Second Date Update Classic: Secret Mission

Summary

Podcast Summary: Brooke and Jeffrey: Second Date Update Classic: Secret Mission

Episode Details:

• Title: Second Date Update Classic: Secret Mission
• Hosts: Brooke and Jeffrey
• Release Date: March 8, 2025
• Platform: iHeartPodcasts

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Introduction

In this episode of Brooke and Jeffrey in the Morning, the dynamic hosts delve into the intricacies of modern dating, focusing on the challenges of securing a second date after an initial encounter. The episode centers around a listener named Michael, who seeks guidance after a perplexing date experience with a woman named Megan. Brooke and Jeffrey aim to unravel the mystery behind Megan's sudden ghosting and provide Michael with actionable advice to navigate his love life.

The Initial Encounter and Date Setup

Timestamp: 02:50

Brooke introduces the segment by recounting Michael's previous interaction with the show, where he sought help in convincing his best friend to date a lonely female friend. Michael returns almost a year later, now ready to re-enter the dating scene after a messy breakup.

• Brooke: "Second date update. Not sure if you remember this, but a few months ago, one of our listeners named Michael did an awkward Tuesday phone call because he had this female friend who was complaining to him about how lonely she was all the time."

Michael explains that unlike his previous venture into dating through apps, he met Megan organically at a grocery store—a setting Brooke humorously labels as stereotypical.

• Michael: "Someone I met in real life, not on the apps... her name's Megan, and I met her at the grocery store."

The Date and Unexpected Turn of Events

Timestamp: 05:22

Michael describes his initial date with Megan, which began promisingly with mutual grocery store encounters leading to an invitation for a "Netflix and chill" evening at his apartment. The date proceeds smoothly, with both parties appearing comfortable and relaxed.

• Michael: "We just ended up doing was just watching a movie, had a couple of drinks."

However, the evening takes an abrupt turn when Megan excuses herself to retrieve something from her car and subsequently disappears without explanation. Michael's confusion escalates as Megan later sends a terse text ending their budding relationship.

• Michael: "She just sent a text over and it just said, hey, sorry, it's not going to work out between us. That was it."

Seeking Clarity: Calling Megan on Air

Timestamp: 11:08

Determined to understand what went wrong, Brooke and Jeffrey decide to call Megan live on the show. This bold move aims to provide Michael with transparency and closure.

• Brooke: "We're trying to help him figure out if when you two hung out and did Netflix over at his apartment, if something went wrong during that night."

Megan answers the call, visibly embarrassed, and reveals startling information about the true nature of her encounter with Michael.

Revelations and the Secret Mission

Timestamp: 15:00

Megan discloses that her meeting with Michael wasn't as coincidental as it initially appeared. Instead, it was orchestrated to retrieve her ex-girlfriend's guitar, which Michael had been holding onto.

• Megan: "I don't even know where to begin. I really don't even know if I should tell you."

She admits that her actions were motivated by a desire to reclaim the guitar, not by romantic disinterest.

• Megan: "I kind of didn't bump into Michael at the grocery store. I know his ex-girlfriend. We're in a book club together... so, yeah, we kind of set up to run into Michael at the grocery store."

This revelation paints Megan's ghosting not as a lack of interest but as part of a calculated plan to retrieve the guitar under the guise of a romantic encounter.

Conclusion and Lessons Learned

Timestamp: 18:44

The episode culminates with Michael processing the unexpected twist. Brooke and Jeffrey emphasize the importance of awareness and caution in dating, highlighting how well-intentioned actions can sometimes have unintended consequences.

• Brooke: "Lesson learned here."

Megan’s involvement reveals a complex layer of motivations beyond typical dating misunderstandings, prompting Michael—and listeners alike—to consider deeper aspects of trust and intentions in romantic pursuits.

