Brooke and Jeffrey: Second Date Update - Second Date Update: Taylor Where'd Ya Go

Episode Date: May 8, 2026

Dennis wrote a SONG for Taylor after their night out and he’s not getting a call back. In exchange for our help with a Second Date Update he’s gonna let us PLAY IT on air too!See omnystudio.com/listener for privacy information.

Another podcast from some SNL late-night comedy guy, not quite. Unhumor me with Robert Smygel and Friends. Me and hilarious guests from Bob Odenkirk to David Letterman help make you funnier. This week, my guest, SNL's Mikey Day and head writer, Streeter Seidel, help an a cappella band with their between songs banter. Where does your group perform? We do some retirement homes. Those people are starving for banter.

Listen to humor me with Robert Smigel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcast. Imagine an Olympics where doping is not only legal but encouraged. It's the enhanced games. Some call it grotesque. Others say it's unleashing human potential. Either way, the podcast's Superhuman documented it all, embedded in the games and with the athletes for a full year.

Within probably 10 days, I'd put on 10 pounds. I was having trouble stopping the muscle growth. Listen to Superhuman on the I-Hard Radio app, Apple Podcasts, or wherever you get your podcasts. My mother-in-law spent years sabotaging our relationship until karma made her pay for it. All right, Sophia, tell me about how we started this story. She moved in for two weeks, lasted five days, left a mess, and then pressed her ear against their bedroom door and burst in screaming. When kicked out to a hotel, she called her son-in-law's workplace, pretending his partner had been rushed to the hospital by ambulance.

She faked a medical emergency? And spoiler, that was just the beginning. To find out how it ends, listen to the OK Storytime podcast on the IHeart Radio app, Apple. podcast or wherever you get your podcasts. Hey, this is Robert from the Stuff to Blow Your Mind podcast. Joe and I are both lifelong Star Wars fan, so we're celebrating May the 4th with a brand new week of fun, thought-provoking Star Wars-related episodes. Join us as we tackle science and culture topics from a galaxy far, far away, such as the biology of tauntons and wampas on the ice planet hot, or the practicality and corporate business sense of the Sith rule of two. Listen to stuff to

your mind on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. On the Look Back at it podcast. From 1979, that was a big moment for me. 84 was big to me. I'm Sam J. And I'm Alex English. Each episode, we pick a year, unpack what went down, and try to make sense of how we survived it with our friends, fellow comedians, and favorite authors.

Like Mark Lamont Hill on the 80s. 84 was a wild year. I mean, it was a wild year. I don't think there's a more important year for black people. Listen to look back at it on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, welcome to it 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, that was really nice of you guys. Thank you. I love feeling so loving at the same time. I'm like, stop! Too much! But anyways. Compliments are not her forte. Yeah, that's the way to describe it.

Alexis, you're stupid. That's better. There you go. What a gift. But more about the blind love is we did yesterday. Oh, my God. And the guy who wanted to do one with Alexis. Oh, of course it's a Brad.

Do you know his name because you guys have been texting? 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 a shot if he didn't think there was a chance. 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. So can I just make an assumption these are all men. We're not good at reading vibes. Maybe that's it. This is why when the server's like, hi guys, having a good day, they're like, she's hitting on me. Yeah, you're right. So I will just make a blanket statement and say those are probably all guys misreading. You're right.

I'm going to go look for the female comments. Yeah, see, my take was that they were rage-baiting you and you completely fell for the Lexus. You got trolls. Either way, it's not good. No, it's not. It's not good. All right. Let's get to your brand new episode starting right now.

Brooke and Jeffrey in the morning. Second date update. We've heard of people using chat GPT to write their dating profiles for them. Yeah. People photoshopping themselves with the help of AI looking taller and skinnier. Ooh, even my wallet looks fatter. Oh, no. Thanks, AI.

Please tell me for the first time ever we're actually getting AI on the phone because they couldn't get a second date. Oh, no. We're not quite there yet. But how would you use? would you use AI after a date to help you get a call back? Huh. 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. Hey, thanks. Thanks for having me. Did you type in to chat, GBT, what to say back to us just then? Are you that reliant? No, that was me.

That was all me. Oh, wow. A freestyle. Good for you, Denny. 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. All right. Well, I met Taylor on a dating app.

We bonded over my chat TVT script that I wrote. It was really good. Hold on. What do you say really good? Like, she knew it was chat GPT or just in general? She loved your bio. I didn't ask her. I don't know.

