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Bowen Yang
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Unidentified Speaker 1
Why is it always chaos when we link up?
Jeffrey
Because nobody plans anything, bro.
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Brooke
Just when we're about to start this, our producer calls Jose out of the room. Yeah, Come on, Boyd.
Unidentified Speaker 2
Come on.
Sheena
It's like right when we go to
Unidentified Speaker 2
start recording, he's always like, and I'm gon interrupt right now.
Brooke
Hey, you know what? We're doing it anyway. It's Brooke and Jeffrey and we've got a brand new episode for you on your second date podcast. Thanks so much for being here. And before we get to it, let's do comments.
Unidentified Speaker 2
Yeah, Debo77 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.
Brooke
Oh, my gosh. Yeah, you're one of those that loves our back to back classics on Saturdays.
Unidentified Speaker 2
Yeah, you are, Debo, for sure.
Brooke
All right, let's get to just your one new episode. It's gonna start right now.
Sheena
Brooke and Jeffrey in the morning, second date update.
Jeffrey
When was the last time someone in this room picked up the book? The Great Gatsby.
Brooke
Yeah, my junior year maybe.
Jeffrey
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.
Brooke
I thought it was more of a societal look on what wealth does to people. I don't know.
Jeffrey
Yeah, I mean, it's sort of. I'm more focused 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.
Brooke
I'm glad you did, but probably half of our listeners just tuned out. But that's cool.
Unidentified Speaker 2
Including me. Yeah.
Jeffrey
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.
Sheena
Thank you for having me.
Brooke
Okay, so this guy was going full in.
Jeffrey
He was going full Gatsby on full Gatsby?
Sheena
Yeah. I mean, he was pursuing me for quite a while, like hard. But I think maybe accidentally I turned him off.
Brooke
Okay. What's his name, by the way?
Sheena
His name is Matt, we met on Bumble.
Brooke
Okay.
Jeffrey
Okay.
Sheena
And I have to be honest, I really loved his directness. Like, one of his very first messages was Saturday, noon coffee, you and me.
Unidentified Speaker 2
Oh, okay.
Unidentified Speaker 3
Some people don't like that. I could never just be like, hi, stranger, let's link up.
Jeffrey
Yeah. But some people really appreciate, you know, no nonsense, just like, let's hang out.
Sheena
Yeah. I appreciated the way he did it. I mean, I didn't respond. Oh, but I did appreciate it.
Jeffrey
Wait, what?
Brooke
Why didn't you respond if you appreciated it?
Sheena
I don't have a lot of time for dating, but for the right person, I could hopefully squeeze in a little bit of time in my schedule.
Brooke
I mean, 20 minutes of coffee was too much. Yeah, okay.
Sheena
At that time when he was asking. Yeah, it was okay.
Unidentified Speaker 2
Okay.
CarMax Advertiser
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Sheena
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, like,
Unidentified Speaker 3
so how did you show him? You left him on red.
Sheena
I let him pursue me.
Brooke
So. So, so there was no response from you, but you didn't delete him. And I assume he messaged again.
Sheena
He probably messaged me like, I don't know, six or seven times. Clearly not getting a reply doesn't bother him. Essentially I said no, though eventually I did respond.
Brooke
Why did you say no, though? Like, he's pursuing you like you want. Why the no?
Jeffrey
What's stopping you?
Sheena
My work has been crazy. I had vacation coming up. I was away for a week.
Unidentified Speaker 3
Oh, that's bad.
Jeffrey
Okay. Are you saying that been out on a date with him yet at all?
Sheena
No.
Brooke
What?
Unidentified Speaker 2
What?
Sheena
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.
Jeffrey
You said ew?
Matt
Wow.
Sheena
Yes. Because wanting him to come to my work is kind of weird, don't you guys think?
Jeffrey
Yeah, I mean, I can understand. You don't want a strange guy showing up at your work unannounced.
Unidentified Speaker 2
Yeah, he.
Jeffrey
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.
Sheena
I told you guys I made a mistake. I probably should not have responded that way.
Jeffrey
Yeah, okay.
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Jeffrey
So that's self awareness. That's nice. So what happened after the ew. No text?
Sheena
He wrote back. Okay. And then I left him on. I left him on Read for like three days.
Brooke
Oh, man, this is exhausting.
Unidentified Speaker 3
Yeah.
Brooke
You guys haven't even seen each other in person, and I'm already tired.