Key Takeaways:

• Awareness in Dating: Always be mindful of the other person's intentions and be cautious when inviting someone to a personal space like your home.
• Communication: Clear and honest communication is crucial to avoid misunderstandings and ensure both parties are on the same page.
• Resilience: Even when faced with confusing or disappointing experiences, maintaining a positive outlook and seeking constructive feedback can aid personal growth.

Notable Quotes:

• Brooke (02:05): "It's our honor and privilege to be able to assist you with your love life today, Michael."
• Michael (03:48): "I want to know what was the turn off? Because I'm confused. Was it my apartment? Was it something I did?"
• Megan (15:00): "I don't even know if I should tell you."
• Jeffrey (17:00): "You got finessed."

Final Thoughts

This episode of Brooke and Jeffrey in the Morning masterfully blends humor with heartfelt advice, shedding light on the unpredictable nature of dating in the modern age. Through Michael and Megan's story, listeners gain insights into the complexities of human relationships, the importance of genuine connections, and the value of seeking clarity in romantic endeavors.

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Connect with the Show:

• Listen on iHeartRadio: Brooke and Jeffrey
• Apple Podcasts: Brooke and Jeffrey
• Spotify: Brooke and Jeffrey

Transcript

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You know only the OGs are here on the weekend so yeah. Thank you. You're our favorite. Yeah, it's Brooke and Jeffrey in the morning. The home of the second Date Update. And if you haven't heard, we do have brand new merch for a Cause Second Date Update Edition. First time ever. I know and it's so cute. And the best part of it is 100% of proceeds are going to LA Wildfire Relief. I know that that feels like ago that it happened, but the work is really being done right now to build back.

[Brooke]

Yeah.

[Jeffrey]

So. So go to the show links notes. What is show notes? Thank you. There's a link in the show notes. There it is. That's what I'm trying to say. And purchase for you, your loved ones. Thank you so much for your support. Again, 100 of proceeds going to convoy of hope. And here is your classic second date update.

[Brooke]

Second date update. Not sure if you remember this, but a few months ago, one of our listeners named Michael did an awkward Tuesday phone call because he had this female friend who was complaining to him about how lonely she was all the time.

[Jeffrey]

Yeah.

[Brooke]

So he wanted to convince his best friend to date her just to get miss sad face out of his hair.

[Jeffrey]

I do remember this. I can't remember how it turned out.

[Brooke]

But I remember it doesn't really matter. I guess we did a good enough job helping him with that situation that Michael now trusts us completely. So much so that almost a year later, he wants us to do a second date update. Michael, it's good to have you back on on the show, dude.

[Michael]

Hey, it's great to be back. Thanks for having me.

[Jeffrey]

How does it feel to, like, lower your standards of advice this low?

[Michael]

Well, I think you guys are gonna help me out.

[Jeffrey]

Oh, okay.

[Brooke]

It is our honor and privilege to be able to assist you with your love life today, Michael. So tell us what's going on.

[Michael]

I want you to know that before I started dating, even before I had you guys help me advice with my friend, I was in a long relationship before then it ended messy. So I was definitely taking a long break from dating. But now I'm back out there.

[Jeffrey]

Okay. How's it feel?

[Michael]

I feel all right. I mean, I finally got on the apps, but why I need your advice is somebody I met in real life not on the apps.

[Jeffrey]

That's fun. How'd you do that?

[Michael]

Well, her name's Megan, and I met her at the grocery store.

[Brooke]

Dude, that's like, such a stereotype. People say the best place to meet a chick.

[Jeffrey]

Do they really say that?

[Michael]

The grocery?

[Brooke]

Yeah. Well, I don't know why, but they.

[Jeffrey]

Say that I stop wearing my AirPods to the grocery store.

[Brooke]

Romantic at the grocery store. Especially when they have the thunder over by the produce section setting the mood in the rainstorm. That's hot. Dude, the timing was this. How did you meet Megan there?

[Michael]

Just. We caught each other's eyes, and then we kept finding each other on almost every aisle.

[Jeffrey]

Oh, you need bread, too? I needed bread. Okay. That's kind of cute.

