Brooke and Jeffrey: Second Date Update - Second Date Update: Pursue Me Please

Episode Date: June 24, 2026

Sometimes in the dating world, you have to decide if the pursuit is WORTH the prize at the end of the journey. In today’s Second Date Update we’re figuring out just HOW FAR one man will go for just one, single date. See omnystudio.com/listener for privacy information.

Joy is essential and it's also elusive, but now there's a new and exciting way to start your journey toward a more joyful existence, Joy 101. It's a new podcast hosted by me, Hoda Kotby. If you're craving inspiration to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Open your free Iheart radio app. Search Joy 101 and listen now. Joy 101 with Hoda Kotby is presented by CVS. My first guest is Territ Hilton, Shakira, Luke, and Yerrin. Have surprises? Many surprises.

Welcome to the Sweet 305 podcast where the group check comes to life. What on? You're the only person I know that loves a yellow starburst. It's lemonade. This is Sweet 305. Here, oversharing is encouraged. Listen to Sweet 305 with Lele Pons on the IHard Radio app, Apple Podcast, or wherever you get your podcasts. Hey, this is Chuck from Stuff You Should Know, and we're submitting our most sciencey episodes for your peer review with our new Stuff You Should Know Doing Science Playlist.

Out now. You want to know about Occam's Razor? Simplest explanation is usually the right one? We got you covered. Wondered what chaos theory is ever since the first time you saw Jurassic Park? Well, come on down. So distill a nice pot of tea, everybody. Turn down the gas on your Bunsen burner and slip into your most comfortable lab coat and listen to the Stuff You Should Know doing science playlist on the IHeart Radio app.

podcasts or wherever you get your podcasts. It just came out. Jeremy, what did you just do? You just sit yourself up for failure. I've never heard you tell this story. I've never told this story. This must have been tucked deep, deep in the Jeremy Lynn file. My name is MC Jin.

I'm excited to tell you about laugh but not least. I'll be chatting with guests from all walks of life about the power of humor when it comes to facing difficult times. These will be conversations that remind us all, life is hard. Laugh harder. Listen, and laugh but not least with MC Jen on the I. I Heart Radio app, Apple Podcasts, or wherever you get your podcast. Happy Pride from the Outspoken Podcast Network.

All month long and all year round, we're celebrating being loud, proud, and always original. It's me, Brandon Kyle Goodman, host of the podcast, Tell Me Something Messy. Check out my show for unfiltered takes on dating, relationships, and adulting. Listen to High Key for the best pop culture takes, and there are no girls on the internet for all your tech news. For your favorite celebrity key keys, check outlaws with T.S. Madison. Learn to love yourself unapologetically with BFF, Black Fat Fem, and start your day with intention with waking up with Ryan coming in July. Celebrate Pride with the Outspoken Network.

Open your free IHeart Radio app. Search Pride and listen now. Just when we're about to start this, our producer calls Jose out of the room. Yeah. Come on, Boyd. Come on. It's right when we go to start record, he's always like, and I'm going to interrupt right now.

All right. Hey, you know what? We're doing it anyway. It's Brick and Jeffrey, and we've got a brand new episode for you on your second date podcast. Thanks so much for being here. Yes. And before we get to it, let's do comments. Yeah, Debo 77 said, I've purposely

been slacking on listening. So I have a nice chunk of five to six episodes to listen to all at once. Oh my gosh. Yeah, you're one of those that loves our back-to-back classics on Saturday. Yeah, you are, Debo. For sure. All right, let's get to just your one new episode. It's going to start right now.

Brooke and Jeffrey in the morning. Second Date Update. When was the last time someone in this room picked up the book The Great Gatsby. I'd say, yeah, my junior year, maybe. Oh, perfect. Then you obviously remember the entire novel is basically following Gatsby's pursuit of Daisy.

While Daisy, the entire time, plays hard to get, much like Elizabeth Bennett from Pride and Prejudice and Mr. Darcy. I thought it was more of a societal look on what wealth does to people. I don't know. Yeah, I mean, sort of. I'm a more Focus on the courtship aspect of it.