Unidentified Speaker 2
But he doesn't care. Look at him. He keeps trying.
Jeffrey
Okay, she's enjoying the pursuit, clearly.
Brooke
But after three days, what do you write?
Sheena
Finally, I just uncharacteristically wrote to him and I said, well. And then nothing.
Jeffrey
Oh, you just said the word well.
Unidentified Speaker 3
That is kind of funny that you're just like, hello.
Brooke
Why on earth do you think he'd want to go out with someone who can't make any time for him at all?
Sheena
It's not that I don't like him. Trust me. I would have never, ever even wrote that. The word wells 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 hint and just keep pursuing me, because that's what I feel a woman deserves of my caliber.
Brooke
I just don't feel like there's any hint in any of your messaging.
Jeffrey
Brooke. She said, well, oh, probably with some doctors.
Sheena
Thank you. That means I wanted him to say something.
Jeffrey
She cracked the door open for him. Why isn't he pulling it, like, all the way down?
Unidentified Speaker 2
I feel like he got what he wanted. He was just chasing till he got a reply, and now he's like, game over. I got it.
Jeffrey
Are you actually wanting us to call him now and ask him to go on a date with you?
Brooke
Because we can't ask him why he's not calling you back. It feels just blatantly obvious.
Sheena
I would really like you to call him and tell him to start pursuing me again, to not give up on me.
Brooke
Is there any sell that we could have of why he should do that?
Jeffrey
What does he have to look forward to?
Sheena
Yeah, that I'm interested. That's what he has to look forward to, which is I have to find a place to fit him in my schedule.
Jeffrey
Okay, well, it doesn't get any easier than that. What guy's going to say no to that sort of opportunity?
Unidentified Speaker 2
I like how all the time she spent on the phone with us, she could have got coffee with him.
Jeffrey
Well, I'm sorry that you're going through this right now. First of all, Sheena, this must be
Brooke
very tough on you, but it is.
Jeffrey
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.
Sheena
I knew I loved you guys. So you understand me?
Jeffrey
We Do.
Brooke
She does show affection eventually.
Jeffrey
We're doing it with your second date update right after this. Hold on.
Sheena
Brooke and Jeffrey in the morning. Second date update?
Jeffrey
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.
Matt
Wow.
Unidentified Speaker 1
Wow.
Jeffrey
Talk about being clear and respecting boundaries.
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Jeffrey
Am I right, Sheena?
Sheena
Yes, that's right.
Brooke
No, I don't want to reverse of that.
Jeffrey
No, he's. He's given 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
Brooke
too crazy that the text well meant.
Jeffrey
Yeah, keep going. Yeah, 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. Yeah, 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?
Sheena
I mean, I do want to go out with him. It just has to be under my terms and fit my schedule.
Brooke
Oh, God, please, let's not do the back and forth of what day works for you because that sounds exhausting. You can do that separately if this works out fair. Thank you.
Jeffrey
I like your energy, Sheena. Don't lose your spark, because I won't.
Unidentified Speaker 2
Good.
Jeffrey
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.
Matt
Hello?
Jeffrey
Hey, is this Matt?
Matt
Yeah, this is Matt. Who's this?
Unidentified Speaker 3
Hey, man.
Jeffrey
This is a radio show. We're called Brooke and Jeffrey in the Morning.
Brooke
It's probably going to be a very surprising call to you.
Unidentified Speaker 2
True.
Matt
Okay.
Jeffrey
I think she meant very exciting call for you both, I'm sure, because we're doing this segment. It's called a second date update. Super exciting.
Matt
Okay, okay.
Jeffrey
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 is a reason why.
Brooke
Why the date hasn't happened, materialized.
Matt
I feel like I know where you guys are going with this, but maybe
Brooke
that would be shocking to me if you knew what we were talking about.
Unidentified Speaker 3
Let's give him a hint. Well, yeah, you got it now, right, bro?
Jeffrey
That's pretty good. Because we're talking about a girl you've been talking to named Sheena.
Matt
What?
Brooke
Okay, he did not expect Sheena.
Jeffrey
Okay, well, we've heard that there's been developments in this relationship. We're trying to figure out where your head's at.
Matt
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.
Brooke
Can I just ask, after she first said no to the coffee date, why did you keep pursuing her?
Matt
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.
Brooke
I thought that was like emo.
