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Brooke
Hey, welcome to in a brand new episode on your second date update podcast. Thanks for being here. And I'm sure Alexis has something to say about all of the birthday wishes she got yesterday. Oh, yeah.
Alexis
That was really nice of you guys. Thank you. I love feeling so lovely at the same time, like, stop too much, you know?
Brooke
But anyways, compliments are not.
Alexis
Yeah, that's the way to describe it.
Brooke
Yes, Alexis, you're stupid. That's better.
Alexis
Thank you. What a gift. But more about the blind love is we did yesterday.
Brooke
Oh, my God. And the guy who wanted to do one with Brad says, oh, of course it's a Brad. Do you know his name? Because you guys have been texting.
Alexis
I know his name because I'm reading the comments right now and I thought I made it pretty clear during the break. The vibe. Okay, but I don't know why the comments aren't really getting the vibe we got. I hope she gives Brad a chance. He wouldn't shoot his shot if he didn't think there was a chance.
Dennis
Yeah.
Alexis
Or I think Alexis likes him. Or Alexis. I feel the chemistry there and I'm like, are you people being for real? I feel like I can't even.
Jeffrey
So can I just make an assumption? These are all men. We're not good at reading vibes.
Alexis
Maybe that's why when the server is
Jeffrey
like, hi, guys, having a good day? They're like, she's hitting on.
Alexis
Yeah, you're right.
Jeffrey
So I will just make a blanket statement and say, those are probably all guys misreading.
Alexis
You're right. I'm going to go look for the female comments.
Matt Rogers
Yeah, see, my take was that they were rage baiting you and you completely fell for exos.
Alexis
You got me, everybody.
Matt Rogers
You got trolled.
Brooke
Either way, it's not good. No, it's not good. All right, let's get to your brand new episode. Starting right now.
Second Date Update Announcer
Brooke and Jeffrey in the morning. Second date update.
Matt Rogers
We've heard of people using chat GPT to write their dating profiles for them. People photoshopping themselves with the help of AI looking taller and skinnier and ooh, even my wallet looks fatter. Thanks, AI.
Brooke
Please tell me for the first time ever, we're actually getting AI on the phone because they couldn't get a Second date?
Jeffrey
Oh, please.
Matt Rogers
We're not quite there yet. But how would you use AI after a date to help you get a call back, huh? Well, apparently our listener Dennis figured out a creative way that didn't really work because he needs our help. So I guess we'll get to that in a minute. But first, we do have to get a little bit more information out of him. So first, Dennis, welcome to the show.
Dennis
Hey, thanks. Thanks for having me.
Brooke
Did you type into Chat GPT what to say back to us just then?
Matt Rogers
Are you that reliant?
Jeffrey
It's just listening.
Dennis
No, that was me. That was all me. Oh, wow.
Matt Rogers
Good for you, Dennis. Well, you must be pretty desperate if you're going to AI before coming to us. But tell us about this girl that you want us to call today and how you met her.
Dennis
All right, well, I met Taylor on a dating app. We bonded over my Chat GBT script that I wrote. It was really good.
Jeffrey
Yeah, really good. Like, she knew it was Chat GPT or just in general. She loved your bio.
Dennis
I didn't ask her. I don't know. I mean, she was just getting along. It was working.
Matt Rogers
So did you meet up for a date irl?
Dennis
We met up for a date. We did. We had dinner.
Matt Rogers
Now the pressure's on you to come up with your own questions and talk to her directly. How did that go?
Dennis
Well, I mean, I only use ChatGPT a couple times, you know, during my day to look down at the screen. I don't think she noticed, though.
Brooke
What were you looking for, though? Like, were you looking for, like, cool question prompts or something?
Alexis
Notice you typing a prompt Conversation?
Dennis
Yeah, Things to ask and talk about. Oh, how.
Matt Rogers
How do I compliment her sparkly eyes again without saying the same thing?
Brooke
I mean, it's interesting because you sound like a real charismatic guy that you would be that reliant on this.
Dennis
Well, I get a little shy around girls. Women.
Jeffrey
Got it. Yeah, I understand that.
Matt Rogers
So what did you and ChatGPT talk to Taylor about?
Brooke
I like how it's. We know.
Matt Rogers
Yeah.
Brooke
Two of them on a date.
Matt Rogers
What the two of you come up with?
Dennis
Well, you just gave me some great surface talk, and we talked about family and stuff. Family Also, I wasn't using it the whole time. I would kind of gauge the conversation and figure out where to go, you know?