I hope you don't mind me using early literary references of it, where the man must prove himself through persistence in order to gain her affection. I'm glad you did, but probably half of our listeners just tuned out, but that's cool. Including me. Yeah. Perfect. We're right where we normally are, and I only bring it up because our listener, Sheena, says she had a guy like that, someone she really liked, and now he's not calling her back.

Okay. The persistence has stopped. Sheena, welcome to the show. Thank you for having me. Okay, so this guy was going full in. He was going full Gatsby on you. Full Gatsby. And what happened?

Yeah, I mean, he was pursuing me for quite a while, like hard. But I think maybe accidentally I turned him off. Okay, what's his name, by the way? His name is Matt. We met on Bumble. Okay. And I mean, I have to be honest, I really loved his directness. Like, one of his very first messages was

Saturday, noon, coffee, you and me. Oh, okay. Wow. Some people don't like that. I could never just be like, hi, stranger, let's link up. Yeah, but some people really appreciate, you know, no nonsense, just like, let's hang out. Yep. I appreciated the way he did it.

I mean, I didn't respond. Oh. But I did appreciate it. Wait, what? Wait. Why didn't you respond if you appreciated it? I don't have a lot of time for dating, but. Oh.

For the right person, I could hopefully squeeze in for a little bit of time in my schedule. I mean, 20 minutes of coffee was too much. Yeah. Okay. At that time when he was asking, yeah, it was. Okay. Okay. Again, if I felt like he was worth it right at the jump, maybe I would have made the time.

I mean, I didn't delete him. I do want you to know. So how did you show him that you left him on red? Well, I let him pursue me. So, wait, so there was no response from you, but you didn't delete him. And I assume he messaged again. He probably messaged me like, I don't know, six or seven times. Clearly not getting a reply.

It doesn't bother him. Eventually, I said no, though. Eventually, I did respond. Why did you say no, though? Like, he's pursuing you like you want. Why the no? What's stopping you? My work has been crazy.

I had vacation coming up. I was away for a week. Oh, that's bad time. Okay. Are you saying that you haven't been out on a date with him yet at all? No. What? No.

What? I would like to see him in person when I have some time. But actually, he asked me if he could stop by my work and see me. And I said, ew, no. Like, I barely know you. You said, ew? Yes, because wanting him to come to my work is kind of weird. Don't you guys think?

I mean, I can understand you don't want a strange guy showing up at your work unannounced. But, I mean, he's providing a solution to meet your seemingly impossible schedule that you're offering. You have to at least consider that aspect of it. I told you guys I made a mistake. I probably should not have responded that way. Okay. That's self-awareness. That's next.

So what happened after the e-no text? He wrote back. Okay. And then I left him on read for like three days. Oh, man. This is exhausting. Yeah, it is. You guys haven't even seen each other in person and I'm already tired.

But he doesn't care. Look, he keeps trying. Okay. And she's enjoying the pursuit, clearly. But after three days, what do you write finally? I just uncharacteristically wrote to him and I said, well, and then nothing. Oh, you just said the word well? That is kind of funny that you're just like, uh, hello?

Why on earth do you think he'd want to go out with someone who can't make any time for him at all? It's not that I don't like him. Trust me, I would have never ever even wrote the word well to him. I would have never initiated a text, but I really haven't had the time, and I was kind of hoping that he would get the hints and just keep pursuing me, because that's what I feel a woman deserves of my caliber.

I just don't feel like there's any hint in any of your messaging. Brooke, she said well. Oh. Probably with some dots afterwards. Thank you. Thank you. That means I wanted him to say something. She creaked the door open for him.

Why isn't he pulling it all the way through? I feel like he got what he wanted. He was just chased until he got a reply. And I was like, game over. Are you actually wanting us to call him now and ask him to go on a date with you? Because we can't ask him why he's not calling you back. It feels just blatantly obvious. I would really like you to call him and tell him to start pursuing me again, to not give up on me.

