Second Date Update Classic: Five Finger Hangout

Summary

Brooke and Jeffrey: Second Date Update – Episode Summary: "Second Date Update Classic: Five Finger Hangout"

Release Date: May 3, 2025
Hosted By: Brooke and Jeff
Podcast Platform: iHeartPodcasts

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Overview

In this engaging episode of Brooke and Jeffrey: Second Date Update, hosts Brooke and Jeff delve into a compelling listener story that highlights the unpredictable nature of online dating. The episode centers around Jack’s perplexing experience with a date named Naomi, unraveling themes of trust, manipulation, and the quest for clarity post-date.

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Listener's Story: Jack and Naomi

Timestamp [01:37] – Introduction to Jack’s Date

The episode begins with Jeff posing a question to their regular contributors, Jose and Alexis, about the fastest transition from online matching to meeting in person. This leads to Jack’s introduction:

• Jeff: “Second date update Question for Jose and Alexis. What is the quickest that you've ever gone from matching with someone to meeting up with them?”

Jack shares his experience of matching with Naomi online and agreeing to meet within 10 minutes of connecting.

• Jack: “We matched and, like, within 10 minutes, she was asking me to meet up.”

Brooke and Alexis express amazement at the rapid progression, highlighting it as a potential red flag:

• Brooke: “10 minutes.”
• Alexis: “That's a record.”

Timestamp [03:25] – Excitement vs. Red Flags

As Jack describes his excitement about Naomi’s interest, the hosts question whether moving so quickly could indicate underlying issues.

• Jeff: “Isn't that kind of a red flag, though, where it's like, they instantly want to see you?”
• Alexis: “It's at least, like, a pink flag.”

Jack reassures them that Naomi seemed genuine and interested, mentioning that he considered meeting her in person to validate her authenticity.

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The Deception Unfolds

Timestamp [05:23] – The Date’s Progression

Jack recounts how the date unfolded:

1. Meeting Spot: They met at a bar.
2. Apartment Viewing: Naomi suggested visiting an apartment she was interested in.
3. Brief Interaction: After the apartment visit, they returned to the bar, where Naomi suddenly had to leave due to an alarm she set on her phone.

• Jack: “She had set an alarm on her phone and it was probably like 15 minutes of the date had gone by.”

Confusion ensues as Brooke and Jeff probe deeper into the abrupt departure, questioning the nature of the alarm and the haste in Naomi’s actions.

Timestamp [07:57] – Attempts to Reconnect

Three weeks after the date, Jack hasn’t heard back from Naomi. Desperate for answers, he even visits her former apartment, leading to suspicions that he might have been deceived.

• Jack: “If she never gets back to me, I'll just always kind of be wondering what could have happened. And what did happen.”

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Confrontation and Revelation

Timestamp [09:22] – Calling Naomi

In a dramatic turn, Brooke and Jeff decide to call Naomi live on air to seek clarity for Jack. Naomi reveals her true intentions:

• Naomi: “I basically just used him.”
• Jeff: “How?”
• Naomi: “I was going to go look at the apartment, but I needed someone to distract whoever was showing the apartment so I could get the necklace.”

Naomi explains that she orchestrated the meeting with Jack to retrieve a locket from her ex-boyfriend’s apartment. Her plan involved distracting Jack, placing the locket in his jacket pocket, and later retrieving it discreetly.

• Naomi: “I slipped the locket in his jacket pocket while I kissed him.”

Despite her manipulative actions, Naomi claims the locket retrieval was successful and expresses regret for using Jack:

• Naomi: “I'm not interested in dating him. You... sorry.”

Timestamp [15:09] – Host Reactions

Brooke and Jeff react to Naomi’s confession with a mix of disbelief and criticism, emphasizing the unethical nature of her actions.

• Brooke: “I don't get it. Like, I don't either.”
• Jeff: “It's an extremely intricate plan just to get a piece of jewelry back.”

Jack expresses his confusion and disappointment, highlighting the emotional toll of the interaction.