I mean, she was getting along. It was working. Oh, yeah. Don't stop them. Yeah. All right. So did you meet up for a date, IRL? We met up for a date.

We did. We had dinner. Now the pressure's on you to come up with your own questions and talk to her directly. How did that go? Well, wow. I mean, I only use chat CBT a couple times, you know, during my day to look down of the screen. I don't think she noticed, though.

What were you looking for, though? Like, were you looking for, like, cool question prompts or something? She didn't notice you're typing a prompt to chat. Conversations. Yeah, things to ask and talk about. How do I compliment? her sparkly eyes again without saying the same thing. I mean, it's interesting because you sound like a real charismatic guy that you would be that reliant on this.

Well, I get a little shy around girls women. Got it. Yeah. I understand that. So what did you and chat GPT talks to Taylor about? I like how it's we now. There's two of them on a day. What would the two of you come up with? Well, it just gave you 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. Okay, so like only if you got stuck or there was a lull. 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. Exactly. And it was chat TBT that reminded me that I have an older sister and she does too. You didn't remember that you had a sister? Well, I mean, it just reminded me to bring

up. The connection. It's like AI Brownie points. And we're both close to her older sisters, so that was nice, you know. We bonded over she loves country music like I do. I mean, listen, 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. What did chat GPT tell you to do at the end? Did it tell you to go in for a kiss? It suggested maybe to go for a walk. I didn't know we were actually still going to ask it what to do. Okay, I was kind of a joke.

Give me a walking path to get a kiss. Well, that could be romantic. How did the walk go? 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, eh.

Did chat GPT think it was a good idea? Dude, you're not writing still at this point. Please tell me. No, I'm not on my phone at this time. Oh, thank you. Okay. So you're making the decision. go in for the kiss.

Yeah, well, I was going to, but right before I was going to do it, she kind of like snatched or swatted like a bug out of the air. And I was like, is that a sign for me not to? Like she was swatting you away? Go, shoot. Yeah. I wasn't sure. So I just went in for the hug at the end.

Okay, I think that's fine. Was there any talk about future hangouts? Other than her texting me that she got home safely, it's been silence. from her since then it's been like three days 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 i did i thought it'd be really creative if i had AI helped me make like a 30 second song about our date and then send it to her oh yeah you can make music on AI an AI generated song Brooke, you're wincing right now at the thought of it.

Why? 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... Well, I thought the song was great. Well, you did. Maybe we'll play it later. I'd love to hear it, you know?

Well, he actually sent us the song. Yeah, I said you guys the song. Is it cool if we played it right now so that we can hear it? Yeah, absolutely. Okay. Oh, my gosh. We're going to load it up. Here's the AI-generated song he created called

Taylor, where'd you go? Oh, wait, that's what we titled it? That's what he titled it. I thought it was a reflection of what a fun night he had. Well, let's listen. I haven't heard you. 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? Uh-oh. Oh, Taylor. Wow.

Is that the new Taylor Swift? No, it was a sad song. It's upbeat, but the lyrics are sad. I'd be calling you back after that song. Come on, it was good. No, it was good. I mean, those AI songs were cute. The girl makes them all the time.

I think it's funny or clingy. Like, I don't know which way you'd take it. You don't find it romantic in any way that he put in all the extra effort to have AI write a song for it. It could be funny. I like that spin on. We'll see what Taylor actually thinks about it. Where'd you go? I'm so alone.

Let's play it. Radio silence. Man, it's laugh for me. We're talking of families. Oh, yeah. Mom's name. A name. He's jamming out to it.

We're going to come back and then we'll try to get you your second date, update, AI style with Taylor. Right, I do this. Hold on. Brooke and Jeffrey in the morning. Second Date Update. I'm not going to lie, our listener Dennis had a big impact on me just now. Did he? Really?

Because he made me want to make an AI-generated song for our show. Oh. Hit it! It felt so great. Now they won't even communicate. You're staring at your lone lone. Don't you worry, don't you fear. Broken Jeffrey.

Second date and Jeffries. Second date update. Yeah. It's like a Disney channel entry. You got the kids cheering at the end. Is it like kids in quarantine? If you're old enough to know. Like I said, they all kind of sound the same.

Well, not enough references to how handsome I am in the song, but I'll take it. You're one who made it. You could have told it. Yeah, you're fairly. Literally sings what you say. 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.

Because... Oh, here we go, tell you have. Give the people what they want. Actually, the voice is exactly the same. I'm telling you. That's why the recording artists don't have to be worried. Yeah. Okay.

