Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Worst Best Man

Episode Date: March 18, 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 wants to STOP her future husband’s best man from giving a speech at their wedding. Not only would is ruin the wedding but it would reveal a secret she’s been hiding for 10 years!See omnystudio.com/listener for privacy information.

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

Be more you this year and find them on Bumble. Hey, it's Amartines. The news can feel like a lot on any given day, but you can't just ignore las noticias when important world-changing events are happening. That is where the Up First podcast comes in. Every single morning in under 15 minutes, we take the news and boil it down to three essential stories so you can keep up without feeling stressed out. Listen Up First from NPR on the iHeartRadio app or wherever you get your podcasts. Are you hungry?

Colleen Witt here and Eating While Broke is back for season 4. radio app or wherever you get your podcasts. October, London and Carrie Harper Howie turning Big Macs into big moves. Catch Eating While Broke every Thursday on the Black Effect Podcast Network, iHeartRadio app, Apple Podcast, wherever you get your favorite shows. Come hungry for season four. My name is Brendan Patrick Hughes, host of Divine Intervention. This is a story about radical nuns in combat boots and wild haired priests trading blows with J. Edgar Hoover in a hell bent effort to sabotage a war. J. Edgar Hoover was furious. He was out of his mind

and he wanted to bring the Catholic left to its knees. Listen to Divine Intervention on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. All right, it's time for your brand new awkward Tuesday phone call. Welcome to the Second Date Update podcast with Brooke and Jeffrey, of course, the home of the Second Date Update. And I'm just saying, you are in for a treat

because a bride is trying to stop a best man speech before it outs her 10-year secret she's been keeping. Yeah. We're gonna get to that in just a second, but first, Bibi wrote wrote us greetings from the UK I'm so obsessed with your show and got my best friend hooked as well I just think it's so cool how people all over the world are into this yeah Seriously Marie Airstead said this show is all I listen to when coming home from work greetings from Denmark

Hey, I have a guy on my stream almost every day now from Germany. Oh really? Forgot your name though, but shout out to you. It's so good that the rest of the world can speak multiple languages, where we'll hear just being idiots. Yeah. Yeah, seriously.

Another one from Corrin wrote, I look forward to this every day listening from South Africa. Aw. Thank you so much for being part of it. We should shut it down in America. I say we just do all international. What do you guys think? That's not a bad idea. Okay, let's get into this brand new awkward Tuesday phone call. It starts right now.

When you think of best man speeches, they're always so well thought out, so sincere, concise, never weird or inappropriate. Oh my god, are you kidding me? They don't even scribble down anything on a napkin, they're like, oh, we're gonna... Yeah, I'll just fart into the mic, it'll crack the whole place up. That would be so funny. Shakespeare in bro form, am I right? That's why when one of our listeners emailed us saying she has to stop her husband's best man from giving a speech at all costs I was like what?

What are you talking about? I am shocked Because apparently his speech could ruin not only her wedding But maybe out a big secret that she's been hiding for the last ten years Wait what? What? She's willing to share it in exchange for some help in your brand new Awkward Tuesday phone call coming up

right after this. It's Awkward. It's Tuesday. It's Awkward Tuesday phone call. Brooke, you got married once. Yeah, I did. And I'm curious, how much of a say did you have in picking Michael's groomsmen?

Was that 100% your choice, or did you give him like 5% say? 0%. Zero? You gave him zero? No, no, I had 0%. Oh, I thought you were saying. Why are you putting up air quotes when you say that?

It was all his choice, I don't know. You let him pick out his own groomsmen? Who doesn doesn't do that giving away all the power to the man how 1940s But I only asked One of our listeners is recently engaged and she is having an issue with someone selected for their wedding party So let's talk to her about it Maria welcome to the show. I think oh So let's talk to her about it Maria welcome to the show I think oh you already sound a little annoying Yeah, well, okay, so yeah, you teed it up my fiance just told me who the best man's gonna be I Instantly hated it. I instantly hated it

Obviously like his best friend or his brother? Yeah, it's gonna say. I mean you kind of just know who that person's person is, right? Or might be. Yeah, I mean we have a really large friend group, so honestly it could have been two or three different people. So wait, was it at this point where you were like hoping it wasn't this one person, like anyone but them kind of thing?

