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Maria
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Jeffrey
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Jose
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Brad
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Maria
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Jeffrey
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're 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, BB 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.
Alexis
Yeah, seriously.
Jeffrey
Marie Airstead said this show is all I listen to when coming home from work. Greetings from Denmark.
Alexis
Hey, I have a guy on my stream almost every day now from Germany.
Jeffrey
Oh, really?
Alexis
Forgot your name though. But shout out to you.
Jeffrey
It's so good that the rest of the world can speak multiple languages while we'll hear Just being idiots. Yeah, seriously. Another one from Corin Wrote. I look forward to this every day. Listening from South Africa. Thank you so much for being part of it.
Alexis
We should shut it down in America. Yeah, I say we just do all international. What do you guys think?
Jeffrey
That's not a bad idea these days. Okay, listen, let's get into this brand new Awkward Tuesday phone call. It starts right now.
Brooke
When you think of best man speeches, they're always so well thought out, so sincere, concise, never weird or inappropriate.
Jeffrey
Oh my God, are you kidding me? They don't even scribble down anything on a Napkin. They're like, oh, wing it.
Alexis
Yeah, I'll just fart into the mic. It'll crack the whole place up.
Jeffrey
Oh, it'd be so funny.
Brooke
Yeah. 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, oh, no. I was like, what? What are you talking about?
Alexis
I am shocked.
Brooke
Cause apparently his speech could ruin not only her wedding, but maybe out a big secret that she's been hiding for the last 10 years.
Jeffrey
Wait, what? Now I'm like, what?
Brooke
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.
Jose
It's Tuesday.
Brooke
It's awkward Tuesday phone call. Brooke, you got married once.
Jeffrey
Yeah, I did.
Brooke
And I'm curious, how much of a say did you have in picking Michael's groomsman? Was that a hundred percent your choice, or did you give him, like, 5%, say, 0%? Zero.
Alexis
You had him zero.
Jeffrey
No, no, I had 0%.
Brooke
Why are you putting up air quotes.
Jeffrey
When you say that it was all his choice? I don't know.
Brooke
You let his pick out his own groomsmen.
Jeffrey
Who doesn't do that?
Brooke
Giving away all the power to the man. How 1940s of you. But I. I only asked because one of our listeners is recently engaged, and she is having an issue with someone selected for their wedding party.
Jeffrey
Oh.
Brooke
So let's talk to her about it. Maria, welcome to the show.
Maria
Hi. Thanks.
Jeffrey
Oh, you already sound a little annoying there, Maria.
Maria
Yeah, well, okay, so, yeah, you teed up. My fiance just told me who the best man's gonna be, and I instantly hated it. I instantly hated it.
Jose
It's not even a him.
Jeffrey
It's an it. Okay, isn't it obvious? His best friend or his brother? Like, didn't you. I mean, you kind of just know who that person's person is, right?
Alexis
Or might be?
Maria
Yeah. I mean, we have a really large friend group, so honestly, it could have been two or three different people.
Alexis
Oh, 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?
Maria
I just really wish I would have been asked before picking this guy.
Alexis
Can I. Oh, to help guide the selection?
Jeffrey
Why does it matter to you?
Maria
Well, here's the deal. So my fiance doesn't know this, but I used to date the best man.
Jeffrey
What?
Brooke
Oh, no, no.
Alexis
And you never told.
Brooke
Okay. And it's not his Brother, though.
Maria
No, it's not a family member.
Brooke
Okay. Okay. Because that would be more of a red flag to me.
Jeffrey
That's still a red flag.
Brooke
How does he not get.
Jeffrey
Yeah, that's the red flag.
Alexis
You gotta have all that out in the open.
Jeffrey
What are you talking about?
Maria
No, I didn't want it to get messy or weird. Hi.
Alexis
It's messy now.
Jeffrey
Long ago. Are we talking.
Maria
We're talking like 10 years. This is like back in high school.
Jeffrey
Back in high school. It feels a little more innocent, right?
Brooke
Yeah.
Maria
Well, I didn't know that the guy that I'm dating now, now is my fiance was gonna be my fiance either.
Alexis
Yeah.
Jeffrey
So were you all high school friends?
Maria
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 gonna stick around.
Brooke
Oh.
Alexis
Yeah.
Brooke
Okay, so. But he's made his choice. Like, what are you wanna do now?
Maria
Here's the deal. Like, this guy that's gonna be the best man, he really liked me. Like, he was super into me and I broke it off in high school.