Jeffrey
Okay, so, like, only if you got stuck. There was a lull.
Brooke
I'll say. I don't know about using it during it, but I don't think it's bad to come up with a list of like, five questions to get you out of a awkward moment in a date. I think that's being prepared.
Dennis
Exactly. And it was ChatGPT that reminded me that I have an older sister and she does too.
Matt Rogers
You didn't remember that you had a sister?
Dennis
Well, I mean, it just reminded me to bring it up, the connection.
Jeffrey
It's like, AI Brownie points.
Dennis
And we're both close to her older sister, so that was nice. You know, we bonded over. She loves country music like I do. I mean, listen, I. I've been on a lot of dates, and there was a lot of sharing and a lot of laughing on this date between us, and it just really felt great.
Brooke
What did ChatGPT tell you to do at the end? Did it tell you to go in for a kiss?
Dennis
It suggested maybe to go for a walk.
Brooke
I didn't know we were actually still going to ask him what to do. I was. That was kind of a joke to get a kiss.
Matt Rogers
Well, that could be romantic. How did the walk go?
Dennis
We're underneath the moonlight. I mean, it was just really pretty and beautiful. I mean, I was just feeling so good, and then I was like, you know, wow, should I go in for the kiss? You know, I was like, did ChatGPT
Matt Rogers
think it was a good idea?
Brooke
Do. You're not writing still at this point? Please tell me.
Dennis
No, I'm not. I'm not on my phone at this time.
Brooke
Oh, my God.
Matt Rogers
Okay, so you're. You're making the decision to go in for the kiss?
Dennis
Yeah. Well, I was going to, but right before I was gonna do it, she kind of, like, snatched or swatted like a bug out of the air, and I was like, is that a sign
Brooke
for me not to, like, she was swatting you away?
Alexis
Go.
Brooke
Shoot.
Dennis
Yeah, I wasn't sure, so I just went in for the hug at the end.
Brooke
Okay, I think that's fine. Was there any talk about future hangouts?
Dennis
Other than her texting me that she got home safely? It's been silence from her since then. It's been like three days.
Matt Rogers
That is weird. Now, going back to what we were saying earlier about using AI after the date to help get you reconnected. You came up with a way to do that? What did you do?
Dennis
I did. I thought it'd be really creative if I had AI help me make, like, a 30 second song about our date and then send it to her. Oh, yeah.
Jeffrey
You can make music on AI?
Matt Rogers
An AI generated song?
Brooke
Yeah.
Matt Rogers
Brooke, you're wincing right now at the thought of it. Why?
Brooke
It's like giving a collage picture book after the first date. It's just a little too quick, too soon. I know it didn't take much effort, but.
Dennis
Well, I. I thought the song was great.
Matt Rogers
Oh, well, you did?
Brooke
Yeah. Maybe we'll play it later. I'd love to hear it.
Dennis
Oh, my God.
Matt Rogers
You know, well, he actually sent us the song.
Dennis
Yeah, I said I sent you guys a song.
Matt Rogers
Is it cool if we played it right now so that you can hear it?
Dennis
Yeah, absolutely.
Matt Rogers
Okay.
Brooke
Oh my gosh.
Matt Rogers
We're load it up. Here's the a generated song he created called Taylor, where'd you go?
Brooke
Oh, oh, wait. That's what we titled it.
Matt Rogers
That's what he titled it.
Brooke
I thought it was a reflection of what a fun night he had.
Matt Rogers
Well, let's listen. I haven't heard
Second Date Update Announcer
talked about our families. You even know my mom's name. You said you loved my playlist playing country in the rain. Then we walked beneath the moonlight. It felt like a movie scene. So Taylor, where'd you go? What does this radio silence mean?
Jeffrey
Is that the new Taylor Swift?
Brooke
No, it was a sad song.
Jeffrey
It's upbeat, but the lyrics are sad.
Matt Rogers
I'd be calling you back after that song.
Dennis
Come on, it was good.
Jeffrey
No, it was good. I mean, those AI songs were cute. The girls.
Alexis
I think it's either funny or clingy. Like I don't know which way you'd take.
Matt Rogers
You don't find it romantic in any way that he put in all the extra effort to have AI write a song for them?
Brooke
It could be funny. I like that spin on it.
Matt Rogers
We'll see what Taylor actually thinks about it.
Brooke
Where'd you go?
Matt Rogers
I'm so alone.
Brooke
Let's play it. Radio silence, man.