I just really wish I would have been asked before picking this guy Why does it matter to you? Well, here's the deal. So my fiance doesn't know this but I used to date the best man And it's not his brother though, no, it you never told him? What? And it's not his brother though? No, it's not a family member. Okay, okay. Because that would be more of a red flag to me. It's still a red flag, Jack. It's how does it not go?

Yeah, that's the red flag. You gotta have all that out in the open. What are you talking about? No, I didn't want it to get messy or weird. Uh-huh, it's messy now. Wait a minute, wait a minute. How long ago are we talking? We're talking like 10 years. Messy or weird. Uh-huh, it's messy now. Wait, wait, wait. How long ago are we talking?

We're talking like 10 years. This is like back in high school. Back in high school. Okay. Okay. It's better, makes you feel better. It feels a little more innocent, right? Yeah, well, I didn't know that the guy

that I'm dating now, now is my fiance, is gonna be my fiance either. Yeah, duh. So were you all high school friends? Yeah, some of us were friends since high school. Others came around in college. Like I didn't think that this friend from high school was necessarily going to stick around. Oh, yeah. Okay. So, but he's made his choice. Like what are you want to do now? Here's the deal. Like this guy that's going

to be the best man. He really liked me. like he was super into me and I broke it off in high school You mean you broke his heart? Yeah, and now so this same person's gonna be making a best man speech at my wedding with a microphone and Flip that we dated and I could just I could just see him doing that. That's interesting So you're actually worried about him outing you for being a liar about back to right Yeah, but sometimes drunk guys don't think they'll yeah But it makes her I don't know you're right. It makes them both look bad

Does it make worse? I just so you know, like I never lied to my fiance It just never came up like I I kept thinking every year every maybe six months like I'll tell him now and then Now here we are Yeah, like like on his deathbed You think it's too late to tell your fiance now? God, yes. I think it's gonna be too much. Okay, you don't think he would laugh if it came up in the speech at the wedding? No. That's not the timing.

Exactly. It might be funny in a different... No, this is good because I clearly need to adjust my wedding speech that's coming up. I'm learning. Yours will base all on your exes. Yeah, so wait, you don't want us to call your fiance about this No, we're gonna call the guy we I used to date We're calling the best man Yeah, you know, I know it's awkward Tuesday. I've heard you guys help other people

How close are you friendship wise with this guy like when was the last time you saw him? I mean, I see him all the time We're out in a group, but it's not like we're spending one one time together You're familiar with each other obviously so what in the group chat what advice do you want like what do you want to say to this Guy I don't know maybe What exactly to say tell him in a nice way? I Don't know. I just maybe don't be the best man. What?

His best man job You can't do that to your fiance. Oh Lex is right your fiance be crushed This is gonna be coming out of the blue to this guy like don't you think this guy's gonna be like what are you talking about? We did it in high school who cares? I don't know I I think he might still have feelings. That's why I want to get ahead of it That's a different situation The truth is coming out slowly. I don't know about asking him to completely bow out Yeah, has he like hit on you or has there been a moment or something? Why do you think he has feelings? I mean I have felt like there's been some tension Well, I mean it is kind of like you're both in on a little lie because you're not telling

I mean Brooke think of the vibe when you hang out with me. It's kind of like that same thing You know, I see the look. Yeah, we never dated I know you want to but I'm not gonna let it happen. I think you miss you you're misremembering that segment Tension yeah feel that I feel like Jeff is her in this Coming from over on that side of the room, and I need to cut this off because we have an important thing to do here Let's just you take some time to think some of quality advice to give to Maria here so we can come back dial this best man and Politely let him know that he needs to either

Bow out of the wedding or at least not bring up their past relationship during the speech yeah yeah alright easy for you so let's do it with your Awkward Tuesday phone call right after this hold on weddings are supposed to be one of the most joyous fun times of your life but we have a supposed to be one of the most joyous fun times of your life But we have a bride to be who is stressed out and not for the normal wedding reasons It's cuz her fiance picked out his best man, and he doesn't know this but she used to date that guy back in high school They've been keeping the secret her and the guy for 10 years. The worst part though is she feels like the guy still might even like her. Oof.