Matt
All right, but she's pretty and like, gotta give it a chance when you actually get a response on there because it's desert, so it's, you know, it's rough.
Brooke
Emujin. Desert is the dating landscape right now.
Jeffrey
Beautiful metaphor. So we heard you two met on Bumble. You chatted for a long time. You said a whole month.
Brooke
It was mostly one sided. It was sending her messages and her every once in a while saying, no,
Jeffrey
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.
Matt
I mean, I really tried with her. I even sent her flowers.
Brooke
You did? Oh, wait, she didn't say that she
Jeffrey
gave you her address?
Unidentified Speaker 2
Yeah.
Brooke
What?
Matt
No, I mean, I. I had to send them to her sister's place.
Brooke
How do you know her sister?
Jeffrey
She gave you her sister's address?
Matt
She said just to be safe. So I did. And you know, I still got like heard nothing back.
Brooke
Wait, just. Just to be safe, I don't want you to find me. But if my sister. That's fine.
Unidentified Speaker 2
She.
Brooke
She was like a sacrificial lamb.
Jeffrey
She's got a machete by the door. She'll be fine.
Matt
Yeah, and I mean like I just asked to a casual coffee date and then tried dinner. I tried an activity and she. So I couldn't make any of it.
Brooke
Okay.
Jeffrey
Sounds like the sister.
Matt
Probably.
Sheena
Matthew, that doesn't mean I want you to stop pursuing me.
Unidentified Speaker 2
I heard it too.
Brooke
Good one.
Jeffrey
Oh, God.
Matt
Okay, what's going on?
Jeffrey
Yeah, man. So that's Sheena, who has been waiting quietly on the other line until she wasn't.
Brooke
I mean, it makes Sense you'd never heard her voice before, so that's fair. This is what she sounds like.
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Jeffrey
She's been waiting to talk to you.
Matt
Oh my God.
Sheena
Seriously, I can't believe you right now.
Brooke
What? You're mad?
Matt
What do you want from me?
Sheena
I'll be honest. With my looks, I match with a lot of idiots on dating sites.
Matt
I believe a lot of people idiots insult them.
Jeffrey
Hold on. Let her cook.
Sheena
And you're the first one in a while who's been able to keep up and to stay with me. Like you were fighting to see me for, I don't know, like an entire month. And I really appreciated that. It meant a lot to me.
Jeffrey
Aw, come on, Ruma.
Brooke
How would he.
Jeffrey
That was the first nice thing she said.
Brooke
Is that.
Sheena
Yeah, but like eight times.
Matt
And you could never, never do it.
Sheena
And you know what? If you really like me, you don't quit. You ask me out eight more times. It doesn't matter.
Brooke
You sound like a woman who's got a great career. You 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 5 or whatever works in your schedule?
Unidentified Speaker 3
Yes.
Sheena
Excuse me, I am not the man here. That is the man's respons.
Brooke
Okay, yeah, to know your schedule, find the date that works.
Jeffrey
Why are you telling women to do everything and men can sit back and do nothing?
Brooke
Sounds like an incredibly independent woman who's got her stuff together. I don't understand.
Jeffrey
Not enough, apparently. Now she needs to be scheduling all the dates for the man.
Sheena
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, the guy that I want to go out
Brooke
with, I mean, that's the first time Matt's probably heard that he's wanted, which is, I assume, nice feeling. No.
Matt
Matt, I'm mind blown and you want me to ask you out eight more times? Yes.
Sheena
Well, it doesn't matter. There's no number on it. I just want you to pursue me so I know you're serious.
Jeffrey
Yeah, 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.
Unidentified Speaker 3
Coaches, I'm going to pull you from the usually.
Brooke
Usually means you get sent down to a lower team.
Jeffrey
Well, she's not ready to send them down. She Wants you to strike out more.
Sheena
It's not.
Matt
How about strikeout again?
Sheena
You don't know. I'm gonna say no.
Jeffrey
That's a good point.
Matt
Are you free on Friday?
Sheena
No, I have, like, a work thing.
Matt
Okay. How about Saturday?
Sheena
Actually, the thing Friday. I have to go away for a few days. I'm like, kind of gone the whole weekend. For the work thing.
Unidentified Speaker 2
Don't choose weekend.
Matt
Weekends. Yeah.
Brooke
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.
Unidentified Speaker 2
Monday could be good.
Jeffrey
Or future months.
Sheena
Monday might be possible. Who knows?