Alexis
You mean you broke his heart.
Maria
Yeah. And now. So the same person's gonna be making a best man speech at my wedding with a microphone and have a couple drinks, let it slip that we dated, and I could just. I could just see him doing that.
Jeffrey
Interesting. So you're actually worried about him outing you for being a liar about. But it makes him look bad too, right? I mean, yeah, but sometimes drunk guys don't think they'll.
Alexis
But it makes her. I don't know.
Ryan Seacrest
You're right.
Alexis
It makes them both look bad. Does it make her look worse?
Maria
Just so you know, like, I never lied to my fiance. Just never came up. Like, I, I kept thinking every year, every, maybe six months, like, I'll tell him now. And then just, now, here we are.
Alexis
Or like, it'll naturally come up.
Brooke
Yeah, like, like on his deathbed as he's passing. Like, by the way, I was in love with Evan. Enjoy. Evan.
Jeffrey
You think it's too late to tell your fiance now?
Maria
God, yes. I, I, I, I think it's gonna be too much.
Brooke
Okay. You don't think he would laugh if it came up in the speech at the wedding?
Jeffrey
No, that's not the timing.
Alexis
No, exactly.
Jeffrey
It might be funny in a different.
Brooke
No, this is good because I clearly need to adjust my wedding speech that's coming up. So I'm learning your space.
Alexis
All on your exes.
Brooke
Yeah. So wait, you don't want us to call your fiancee about this?
Maria
No, we're going to call a guy I used to date.
Brooke
We're calling the best man.
Jeffrey
Yeah.
Maria
You know, I know it's awkward.
Jeffrey
Tuesday.
Maria
I've heard you guys help other people.
Alexis
This is perfect.
Jeffrey
I have a question. How close are you friendship wise with this guy? Like when was the last time you saw him?
Maria
I mean, I see him all the time. We're out in a group, but it's not like we're spending one on one time together.
Brooke
Yeah, okay.
Alexis
Like Texas friends or anything.
Brooke
You're familiar with each other obviously.
Maria
So he's in the group chat.
Brooke
What advice do you want? Like what do you want to say to this guy? Guy?
Maria
I don't know. Maybe what exactly to say? Tell him in a nice way.
Alexis
Oh, tell him.
Ryan Seacrest
Tell him what?
Maria
I don't know, I just. Maybe don't be the best man.
Jeffrey
What?
Nathan Lane
Oh no.
Brooke
Quit his best man job.
Jeffrey
You can't do that to your fiance.
Alexis
Alexis is right. Your fiance will be crushed. Like that's his best friend.
Jeffrey
This is going to be coming out of the blue to this guy. Like, don't you think this guy is going to be like, what are you talking about? We dated in high school. Who cares?
Maria
I don't know. I think he might still have feelings. That's why I want to get ahead of it.
Brooke
Oh, Jeff, that's a different situation.
Jeffrey
That truth is coming out slowly.
Brooke
I don't know about asking him to completely bow out.
Maria
Yeah.
Jeffrey
Wait a minute. Has he like hit on you or has there been a moment or something? Why do you think he has feelings?
Maria
I mean, I have felt like there's been some tension.
Jeffrey
Well, I mean, it is kind of like you're both in on a little lie because you're not telling.
Brooke
I mean, Brooke, think of the vibe when you hang out with me.
Jeffrey
Me?
Brooke
It's kind of like that same thing.
Alexis
You guys got the secret, you know?
Brooke
Yeah, I see the look.
Jeffrey
Yeah. We never dated. Love.
Alexis
Yeah, they just went right to it.
Brooke
I know you want to, but I'm not gonna let it happen.
Jeffrey
I think you miss you. You're misremembering that segment.
Brooke
Tension.
Maria
Yeah.
Brooke
Feel that.
Jeffrey
I feel like Jeff is her in the situation.
Brooke
It's all 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, bro.
Jeffrey
Yes. I don't want to have to call my husband. That will be awkward.
Alexis
I know.
Brooke
You never want to call him.
Alexis
You always want to talk to me.
Brooke
So look, 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, bow out of the wedding, or at least not bring up their past relationship during the speech. Yeah, yeah.
Jeffrey
Okay.
Brooke
All right. Easy for you. So let's do it with your awkward Tuesday phone call right after this. Hold on. It's awkward?
Jose
It's Tuesday.