• Jack: “I just want you to know, like, I do think you're a pretty bad person.”
• Jeff: “You're a very pretty, but bad person.”

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Hosts' Reflections and Final Thoughts

Timestamp [16:40] – Moving Forward

Brooke and Jeff discuss the implications of Naomi's actions, pondering whether Jack could find closure or if similar situations are inevitable in the dating landscape.

• Jeff: “Now's your chance, because Naomi Jack's been listening this entire time on the other line and wants to hear you tell him off to his face.”

They touch upon the potential for listeners to learn from Jack’s experience, emphasizing the importance of intuition and caution in online dating.

• Brooke: “I am so sorry. This has gotta be sucky.”

The episode concludes with a reflection on the unpredictability of dating and the value of seeking answers post-date, reinforcing the podcast’s mission to provide insights and closure for its listeners.

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Notable Quotes with Timestamps

• [03:25]
  Jeff: “Isn't that kind of a red flag, though, where it's like, they instantly want to see you?”

• [09:43]
  Jeff: “We are a morning radio show called Brooke and Jeffrey in the Morning.”

• [11:00]
  Naomi: “It was totally using him. It was exactly the same.”

• [13:27]
  Brooke: “I don't. Like.”

• [14:20]
  Jeff: “I didn't mean it as a compliment.”

• [15:32]
  Jeff: “Hey, he called you pretty, Naomi.”

• [16:22]
  Jeff: “Just imagine how effective he would be if he was in on the plan.”

---

Conclusion

This episode of Brooke and Jeffrey: Second Date Update masterfully navigates the complexities of online dating through Jack’s unsettling encounter with Naomi. By providing a platform for confrontation and seeking the truth, the hosts illuminate the challenges individuals face in discerning genuine connections from manipulative intentions. The episode serves as a cautionary tale, encouraging listeners to remain vigilant and trust their instincts in the ever-evolving landscape of modern romance.

Transcript

[Ryan Seacrest]

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[Unknown]

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[Brooke]

Maybe get a little Saturday treat for you. This is a classic. Okay, so if you have binged all, what, 5,000 second dates that we have, somehow so many of you have. Yeah, I'm impressed. You may have heard it, but if you haven't and you're a normal person, then enjoy it because I think you're gonna love it. And don't forget, we do have second date update merch for sale right now with 100 of proceeds going to a great charity called Convoy of Hope. So we don't see any money from it. And you look really cute, very SoCal style. We got hoodies, we got the crew neck sweatshirt, we got T shirts. So check it out. The link is in the show notes. And hey, enjoy this podcast.

[Jeff]

Second date update Question for Jose and Alexis. What is the quickest that you've ever gone from matching with someone to meeting up with them? Oh, wow, like a couple days. Couple seconds.

[Brooke]

Seconds. I saw minutes in Alexis's eyes.

[Jack]

Hey, cutie.

[Jeff]

What's up? I'm here.

[Brooke]

It depends if I'm already stalking them or not. Probably a week. A week, around the same.

[Alexis]

I. I normally just match to feel like I'm attractive and then I never meet up.

[Brooke]

You guys don't just like go to the bar and find out who's closest and then figure it out? Okay, we're not. I never done. I never got to do dating apps. I just thought that would always be my plan.

[Jeff]

Well, I bring it up because one of Our listeners. Jack says he was surprised at how fast he got the green light to see his date in person.

[Ryan Seacrest]

Wow.

[Jeff]

So, Jack, welcome to the show.

[Jack]

Hello. Thank you.

[Jeff]

I am excited to hear about your date. And then after this, you want to grab a drink or something?

[Brooke]

I'm just saying, he's looking for a man that moves fast.

[Jeff]

Jack, what's the name of the person that you matched with?

[Jack]

I matched with this girl named Naomi online.

[Alexis]

Jack and Jeff sound better. That is also a pretty name.

[Jeff]

And how long did it take for you and Naomi to agree to meet up?

