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

Episode Date: March 4, 2025

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',  that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners said his buddy called him to drop a HUGE piece of news about his girlfriend. Now he wants our help getting the truth out of her about what really happened!See omnystudio.com/listener for privacy information.

Hey, what's up y'all? This is Eric Andre. Well, I made a podcast called Bombing about absolutely tanking on stage. I tell gnarly stories and I talk to friends about their worst moments of bombing in all sorts of ways. Bombing on stage, bombing in public, bombing in life. I want to know what's the worst way they ever bombed or have they ever performed way too drunk or high or was there ever a time where they thought they were going to crush and they stunk it up. Listen to Bombing with Eric Andre on Will Ferrell's Big Money Players Network on the I Heart Radio app, Apple Podcasts, or wherever you get your podcasts.

Bombing with Eric Andre. Why would you do that to me? Los Angeles, 2021. A friendly neighbor appears out of nowhere and promises to make all my dreams come true. Let's not forget that David Blum was a professional con artist, so you didn't stand a chance. But my dreams soon turned into a nightmare. I'm Caroline DeMore.

Listen as I take down my scammer on Once Upon a Con on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Alec Baldwin. This past season on my podcast, Here's the Thing, I spoke with more actors, musicians, policymakers, and so many other fascinating people, like writer and actor Dan Aykroyd. I love writing more than anything.

You're left alone. You know, you do three hours in the morning, you write three hours in the afternoon, go pick up a kid from school and write at night and after nine hours you come out with seven pages and then you're moving on. And actor and comedian Jack McBrayer. The most important aspect is the collaboration with people that I like, I trust, are talented. That has been the most amazing gift to me about this crazy business that we've chosen. Meeting these people who have such diverse talents and you're able to create something together.

Listen to Here's the Thing on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, you guys. I'm Catherine Legge. Apple podcasts or wherever you get your podcasts. Thrustle Therapy with Katherine Legg, an iHeart women's sports production in partnership with Deep Blue Sports and Entertainment. You can find us on the iHeart radio app, Apple podcast, or wherever you get your podcast. Presented by Capital One, founding partner of iHeart Women's Sports. All right, we polled you last week.

Hey, welcome to the Second Date podcast, by the way. It is Brooke and Jeffrey in the morning. We follow with a Second Date update. We said in a poll that we moved Awkward Tuesday from Sunday to? Tuesday! Hey! Did you think it was brilliant or a terrible choice?

Believe it or not, 71% of people said brilliant. Hey! They can keep track of the day of the week now. It makes a lot more sense. It's happening right now. Welcome to your Awkward Tuesday phone call. If a friend calls you at 11 o'clock at night and demands to come over,

because they have to tell you something in person and it can't wait. Oh my gosh. It's probably good news, right? I would hope. Oh, maybe they just finished watching Love Island. A lot of gossip. Yeah, or maybe they found an extra McNugget

in their McDonald's bag. Oh, guys. They just save 15% by switching insurance providers. Yeah, or maybe they found an extra McNugget in their McDonald's bag. Oh, no guys. Did they save 15% by switching insurance providers? Yeah, no. No? It's not an 11pm call kind of thing. Okay, well unfortunately for our listener, his buddy called him to drop a huge bomb about his girlfriend. Oh no.

And now he needs our help getting the truth from her about what really happened. Oh. Too bad it wasn't a chicken nugget. Maybe it's a good thing that happened. We're gonna find out when we do your brand new Awkward Tuesday phone call right after this. It's Awkward. It's Tuesday.

It's Awkward Tuesday 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 Because you 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 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 seen It's just like you caught a meeting 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 it depends? It depends on the relationship with your Grocery shopping with somebody. I don't know are they literally making out? Why, did you guys see something? No, we didn't see anything. I just saw no listeners. Why, why aren't you telling? Why aren't you sure? I don't think I would tell you. Oh. No.

Oh, wow. Oh, yeah. Thanks, friend. I'd tell you 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.

Oh, geez. Jacob, hey man, are you holding up okay? 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, where, where, all of it? Okay, so I've been seeing this woman, her name is Shannon, for about 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 gonna 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. Shannon and I will have nights where we hang out, we do stuff together, but then other nights we're apart through things where we hang out with your friends stuff together. But then other nights were apart, do things where we hang out with your friends and it's healthy, you know? I disagree. You should be spending 24 seconds with them, but you know, that's just my clingy nature. I mean, like I said, we're not

living together. Schedules are not framed around one another. Right. You have your own lives. That's totally normal. 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? Cause I gotta come over and tell you something. And he was like, like really kind of on edge about it. Come over too is huge.

Exactly what I was gonna say. If a friend says I need to tell you something to your face, I'll be like, friendships over, dude. Sorry. I don't like anything. 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 stops by. He tells me that he saw Shannon out at this place called Crystal Lounge. Sounds like a shady place. She was with a guy and she was wearing an engagement ring. Huh? On her ring finger? Are you sure that this guy's good at left and right?

Because I have made that mistake before. I have friends that don't even know what that finger is. And that's the thing, I was trying to defend Shannon, I was like, nah, you know, you're wrong. But he was pretty adamant, and that's why he had to tell me face to face. He saw what he saw. Well did he mention anything specific, like if they were kissing or holding hands? She was wearing an engagement ring, Jeff.

You never put a ring on a person's leg. Well maybe it was just like her friend's engagement ring that she was trying on for fun. No, no. You girls are always swapping jewelry and clothes. Always at the bar, just casually putting on my friend's wedding ring. Oh, which reminds me, Brooke, I'll take your wedding ring off right now. Thanks for letting me wear it before the break. That doesn't happen.

Did he mention anything specific like that? So Walmart said they were like physically close to each other, but he didn't see any overly romantic gestures happen. So I'm like, all right, it's probably just a friend and she's wearing some kind of fake engagement ring. I mean, I will say, I will say I have some really hot friends that will wear fake engagement rings so they don't get hit on.

And I totally get that. And don't get me wrong, you guys, like I feel like I'm dating up. She is very attractive So I see her the next day and I bring it up thinking it's gonna be you know, like 30-second conversation She's gonna laugh. She's gonna you know, but she Was like I don't want to talk about that I want to talk about that. Oh, no. What kind of answer is that?

Oh, that's an immediate feeling of guilt. I tried to bring it up a few more times, and then Shannon got upset, and she stormed out. What? Why would she get upset? She got mad at you? Yeah, because you know when it's caught in a lie, it's upset. That's how it works.

It's like anybody who's accused of cheating will be like, no, you were cheating. Yeah. Oh, you're spying on me? But that's the thing is I wanted to give her like the medicine of the doubt And I wasn't trying to be aggressive about it or like it like accusing her right and now she's not answering my calls this was just the other night just this week and So I need advice. I need advice on how to handle it cuz you 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. I feel like we have not discounted the fact She could be a jewelry heist person That is a pretty frequent thing that we get on the show

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 that 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 have. Yeah. They probably haven't gotten married yet. Yeah, she's close with him anyway.

Now I can see a wedding band. Yeah, totally different. No, Jay, I'm sorry that you're going through this but we're gonna 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 friends 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. Okay, you don't have to hit on him now.

He's still with somebody. Yeah. We'll get to that in a second. Your Awkward Tuesday phone call is coming up right after this. It's awkward. It's Tuesday. It's Awkward Tuesday phone call. If you're just joining us for the Awkward Tuesday 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. Uh-huh. 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. Yeah, the least that he deserves right? What's your advice to Jacob man Jacob? It's not looking good. That's not really advice If all of those things are what happened for real then it's a hundred percent she's cheating like there's no way Right like all right Brooke. Can I get advice on how to handle this yes this has been pretty hopeless so far you just told him the situation you are gonna take control of this situation okay all right and you were gonna tell her you need to tell me the truth now you need to

rip it off like a bandaid rip it off like a bandaid because if she waits any longer it's only gonna 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, thank you. There was actually a little bit of advice in there good job Every week I give great advice What about you? What do you think? Remember you need to make her feel comfortable remind her honey. I want you to know 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 up to you. 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 gonna look really stupid if we're being as hateful as Brooke is towards Said the logical thing if it was logical Jeff. She wouldn't have like run out of the room

You know, I don't look stupid. So I'll listen and then judge I don't want to look stupid, so I'll listen and then judge. Okay, yes. And then we can mix. Ivor, that's normal life. Whatever it was. Don't get me wrong, you guys. If this doesn't go my way, I am fully welcome to judge. Yes.

Okay. 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. You'll be here if you feel like you need a little bit of help. Okay, good luck.

Hello? Hey, uh, 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? Like what, 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? Yeah, what is that? No, I'm sorry.

What do you think? I'm serious, all right? I deserve an explanation here. Like, it's my understanding, we've been together for six months now. Like we're boyfriend and girlfriend. And my understanding, we're not seeing other people. So am I wrong here?

Ah. Jacob, I don't want to hurt you. It's a little late for that. 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 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. Could I just come and catch up? What does this have to do with us? I'm getting there. This is not, this isn't easy, okay? 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.

Oh. And I didn't know what to say to you, because you're so sweet to me. Oh, my God. And I started dating him again. And I know it's messed up. I know, but in my head, I was like, I've always just wanted to have a forever relationship, be married.

And so I had it in my head that I was just gonna say yes to whoever proposed first. Oh, what? And he proposed a whoever proposed first. Oh! What? What? And he proposed a few nights ago. Oh my God! So, 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 What is that what's going on? Okay, oh my god Shannon We've been listening to this call 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 yeah what look yeah 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 and maybe Maybe you should 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 misunderstandings for the funny part me too. Yeah, but it turns out Shannon. You're just a two-timing cheater And you're just a two-timing cheater I'm sorry. She said that she can't believe this no. I'm sorry. I can't believe

Engaged and you hid all of this from me like how long were you dating for 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 gonna answer some questions for some people I've never talked to before well. It's pretty valid to the situation Jacob's friend and we're defending you're not a friend. He called the radio station now. He's your friend We're really clingy you don't know us Jacob is my friend like I still want him to be part of my life After all of this you think Jacob would still want to be around you Couldn't we stay friends like I even

Asked my fiance to have our wedding in like a year so you could have some time to heal cuz you are a good friend And I want you in my life to heal cuz you are a good friend and I want you in my life You're gonna delay your wedding a year so that your current boyfriend can get over you so that he can go to the wedding? I have never heard of that Jacob? I mean are you insane? It's gotta be a joke

Well what does your schedule look like next time? I would joke! I wouldn't joke! You're a special guy! Get out of here! Okay I was joking Oh jeez I wouldn't joke you're a special guy My schedule next year is figuring out when she's on her honeymoon and burning up her apartment

We're on tape here so this can be used in the court of I can help you Okay, yeah You're not helping me. Listen, the best revenge is to move on, okay? Yeah. Okay. Listen. 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. Hey, I wish Jacob well I hope he has a great life I don't know what to say to you Shannon honestly but Jacob sure Jeff he's gonna send you a wedding present yeah I do I do perform at weddings so you can hire me but, 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. But I mean, that's another positive. Well, hey, you know what? 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 ask her? Oh, you mean us, right? Yeah, yeah, yeah. Oh, okay. Okay. Yes, drinks on Jacob, right? Yeah. Yeah. Oh, okay. Yes. Drinks on Jacob.

Cool. Brooke and Jeffrey in the morning. Hey, what's up, y'all? This is Eric Andre. Well, they made a podcast called Bombing about absolutely tanking on stage. I tell gnarly stories and I talk to friends about their worst moments of bombing in all sorts of ways. Bombing on stage, bombing in public, bombing in life.

I want to know what's the worst way they ever bombed or have they ever performed way too drunk or high or was there ever a time where they thought they were going to crush and they stunk it up. Listen to Bombing with Eric Andre on Will Ferrell's Big Money Players Network on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Bombing, bombing with Eric Andre. Why would you do that to me? Los Angeles, 2021. A friendly neighbor appears out of nowhere and promises to make all my dreams come true. Let's not forget that David Blum was a professional con artist, so you didn't stand a chance. But my dreams soon turned into a nightmare. I'm Caroline DeMore. Listen as I take down my scammer on Once Upon a Con on the iHeartRadio app, Apple podcasts,

or wherever you get your podcasts. Hey, it's Alec Baldwin. This past season on my podcast, Here's the Thing, I spoke with more actors, musicians, policymakers, and so many other fascinating people, like writer and actor Dan Aykroyd. I love writing more than anything. You're left alone. You do three hours in the morning, you write three hours in the afternoon, go pick up a kid from school, and write at night. And after nine hours, you come out with with seven pages and then you're moving on.

And actor and comedian Jack McBrayer. The most important aspect is the collaboration with people that I like, I trust, are talented. That has been the most amazing gift to me about this crazy business that we've chosen. Meeting these people who have such diverse talents and you're able to create something together. Listen to Here's the Thing on the iHeartRadioApp Apple Podcasts or wherever you get your podcasts. Hey you guys, I'm Catherine Legge. I'm a racing driver who's literally driven everything with four wheels across the planet. And I've got a new podcast.

It's called Throttle Therapy. This season, I'm competing in some of the world's most notorious racing events. Tune into my new podcast, Throttle Therapy, with Catherine Legg, an iHeart women's sports production in partnership with Deep Blue Sports and Entertainment. You can find us on the iHeart radio app, Apple podcast, or wherever you get your podcasts. Presented by Capital One, founding partner of iHeart Women's Sports.