[Michael]

Yeah. To the point where, like, she jokingly had to ask me, are you following me? With a smile?

[Jeffrey]

I love she's joking. Well, I mean, I'll tell you, when women say that, it's like joking. But also, we also need to know one hand.

[Brooke]

One hand on the pepper spray. Yeah. All right.

[Michael]

You know, I asked her right back, though. Are you following me? And that started up like a mall conversation. We just talked about what was in our cart, you know?

[Jeffrey]

Oh, yeah, you're going to make tacos tonight, huh? Yeah.

[Brooke]

You guys went deep on that first convo. My God. Yeah.

[Michael]

And that led to me asking her her number.

[Jeffrey]

I just went for it.

[Brooke]

Yeah.

[Michael]

And so, yeah, I got her number.

[Brooke]

Wow. Well, that must make you feel really confident after, like, you said, you went through that tough breakup for a. Like a year ago. Finally going out into the world and meeting somebody that you connect with instantly.

[Jeffrey]

What have people been complaining about? This is so easy.

[Brooke]

Did it lead to an actual date?

[Michael]

It did. Yeah.

[Jeffrey]

And there was no ghosting involved. Well, except for now.

[Brooke]

Look how jaded we all are in this room. Like, you met again. Oh, my God.

[Michael]

Well, you're jumping ahead. There was some ghosting, so. Okay, yeah, I mean, we. We did meet up. I suggested we go out for dinner, like at a restaurant just to get to know her more, but she countered with just like, I don't feel like going out. Can we just watch a movie? And I said, sure. And she suggested my place.

[Brooke]

Suggested your place? That's a great sign, bro.

[Jeffrey]

Is it? Or I mean, like, are you. Because I feel like it's a good sign for just like a one night hangout situation. It's not a good sign if you're.

[Brooke]

I just meant it's a good sign that she's comfortable enough to come to you. I can be that she stole Brooks line. I think it's a very good sign. So how did it go?

[Michael]

I felt very comfortable and relaxed. We just. All we ended up doing was just watching a movie, had a couple of drinks. Oh, that's.

[Brooke]

Wait, you guys didn't fool around? That's.

[Michael]

No. Didn't lead to any of that.

[Jeffrey]

That's okay. It's the first hangout.

[Brooke]

Okay. This isn't like Brooks hangout.

[Jeffrey]

Yeah, you're not wr. Wrong, Jeff.

[Michael]

So then I thought the night would go on a little longer, but she said she had to go and get something from her car real quick. She's like, I gotta run to my car real quick. I didn't even think of It. I was having a good time and that's when she just never came back.

[Brooke]

What a dramatic way to leave.

[Michael]

Whoa.

[Jeffrey]

I feel like that's something Alexis would do. Like she just doesn't know how to say, I really would literally dip out.

[Brooke]

Or is this a trail? Like, oh, wait, I left it at home.

[Jeffrey]

It's same with when you're meeting someone at a second bar, like a restaurant to a bar. It's like, see you there. Yeah.

[Brooke]

It's a little concerning though. Did you reach out to her afterwards?

[Michael]

Yeah, I was concerned. I'm like, I hope no one snatched her up or something. I call. I even called the number. I mean, no. No reply for quite a bit. And then she finally got back to me and all. She just sent a text over and it just said, hey, sorry, it's not going to work out between us. That was it.

[Brooke]

We're so jaded. You're right, because I think that's polite. I'm like, oh, that's nice of her.

[Jeffrey]

But she ditched him into his face.

[Brooke]

But it's weird that there's no explanation for why.

[Michael]

Yeah, exactly.

[Brooke]

After she invited herself to hang out at your apartment.

[Jeffrey]

But I don't feel like your own explanation after only one hangout, Jeff. Like, yeah, that's.

[Brooke]

That's a good point too. It's not like going out.

[Jeffrey]

That's the thing. Like, oh, but we want it. Do you want. Do you want to see her again?

[Michael]

I just want to know what was the turn off? Because I'm confused. Was it my apartment? Was it something I did? I don't know. It just.