[Jack]

It was really quick. We matched and, like, within 10 minutes, she was asking me to meet up.

[Brooke]

10 minutes.

[Alexis]

That's a record.

[Jeff]

She must be quite the smooth talker.

[Brooke]

Either that or it was, like, two in the morning and she was drunk.

[Alexis]

And Brooke is right. You were, like, at the same bar.

[Brooke]

Sitting next to each other.

[Jeff]

I didn't think about that. That's a good question.

[Brooke]

What time of day did this happen?

[Jack]

This is kind of like early morning. And then she wanted to beat up that afternoon.

[Brooke]

Oh, wow. Cool. I mean, were you excited about that, or were you freaked out?

[Jack]

No, I was excited. She was really cute, and she seemed interested.

[Brooke]

Oh, yeah.

[Jeff]

Isn't that kind of a red flag, though, where it's like, they instantly want to see you?

[Alexis]

It's at least, like, a pink flag.

[Brooke]

I don't know. Maybe she had a date planned and the other guy bailed, and she's like, well, let's fill in the blank again.

[Jeff]

I'll take anybody.

[Alexis]

I don't have standards.

[Jeff]

As long as it's a warm body.

[Jack]

Well, she explained that she was, like, new on the app, and she's looking to date someone, and I seem like a nice guy, so she wanted to grab a drink with me at this bar.

[Brooke]

Okay, and you didn't at any point think you were getting catfished? Like, too convenient? You must be a robot.

[Jack]

Yeah, that thought definitely crossed my mind. But it's not like she wanted a phone number or anything. She wanted to meet up, so I was gonna find out that day.

[Jeff]

Okay, cool.

[Brooke]

I think it would be kind of refreshing, because suddenly you're just meeting with this person, and you don't know a lot about them. Instead of having all of that small talk out of the way, like, you have a lot to discuss.

[Jeff]

How did it go?

[Jack]

It was amazing. She was, like, really, really pretty, and she laughed at all my jokes. But we really weren't there long until some alarm went off, and she said she had to go.

[Brooke]

What?

[Jeff]

Wait, what type of Alarm.

[Jack]

She had set an alarm on her phone and it was probably like 15 minutes of the date had gone by.

[Brooke]

Was she doing her own speed dating?

[Jeff]

Another guy came in and took her seat.

[Alexis]

She's like, I've to ask you to get up, actually.

[Brooke]

Well, she didn't give you any other explanation?

[Jeff]

Yeah. What happened?

[Jack]

She's like, I'm supposed to go check out this apartment nearby. Do you want to go with?

[Brooke]

That's great.

[Jeff]

She does move fast. Already asking you to move in.

[Alexis]

Is that weird? I think a lot of people would think that's a fun idea to go check out apartments or like a house.

[Jeff]

Together on a date. Is that what you thought, Jack?

[Jack]

Yeah, it was a little surprising that first she wanted to meet really quickly and then she wants to check out this apartment. So I didn't really know what was coming next.

[Brooke]

I have a baby to deliver later. Do you want to come with me?

[Jeff]

Let's go to this tuxedo shop and then go to the church right after. What do you think?

[Alexis]

The wedding officiants waiting in the apartment.

[Jeff]

That's weird to us. But tell us how it went.

[Jack]

Well, we went to this apartment together and I'm talking with the lady showing her around and imagine. So Naomi, she loves the place and she actually like, gave me a big kiss in front of the apartment manager and.

[Brooke]

Oh, it's awkward for the apartment manager.

[Alexis]

I would be like, I need you to leave. Actually, this is ours now.

[Jeff]

We really need to test this place. The floors.

[Brooke]

That had been unexpected. What happened next?

[Jack]

So we just went back to the bar and the chemistry felt really good. And she just went to the bathroom and never came back.

[Brooke]

No.

[Jeff]

Wait, what?

[Brooke]

Why did you say that so casually?

[Jeff]

We were vibing and clicking and then she was gone.

[Unknown]

What do you mean?

