Second Date Update Classic: High Stakes Higher Stacks

Summary

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Episode Overview: "High Stakes Higher Stacks"

Podcast: Brooke and Jeffrey: Second Date Update
Air Date: January 5, 2026

This "Second Date Update Classic" dives into the real reason why Jennifer was ghosted after what she thought was a great first date with Joshua. The episode centers around themes of modern dating practices—specifically "stacking" (going on multiple dates in a single night)—and how different perspectives on dating etiquette can make or break potential relationships. The conversation is characteristically lively, cheeky, and empathetic in tone.

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Key Discussion Points & Insights

1. Setting the Stage: Jennifer’s Story

• Meet-cute: Jennifer met Joshua on a dating app and made the reservation for their first date herself, wanting to ensure a good spot.
• Mishap: The restaurant overbooked and lost their reservation ([03:29]), so they pivoted and grabbed street burgers instead, turning a potential disaster into a charming evening ([04:04]).
• Bonding Moment: While eating, the two commiserated over bad dating stories. Jennifer told about a date Venmo-requesting $2.47 for half an appetizer, while Joshua shared about a woman who brought her mom to the date ([04:56]).
• Post-date confusion: Jennifer felt a great vibe but was surprised when Joshua didn’t try to extend the date or reach out afterward ([05:46]-[06:05]).

Notable Quote:

“We ended up just wandering around the city and getting burgers at a takeout place and just talking about our bad date experiences.”
– Jennifer ([04:04])

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2. The Ghost & The Reveal

• Joshua Goes Silent: Jennifer reached out several times post-date but got “radio silence” ([07:32]-[07:35]).
• Hosts' Hypotheses: Panel speculates humorously that maybe the burger was bad, or maybe he's just playing it “too cool” ([06:30]).
• Jennifer’s Discomfort: She expresses embarrassment over having to call the show for help ([08:31]).

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3. Joshua’s Perspective: The Truth About “Stacking”

• Joshua Joins: Initially quiet but polite on the phone, Joshua eventually opens up.
• The Stacking Moment: Joshua reveals that Jennifer mentioned she “missed stacking”—having three to four dates a night ([11:16]-[11:36]).
  • Joshua explains: “To me, I just think it's kind of rude to say, like, I miss stacking.” ([11:44])
• Hosts Clarify: Confused at first, the hosts joke about speed cup stacking, then realize she meant serial-dating in the same evening ([11:17]-[11:36]).
• His Takeaway: He interpreted her nostalgic tone as a red flag—he wants long-term, while she seemed to fondly recall the “stacking” lifestyle ([12:16]).

Notable Quote:

“She said she used to stack, which means, like, have three to four dates a night...she literally said she misses it.”
– Joshua ([11:32]-[11:55])

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4. Jennifer Defends Herself

• On the Line: Jennifer is brought into the conversation and surprised by Joshua’s strong reaction ([12:48]).
• Clarification: She insists stacking was in her past and that she's looking for a relationship now, not playing the field ([13:13])
• Hosts Weigh In: Discussion about the pros and cons of “stacking,” and whether it's possible to be truly present when “stacking” ([14:04]).
• Jennifer’s Defense:
  • “I gave every guy I was with an hour and a half. I was fully present in the moment, and I was not thinking about the next guy.” ([14:20])
  • But the hosts express skepticism about emotional investment.

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5. The Resolution: The “Ick” and No Second Date

• Joshua’s Final Word: Even with encouragement and the offer of a paid second date, Joshua stands firm:
  • “No, I got the ick. I'm sorry.” ([15:52])
• Jennifer’s Reaction:
  • “Do you realize no one says no to me?...Whatever. I'll just keep stacking. I'll stack this weekend.” ([15:58]-[16:14])
• Panel’s Epilogue:
  • Empathy for both sides; acknowledgment that “stacking” works for some, not for others ([16:50]).
  • Hosts joke about “dozens of guys on the text board who are DTS—down to stack whenever.” ([17:19])

Notable Quotes:

“I see it like that's your default setting. So I think the anomaly is you having a long-term relationship and that's what I'm looking for.”
– Joshua ([14:46])