Is there any cell that we could have of why he should do that? What does he have to look forward to? Yeah. That I'm interested. That's what he has to look forward to. It's just I have to find a place to fit him in my schedule. Well, it doesn't get any easier than that. What guy's going to say no to that sort of opportunity?

I like how all the time she's about the phone with us, she could have got coffee with them. He would call us instead. I'm sorry that you're going through this right now, first of all, Sheena. This must be very tough on you. It is. Well, we understand. That's why we're going to come back. We're going to call this quitter of a man and tell him to pull his head out of his butt and get back to pursuing you.

Like real men do. I knew I loved you guys. So you understand me. We do. She does show affection eventually. Yeah. We're going to do it with your second date update right after this. Hold on.

Brooke and Jeffrey in the morning. Second date update. What happened to men? I don't get it. I mean, one day you're telling them, no, don't show up at my place of business. And then the next thing, they're not doing that. Wow. Talk about being clear and respecting boundaries.

Yuck. Am I right, Sheena? Yes. You are right. That's right. No, you don't want the reverse of that. No, he's giving up. Matt asked her out multiple times. Sheena has reluctantly been forced to turn him down over and over again

because her schedule is just too busy and too crazy. You should have known that the text well meant. Keep going. Don't give up. But for some reason, Matt's thrown in the towel. He's waving the white flag. And Sheena does not appreciate that. That's why she's come to us for help today.

And just to clarify, Sheena, at the end of this, are you saying that you want us to ask to send Matt on a date with you? I mean, I do want to go out with him. It just has to be under my terms and fit my schedule. Oh, God. Please let's not do the back and forth of what day works for you because that sounds exhausting to me. You guys can do that separately if this works out. Fair. Thank you.

I like your energy, Sheena. Don't lose your spark. I won't. Good. Yeah, you deserve all the things that are coming to you. So let's just dial Matt's number, and we'll see what happens. Here we go. Hello. Hey, is this Matt? Yeah, this is Matt. Who's this?

Hey, man, this is a radio show. We're called Brooke and Jeffrey in the morning. It's probably going to be a very surprising call to you. True. Okay. I think she meant very exciting call for you. Both. Yeah, both, I'm sure. Because we're doing this segment. It's called a second date update. Super exciting.

Uh, okay. Okay. So what that is, is if we have a listener who's gone out on a date with somebody or in your case has just been talking to someone for a really long time and they've never met up in person, we can reach out on their behalf to figure out if there's a reason why. Yeah, why the date hasn't happened, materialized. I feel like I knew where you guys are going with this, but, uh, maybe. That would be shocking to me if you knew what we were talking about. Hold on, let's give him a hint. Well, we got it now, right, bro?

That's pretty good. Because we're talking about a girl you've been talking to named Sheena. What? Okay. He did not expect Sheena. Okay. Well, we've heard that there's been developments in this relationship. We're trying to figure out where your head's at.

I tried to hang out with that girl for almost a complete month. And that's just a month that I will never get back. Can I just ask after she first said no to the coffee date, why did you keep pursuing her? Well, listen, you see on social media that there's this push where it's like, well, guys need to pursue more. Like, you hear it be said. I'm not an emu. My head's not in the sand. I thought that was like emo.

No, you know, not a lot. Yeah. All right. But she's pretty. And, like, you got to give it a chance. And you actually get a response on there because it's desert. So it's, you know, it's rough. Emuven Desert is the dating landscape right now.

Beautiful metaphor. So we heard you two met on Bumble. You chatted for a long time. You said a whole month. It was mostly one-sided. You chatted. You sending her messages and her every once in a while saying, no, that won't work. In different ways because it doesn't fit her schedule.

And then you suggested visiting her at work because she was so busy and she responded with, ew, and that was kind of how it dissolved. I mean, I've really tried with her. I even sent her flowers. You did? Oh, that's nice. Wait, I didn't say that. She gave you her address?

Yeah, what? No, I mean, I had to send them to her sister's place. How do you know her sister? She gave you her sister's address? She said, just to be safe, so I did, and you know, I still got like, heard nothing back.