Matt Rogers
It's slap for me, but talking with families. Oh yeah, He's jamming out to it. Okay, we're going to come back and then we'll try to get you your second date update AI style with Taylor right after this hold.
Taylor
Brooke and Jeffrey in the morning.
Second Date Update Announcer
Second date update.
Matt Rogers
I'm not gonna lie. Our listener Dennis had a big impact on me just now.
Brooke
Did he really?
Matt Rogers
Cuz he made me want to make an AI generated song for our show.
Jeffrey
Hit it.
Second Date Update Announcer
The first date felt so great. Now they won't even communicate. You're staring at your lonely phone they left you hanging all alone. Don't you worry don't you fear the answers that you need are here. It's the Brooke and Jeffrey second date update. Brooke and Jeffrey's second date update.
Alexis
Yeah, it's like a Disney Channel entry.
Matt Rogers
You got the kids cheering at the end.
Brooke
It did feel like kids incorporated if you're old enough to know.
Jeffrey
Like I said, they all kind of sound the same.
Matt Rogers
Well, not enough references to how handsome I am in the song, but I'll take it.
Brooke
I you who made it.
Alexis
You could have told it.
Brooke
Yeah, you're fairly Literally sings what you say.
Matt Rogers
Room for improvement. But the whole reason I did that, if you missed part one, is because Dennis sent an AI generated country song to his date, Taylor, three days after they met up.
Dennis
Because
Matt Rogers
give the people what they want. Actually, the voice is exactly the same.
Brooke
That's why recording artists don't have to be worried.
Matt Rogers
Yeah.
Dennis
Okay.
Brooke
Where'd you go?
Jeffrey
Yeah. Oh, man. Do we have to call, or can we just listen to AI music the whole day?
Matt Rogers
I wish. He thought that song would be a fun way to help restart the conversation between them. Unfortunately, no dice.
Brooke
I am glad you said it after she had already ghosted you.
Matt Rogers
Yeah. So what else do you have left to lose?
Jeffrey
We know that's not the reason.
Matt Rogers
Something must be up. We're gonna try to figure out what that is and just dial her right now. You ready to do this, Dennis?
Dennis
I am. Thanks.
Matt Rogers
Okay. All right, let's see what she has to say. Here we go.
Brooke
Hello.
Matt Rogers
Hi. Is this Taylor?
Taylor
This is she. Who's this?
Matt Rogers
This is a radio show. We're called Brooke and Jeffrey in the morning.
Brooke
Real people.
Dennis
Hi.
Jeffrey
Good morning.
Brooke
Real radio. Well, I mean, she's gotten a lot of weird stuff sent to her in the last.
Dennis
Yeah.
Matt Rogers
So sorry to, like, burst in on your day, but we're doing this segment right now. It's called the second date update date.
Taylor
Okay.
Matt Rogers
Okay. So basically what that is is where if someone goes out on a date and they're not getting a call back afterwards, we can try to reach out on the person's behalf to see if there's a reason for it. And in this case, we're trying to help out a guy named Dennis.
Taylor
Okay.
Matt Rogers
Okay.
Dennis
Okay.
Brooke
There's somewhat of a smile on your face. It sounds like when we mentioned Dennis
Taylor
a little bit, I would say maybe an awkward feeling.
Brooke
Awkward feeling. That's not always bad, though.
Matt Rogers
No, but Dennis feels like you've been kind of avoiding him because you haven't really been responding to any of his messages. And he isn't sure why he does
Brooke
not feel like it. He knows that she's in voice.
Matt Rogers
That adds to the feeling.
Brooke
Yeah. Is there a reason?
Taylor
I'm. I'm. I'm. I don't know if I feel comfortable discussing this on the radio.
Matt Rogers
Well, you don't have to say anything if you feel uncomfortable with it. It's just Dennis feels very confused because he felt like your date went really, really well.
Taylor
Yeah.
Matt Rogers
So why'd you say, oh, God?
Taylor
Well, I'll give him some creativity points.
Brooke
All right.
Dennis
But good.
Jeffrey
Those are important.
Brooke
For what? What did he do that was creative?
Taylor
I mean, there was a song, but I just kind of felt like our date didn't. It just wasn't what I was expecting. It didn't sit right with me.
Jeffrey
Sit right.
Taylor
I'm not sure if you've ever had this, but I kind of felt like maybe we had more of a connection over the phone, and it's just I'm looking for something more in person.
Brooke
Interesting.
Jeffrey
You guys had more, like, text chemistry than, like, real physical chemistry.