[Jack]

I don't know. I don't know what happened.

[Alexis]

We knew she was.

[Brooke]

Red flags. Just saying. That's so strange. Yeah, because it's not like she was using you for anything. Right? Like, she didn't ask for any money. Right. She didn't ask you to co sign on the apartment.

[Jeff]

She went so fast with everything else. Maybe that's just how long her relationships normally. Normally last. Like, she can't go a full 24 hours.

[Alexis]

It's been 34 minutes. We're broken.

[Jeff]

How long ago was that?

[Jack]

That was like three weeks ago. And whoa, she hasn't called me back or anything. I even went to the apartment to see if she had moved in and.

[Brooke]

Creepy.

[Jack]

I know, I know, but that's the only thing I could think of to try and get a hold of her because she wasn't answering.

[Brooke]

Weird.

[Jeff]

I mean, so it's been three weeks.

[Brooke]

This is like a mystery.

[Jeff]

It is. It's a big mystery.

[Jack]

Rol.

[Alexis]

Roller coaster, highs and lows.

[Jeff]

With the pace that she moves through things, who knows? She probably could have been married and divorced six times over in that span of time. But we'll call her and try and figure out the real reason when we do your second date update right after this.

[Jack]

Awesome. Thank you.

[Jeff]

All right, hold on, man. Second date update. We just heard maybe the quickest hangout in second date history.

[Alexis]

Yes.

[Jeff]

I mean, I know I've had a few lightning rounds, and I'm not calling a radio station after those to find out what happened.

[Brooke]

No, you're just talking about him now.

[Jeff]

Definitely. I mean, that's a mess for them to clean up. That's their deal. But one of our listeners, Jack, met a girl named Naomi online. They met up the same day that they matched, saw an apartment together, went back to a bar, and then she disappeared into the bathroom forever, Never to be seen or heard from again.

[Brooke]

That's so crazy.

[Jeff]

Actually, some of my lightning rounds happened in public bathrooms, so don't even get me started on that.

[Brooke]

Thank you.

[Alexis]

I think we're already done with those.

[Jeff]

It's over. It's been three weeks, though, since that happened with Jack. And we never asked, though. Is there anything, Jack, that you think you may have done wrong? Like when she kissed you, did you hold eye contact with the lady showing the apartment?

[Brooke]

No.

[Jack]

No, I did not.

[Brooke]

Thank God.

[Jeff]

Oh, maybe you should have.

[Jack]

No, I really don't think I did anything wrong. It was a really nice date.

[Brooke]

How come now you don't sound angry? I'd be a little mad if somebody ditched me in the middle of the date. That's humiliating.

[Jack]

I'm just kind of confused more than anything.

[Brooke]

Okay.

[Jack]

Like, if she never gets back to me, I'll just always kind of be wondering what could have happened. And what did happen.

[Brooke]

Was she even real?

[Jeff]

Just like what my lightning rounds think of me. Yeah, let's get some answers for you here. I'm going to dial Naomi right now, and hopefully she picks up. We'll see what she has to say. Here we go.

[Unknown]

Hello?

[Brooke]

O, she's there.

[Jeff]

Hey, is this Naomi?

[Unknown]

Yeah. Hi.

[Alexis]

Quick, ask her questions before she answers.

[Brooke]

You gotta move fast, Jeff.

[Jeff]

I'm not good under pressure. What?

[Unknown]

What?

[Alexis]

Oh, no.

[Brooke]

This is like the lightning rounds.

[Unknown]

Come on.

[Brooke]

Hi, Naomi.

[Unknown]

Hi. Who is this?

[Alexis]

Sorry.

[Jeff]

Thank you for asking a question. I can Answer that. We are a morning radio show called Brooke and Jeffrey in the Morning.

[Unknown]

Okay.

[Jeff]

And we're reaching out on behalf of one of our listeners that you went on a date with the other day.

[Brooke]

A couple weeks ago. Three weeks ago.

[Jeff]

Three weeks ago. His name's Jeff.