“Whatever. I'll just keep stacking. I'll stack this weekend.”
– Jennifer ([16:13])

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Memorable Moments & Quotes with Timestamps

• Joshua defining “stacking”:

  “She said she used to stack...have three to four dates a night...she misses it.” ([11:32]-[11:55])

• Jennifer defending presence on stacked dates:

  “I gave every guy I was with an hour and a half. I was fully present in the moment...” ([14:20])

• Joshua’s dealbreaker:

  “No, I got the ick. I'm sorry.” ([15:52])

• Jennifer’s confident comeback:

  “Do you realize no one says no to me?...I'll just keep stacking.” ([15:58]-[16:14])

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Important Timestamps & Segment Guide

| Timestamp | Segment Description | |-----------|-------------------------------------------------------------| | 00:59 | Hosts set up Jennifer’s scenario | | 02:16 | Jennifer explains how she met Joshua | | 04:04 | Mishap with reservation—date turns to city walk & burgers | | 04:56 | Bad date stories exchanged (Venmo/appetizer, the mom) | | 06:05 | Jennifer reflects on the shortness of the date | | 07:32 | Jennifer reveals she’s been ghosted | | 09:07 | Hosts call Joshua | | 11:16 | “Stacking” explained | | 12:48 | Jennifer enters conversation, defends her comments | | 14:20 | Jennifer: “I gave every guy...fully present in the moment” | | 15:52 | Joshua delivers the dealbreaker (“I got the ick”) | | 16:13 | Jennifer: “I'll just keep stacking.” |

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Tone & Takeaways

• Hosts’ Attitude: Playful banter mixed with genuine curiosity and occasional ribbing.
• Dating Culture Reflected: Sometimes honesty about past dating behavior is interpreted differently depending on viewpoint and timing.
• Key Message: Even a great first date can be derailed by mismatched expectations or values—especially when it comes to how openly we talk about our dating pasts.

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This episode is a perfect example of the show’s entertaining but real exploration of contemporary dating drama—full of mishaps, misunderstandings, and memorable one-liners. With humor and empathy, the panel illustrates just how much our words and histories matter in the unpredictable world of modern romance.

Transcript

[A]

Hey, thanks so much for being here in 2026.

[B]

Wow. Crazy.

[A]

Okay, listen, listen. All right. A little housekeeping. We do have a couple of classics. Okay. Today and Wednesday, and then our brand new second dates are going to start on Friday. Friday, I think. But I think we also have a brand new episode on Thursday.

[C]

Yeah, there will be some new stuff, so just you have to listen every.

[D]

Day to find out.

[A]

Yes. We'll be doing tons of recording and making sure that we've got it stacked for you guys coming up this January. So thank you for being here. Enjoy this classic. And we always love to start with a comment.

[C]

Yes, Liliana said, I just broke up with my boyfriend and as I was stressed waiting for a reply, all I could do was listen to you guys and all I got was a alr. Not even the full word.

[D]

All right.

[C]

Just shortened it.

[A]

Okay, well, you did break up with him via text.

[B]

Yeah.

[A]

So I don't know what you expected back. Like just a thumbs up emoji.

[B]

True.

[C]

But New year, new guys. Liliana. Okay, there we go.

[A]

All right. Enjoy this classic second date.

[B]

Second date update. Is it ever a good idea to talk about your other dates while you're on a date? No.

[A]

I mean, I don't know if you're like commiserating and sharing funny stories back and forth.

[E]

Yeah, that's convo.

[B]

I would say the short answer is no. The longer answer, absolutely not. No. Unless you plan to be on with us because we love to hear the dirt. And I'm just thankful that Jennifer, our listener, is on the phone with us today because apparently she talked about her other dates on her date.

[E]

So unattractive.

[B]

Jennifer. I disagree. I admire your class. Welcome to the show.

[D]

Thank you.

[A]

It's not like talking about, like her ex boyfriend that she's still in love with. Right, Jennifer?

[B]

We don't know.

[A]

That's why I'm asking. Right, Jennifer?