Brooke
It's awkward Tuesday phone call. Weddings are 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 because her fiance picked out his best man. And he doesn't know this, but she used to date that guy back in high school.
Alexis
Dude, how awkward. Like, she'll always know this.
Jeffrey
And they been keeping the secret, her and the guy, for, like, 10 years.
Brooke
The worst part, though, is she feels like the guy still might even like her. So it all comes. It 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?
Alexis
Oh, my gosh.
Brooke
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?
Alexis
Yeah.
Brooke
Is that right, Maria?
Maria
Yeah, that's right.
Jeffrey
Okay, so, like, I'm even more stressed.
Brooke
I know. I can sense that you're nervous. So let's get you some advice. Brooke, what do you got for.
Jeffrey
Okay, first, do not tell him to not be the best man. I'm gonna tell you, that is just going to create so much drama.
Brooke
Right?
Jeffrey
Yeah.
Brooke
Ask him to be your husband.
Jeffrey
Yeah. 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. Oh, you know, information.
Brooke
Okay.
Jeffrey
Just a little threatening.
Brooke
How do you feel about threatening the best man before the wedding?
Jeffrey
You made your bed.
Jose
I agree with you.
Jeffrey
The high school relationships, there's got to be something cringy you have. Thank you. That's fair.
Maria
That's fair. I mean, it'd be like a last resort, I'd want to say.
Jeffrey
Absolutely, I agree.
Brooke
So idle threats are on the table. Jose, what do you think you should just say?
Alexis
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.
Jeffrey
Oh, so he doesn't have to buy anything. I kind of like it, Jose. I would say what any bride wanted me to if I didn't have to buy a gift.
Alexis
Saved you hundreds.
Brooke
Maria, what do you think about that?
Maria
That I didn't even think about the trade off of the wedding gift.
Brooke
Right. I think it's actually really smart.
Jeffrey
I mean, honestly, I'm smart.
Alexis
Everyone tell me.
Jeffrey
I don't know. I don't know who this guy was, but was he planning on buying a gift? Anyway, I'm gonna let you know, at least half of my husband's groomsmans did not get us anything.
Alexis
You tell him. He's like, wow. Yeah, we gotta buy a gift.
Jeffrey
Yeah.
Brooke
Brook's almost threatening her husband's groomsmans now, so taking her own advice.
Alexis
Good threatener.
Jeffrey
Yes, thank you.
Brooke
So we will have Brooke on deck to pass out all the threats that you need, but I don't think you're gonna. But I'm going to dial this best man and let you talk to him, okay?
Maria
Okay.
Brooke
What is his name, by the way?
Jeffrey
Oh, yeah, his name's Brad.
Brooke
Brad. Okay, I'm going to call Brad for you. Brad is not going to see this coming, but I'm dial his number right now. Here we go.
J
Hello?
Maria
Hi, Brad, it's me.
J
Who?
Maria
Maria. You know.
J
Oh, okay. Hey. Yeah, I didn't have your number saved or something. I didn't recognize it. What's up?
Maria
Yeah, no, I was just looking to see if you had, like, some time to talk or.
J
Yeah, sure. Is everything okay? What's going on?
Maria
Yeah, no, everything's fine, you know.
Jeffrey
Okay.
J
You sure?
Maria
You are getting married Excited? Yeah, yeah, yeah. It's just. Well, you know, it's just a little awkward with everything, you know?
J
What do you mean? Something wrong with, like, the venue or something?
Maria
No, no, nothing. Venue is fine. It's. It's just like with us, with our history. History, right. Like our relationships.
J
I mean, if you even want to call it that. I didn't even think about it. Like, what about it?
Maria
I mean, we went out. What are you talking about? Like, it was like seven or eight months.
J
I mean, I wouldn't even call that a relationship. Like, almost a joke. And it was a long time ago.
Maria
So, I mean, we. We went out. It's like the longest relationship that I had had in all of high school.
J
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.
Maria
You're joking, right? It was a real thing.
J
I guess to you, maybe, but I never thought we were, like, official, like I said.
Maria
Okay, well, it was real. But listen, we just need you to not bring it up at the wedding, okay?
J
I didn't plan on it because nothing even happened.
Maria
Did you get hit in the head? Like, are you forgetting you were in love with me?
J
I don't remember it like that. I'm pretty sure you were obsessed with me.
Maria
Oh, okay, listen. I had to break up with you.