Brooke
Why, in this day and age, do you need something more in?
Matt Rogers
Chemistry is really overrated.
Brooke
Yeah, I mean, you're gonna have to
Jeffrey
have a lot of personal moments you need to click.
Brooke
Could do those online.
Matt Rogers
But. But you did say you gave him creativity points for the song that he sent.
Brooke
Good.
Taylor
I'm saying creativity points, but I didn't find it a little weird.
Jeffrey
Got it.
Dennis
Okay.
Matt Rogers
Both things, like creativity, weirdly close to the heart in that sense, I think
Brooke
maybe more funny, right? You would find it funny.
Taylor
You know, I'm just gonna say that I've been considering other dates at this time. I just feel like something was off with him.
Matt Rogers
Well, you know, before you start doing that and throwing yourself back into the awkwardness of the dating pool, you said that the chemistry with Dennis was off on that date night. Maybe it'll be better right now because he's on the other line listening, waiting to talk to you.
Jeffrey
I can feel the chemistry.
Dennis
Hey. Hi, Taylor.
Matt Rogers
There he is.
Taylor
Like, what are you doing?
Dennis
Hold on, hold on,
Matt Rogers
hold on.
Brooke
What?
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Us.
Dennis
I'm reaching out to see how your lovely day is.
Brooke
Dennis, put the. I mean, I guess don't put the phone down because you're probably talking on
Jeffrey
it, but, like, close the speaker.
Matt Rogers
Just talk to Taylor without help. Brooke, she doesn't know what the situation is.
Jeffrey
How could you not?
Taylor
Okay, I'm just a little confused.
Dennis
About what?
Taylor
I don't know. But, Dennis, you didn't feel like things were off on our date. Hold on,
Jeffrey
Hold on. Let him cook.
Matt Rogers
Let him cook.
Dennis
Things were all. But then we can turn it to on.
Brooke
That is the stupidest line. Dennis, don't read that.
Alexis
And he said she wouldn't notice it on the Phone.
Taylor
Dennis, I'm not really sure if you're understanding what I'm saying, but I feel like there is a disconnect here, Helen.
Dennis
It's just so. Sometimes I get nervous, you know, and like, you like the song, right? The song was okay and.
Jeffrey
Oh, change subject.
Dennis
Well, sometimes. Sometimes I use AI like before our date to start out and a couple times, you know, during the day and you know, then the song, of course.
Matt Rogers
I kind of wish Chat GPT had written that shorter for him.
Jeffrey
Yeah, you see why.
Matt Rogers
Yeah, now I get it.
Taylor
So you're saying the song and when we're talking, everything is AI.
Dennis
Well, I'm not. I mean, a lot. A lot. I mean, me too, but I feel
Jeffrey
like it's just thinking right now.
Brooke
Well, dude, I feel like AI has stunted your emotions as a human.
Jeffrey
Yeah.
Taylor
Is your profile all AI Then?
Brooke
We didn't need to bring that up.
Taylor
AI helped.
Brooke
Yeah, but listen, AI is only as good as the prompt you give it. So he must be a good prompt giver.
Taylor
You guys know this is really weird, right?
Brooke
According to him, everybody uses it to write their dating profiles. Yeah.
Jeffrey
Do you ever use it in your life?
Taylor
I don't think everyone. I mean, I especially don't. I just. I feel like if going to have one on one interactions with another human, maybe AI isn't the best. Like especially on our dates.
Matt Rogers
But the song.
Taylor
No, but the song was also AI. Okay, great.
Matt Rogers
I mean, no other human has asked AI to write a song for you before, right? God, I hope.
Taylor
I guess I wouldn't know, would I?
Jeffrey
Yeah, that's okay.
Brooke
Well, I mean, the thing is, like, you didn't get a good gauge of who he is because he was too reliant. Maybe. Maybe he can back off of AI and you guys can actually see if you're compatible.
Alexis
Can he do that?
Brooke
I don't know.
Dennis
Did you hear what she said? We both have older sisters, you know.
Matt Rogers
No, I don't think Brooke said that just now.
Jeffrey
He just remembered.
Brooke
He's just reading old AI prompts.
Matt Rogers
You're looking at your phone again. Okay, well, he's great at prompts. And maybe this is a good time to prompt you with a question, Taylor, because we'd like to offer to send you on another date with Dennis. And we would pay for it.
Dennis
Come on, Taylor. I'll try to talk to you. Just, you know me.
Matt Rogers
Okay?