[D]

Right. We were just sharing like, funny stories.

[E]

You both were, right?

[D]

Yeah.

[B]

Good.

[E]

Then that's okay.

[B]

Okay, well, who are you sharing these stories with? What's this guy's name?

[D]

His name is Joshua.

[B]

Okay.

[D]

I met him on the coffee and bagel app.

[A]

Oh, is that still around? We haven't heard of that one in a while.

[B]

I know about the bangle and the candle app, but the coffee one is a different one.

[E]

Coffee meets Bengal. Yeah, I like that one.

[B]

Okay.

[D]

He just looked cute. He had like a. A dog with him in his photo and.

[A]

Okay.

[B]

You know, actually I've heard that guys who have dogs in their photos get 90% more matches no way that makes sense.

[E]

Borrow your dog, bro. I need your attention.

[A]

The whole point is that you can actually keep something alive and care for something outside of yourself. That's the attractive point of it.

[B]

Men, women, are not going to be able to tell if it's your dog and how well it's taken care of. As long as it's in the photo. Just Photoshop one in.

[A]

They're going to know after date one.

[B]

Yeah. Okay.

[E]

Or put a little neck brace on it.

[A]

It is said.

[B]

All we're trying to do is accomplish.

[A]

Sick dog. Dog sick.

[E]

I just want the trick.

[B]

Guys, could you determine his dog's health from the photo?

[D]

Jennifer, it definitely looked like a healthy, cute.

[B]

This is what you're talking about right here.

[E]

You don't need a sick dog.

[B]

I see what you're saying. Okay, now take us to the date with Joshua.

[D]

So I wanted to make the reservation. I said I would make it.

[A]

Is there a reason for that?

[D]

I just, in particular, like, I love food. I love eating out.

[E]

I could relate to that. You're like, I have my favorites. Let me pick the spot.

[A]

You like certain tables. You like all the things.

[D]

Yeah. So I called and made a reservation, but when we got there, they had lost our reservation.

[A]

Oh, no.

[D]

So I guess I should have made it online.

[A]

Did that, like, throw the night off? Did it make you upset?

[D]

I wasn't upset. Like, they apologized, but they were just, like, overbooked.

[A]

Oh, no, that's rude.

[E]

It sounds like it's a popular restaurant.

[A]

I know there's only two of you. It's like, can you squeeze us in somewhere? We'll sit at the end at somebody else's table. No big deal.

[E]

Literally, make a table.

[B]

We'll eat in the alley back behind the restaurant.

[A]

If I get the good food. Jeff. Absolutely.

[D]

It totally turned out to be a good thing because we ended up just wandering around the city and, like, we ended up getting burgers at a takeout place and just talking about our. Our bad date experiences.

[B]

You lumped this experience as to one of the many bad date experiences that you've gone on?

[D]

No, this was just, like, a little bump in the road compared to, like, one time this guy venmoed me, like, $2.47 for half of his appetizer.

[E]

Oh, my gosh.

[C]

Venmo requested you.

[E]

Wow.

[D]

Yeah.

[E]

I was still offended at the.

[B]

Sorry.

[E]

$2, bro.

[B]

Okay, okay.

[A]

So you shared stories like that with him. Did he share stories back with you? Joshua did.

[D]

So he said he had, like, a date who brought her mom and the mom was, like, critiquing his posture on the date.

[A]

Sit up straight, honey.

[B]

Sit up.

[A]

Pull your shoulders back.

[B]

I actually think that's some nice feedback. He probably benefited from it.

[E]

Jeff, you'd be doing that on the date. Excuse me. You're slouching a little.

[B]

So. Okay, now this is a way to be like, you're actually way better than a lot of the D that I go on. It's supposed to make him feel good.

[D]

Yes. Like, we were having a great time, just, like, laughing a lot, and it was just, like, fun.

[A]

And anytime you have, like, a shared experience, whether it's like, a bad day or anything, it can bring you closer to somebody.

[B]

Totally. But this wasn't a bad.

[A]

No, I know, but they're both commiserating over the same thing.