[Jeffrey]

I like that you're blaming yourself. That's a good start.

[Michael]

Okay, this might lead to me being embarrassed. Who cares? Let's find out what I did so.

[Brooke]

I can, you know, if there's something wrong that you're doing, it's good to know it up ahead of time. So let's come back. We're gonna call Megan for you, Michael. Oh, so weird. Brooke's husband and Brooks best friend's name. Don't think about that when we do our next call here. You took her line ye telling me it's gonna be bad when we do Here. Second date update right after this. Hold on. Second date update. It was the comeback after the romantic setback. Followed by a slight drawback. Oh, okay. Cuz our listener Michael finally got back into the dating game after going through a tough breakup about a year ago.

[Jeffrey]

Yeah.

[Brooke]

Didn't find his match online though. Found her in the grocery store.

[Jeffrey]

Yes.

[Brooke]

Holding two big. Cantaloupes What? At least that's Jose's dream of how they met. But her name was Megan. And eventually they arranged a little Netflix and chill night back at Michael's apartment, which went really well and was her idea.

[Jeffrey]

That was her idea. It's very important to mention.

[Brooke]

Things kind of fell apart, though, when she said she had to grab something from her car and never returned.

[Jeffrey]

Yeah. I'm wondering if she was. Was hoping for something more that never was materializing.

[Brooke]

Oh, that he didn't.

[Jeffrey]

Yeah. Yeah. They watched the whole movie. Yeah.

[Brooke]

I was like, you guys didn't do anything. Was the had to grab something from the car thing a lie? Alexis says yes, from experience. But we don't know that.

[Jeffrey]

Yes, we do. She didn't.

[Brooke]

We don't know anything for sure. We do know it's not a good sign. Alexis is still confused on what a lie is.

[Jeffrey]

The point is she didn't want to be there.

[Brooke]

Okay. That would mean that she lied.

[Jeffrey]

Yes.

[Brooke]

Okay. But again, we don't know. We just know it's not a good sign. Also not a good sign. Megan texted him days later confirming it's not going to work. That's why.

[Jeffrey]

No. After all of those things, Jeff, I think it's very.

[Brooke]

We need to be impartial people in the middle here. Isn't that right, Michael? You want an impartial audience.

[Michael]

Like, I am very hopeful that I'm going to get something positive out of that. It'll be an easy correction to make.

[Jeffrey]

I think your positivity is really sweet.

[Brooke]

Do you hear the condescending tone in her voice? Yeah.

[Michael]

I'm not hopeful to get another date out of this. It's not like trying to get her back with me. I just want to become better at dating.

[Jeffrey]

Okay. And that's sweet. Yeah.

[Brooke]

Sweet that you think you can get better.

[Jeffrey]

Yeah.

[Brooke]

Okay, well, we're all gonna try our best for you here, Michael. Let's call Megan for you and see if she answers and what she has to say. Here we go.

[Jeffrey]

Foreign.

[Brooke]

Hi, we're looking to talk with Megan.

[Megan]

Speaking.

[Jeffrey]

Oh, hey, Megan.

[Megan]

Hey. Hello.

[Brooke]

You're awfully chipper.

[Jeffrey]

I'd be so scared if I got.

[Brooke]

A group phone call. Yeah, because I don't know if you realize you're on the radio right now with a show called Brooke and Jeffrey in the Morning.

[Megan]

Are you serious?

[Brooke]

Yes.

[Jeffrey]

Welcome to the show, Megan.

[Megan]

Oh, hi, guys. I guess thanks for answering.

[Michael]

Okay.

[Brooke]

I don't know how to deal with this positivity on the other end. We don't normally get this We've got.

[Jeffrey]

Two positive people that we've talked to today.

[Brooke]

That's true. You don't know this, Megan, but earlier, the other positive person we spoke to was a guy named Michael that you went on a date with.

[Megan]

Are you serious?

[Jeffrey]

Yeah.