[Unknown]

Wait, why are you calling me about him?

[Jeff]

Well, because he reached out to us because he's a little bit confused about what happened when you disappeared. And that's what we do in this segment called A Second Date Update. We try and help give some answers to people who have questions after a date.

[Unknown]

Oh, yeah. Yeah, he probably does have questions.

[Brooke]

Okay. So you. You would understand why he's so confused.

[Jeff]

Yeah.

[Unknown]

Yeah, totally.

[Jeff]

Could you help maybe shed some light on what went down? Because he has no idea.

[Unknown]

Yeah.

[Alexis]

Think from his perspective.

[Jeff]

He had a lot of nice things to say. He thought you were a really great person.

[Brooke]

Yeah, I think he's a great person.

[Unknown]

No, he is. He is nice. He's really nice. That's. That was part of it.

[Brooke]

That was part of it.

[Unknown]

This is so weird to say. I don't really want to say it. Like, I basically just used him.

[Brooke]

What?

[Alexis]

Oh, man.

[Jeff]

Wow. How?

[Brooke]

That was like a band aid just got ripped off.

[Jeff]

I don't understand. From what we've heard, you guys went to a bar. He went and checked out an apartment with you, you guys went to a bar again, and then you left. How is that using him?

[Unknown]

It was totally using him. It was exactly the same.

[Brooke]

Free drink.

[Unknown]

Yeah.

[Jeff]

For what?

[Alexis]

If it was just for drinks, why take him to the apartment?

[Unknown]

I know. That was fine, though. I'm not. I'm not, like, proud of using him.

[Brooke]

But I sound a little proud.

[Unknown]

I am kind of. I'm kind of proud of my plan. Like, I. I think I had a really good plan.

[Brooke]

I don't get it. Like, I don't either.

[Jeff]

Yeah.

[Brooke]

You didn't even get the apartment. He went back there.

[Unknown]

No, I know, I know. No, it wasn't. It was. Here's what happened. So that apartment that I was looking at was actually my ex boyfriend's apartment. So he was moving out. I knew he was moving out, and I used to stay there a lot. Obviously we were together. And I had left a locket, a really awesome locket that my dad had given me there, and he had refused to give it back to me.

[Brooke]

I don't know why exes do this. Okay.

[Unknown]

Total jerk. Like, just a total jerk move right there. He wasn't giving it back to me, so I figured out a way to get it back which was basically, I was going to go look at the apartment, but I needed someone to distract whoever was showing the apartment so I could get the necklace.

[Brooke]

Why wouldn't you just invite a girlfriend or something?

[Unknown]

No, no, no, no. Scratch. Just wouldn't be as fun. So I go online.

[Jeff]

Okay, you get Joy out of this.

[Unknown]

It was a good plan. It's a good plan. It was, like, sneaky.

[Jeff]

It is very sneaky. Not arguing that.

[Unknown]

So I go online and I find this guy who seems really nice and truthfully, a little easy to manipulate. And he's available that day, which is perfect. That's what I need. And so, you know, I haven't. Meet me at this bar. We, like, kind of get to know each other, and then we go look at this apartment. And the only thing I hadn't, like, thought out the one little, like, snafu, was that I did not have a jacket with my pockets. And I had, like, no other pockets. So I'm like, thinking on the fly. And at the end of this apartment viewing, I reach in and I, like, give him a kiss, and I slip the locket in his jacket pocket while I kiss him. I'm thinking, is brilliant. So smart, right?

[Brooke]

I don't. Like.

[Unknown]

He's totally feeling it. The apartment lady's like, oh, yeah, they're such a cute couple. Also, by the way, if she happens to, like, suspect anything, he has the luck and he gets in trouble. And, like, I don't get in trouble. It's smart. It's smart.

[Jeff]

Yeah, you always need a fall guy whenever you're getting your stuff back.

[Brooke]

How would you get it back out of his apartment? Out of his pocket. Pocket, though, because you left him.