So it all comes down to this. She's asked us to give her advice about, do you ask him to not come to the wedding at all and relieve himself of his best man duties? Oh my gosh. Or can we ask him to go through with it and just keep his mouth shut and don't say a word, especially with a microphone in his hand? Yeah. Is that right, Maria? Yeah, that's right.

Okay, so- She's like, I'm even more stressed now. I know. I can sense that you're nervous, so let's get you some advice. Brooke, what do you got for her? Okay, first, do not tell him to not be the best man. I'm going to tell you that is just going to create so much drama right ask him to be your husband No, no, I would say ask him nicely to not bring it up in the speech and

If you have to play a little dirty, okay It's just like you've known this guy for over 10 years. You've got to have some like something you can blackmail him with information Okay, just a little threatening. How do you feel about threatening the best man for the wedding? You made your bed I agree to the high school relationships there's gotta be something cringy you have of it. Thank you. That's fair That's fair. I mean it'd be like a last resort. I'd want to say absolutely I agree so idle threats are on the table What do you think you should just say look because of our history my request to you is you show up?

But you shut up okay. Don't say anything about us dating and that I will consider your official wedding gift to us I will consider your official wedding gift to us. Oh. So he doesn't have to buy anything. Thank you. I kind of like it, Jose. It's a good compromise. I would say what any bride wanted me to if I didn't have to buy a gift.

Yeah, save you hundreds. Maria, what do you think about that? I didn't even think about the trade-off of the wedding gift. Right. I think it's actually really smart. I mean, honestly. Okay, I'm smart, everyone tell me. I don't know who this guy was,

but was he planning on buying a gift anyway? Well, we're dudes. I'm gonna let you know at least half Tell me I don't know who this guy was but was he planning on buying a gift anyway? At least half of my husband's groomsman did not get us anything Yeah, brook's almost threatening her husband's groomsman's now so taking her own advice We will have Brooke on deck to pass out all the threats that you need, but I don't think you're gonna need that But I'm gonna dial this best man and let you talk to him. Okay, okay. What is his name by the way? Oh, yeah, his name's Brad Brad. Okay, I'm gonna call Brad Brad is not gonna see this coming, but I'm Dallas number right now. Here we go. Hello. Hi, Brad. It's me. Who? Maria, you know. Oh, okay. Hey,

yeah, I didn't have your number saved or something. I didn't recognize it. What's up? Yeah, no, I was just looking to see if you had like some time to talk or. Um, like, yeah, sure. Is everything okay? What's going on? Yeah, no, everything's fine. Um, you know, okay.

I did. I'm not sure you're getting getting married, excited. Yeah. Yeah. Yeah. Yeah. Well, you know, it's just a little awkward of everything, you know, what do you mean something wrong with like the venue or something?

No, no, no, they don't need fine. It's, um, it's just like with us, with our history. History? Right. Like our relationships. I mean, if you even want to call it that, I didn't even think about it. Like, what about it? I mean, yeah, like we went out.

What are you talking about? Like, it's like seven or eight months. I mean, I wouldn't even call that a relationship. Like almost a joke. And it was a long time ago. So I mean, we went out. We were like the longest relationship that I had had in all of high school. If it was good for you, that's awesome and stuff.

But like, I never thought we were like, I don't know, official or anything. I thought we just hung out a few times. Oh, you're joking, right? It was a real thing. Hmm. I guess to you, maybe. But I never thought we were like official like I said. Okay. Well, it was real.

Um, but listen, we just need you to not bring it up at the wedding. Okay. I didn't plan on it because nothing even happened. Did you get hit in the head? Like, are you forgetting? You were in love with me. I don't remember it like that. I'm pretty sure were in love with me. Oh. I don't remember it like that. I'm pretty sure you were obsessed with me.

Okay, listen, I had to break up with you. Why are we even talking about this? That was a long time ago. That was high school, like who cares? Yeah, it was a long time ago, but it was a real relationship. You were really into me and I'm now worried you're gonna ruin my wedding.

You know, just say something stupid. Again, my fiance doesn't know. Yeah, and I planned on keeping it that way because I didn't think anything happened. Like, if you wanna say you broke up with me, I kinda just led you to do that because I was just not showing any interest because I didn't even know if I was into you.