Here's you go. Oh, man. Do we have to call or can we just listen to AI music the whole day? I wish. He thought that song would be a fun way to help restart the conversation between them. Unfortunately, no dice. I am glad you sent it after she had already ghosted you. Yeah.

So, because it was like, what else do you have left to lose at that point? We know that's not the reason. Something must be up. We're going to try to figure out what that is and just dial her right now. You ready to do this, Dennis? I am, thanks. Okay. All right, let's see what she has to say. Here we go.

Hi, is this Taylor? This is she who says? This is a radio show. We're called Brooke and Jeffrey in the morning. Real people. Hi, good morning. This is a real radio. Thanks for clarifying.

Well, I mean, she's gotten a lot of weird stuff sent to her at the last year. Yeah. So, sorry to like burst in on your day, but we're doing this segment right now. It's called the Second Date Update. Okay. 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.

Okay. Okay. Okay. Okay. There's somewhat of a smile on your face. It sounds like when we mentioned Dennis a little bit. I would say maybe an awkward feeling. An awkward feeling.

That's not always bad, though. 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 not feel like it. He knows that she's in voice. That adds to the feeling. Yeah.

Is there a reason? I don't know if I feel comfortable discussing this on the radio. 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. Yeah. So, did you feel that way? Wait, why did you say, oh, God? Well, I'll give him some creativity points.

All right. Good. Those are important. For what? What did he do that was creative? I mean, there was a song. But I just kind of felt like our date didn't. It just wasn't when I was expecting.

It didn't sit right with me. Sit right. I'm not sure if you 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. You guys had more like text chemistry than like real physical chemistry. Why in this day and age do you need something more in person? Chemistry is really overrated. Yeah. I mean, you're going to have to have a lot of personal moments.

You need to click. You could do those online. But you did say you gave him creativity points for the song. that he sent. I'm saying creativity points, but I didn't find it a little weird. Got it. Okay. Both things are going to be true.

Weirdly close to the heart in that sense. I think maybe more funny, right? You would find it funny. You know, I'm just going to say that I've been considering other dates at this time. I just feel like something was off with him. 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.

I can feel the chemistry. Hey, hi, uh, hi, Taylor. There he is. Like, what are you doing? Hold on, hold on. Hold on what? Us? I'm reaching out to see how your lovely day is.

Dennis, put the, I mean, I guess don't put the phone down because you're probably talking on it. But like, close. Yeah, just talk to Taylor. Without help. Brooke, she doesn't know what the situation is. How could you not? It doesn't matter.

Okay. I'm just a little confused about what I don't know. But Dennis, you didn't feel like things were off on our date? Hold on. Oh, my. No, you can't do this. Oh, God. Wait, wait.

Hold on. Let him cook. Let him cook. The things were off, but then we can turn it to on. That is the stupidest line. Dennis, don't need that. And he said you wouldn't notice it on the phone. Dennis, I'm not really sharing if you're understanding what I'm saying, but I feel like there is a disconnect here.

Hell, it's just, so sometimes I get nervous, you know, and like you like the song, right? The song was okay. I would change subject. Well, sometimes I use AI Like before our date To start out And a couple times

You know, during the day And then the song, of course I kind of wish Chow GPT had written that shorter for him Yeah, you see why you're saying The song And when we're talking Everything is AI Well, I'm not

I mean a lot A lot. I mean, me too. I feel like it's just thinking right now. I feel like AI has stunted your emotional growth. Yeah, as a human. Is your profile all AI then? We didn't need to bring that.

Um, AI helped, yeah. But listen, AI's only as good as the prompt you give it. So he must be a good prompt giver. You guys know that this is really weird, right? According to him, everybody uses it to write their dating profiles. Yeah, do you ever use it in your life? I don't think everyone. I mean, I especially don't.

I just, I feel like if you're going to have one-on-one interactions with another human, maybe AI isn't the best, like, especially on our dates. But the song, no. The song was also AI. Okay, great. We got a lot of courage. I mean, no other human has asked AI to write a song. for you before.

Right? Like, God, I hope. I guess I wouldn't know what I. Oh, that's okay. Well, I mean, the thing is, like, you didn't get a good gauge of who he is because he was too reliant. Maybe he can back off of AI and you guys can actually see if you're compatible. Can he do that?

I don't know. Did you hear what she said? We both have older sisters, you know? No, I don't think Brooke said that just now. He just remembered. He's just reading old AI prompts. 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. Come on, Taylor. I'll try to just to talk to you just, you know, me. Okay. Okay. Talk to you just me. He's just nervous.