Just to be safe, I don't want you to find me, but if you find my sister, that's fine. She was like a sacrificial lamb. She's got a machete by the door. She'll be fired. Yeah. And I mean, like, I just asked to a casual coffee date and then tried dinner. I tried an activity. Jeez.

So I couldn't make any of it. Okay. Sounds like the sister probably kept the flower. That doesn't mean I want you to stop pursuing me. Oh. Oh. Yeah. I heard it, too.

Good one. Oh, God. Okay, what's going on? Yeah, Matt, so that's Sheena, who's been waiting quietly on the other line until she wasn't. I mean, it makes sense you'd never heard her voice before. So, yeah. That's fair. This is what she sounds like.

Yeah, she's been waiting to talk to you. Oh, my God. Seriously? I can't believe you right now. What? You're mad? Yeah. What do you want for me?

Oh. Listen, I'll be honest. With my looks, I match with a lot of idiots on dating sites. I do a lot of people. A lot of idiots insults them. Hold on, let her cook. And you're the first one in a while who's been able to keep up

and to stay with me, like, you are fighting to see me for, I don't know, like an entire month. And I really appreciated that. It meant a lot to me. Oh. How would he do that? How would he do that? What's happening?

That was the first nice thing she said. Is that nice? Yeah, but I have you out like eight times, and you could never, you could never do it. Yeah. And you know what? If you really like me, you don't quit. You ask me out eight more times. It doesn't matter.

Sheena, you sound like a woman who's got a great career. You've got a lot of things going for you. Why wouldn't you take control and just say, oh, that doesn't work for me. How about Wednesday at five or whatever works in your schedule? Yes. Excuse me. I am not the man here. That is the man's responsibility.

Okay. Could know your schedule to find a date that works? Why are you telling women to do everything? And men can sit back and do nothing. She just sounds like an incredibly independent woman who's got her stuff together. I don't understand. Not enough, apparently. Now she needs to be scheduling all the dates for the man.

I'm really busy and I want to fit him into my schedule, but he needs to keep pursuing me until the time is right and I can find space. And then when I do, Matt's the guy that I want to go out with. I mean, that's the first time Matt's probably heard that he's wanted, which is, I assume, nice feeling, no, Matt. I'm mind-blown. And you want me to ask you out eight more times? Yes.

10, 12. It doesn't matter. There's no number on it. I just want you to pursue me. So I know you're serious. It's like a baseball player, Matt. You've swung at eight pitches. You've striked on all eight.

But that doesn't mean you don't go back to the plate and keep swinging. Thank you. coach isn't going to pull you from the game. Right. You don't hold for 37. Usually means you get sent down to a lower team. Well, she's not ready to send them down yet. She wants you to strike out more.

It's not a how about that? How about that? You don't know I'm going to say no. That's a good point. Are you free on Friday? No. I have like a work thing. Okay.

How about Saturday? Actually, the thing Friday, I have to go away for a few days. I'm kind of gone the whole weekend for the work thing. Don't choose weekends. Yeah. Is that it? Matt, you don't want to. try another day. We don't want to go through all seven days of the week. Monday could be good.

Or future months? Monday might be possible. Who knows? I feel like the person that would know would be you, Sheena. I know, but my schedule just changes so rapidly and there's so much being on. But don't give up, Matt. Don't give up. Don't give up. I like to keep asking. You know what? I think maybe I'll just take it from here. So we would love to have you guys go out on a date. Oh, how do we I don't know how to do that, but maybe we can agree to send you on a date at a future time to be determined. And when that time is determined, we would pay for it. I mean, you're talking to the most important woman in the world right now who has the busiest schedule that's ever been. Yeah.

You understand me. I love you guys. I'm not calling you with the right thing. You get me. We do. The question is Matt up for it. Yeah. Yes.

Okay. Beautiful. Way to go, Matt. I don't think that was the response, but I like that you took it. We got it into here. We got a yes. Whatever it was. Thank you, guys.

Okay. I can't wait to get an update in two years. Yeah. If it's happened yet. Uh-huh. I don't even know what happened just now. Yeah. Yeah.

