tell me things. To face. Oh, my gosh. Well, did he mention anything, like, specific, like, if they were kissing or holding hands or doing... She was wearing an engagement ring, Jeff.

You never put a ring on that thing. Well, maybe it was just, like, her friend's engagement ring that she was trying on for fun. You girls are always swapping jewelry and clothes. Always at the bar, just casually putting on my friend's wedding ring. Oh, which reminds you, Brooke, I'll take your wedding ring off right now. Thanks for the break. And I'll give you your shirt back after the second. Did he mention anything specific like that?

So Walmart said they were, like, physically close. but he didn't see any overly romantic gestures happen. So I'm like, all right, it's probably just a friend. And so I see her the next day and I bring it up thinking it's going to be, you know, like 30 second conversation. She's going to laugh. She's going to, you know. But she got upset and she stormed out. Why would she get mad at you?

Yeah, because he got mad at me. It's not in a lie. It's upset. That's how it works. It's like anybody who's a. cues that cheating will be like, no, you were cheating. Oh, you're spying on me? But that's the thing. I wanted to give her, like, the medicine of the doubt, and I wasn't

trying to be aggressive about it or, like, accusing her, right? And now she's not answering my calls. And so I need advice. I need advice on how to handle it. Can I ask you, are you still hoping that she's not cheating? Like, there's still a possibility for that? No, he's hoping that she is cheating. What kind of question is that? In my mind, there's no possibility that she's not cheating.

Okay. I see what you're saying. Everybody in this room is kind of in agreement. It looks really bad for her right now, and it's very, very likely that something is happening behind your back here. I feel like we have not discounted of the fact she could be a jewelry heist person and have access to lots of jewelry and she's scared because we just caught her. That is a pretty frequent thing that we get on the show. Thank you. I mean, like, you want to what? You want to get the truth out of her?

Well, yeah. I really am still holding out hope for it to just be something that she's like, embarrassed about doesn't know how to bring it up yeah i mean it's embarrassed and i was with my fiance yeah my other family i think that's a highly likely possibility when we call her here did her husband may answer yeah well they probably haven't gotten married yet yeah oh god it she's close with him anyway now i get it you can see a wedding band right yeah that's totally different no jay i'm sorry that you're going through this but we're going to try and give you a little bit of advice here before we call your girlfriend Shannon

and let you ask her the question what was going on when my friend saw you out the other night at a lounge wearing an engagement ring with another guy no matter what happens like you're the winner out of this she's the sucky one you don't have to hit on him now he's still with somebody we'll get to that in a second

your awkward Tuesday phone calls coming up right after this hey we're in the middle of an awkward Thursday phone call updates which means you don't want to miss the part three where we get the couple back on the phone to find out what's happened since. It's awkward. It's Thursday. Thursday.

If you're just joining us for the awkward phone call, this is what we know. Our listener, Jacob, has a girlfriend of about half a year. She was spotted out recently at a lounge with a different guy wearing an engagement ring. I feel like I need to be taking notes, Jeff. So right there. That's weird.

Not good. When Jacob brought it up to her in a fun way, he expected her to laugh and explain, oh, it's just a stupid situation I had to wear it. It was a big joke. But no, she got upset and left and has not spoken to him since. That's why he needs our advice today on what to say to get his girlfriend to just tell him the truth of what is really going on. It's the least that he deserves. What's your advice to Jacob? You are going to take control of this situation.

Okay. All right. And you were going to tell her, you need to tell me the truth now. You need to rip it off like a bandit. Rip it off like a band-aid because if she waits any longer, it's only going to get worse. Like, you deserve the truth. And if she has ever respected you ever in the time that she's known you, now is the time to show that. There it is.

All right. Yeah. Yeah. Okay. There was actually a little bit of advice in there. Good job. Every week I give great advice. Okay.

Jose, what about you? What do you think, Jacob needs to remember? You need to make her feel comfortable. Remind her, honey, I want you to know. No, first, I love you. Okay? And whatever you say, in this conversation, I promise not to judge. What?

We listen and we don't judge. That's a TikTok trend. It's an internet therapy trend, not TikTok. You know what? And I think if you practice it, then maybe she will be comfortable to open. I think actually all of us could take that advice in this room. We should listen and not judge her yet. Because there could be a logical explanation for this.

We're all going to look really stupid. if we're being as hateful as Brooke is towards her all race. She would have just said the logical thing if it was logical, Jeff. I don't want to look stupid, so I'll listen and then judge. Okay, yes. And then we can look stupid. Whatever it was. If this doesn't go my way, I am fully welcome to judge.

Yes, exactly. We give you permission. That's actually what we do best on the show. Let's call her. We'll see if Shannon picks up, and then we'll step away and let you make your awkward call. We'll be here if you feel like you need a little bit of help. Okay, good luck. Hello?