So I just kinda made you break up with me. Wow. Okay. Gross. Because I didn't even know if I was into you so I just kind of made you break up with me Wow Okay Okay What was that what's going on? You know what's going on Brad is you're on the radio right now with a really fun show called Brooke and Jeffrey in the morning Hi Brad Seriously with a really fun show called Brooke and Jeffrey in the morning. Oh, yeah. Hi, Brad. Seriously? This is a segment that we do. It's called Awkward Tuesday Phone Call.

Oh, it should be embarrassing. Tuesday, for all day. Yeah. Kind of cringe right now. Yeah. They're saying for him. Oh, well, yes, we're going to go with that because you are our listener. The whole thing, Brad, is that Maria was really worried that because of the past It might come up like at the wedding and make things awkward for her fiance and the family So she didn't know how to bring it up. She asked for help. Yeah

That is literally the dumbest thing I've ever heard like I haven't thought about her in like ten years Well, okay, you don't have to be rude. Don't you guys like hang out? Yeah, but like she's like the little sister I don't even like. Whoa! You dated this woman. She can't be your sister. Gross! I mean step sister.

Chara, that's hot. Gross. It's a joke! It's clueless. I don't hate her or anything. It's a joke. It's clueless. Come on. I mean, I don't hate her or anything. She's just there. She's my buddy's fiance. Like, I don't think about her like that. Well, that's good.

That's what you want to hear, am I right? Yeah, this should be refreshing, right, Maria? Yeah. You're in a cast. I know. I know, listen. That was probably a lot to hear, because it's not what you expected.

Not at all. Is there, like, a small chance that maybe it was you that had the feeling still? No way. I don't know why he's downplaying it, but Brad, you were in love with me. I still have the poem that you wrote. Oh, really? You still have it? What?

Wait, you still have that dumb poem that I wrote? I mean, it seemed really heartfelt. I feel like Brad gave that to more than one girl. Did it start with roses are red? Copy paste action. So, okay. This is like, this is hard. I know it's probably a little bit of an ego blow

to be hearing all this from Brad, but... You're getting married. Yeah. That's what you need to concentrate on. That's right. And maybe a good exercise is to take that poem and throw it away or set it on fire or something. That would be a good first step.

Okay. I think it would be fine if you told your fiance that you guys dated a long time ago. Obviously, nothing's ever going to happen. I think so now, too. Why? Why would you do that? If you told your fiance that you guys dated a long time ago obviously Yeah, why why would you do that like literally just mess around in that cabin that one time that Maria it should be refreshing to know that your past relationship or I guess Brad would say your your non-relationship Is gonna stay in the past Yes Thanks, I mean it didn't play out like thought I would

My god she said there's tension That's actually cheered me up today. Brad, thanks for your time. Have fun at the wedding, guys. I can bring up this phone call, that's for sure. This is the one time we're asking people not to share this on podcast. Yeah, don't let this one go viral. Brooke and Jeffrey in the morning. Ugh, we're so done with New Year, new you. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes.

More of you finding Geminis because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will, too. Be more you this year, and find them on Bumble. Nellie. Your host. I Heart Radio. LL Cool J. Are you guys ready to have some fun tonight? Plus I Heart Innovator Award recipient, Lady Gaga. I Heart Icon Award recipient, Mariah Carey. And I Heart Breakthrough Award recipient, Gracie Abrams. Watch live on FOX, Monday, March 17th.

At 8, 7 Central. Hey, it's Amartinez. The news can feel like a lot on any given day, but you can't just ignore las noticias when important world-changing events are happening. That is where the Up First podcast comes in. Every single morning in under 15 minutes, we take the news and boil it down to three essential stories so you can keep up without feeling stressed out. Listen Up First from NPR on the iHeartRadio app or wherever you get your podcasts. Baker, Nick Cannon, Melissa Ford, October London, and Carrie Harper Howie turning Big Macs into big moves.

Catch Eating While Broke every Thursday on the Black Effect Podcast Network, iHeart Radio app, Apple Podcast, wherever you get your favorite shows. Come hungry for season four. My name is Brendan Patrick Hughes, host of Divine Intervention. This is a story about radical nuns in combat boots and wild-haired priests trading blows with J. Edgar Hoover in a hell-bent effort to sabotage a war. J. Edgar Hoover was furious. He was out of his mind and he wanted to bring the Catholic left to its knees. Listen to Divine Intervention on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.