Jeffrey
I feel like the person that would know would be you, Sheena.
Sheena
I know, but my schedule just changes so rapidly and there's so much going on.
Unidentified Speaker 3
Darn.
Sheena
But don't give up, Matt.
Brooke
Don't give up.
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Jeffrey
You know what? I think maybe I'll just take it from here. So. So we would love to have you guys go out on a date.
Unidentified Speaker 3
Oh, how do we coordinate it?
Jeffrey
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.
Brooke
I mean, you're talking to the most important woman in the world right now who has the busiest schedule that's ever been.
CarMax Advertiser
Yeah.
Sheena
So understand me. I love you guys. I'm calling you with the right thing because you get me.
Jeffrey
We do. The question is, is Matt got up for it?
Matt
Yeah.
Bowen Yang
Yes.
CarMax Advertiser
Okay.
Jeffrey
Beautiful. Way to go, Max.
Brooke
I don't think that was the response, but I like that you took it.
Unidentified Speaker 3
We gotta end it here.
Jeffrey
We gotta. Yes. Whatever it was.
Sheena
Thank you, guys.
Jeffrey
Okay.
Brooke
Okay. I can't wait to get an update in two years of how your date went.
Jeffrey
If it's happened yet, I. I don't
Matt
even know what happened just now.
Brooke
Yeah, yeah.
Jeffrey
Matt, you're in love. Just send more flowers to her sister. You're gonna love it.
Sheena
Brooke and Jeffrey in the morning.
Bowen Yang
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Jeffrey
And I know this is probably unpopular opinion.
Brooke
Oh.
Jeffrey
But did it seem like maybe she was being a little unreasonable?
Brooke
Oh, weird. Jeff, did you come to that conclusion all on your own?
Kalpen (Hearsay Podcast Advertiser)
I don't.
Jeffrey
I don't want to like go too crazy with it. Alexis, what's your take on if a woman won't 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?
Brooke
Well, you can be honest. Yeah.
Unidentified Speaker 2
I don't know.
Brooke
She's crazy. Okay, there it is.
Jeffrey
All right, maybe in this case she was a little bit on the cuckoo side. But he. He said yes.
Brooke
Did he though?
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He said.
Unidentified Speaker 2
Said yeah.
Jeffrey
He said yeah. And that was all we needed because you 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.
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Bowen Yang
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Brooke
Audible.
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What?
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Bowen Yang
Sisters you've always liked, a little drama,
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Jeffrey
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Unidentified Speaker 1
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Episode Date: June 24, 2026
Podcast: Brooke and Jeffrey: Second Date Update (iHeartPodcasts)
Episode Title: Second Date Update: Pursue Me Please
In this classic "Second Date Update," the hosts call a man on behalf of their listener, Sheena, who feels she deserves relentless pursuit from suitors—and is frustrated that her top pick, Matt, has suddenly stopped chasing after weeks of one-sided messaging. The episode examines modern dating dynamics, expectations around pursuit, and questions of communication and agency, all laced with the show's signature sarcasm and wit.
| Timestamp | Segment | |-----------|-----------------------------------------------------------------------------------------| | 03:37 | Start of Second Date Update segment | | 04:41 | Sheena describes Matt’s "Full Gatsby" pursuit | | 05:01 | Sheena shares Matt’s first message | | 07:28 | Hosts express exhaustion at Sheena’s lack of engagement | | 12:29 | Matt gives his side, shares feeling “a month wasted” | | 13:41 | Matt sent flowers to Sheena’s sister | | 15:04 | Sheena finally reveals to Matt that he’s the first guy to keep up and she appreciated it | | 16:42 | Matt asks if she really wants to be pursued more, Sheena confirms | | 17:17 | Matt attempts to schedule a date; Sheena continues to be unavailable | | 18:12 | Hosts propose a vague "future date, to be determined" as resolution | | 20:38 | Hosts debrief on Sheena’s expectations |
The episode offers an entertaining—and at times head-scratching—look at the pitfalls of modern dating, particularly where traditional gender roles clash with contemporary realities and communication fails. While Sheena's story is unique, the hosts’ skepticism and Matt’s exhaustion are likely relatable to anyone who's been stuck in a non-starter "talking phase." Ultimately, the “second date” never happens, but the laughs and cringes abound.
For more Second Date Updates and the full weekly show, visit the Brooke and Jeffrey podcast.