Hey, it's me. I said I don't feel like talking right now. No, we need to talk right now. What do you mean not feel like talking right now? That's not fair. Because you just seem really upset about something that, honestly, I do not feel like talking about. Well, I don't, how do you think I should feel about it? I want to get this, I want to get this over with.

I want to hash this out. Okay. Okay, then just, you know what? Just move on. What do we have to hash out? We don't have to hash out anything. No, okay, sorry. Am I not supposed to be upset when my buddy comes to me saying that you have an engagement ring on

and you're hanging with some other guy? Like, what is that? Ah. Jacob, I don't want to hurt you. Yeah, it's a little late for that. um you just need to tell me whatever the truth is okay i can handle it it's hard to explain well can you try can you try for me here please shannon well you know my friend sierra right yeah i know sierra okay so a couple months ago she set up this like hangout

with some old friends she was saying we hadn't seen them in a while what does this have to do with us so one of the guys who was there to hang like well he was my ex so what what does that even mean so we hooked up and i i didn't know what to say to you because you're so sweet to me I couldn't go and I started dating him again and I know it's messed up I know but I've always just wanted to have a forever relationship be married and so I had it in my head that that I was just going to say yes to whoever proposed first and he proposed a few nights ago oh so so wait sorry you're Actually, you're really engaged. I thought, I really thought there'd be some other reason to it. No. No.

I am, I'm engaged to someone else. I'm really sorry. I'm sorry. No. Oh, my God. What is that? What's going on? Oh, man.

Okay. Oh, my God. Shannon. We've heard everything, Shannon. We've been listening to this call. Who is this? You're on the radio right now with a show called Brooke and Jeffrey in the morning. We're doing something called Awkward Tuesday phone call.

Oh, what? I'm on the radio. You weren't answering my calls, and I didn't know how to address this with you. I've been trying, and so I called the radio station to help me get a hold of you. Yeah. Don't blame him. I can't believe you did this on the radio. Maybe you shouldn't have been cheating.

Yeah. We do a lot of these phone calls, I'll tell you, Shannon, and we don't normally get a lot that end like this. Usually it's somebody playing a joke. There's some hilarious misunderstanding. I was waiting for the funny part. But it turns out, Shannon, you're just a two-timing cheater. Like, how long are you dating before you're engaged to this guy? Who are you?

Why do I have to answer questions to you? I don't even know who I'm talking to at this point. You think I'm just going to answer some questions for some people I've never talked to before? Well, it's pretty valid to the situation. Because we're Jacob's friend, and we're defending Jacob. You're not a friend. He called the radio station. Now he's your friend.

Yes. He is. He is. No, we're really clinging. You don't know us. Jacob is my friend. Like, I still want him to be part of my life. Sorry.

After all of this, you think Jacob would still want to be around you? That's so insulting to call him your friend. Couldn't we stay friends? Like, I even ask my fiancee to have our wedding in like a year so you could have some time to heal because you are a good friend. And I was there. I want you in my life. You're going to delay your wedding a year so that your current boyfriend can get over you

so that he can go to the wedding. Jacob? I mean, are you insane? It's got to be a joke. Well, what does your schedule look like next? I would joke. I wouldn't joke. You're a special guy.

I was joking. My schedule next year is figuring out when she's on her honeymoon and burning up her apartment. Oh, wait. Let's bring it back a couple of times. Jacob, we're on tape here, so this can be used in the court of law. I can help you. No. Alexis, the best revenge is to move on, okay?

Yeah. Okay. You guys, you don't know me, but I'm not a bad person. Yes, maybe I made a mistake. Maybe I should have broken up with Jacob earlier, but I'm not a bad person. Maybe. Did you say maybe? Jacob, are you willing to call this strike one and give it two more strikes?

You know, in the name of friendship. Yeah. I think all nine innings are over. sports analogy I like it Hey I wish Jacob well I hope he has a great life Oh you are

Someone's a lot of I don't know what to say to you Shannon Honestly but Jacob What's your best in life, Jeff? Yeah sure Knowing Jeff he's going to send you a wedding present Yeah Jeff will feel guilty

I do I do perform at wedding So you can hire me But Jacob The good news is you got the truth Right That's what you were after here The whole time And you only wasted six months

On this relationship I mean that's another positive Yeah. Well, hey, you know, since we're friends legitimately, let's go out, spend the rest of the week drinking. I'm up for it. Wait, what? Did you just talk to us or her? Oh, you mean us, right? Yeah. Yeah. Yeah. Drinks on Jacob. Cool. Brooke and Jeffrey in the morning. No one can resist a rule of culture. So here's one for the dating files. Rule of culture number 72.