[E]

They have to adapt.

[B]

Gotcha. So how long did this go on for?

[D]

Like, a couple hours. And neither of us had, like, planned anything after, so he just, like, walked me back to my car and. Yeah, I'm not used to, like, a short date like that where it was.

[B]

Just like you expected the date to go on longer.

[A]

Like, did you want him to invite you back to his place? Like, what are your expectations there?

[D]

I don't know about that. It's just like, the vibe was so good. He just didn't even attempt to do anything else.

[B]

Okay.

[C]

Bar or something.

[A]

Yeah. Maybe he's just playing it cool, you know? Like, sometimes if you go out on top, you end it on a high note.

[B]

Yeah.

[A]

It obviously leaves you wanting more. So he did something right.

[B]

Yeah, he's playing it so cool that he's not even calling her back anymore.

[A]

So I guess that is playing it cold.

[B]

We're beyond the cool part, and we just want to help you figure out what happened. Okay, Jennifer? Maybe the burger was bad that he ate.

[E]

It was all it is.

[B]

It was a street burger, so those.

[A]

Are the best kind.

[B]

Yeah, but it is risky. So let's just call him and we'll get your second date update right after this second date update. Our listener Jennifer, is the perfect example of when life gives you lemons, turn them into lemon drops.

[F]

Everybody.

[B]

Oh, yeah.

[A]

I don't think they. I mean, or burgers.

[B]

Well, yeah, yeah, whatever it is. Cuz her dinner reservation fell through. The restaurant overbooked, so she took that and turned it into a fun night of wandering the city searching for street burgers and talking about previous bad dates that went even worse than this one did. And her date Joshua shared his worst dates, too, so it really actually bonded them together. But Jennifer how long has it been since that night?

[D]

Yeah, it's been like a week.

[F]

Okay.

[A]

And you haven't heard anything?

[D]

No, and I've sent like some text messages and nothing. Radio silence.

[A]

Okay, so you're definitely being ignored.

[E]

Thank you for the silent shout out.

[B]

By the way, have you tried sending him a photo? Because if he doesn't respond to that, then you know you're in trouble.

[A]

Photo of what?

[E]

You know of anything.

[C]

No, don't do that.

[A]

Don't ever do that. Don't listen to their advice.

[B]

You can.

[A]

Terrible advice.

[B]

You could send him a photo of me. No, if he's a fan of our show, he would definitely respond to that.

[E]

You think he's mad that she was talking about other dates? Now you want her sending pictures of other guys to him?

[B]

Jeff. I'm just saying if she does and he doesn't respond, then you really know something's off.

[E]

That's the final thing.

[A]

I think she knows before the picture, Jeff.

[F]

Okay?

[A]

She's not an idiot.

[B]

Brooke's saying we're not at rock bottom yet. Let's wait till this call happens and see where we end up.

[A]

What is happening to you today, Jennifer?

[B]

Any last words before I dial these numbers?

[A]

Or any last pictures for Jeff that you want to send?

[B]

Either way.

[D]

I just can't believe I have to do this.

[B]

Yeah, I have to do this.

[D]

You had to call us.

[E]

We're a last resort for people. That being said, with Jeff being in a weird mood, do you want call back tomorrow? This may not be a good call.

[D]

Well, we'll see. We'll find out.

[B]

We're already here. Let's just go through with it. How bad could it get? All right, let's do it.

[E]

You tell us.

[B]

I'll tell you about some of the worst second date updates we've ever done and that'll make you feel better about it. Hold on.

[A]

Just call.

[B]

Okay, here we go.

[F]

Hello?

[B]

Hey, is this Joshua?

[F]

Yeah, who's this?

[B]

Hey, man, this is. A whole radio show is calling you right now. We're called Brooke and Jeffrey in the morning.

[E]

Good morning.

[A]

That was a lot. You came in real hot there, Josh. How are you doing?

[F]

It's Joshua.

[A]

Sorry, sorry. I'm married to a Michael who hates Mike. I get it. I apologize.

[B]

I'm sorry that my host is trying to make this segment all about her and her marriage. But we.