J
Why are we even talking about this? That was a long time ago. That was high school. Like, who cares?
Maria
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.
J
Yeah, and I planned on keeping it that way. Cause I didn't think anything happened. Like, if you want to say you broke up with me, I kind of 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 kind of made you break up with me.
Maria
Wow. Okay. Gross.
Jeffrey
Awkward. Oh, this is embarrassing.
Brooke
Oh, my God. Okay. Oh, my God.
Jeffrey
Oh, Maria.
J
What was that? What's going on?
Brooke
Yo, 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.
Jeffrey
Oh, my God. Yeah. Hi, Brad.
Brooke
Seriously, this is a segment that we do. It's called Awkward Tuesday Phone Call.
Jeffrey
Oh, it should be embarrassing Tuesday Phone Call today.
Brooke
Yeah.
Alexis
Cause he's got a cringe right now.
Maria
Yeah, embarrassing for him.
Jeffrey
Oh, yes, we're gonna go with that because you are our listener.
Brooke
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.
Jeffrey
So she didn't know how to bring it up. She asked for help.
Alexis
Yeah, she just wants no drama.
J
That is literally the dumbest thing I've ever heard. Like, I haven't even thought about her in, like, 10 years.
Maria
Well, okay, you don't have to be rude.
Brooke
Don't you guys, like, hang out?
J
Yeah, but, like, she's like a little sister. I don't even. Like.
Brooke
You dated this woman. She can't be your sister.
Alexis
Yeah, I mean, stab sister.
Brooke
Sure. That's hot. It's clueless.
Maria
Come on.
J
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.
Brooke
Okay, good.
Alexis
That's what you want to hear, am I right?
Brooke
Yeah. This should refreshing, right, Maria?
Jeffrey
Yeah, I know. I don't. Listen, that was probably a lot to hear because it's not what you expected. I mean, is there, like, a small chance that maybe it was you that had the feeling still?
Maria
No way. I don't know why he's downplaying it, but, like, Brad, you were in love with me. Like, I still have the poem that you wrote.
Jeffrey
Oh, really?
Alexis
You kept it?
Brooke
You still have it?
Jeffrey
What?
J
Wait, you still have that dumb poem that I wrote?
Maria
I mean, it seemed really heartfelt.
Brooke
Okay.
Jeffrey
I feel like Brad gave that to more than one girl.
Alexis
Didn't start with roses are red.
Brooke
Yeah. Copy paste. Action.
Brad
So.
Brooke
Okay.
Alexis
Oh, geez.
Jeffrey
This is like. This is hard.
Brooke
Yeah, I know. It's probably a little bit of an ego blow to be hearing all this from Brad, but you're getting married.
Jeffrey
Yeah. That's what you need to concentrate.
Brooke
That's right. And maybe a good exercise is to take that poem and throw it away or set it on fire or something.
Ryan Seacrest
That'll be a good first step.
Maria
Okay.
Jeffrey
I think it would be fine if you told your fiance that you guys dated a long time ago. Obviously.
Maria
I think so now, too.
Jeffrey
Happened.
Brooke
Yeah.
Jeffrey
Yeah.
Maria
Why?
J
Why would you do that? Like, we literally just messed around in that cabin that one time. That's it.
Brooke
Okay.
Jeffrey
She really.
Alexis
Okay.
Brooke
All right.
Jeffrey
Maybe don't bring it up.
Brooke
Maria, it should be refreshing to know that your past relationship, or I guess Brad would say your. Your non relationship, is going to stay in the past.
Jeffrey
Past hookup.
Brooke
Yes.
Jeffrey
Yeah.
Maria
Well, thanks. I mean, it didn't play out like thought it would, but at least you.
Alexis
Know, when he's looking at you now, he's not flirting with you.
Brooke
That's right.
Alexis
Said there's tension sometimes, right?
J
Oh, my God. She said there was tension.
Brooke
This actually cheered me up today. So, Brad, thanks for your time.
Alexis
Have fun at the wedding, guys.
Maria
Yeah.
J
Not gonna bring up this phone call, that's for sure.
Brooke
This is the one time we're asking people not to share this on podcast.
Jeffrey
Brooke and Jeffrey in the morning.