Chemistry isn't just vibes. It's values. Because what's the point of matching with someone if you can. can't talk about the shows you binge, the books you dog ear, or all the hot takes you'll defend it brunch. I mean, you definitely have friends who have met their partners on Bumble, and it makes sense. It's not just about matching with someone. It's about finding someone who gets your references, your obsessions, your whole vibe. With shared interests and prompts, you don't just see a profile. You get a glimpse of someone's personality, which makes it even easier to start conversations that actually

lead somewhere. Plus, with photo and ID verification, you can trust that the person you're talking to is real. With that added piece of mind, it's so much easier to show up as your full self. So whether your rule of culture is the best first dates start with the shared hot take on Renaissance or compatibility as having the same hometown bodega order, download Bumble and turn those connections into something bigger. Download Bumble and start

your love story. Did she say Johnny? The kids didn't come home last that. Along the central Texas planes, teens are dying. Suicides that don't make sense. Strange accidents and brutal murders. In

what seems to be, a plot ripped straight out of breaking bad drugs alcohol trafficking of people there are people out there that absolutely know what happened listen to paper ghosts the texas teen murders on the iheart radio app apple podcast or wherever you get your podcasts you know out of all the calls we've done over the past year i never thought this would be the couple that we'd be getting an update from wait both of them I thought we'd just be talking to him. I don't know there are a couple of anymore. Jacob and Shannon are both back on.

Wait, are they actually friends? I don't know. What's going on with you two? Hi, how are you guys? Shot. Yeah, we're surprised. We want to ask you the same. You're both there.

What's the situation? Well, funny story. Jacob and I are engaged now. No way. You and Jacob are? What? Yeah, yeah. We're so happy

Okay, stop talking for him for just one second Jacob How do you feel? I'm happy to Don't get me wrong It's been a crazy couple months That's for sure Wait wait, wait

How did the first engagement With the ex-boyfriend break off Instead of girl's off Maybe she's double-engaged Oh yes, Shannon we go No, no, no, no, I'm not So I guess you guys know how popular your show is And my now ex-fiance

actually heard Oh no And found out you had a boyfriend when he proposed? Right. And he said he was confused. Oh, God. And decided that we needed to take a break.

Yeah. Okay. So, Jacob, where, what, why? Yeah, yeah. I mean, don't you mean congratulations, Brooke? I think you need to say congratulations to the happy couple. I mean, yeah, if that's how it goes. Yes, congratulations, Jacob.

Good for you. Yeah, thank you. I know, I'm very excited. You know, basically, you know, after that whole debacle with, I mean, with the engagement ring and everything, I'm going to refer to it as a debacle. Okay. Shannon came to me and, I mean, she needed kind of guidance. She needed a friend. So, yeah, I was there for her.

We talked and I mean, here we are and we're engaged. I mean, one thing led to another and then so. Aw. It's a sweet story, Brooke. Let's hear you say, oh. Yeah. There you go. Are you giving it a year?

So now your other ex-fiancee can heal and come to your wedding? Oh, yeah, that'd be smart. You know what? We're just, what I realized through this whole thing is that this is the relationship I should have been in the whole time. Jacob is so understanding. And I know I'm not a picnic, but he really gets who I am. And I think we make each other really happy. Okay.

You know, you took the long path to get there, but you arrived at the destination. That's what's important. Yeah, Shannon is definitely my better half. I'm looking forward to everything going forward with her, spending life with So when's the wedding? Oh, my God. Don't say that the year, the old guy may show up. This winter, this winter.

We're just going to keep it small, go to Mexico, and, yeah. I would recommend not doing any, like, best man speeches or anything. No stories. Yeah. Just not do those during the reception. That's fair. Yeah. Too many tears of happiness.

What happened? That's a good call, Brooke. But congratulations you two. Keep us updated on your. wild blossoming relationship. Have good luck in marriage. Thank you for the help. I don't know if we deserve it.

It's Brooke and Jeffrey in the morning. Did she say, Johnny? The kids didn't come home last night. Along the central Texas plains, teens are dying. Suicides that don't make sense. Strange accidents and brutal murders.

In what seems to be, a plot ripped straight out of Breaking Bad. alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to Paper Ghosts, the Texas Teen Murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein,

and we used to host a show called Planet Money. And now we're back making this new podcast called Business History, about the best ideas and people and businesses in history. And some of the worst people. horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hey, I'm Cal Penn. And on my new podcast, here we go again. We'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends like Bill Nye, Lily Singh, and Pete. Buttigieg to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now. But my goal here is for you to listen and feel a little better about the future.

Listen and subscribe to Here We Go Again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day. My fellow Americans, this is Liberation Day. Stories that move markets. Chair Powell opened the door to this first interest rate cut. Impact politics, change businesses. This is a really stunning development for the AI world and how you think about your bottom line.

Listen to the big take from Bloomberg News every weekday afternoon on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Two rich young Americans move to the Costa Rica jungle to start over, but one of them will end up dead, and the other tried for murder three times. It starts with a dream, a nature reserve, and a spectacular new home. But little by little, they lose it. They actually lose it. They sort of went nuts. Until one night, everything spins out of control. Listen to Hell in Heaven on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Thank you.