[E]

I was trying to say.

[A]

I understand.

[B]

Okay, we get it. The real thing that we're interested in though, Joshua, is you. And the date that you went on the other night with One of our listeners named Jennifer.

[F]

Okay.

[B]

Yeah.

[E]

Do you remember her?

[B]

You know what I'm talking about?

[F]

Yeah, I remember her.

[A]

Yeah. It sounds like you guys had a really fun night together.

[F]

Why do you know that?

[A]

Great question.

[B]

Oh, yeah, because that's how this segment works. It's called Second Date Update, and we spoke to her about your date, and she's a little bit confused about why she's not getting a call back for a second meetup.

[F]

Really? Yeah. She said that?

[A]

Yeah, yeah, yeah, she said that she had a great time with you. It sounds like you guys laugh together a lot.

[F]

Yeah.

[A]

Is that not accurate?

[F]

No, it's accurate. She's like, a really nice person. She's cute and everything, but.

[B]

Yeah, Your words are saying nice things, but your tone is saying something else. Yeah, it's like, really, the huh wasn't very good.

[F]

I don't. I don't think I know how to say this, but I just don't think I'm the right person for her, you know?

[A]

We don't know because she. I mean, you don't get to decide that. Right? That's what she gets to decide.

[B]

The woman gets to choose who you end up with. You don't get a choice.

[A]

I mean, that's her choice. Right? And she obviously thinks that there's definitely something between you two if she's calling us.

[F]

Yeah, yeah, Definitely her choice.

[E]

Okay, quiet again.

[B]

Something's going on, like. Yeah, can we get your take on the date? Like, did you feel a connection with her?

[F]

I don't know, man. Like, we're wanting different things. I don't know if you know what she's. She's like, into what's called stacking.

[A]

Stacking.

[B]

Stacking.

[A]

Oh, like the cups thing where you do it in competition? I mean, serious.

[B]

The Anna Kendrick song.

[A]

Yeah.

[F]

No.

[B]

Okay. We don't know what that is. Yeah. What is stacking?

[F]

She said she used to stack, which means, like, have three to four dates a night.

[B]

Wait, per night.

[C]

That sounds exhausting.

[E]

Yeah.

[B]

Seriously, is it back to back to back to back or all at the same time?

[F]

I. I don't think it was, like, at the same. We didn't really get into it, but, like, I don't know. To me that just think it's kind of rude to say, like, I miss stacking.

[B]

Oh, she says she misses it.

[F]

Yeah, she literally said she misses it.

[A]

So. So, I mean, I could see, like, I would interpret that as, oh, you. You wish that you were out with someone else right after me.

[B]

Yeah, like that.

[A]

That. Good to hear. I Could understand that.

[F]

And that's why I took her to her car when we finished our burgers.

[A]

Is there any way you could have, like, misunderstood her or.

[F]

No, I don't think I did. She was, like, looking back on it fondly, and it was very real to her. And she was. She very. You could tell?

[A]

Okay, I could totally understand it.

[E]

Doesn't mean she's doing anything wrong, but it does rub you the wrong way.

[C]

It doesn't seem like she likes you a lot.

[B]

We kind of all see where you're coming from. I wonder if Jennifer sees it the same way, because she is on the other line listening to this.

[E]

Jennifer, if you're on the other line.

[B]

With a show, too, right now, stacking.

[E]

Shows, I'm gonna be mad.

[A]

That's just right after us.

[C]

She's good at timing.

[B]

My bad. Jennifer.

[D]

Hey, Joshua. I didn't think you would be so offended by what I said.

[F]

Oh, so you, like. You set this whole thing up? Like, you're on the phone here and you called him?

[D]

Yeah, because I was so confused. I was like, I thought we had such a good time, but I guess it's because I said I missed stacking, which I was just. I mean, that was just a fun time in my life. Like, it's not something I do anymore. I want the same thing you want, which is a relationship.

[E]

But you missed.

[D]

It was a fun time.

[A]

It just feels like maybe that's a conversation you have with your, like, best friend.