Brad
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Ryan Seacrest
Hey, it's Ryan Seacrest for Albertsons and Safeway. It's Stock up Savings time now through March 25th. Spring in for storewide deals and earn four times the points. Look for in store tags to earn on eligible beverage items from from San Pellegrino and Pepsi or breakfast favorites like Chobani Greek Yogurt Dan and Oikios Yogurt and Pete's Coffee, plus many more. Then clip the offer in our app for automatic event long savings. Stack up those rewards to save even more restrictions apply. Visit Albertsons or Safeway.com for more details.
Jose
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Jeffrey
Lenovo Lenovo.
Nathan Lane
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Jose
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Podcast Title: Brooke and Jeffrey: Second Date Update
Episode: Awkward Tuesday: Worst Best Man
Release Date: March 18, 2025
Host/Author: iHeartPodcasts
In this engaging episode of Brooke and Jeffrey: Second Date Update, hosts Brooke and Jeffrey tackle a particularly delicate and humorous listener dilemma titled "Awkward Tuesday: Worst Best Man." The episode delves into the complexities of past relationships resurfacing at pivotal life moments, offering listeners insightful advice laced with their signature wit and charm.
Timestamp: [03:07]
Maria, a listener from South Africa, reaches out with a stressful situation: her fiancé has chosen his best man, Brad, who happens to be someone Maria dated briefly in high school. Although their relationship was short-lived and occurred over a decade ago, Maria fears that Brad might inadvertently or deliberately reveal their past during his best man speech, potentially jeopardizing her upcoming wedding.
Notable Quote:
Brooke: “When you think of best man speeches, they're always so well thought out, so sincere, concise, never weird or inappropriate.”
[04:31]
Timestamp: [05:05 - 07:02]
Brooke and Jeffrey explore the possible repercussions of Brad mentioning their past relationship. They consider whether Maria should confront Brad directly, ask him to refrain from discussing the past, or potentially remove him from his role as best man. The hosts weigh the emotional and social implications of each option, emphasizing the importance of preserving the joyous nature of the wedding.
Notable Quote:
Jeffrey: “Do not tell him to not be the best man. I'm gonna tell you, that is just going to create so much drama.”
[13:02]
Timestamp: [12:00 - 21:37]
To provide practical assistance, Brooke and Jeffrey decide to facilitate an "Awkward Tuesday Phone Call" to Brad on Maria’s behalf. The call is intended to preemptively address any potential issues and ensure that Brad understands Maria’s concerns without causing undue conflict.
Highlights of the Call:
Maria's Approach: Maria expresses her worries about their past relationship resurfacing at the wedding. She seeks Brad’s cooperation in keeping their history private during his speech.
Brad's Reaction: Initially defensive, Brad downplays the significance of their past relationship, asserting that he never considered it official or impactful. He dismisses the idea that he would bring it up, highlighting the benign nature of their brief relationship.
Resolution: Through the conversation, it becomes evident that there is little to no lingering tension between Brad and Maria. The dialogue wraps up with an understanding that Brad is unlikely to mention their past, alleviating Maria’s fears.
Notable Quotes:
Maria: “I used to date the best man.”
[06:07]
Brad: “I don’t remember it like that. I'm pretty sure you were obsessed with me.”
[17:30]
Jeffrey: “This is the one time we're asking people not to share this on podcast.”
[21:37]
Timestamp: [21:37 - End]
Brooke and Jeffrey reflect on the call, underscoring the importance of open communication and addressing concerns directly to prevent misunderstandings. They highlight that often, fears of past relationships impacting current ones are amplified in our minds, whereas reality may be much more straightforward.
Notable Quote:
Brooke: “This is the dumbest thing I've ever heard.”
[18:58]
Navigating Past Relationships: The episode emphasizes the delicate balance between past and present relationships, especially in significant life events like weddings.
Effective Communication: Brooke and Jeffrey advocate for honest and direct conversations to mitigate potential issues, showcasing how proactive dialogue can resolve anxieties.
Humor in Awkward Situations: True to their style, the hosts infuse humor into the discussion, making the episode both entertaining and relatable for listeners facing similar dilemmas.
Role of Best Man: The conversation sheds light on the responsibilities and expectations placed on a best man, reinforcing the importance of selecting someone trustworthy and understanding.
"Awkward Tuesday: Worst Best Man" serves as both a compelling narrative and a practical guide for listeners grappling with uncomfortable social scenarios. Brooke and Jeffrey adeptly navigate Maria's predicament, offering sage advice while maintaining a lighthearted and engaging tone. The episode ultimately reassures that with the right approach, even the most awkward situations can be managed with grace and humor.
Connect with the Show:
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