Me either. Matt, you're in love. Just send more flowers to her sister. You're going to love it. Perfect. Brooke and Jeffrey in the morning. The newest tracks. Let's go.

We lose it. And the next. Big thing. Always on the new music first. Your first place to hear it all. Because you're going to like it, love, to want to play it twice. Playing now.

Iheart new music. Your digital station for brand new drops, fresh vines, and tomorrow's bangers. Discover IHart new music. Always fresh, always first. Stream now on the free IHart Radio app. Hey, I'm Hoda Kotby, host of the podcast, Joy 101 with Hoda Kotby. Together, we're going to have meaningful conversations with the world's most fascinating people.

Like when actress Olivia Munn shared how she overcame fierce health challenges. I've gone through breast cancer and then helped my mother through breast cancer, and that was more difficult. There's a lot of people who understand postpartner depression. I was not prepared for postpartum anxiety. Listen to Joy 101 with Hoda Kotby on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. For me, and I know this is probably unpopular, opinion. Oh. But did it seem like maybe she was being a little unreasonable?

Oh, weird, Jeff. Did you come to that conclusion all in your own? I don't know. I don't want to like go too crazy with it. Alexis, what's your take on if a woman wants to be pursued? And in her mind, a guy needs to ask her out multiple times to show his interest. Obviously, that's not you. But how do you feel about that situation?

You can be honest. Yeah, I don't know. She's crazy. Yeah. Oh, really? Okay. There it is. All right.

Maybe in this case she was a little bit on the cuckoo side. But he said yes. Did he though? He said, yeah. He said, yeah. And that was all we needed. Because he stopped it. That's right.

So I'm marking it up as a victory for us and everyone involved. And you can be victorious, too, in your dating life. Just email the show. We'll call that person who's not calling you back. Joy is essential and it's also elusive. But now. There's a new and exciting way to start your journey toward a more joyful existence. Joy 101.

It's a new podcast hosted by me, Hoda Kotby. If you're craving inspiration to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Open your free IHeart Radio app. Search Joy 101 and listen now. Joy 101 with Hoda Kotby is presented by CVS. My first guest is Karen Tolton. Shakira

Luke and Yerrin Have surprises Many surprises Welcome to the Sweet 305 Podcast where the group check Comes to Life What on? You're the only person I know

that loves a yellow starburst It's lemonade This is Sweet 305 Here, oversharing is encouraged Listen to Sweet 305 With Lele Pons On the IHeartRadio app Apple podcast or wherever you get your podcasts

Hey this is Chuck from Stuff You Should Know And we're submitting our most sciencey for your peer review with our new stuff you should know doing science playlist. Out now. You want to know about Occam's Razor? Simplest explanation is usually the right one? We got you covered.

Wondered what chaos theory is ever since the first time you saw Jurassic Park. Well, come on down. So distill a nice pot of tea, everybody, turn down the gas on your Bunsen burner, and slip into your most comfortable lab coat and listen to the stuff you should know doing science playlist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. It just came out. Jeremy, what did you just do? You just sit yourself up for failure. I've never heard you tell this story. I've never told this story. This must have been tucked deep, deep in the Jeremy Lin file. My name is MC Jin. I'm excited to tell you about laugh but not least. I'll be chatting with guests from all walks of life about the power of humor when it comes to facing difficult times.

These will be conversations that remind us all. Life is hard. Laugh harder. Listen to laugh but not least with MC Jen on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Happy pride from the Outspoken Podcast Network. All month long and all year round, we're celebrating being loud, proud, and always original. It's me, Brandon Kyle Goodman, host of the podcast, Tell Me Something Messy. Check out my show for unfiltered takes on dating,

relationships, and adulting. Listen to High Key for the best pop culture takes, and there are no girls on the internet for all your tech news. For your favorite celebrity key keys, check outlaws with T.S. Madison. Learn to love yourself unapologetically with BFF, Black Fat Fem and start your day with intention with waking up with Ryan coming in July. Celebrate Pride with the Outspoken Network. Open your free IHeart Radio app. Search Pride and listen now.