[Brooke]

We loved his energy, too.

[Jeffrey]

Yeah.

[Megan]

Oh, my.

[Jeffrey]

Oh, my God. You're just freaking out.

[Brooke]

You sound excited, but. No, that's the word. Well, I don't know.

[Jeffrey]

What.

[Megan]

Okay, wait. You said Michael. Like, Michael called you?

[Jeffrey]

Yeah.

[Brooke]

Yeah.

[Jeffrey]

Well.

[Brooke]

Well, because we're doing something called a second date update. We're trying to help him figure out if when you two hung out and did Netflix over at his apartment, if something went wrong during that night because.

[Jeffrey]

Well, he knows something went wrong because you left and didn't come back.

[Brooke]

Well, we don't know what the problem was, if it was on your end, if something he did.

[Megan]

Oh, my gosh. I cannot believe this is happening.

[Brooke]

Wait, I have a limited time, so we need to have you believe sooner. So start to believe. You're on the radio now.

[Jeffrey]

Are you excited to hear Michael's name again?

[Megan]

I don't know if I'd say excited.

[Jeffrey]

Okay, okay.

[Megan]

Embarrassed.

[Brooke]

Embarrassed for you?

[Megan]

Absolutely. 100%.

[Jeffrey]

Why? I thought it was amazing. Why? What happened?

[Megan]

Okay, I don't even know where to begin. I really don't even know if I should tell you.

[Jeffrey]

Oh, my God. No. We love humiliating stories. We are walking embarrassments to everyone that we know. Like, you are in the right company.

[Brooke]

We're really just trying to help out Michael because he's really concerned, feeling like he did something wrong on the date. Yeah.

[Megan]

So let me just say, I've never done anything like this before.

[Jeffrey]

What do you mean?

[Brooke]

Alexis says that on the first date, too, a lot, so I know that move. Oh, I swear.

[Megan]

But seriously, guys, I'm a good person. I promise.

[Brooke]

What are you talking about?

[Jeffrey]

With anything.

[Megan]

Okay, so I kind of didn't bump into Michael at the grocery store. Like, not by accident.

[Jeffrey]

What do you mean?

[Brooke]

What?

[Megan]

I don't know if he told you, like, we met in a grocery store or not.

[Brooke]

Yeah, he said you guys, like, randomly kept bumping into each other kind of multiple times in the store.

[Megan]

Yeah, well, I'm kind of like, I know his ex girlfriend.

[Jeffrey]

Wait, what?

[Megan]

Yeah, like, we're in a book club together. So, you know, we're girl pals. We chill, we talk, you know?

[Michael]

And.

[Jeffrey]

Wait, so you saw him in the grocery store by chance or you went there because you knew he was going to be there?

[Megan]

Yeah, I kind of followed him there because why? She basically was like venting one day and she was like, my ex boyfriend won't give me back my guitar. So my God, one thing leads to the next and. Yeah, so we kind of set up to, you know, run into Michael at the grocery store.

[Jeffrey]

The whole thing was a setup. So you could go in and steal her guitar back. He didn't see you leave with the guitar?

[Megan]

I didn't steal anything that's hers.

[Jeffrey]

Okay.

[Brooke]

Yeah. At least that's what she says.

[Jeffrey]

Returned it.

[Brooke]

What really happens at book club? You don't read any books.

[Jeffrey]

You do the book for like 15, 20 minutes, you discuss it, and then.

[Brooke]

You plot revenge against all of your exes for the rest of the time.

[Jeffrey]

I mean, if it needs to happen, it needs to happen. I mean, she's not getting revenge. She's just trying to get her guitar back. That's different. I have had reconnaissance missions like this myself. I know.

[Brooke]

That's like another 20 minute long story that we don't need to get into. The important thing that we need to get to here. Megan is letting you know that Michael is actually on the other line right now listening to this conversation.

[Jeffrey]

It's fine. I mean, it's not like you're ever gonna see him again.

[Brooke]

Well, kind of ruins your plan.

[Michael]

I mean.

[Jeffrey]

What do you mean? Didn't she already get the guitar?

[Brooke]

Michael, are you hearing this?

[Michael]

Yeah. I do not know what to say right now.

[Megan]

Michael. Oh, my gosh. I'm so sorry. I really am.

[Michael]

Unbelievable. Tell me, is the guitar from my house gone?

[Megan]

Yeah, I slipped it outside the door when I went to the bathroom.

[Brooke]

That's so. I mean, devious, cunning. I.

[Jeffrey]

But Jeffrey is like, doesn't. You're stunned.

[Brooke]

I'm. I'm shocked. I didn't see this coming because, I mean, what is the history of the guitar? Whose guitar is it?

[Michael]

It's my ex's. Yeah, like why the hell.

[Jeffrey]

Yeah.

[Brooke]

Why are you holding on to it?

[Michael]

It was a gift. I just held on to it. It was a messy end. I don't want to get into it at all, but I'm trying to get better.

[Brooke]

You're trying to get better?

[Jeffrey]

When you say it's a messy breakup, this makes it a messy.

[Brooke]

You're not helping.

[Jeffrey]

It's not like you are the issue.

[Brooke]

Some women like. Some women hold like onto the sweaters from their ex boyfriends and cry. He holds on to his ex girlfriend's guitar and cries into it, which is expensive.

[Jeffrey]

Dirty old sweatshirt.

[Megan]

Yeah, I'm sorry, man. She just said like, basically you kept Making excuses. So I wanted to help her out.

[Jeffrey]

Oh, yeah.

[Michael]

I just didn't want to see her kind of thing. It wasn't really about keeping it out of a spider or anything.

[Jeffrey]

Could have left it somewhere.

[Megan]

I will say, like, you are a really nice guy. Like, you were really hospitable. You were really cordial. You didn't try anything crazy.

[Brooke]

And you're not even mad hearing about this like, elaborate plan to get the guitar back out from under your nose.

[Michael]

It's more amazing that you pulled it off. And why would I be angry about that?

[Jeffrey]

I think it's amazing you didn't know it was missing.

[Brooke]

Yeah, well, he doesn't sounds like he doesn't play. Yeah, that's more his girlfriend's thing. But is there still, like, was there ever romantic connection between you two, Megan and Michael?

[Jeffrey]

Wait, you're going to make that happen?

[Brooke]

Isn't that the goal of this call?

[Megan]

Sorry, Michael, I'm actually engaged, so.

[Jeffrey]

And you went out with a guy.

[Brooke]

Does your engaged fiance know about this?

[Jeffrey]

Probably. It's kind of a funny story.

[Megan]

Oh yeah, he knows all about it and he thinks it's hilarious.

[Brooke]

And you know, oh my God, his Internet is kind of funny.

[Michael]

I'm happy I didn't make a move.

[Brooke]

So. Yeah. Okay, well, clearly there's no connection between the two of you. But Megan, Michael did want to get some dating advice out of this segment. Do you have any that you want to share with him to maybe help him out going forward?

[Megan]

Yeah, Michael, you definitely got to be more aware of your surroundings. And don't bring people to your house.

[Brooke]

Okay, that's.

[Jeffrey]

You didn't notice someone stalked you to a grocery store?

[Brooke]

Just assume every girl you meet wants to steal something from you.

[Jeffrey]

Yeah.

[Brooke]

Oh, man. Wow.

[Jeffrey]

That is a hard reality.

[Brooke]

Your first date, Michael. Back in the dating world after a year. It's a setup to get your guitar out of your apartment.

[Michael]

Lesson learned here.

[Jeffrey]

You got finessed. Brooke and Jeffrey in the morning.

[Brooke]

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[Jeffrey]

Kids are spending with real time notifications. Kids learn to earn, save and spend wisely and parents can rest easy knowing their kids are learning about money with guardrails in place. Try Greenlight Risk free [e-mail] iheartra.