[Unknown]

So we go back to the bar and we're chatting, and he hangs up his jacket. I'm like, oh, this is perfect. So I just reach in stealthily, 007 style, and I get my necklace, excuse myself to the bathroom, and I'm out.

[Brooke]

Wow, that is so cold hearted.

[Jeff]

It's an extremely intricate plan just to get a piece of jewelry back. I mean, you went full Ocean's 11 for this?

[Unknown]

Lock in, yes. Ocean's 11.

[Brooke]

But why?

[Jeff]

I didn't mean it as a compliment.

[Brooke]

But why did you have to ditch Jack? Like, I don't understand.

[Unknown]

I wasn't interested. Like, I didn't want to date him. I like, he's not my type at all.

[Jeff]

Well, you know what? I don't. Don't say that to us. Jack deserves to hear that from you directly. And, well, now's your chance, because Naomi Jack's been listening this entire time on the other line and wants to hear you tell him off to his face.

[Unknown]

Are you kidding me?

[Jeff]

I'm serious.

[Jack]

Wow. Hi, Naomi.

[Brooke]

Oh.

[Unknown]

Oh, my gosh. I didn't know you were on the phone.

[Jack]

I don't even know what to say to you. This is crazy. You could have just told me. I would have been down to do the Ocean's Eleven, Brad Pitt and Clooney style.

[Jeff]

Really?

[Brooke]

I mean, honestly, like, for like a hot girl says, hey, you want to help me?

[Jeff]

Like, you want to help me steal from my ex boyfriend's apartment?

[Brooke]

I feel like.

[Unknown]

No, but it's not stealing. It's my necklace.

[Brooke]

Yeah.

[Unknown]

And I'm not interested in dating him. You. Sorry.

[Jack]

I just want you to know, like, I do think you're a pretty bad person.

[Brooke]

Yeah.

[Jeff]

Hey, he called you pretty, Naomi.

[Ryan Seacrest]

That was nice.

[Brooke]

Is that what you heard, Jeff?

[Jeff]

You're a very pretty, but bad person.

[Brooke]

Yes.

[Unknown]

Sorry you feel that way. I just think it would smart and, like, what? You. You met up with a girl, you got a drink, and then that's it, like nothing bad happened to you?

[Brooke]

It's a good point, Jack. I am so sorry. This has gotta be sucky.

[Jeff]

Well, hold on. There's a. I think there's an opportunity here. You guys are all looking at the negatives here. Jack, are there any items that your ex girlfriends have that you'd like to get back? Naomi seems like the type that be happy to be your accomplice.

[Jack]

Yeah, I am happy. Never talking to Naomi again, actually.

[Jeff]

Come on, Jack, you don't mean that. Ocean's Eleven had at least two sequels.

[Unknown]

We do work well together.

[Alexis]

He didn't know he was worthy.

[Jeff]

Just imagine how effective he would be if he was in on the plan.

[Unknown]

I don't know. I don't know. I don't know. I think he would compromise it.

[Alexis]

Yeah, he'd be nervous.

[Brooke]

Jack. All right, I don't think this is a real loss for you.

[Jack]

Yeah, no, I'm picking up on that. I should have really gone with my gut and known. It was too good.

[Jeff]

Oh, my God. Do you realize that's exactly what Andy Garcia said at the end of Oceans when he found out he got taken for $2 billion. Jeffrey, the prophecy's being fulfilled. It's meant to be.

[Brooke]

We did it.

[Ryan Seacrest]

Brooke and Jeffrey in the morning.

[Unknown]

Time is precious, and so are our pets. So time with our pets is extra precious. That's why we started Dutch. Dutch provides 247 access to licensed vets with unlimited virtual visits and follow ups for up to five pets. You can message a vet at any time and schedule a video visit the same day. Our vets can even prescribe medication for many ailments and shipping is always free. With Dutch, you'll get more time with your pets and year round peace of mind when it comes to their vet care.

[Ryan Seacrest]

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[Unknown]

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