Jeffrey
He's just nervous. You understand that.
Brooke
He really was delightful before you
Taylor
guys. Listen, I'm not feeling the art here.
Jeffrey
Look at Dennis stays logged in and
Brooke
you just dude, no, I think it's a lesson. Dennis, Dennis. Just be yourself. You don't need to rely on artificial intelligence. Use your own.
Dennis
Yeah, I'm gonna answer you guys. Okay, hold on.
Matt Rogers
You know, why don't you email us the response to that?
Jeffrey
Actually, we're gonna email it. Give us three different. Separate responses, different styles.
Matt Rogers
Which one do we like the best?
Dennis
Yeah.
Taylor
Guys, I hope that you're all having a great day, but I think I'm gonna go. This feels a little ridiculous. I need to get back to work right now.
Matt Rogers
Okay.
Brooke
I actually thought she already hung up.
Matt Rogers
Yeah. Okay, well, we're gonna say goodbye to you in just a second. Just hold on. Yeah, I got something really good to say.
Jeffrey
Hit the song.
Matt Rogers
Thanks for being here.
Dennis
Hey, hold on. I finally have something started.
Matt Rogers
We're out of time, Dennis.
Dennis
Ah, shoot.
Taylor
Brooke and Jeffrey in the morning.
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Matt Rogers
into 78592 says, can you play the Taylor where'd you go song again? That slaps again.
Jeffrey
It's kind of catchy.
Matt Rogers
We've literally got half a dozen people who actually want to hear the whole song played on our show.
Brooke
Yeah, it's like a country playlist in the range.
Jeffrey
Okay, if the song blows up around the world, who gets the royalties? It's an AI song.
Matt Rogers
Well, wait a minute. The only person who doesn't want to hear it is just Taylor herself.
Jeffrey
Oh, the one it's made for.
Brooke
Where Taylor go? She left.
Matt Rogers
She's gone.
Brooke
That's the follow up song.
Matt Rogers
So no date for Dennis?
Brooke
No. And no new song for us either. I hated that second date.
Matt Rogers
Yeah, no one is requesting the A.I. brooke and Jeffrey second date theme song to be replayed. I'm offended.
Brooke
Yeah, you wanted like that middle part to be like some sort of breakdown where everybody sings along together.
Matt Rogers
So clutch.
Jeffrey
One day, maybe on the show I'll play you guys my intro song to the Giggle Gang. It sounds exactly like what?
Brooke
We just pass on that one too.
Matt Rogers
Yeah, can't wait. But you know what? AI aside, we can help you with your dating life. If you ever need us, email the show. We'll call that person who's not calling you back. You can go check out all of our second date updates online, wherever you get your podcasts at.
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Date: May 8, 2026
Podcast: iHeartPodcasts
This episode centers around Dennis, a listener who went on a first date with Taylor after connecting on a dating app. The unique twist? Dennis used AI (ChatGPT) both to spark conversation on the date and to follow up afterwards—with a custom, AI-generated country song. Taylor ghosted him, and the hosts (Brooke, Jeffrey, Matt, and Alexis) dig into what happened, trying to get Dennis answers and maybe even a second chance. The episode explores the awkward digital-age intersection of technology, modern dating, and authenticity.
Post-date, Dennis tried to reignite the spark by sending an AI-generated country song summarizing their evening and his feelings. He shares the file with the show:
Hosts’ reactions:
Dennis, nervous, attempts to charm Taylor with lines that seem like AI prompts. The hosts and Taylor pick up on his awkwardness.
Taylor asks for more authenticity and questions Dennis’s over-reliance on AI for everything—from his profile to his conversations.
She says she wants “real, one-on-one interactions with another human”—not with AI assistance.
The hosts offer to pay for another date if Taylor gives Dennis a second chance—this time, promising he’ll talk only as himself.
Taylor gently but firmly declines.
The hosts encourage Dennis to rely less on AI and instead trust his own personality.
This episode showcases a modern tech dating faux pas: Dennis leans so hard on AI to communicate and impress that he loses the human element Taylor was seeking. While his AI song is quirky and innovative, it ultimately fails to connect. Taylor values in-person chemistry and authenticity, declining a second date even after Dennis’s explanations. The hosts, through humor and gentle guidance, encourage listeners to put away the prompts sometimes, showing that in love, human connection still trumps algorithmic assistance.
For fans of real, awkward romance—and anyone wondering if using ChatGPT is the secret to dating success—this episode is a funny, insightful cautionary tale.