[B]

Yeah, I miss my whole face, girl.

[D]

Yeah, that sounds like someone who's never stagged before saying that.

[A]

Well, it is. Because how could you ever, like, be invested enough to find out if you were interested in someone if you were just constantly thinking of the next person you were going to see?

[D]

I hear you guys talk about this all the time. And, Brooke, you've said it's okay to date multiple people to find out who you like.

[A]

That's true.

[B]

It's contradictory to what your advice always.

[E]

Is not what she means.

[B]

Like, you said, get it in as many times as possible before it's gone forever.

[A]

It has. Not what I've said, but I. I think dating lots of people is great. It's just like, if you're gonna ask someone to give you their evening, you also have to invest not just being there, but, like, your presence. Like, how can you be present?

[E]

Well said, Brooke.

[B]

You should have brought her presents.

[D]

Dude, I gave every guy I was with an hour and a half. I was fully present in the moment, and I was not thinking about the next Guy. I gave him that time fully.

[E]

I almost missed my next guy.

[B]

I mean, it worked for her.

[C]

She had a boyfriend after that for years.

[B]

I mean, that's how you see it, Jennifer, but clear Joshua sees it a different way. Right, Josh? Ooh, I don't want to mess that up.

[F]

I see it like that's your default setting. So I think the anomaly is you having a long term relationship and that's what I'm looking for.

[D]

We're looking for the same things. That's what I want. That's just something that's in the past. And by no means did I stack that night when you took me to my car. I was not seeing another person after you guys.

[C]

That's actually cute because she said not. Makes me think she did.

[A]

Yeah, that's how I feel. That's exactly how I feel. I'm just a dumb guy.

[E]

I easily am tricked.

[B]

Not that night, but the next five nights she stacked.

[E]

That's different.

[F]

Brooke.

[D]

You're supposed to be on my side.

[A]

Yeah, well, you said dumb things on a date. I don't know what you're talking about. I mean, the thing is. The thing is, Joshua, she's on the phone with us. She's put in a lot of effort to see you again. So, I mean, maybe that's proof enough that she's over her old ways.

[B]

Yeah, and that's why I would like to ask you, Joshua, if you'd be willing to meet up with Jennifer one more time and we would pay for it. And the next date, and the next date and all the sack dates after that. Just you though.

[F]

No, I got the ick. I'm sorry.

[A]

Oh, can't fix that.

[B]

Oh, no.

[A]

Okay.

[D]

Joshua, do you realize no one says no to me?

[E]

Oh, that's why she's been sad.

[A]

Oh, God, that's not true anymore.

[F]

Yeah, no sign.

[D]

It's his choice. Whatever. I'll just keep stacking. I'll stack this weekend.

[B]

You said you didn't want to do that anymore.

[D]

All right, well, it makes me happy. It's fun. I'm feeling sad now, so it's going to get me out of that funk.

[E]

Back to, back to back to feed ya. Yes, that'll make you happy.

[B]

That's where true happiness comes from. Look at Jeffrey in the morning. All right, so no second date there. And Jennifer has hung up. She's not on the line with us anymore. But Jennifer, if you're listening out there, I just want to say I know you're probably disappointed with one person on this show who didn't support you, but the rest of us here have your back.

[A]

I know you're looking at me, Jeff. She's like, I just really miss dating lots of men at the same night. I mean, no one would feel special.

[B]

Yeah, but you understand where she's coming from, right, bro?

[E]

You miss it, bro.

[A]

I have never had multiple dates in one night.

[E]

Wow.

[A]

I could not pull that off.

[E]

Okay, remember she used to tell us how good of a liar she was?

[B]

Yes, Brooke, unstackable is the definition.

[E]

One at a time.

[B]

There's no lights on there. The good news is we've got dozens of guys on the text board who are DTS and down to stack whenever. So, Jennifer, you stay positive. Yeah, we don't like that. That's weird. It'll happen for you, Jen. And if you're into stacking videos, you can always watch a bunch of ours on YouTube. Got all of our second date updates on there. You can like share and subscribe all of it at Brooke and Jeffrey.