You understand that. He really was delightful before you go. I, you guys, listen, I'm not feeling the bark here. I think it's a lesson, Dennis, just be yourself. You don't need to rely on artificial intelligence. Use your own. Yeah. I'm going to answer you guys, okay?

Hold on. Okay. You know, why don't you email us the response to that? As you were going to email it, give us three different separate responses. You know, different styles. Which one do we like the best? Guys, I hope that you're all having a great day, but I think I'm going to go.

This feels a little ridiculous. I need to get back to work right now. I actually thought she already hung up. Okay, well, we're going to say goodbye to you in just a second. Just hold on. I got something really good to say. Hit the song! Thanks for being here.

Hey, hold on. I thought we have something. I'm sorry. It's a song started. We're out of time, Dennis. Ah, shoot. I'm Cynthia Lois And I'm Josie Dye

And we're done pretending we have it all figured out Each week we laugh, cry And talk our way through life's messiest moments Things you think about but would never say out loud The questions you are always too shy to ask Relationships, regrets, awkward moments And the stuff no one warns you about It's honest, it's funny

And sometimes it gets a little uncomfortable But that's kind of the point This is Cynthia and Josie's Unmentionables Listen on the free IHeartRadio app Or wherever you get your podcast Another podcast from some SNL late-night comedy guide, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman,

help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel, help an a cappella band with their between songs banter. There's the worst singer in the group. The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard, uh, you only got in

because your parents made a huge donation. The group. The yard birds, right? That's the name. The Harvard Yardt Yard's, but they're open. Do you have a name suggestion? We're open. Since you guys are middle-aged, one erection.

Listen to Humor Me with Robert Smigel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcast. Humor me. I need some jokes to make me seem funny. Text in to 785.92 says, Can you play the Taylor Where'd You Go song again? That's slacked. It's kind of catchy.

We've got half a dozen people who actually want to hear the whole song played on our show. It's like a country playlist in the range. If the song blows up around the world, who gets the royalties? It's an AI song. Wait a minute. The only person who doesn't want to hear it is just Taylor herself. Oh, the one it's made for. Where Taylor go?

She left. She's gone. That's a follow-up song. So no. date for Dennis. No, and no new song for us either. I hated that second date song. Yeah, no one is requesting the AI Brooke and Jeffrey's second date theme

song to be replayed. I'm offended. You wanted like that middle part to be like some sort of breakdown where everybody sings along together. So clutch. One day maybe on the show I'll play you guys my intro song to the giggle gang. It sounds exactly like what we just pass on that one too.

We 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 and go check out all of our second date updates online wherever you get your podcast at Brooke and Jeffrey. Another podcast from some SNL, late night comedy guy, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Bob Odenkirk to David Letterman help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel, help an

a cappella band with their between songs banter. Where does your group perform? We do some retirement homes. Those people are starving for banter. Listen to humor me with Robert Smigel and friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts. Imagine an Olympics where doping is not only legal but encouraged. It's the enhanced games. Some call it grotesque.

Others say it's unleashing human potential. Either way, the podcast's Superhuman documented it all, embedded in the games and with the athletes for a full year. Within probably 10 days, I'd put on 10 pounds. honest. I was having trouble stopping the muscle growth. Listen to Superhuman on the I-Hard Radio app. Apple Podcasts or wherever you get your podcasts. My mother-in-law spent years sabotaging our relationship until Karma made her pay for it.

All right, Sophia, tell me about how we started this story. She moved in for two weeks, lasted five days, left a mess, and then pressed her ear against their bedroom door and burst in screaming. When kicked out to a hotel, she called her son-in-law's workplace, pretending his partner had been rushed to the hospital by ambulance. She faked a medical emergency. And spoiler, that was just the beginning. To find out how it ends, listen to the OK Storytime podcast on the IHeart

Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, this is Robert from the Stuff to Blow Your Mind podcast. Joe and I are both lifelong Star Wars fan, so we're celebrating May the 4th with a brand new week of fun, thought-provoking Star Wars-related episodes. Join us as we tackle science and culture topics from a galaxy far, far away, such as the biology of ton-tons and wampas on the ice planet hot, or the practicality and corporate business sense of the Sith rule of two. Listen to stuff to blow your mind on the iHeart radio app, Apple Podcasts,

or wherever you get your podcasts. A win is a win. A win is a win. I don't care which I'm saying. Yep, that's me, Clifford Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast.

The Clifford Show. This is a place for raw, unfills of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to The Clifford Show on the IHeard Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok.