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Kalpen (Bowen Yang)
Amazon Health AI presents Painful Thoughts I
Jeffrey
I can't stop scratching my downtown.
Kalpen (Bowen Yang)
Mm, yeah, but I'm not itching to
Jeffrey
go downtown and tell a receptionist I'm here to talk about my downtown. Some things you'd rather type than say out loud.
Kalpen (Bowen Yang)
There's no question too embarrassing for Amazon Health AI. Chat your symptoms and get virtual care 247 health care just got less painful
Jeffrey
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Brooke
Visit your nearby Lowe's
Jeffrey
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Kalpen (Bowen Yang)
hey everyone, it's Kalpen. I'm inviting you to join the best sounding book club you've ever heard with my podcast, HearSay, the Audible and iHeart Audiobook Club. Every episode, I nerd out with amazing guests and dive into the best new audiobooks available on Audible. It's the book club for your ears. Listen to Earsay, the Audible and iheart Audiobook Club on the iheartradio app or wherever you get your podcasts.
Jeffrey
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Brooke
Hey, you found it. The home of the second date update. It is Brooke and Jeffrey in the morning. And thanks for being here on the podcast. Yes, you know, I love all the comments we've been getting from all over the world, and I think this one really sums up what these second dates are. Nicola Huber in Brazil wrote, the call just gets worse and worse. Oh, it's true. It does it's like a guilty pleasure listening though. You know, Seriously, we love when you comment. We love when you subscribe even more. So please do it. And hey, hey. Just sit back and enjoy the second date update. It starts right now.
Josie
Brooke and Jeffrey in the morning.
Brooke
Second date update.
Jeffrey
Everybody has a different romantic strategy when they're out and they see somebody they're attracted to.
Brooke
Oh yeah, okay.
Jeffrey
Like Jose will name drop himself before breaking down the diet and migration patterns of Pacific soft shell clams.
Brooke
Sorry if we don't make it out
Jeffrey
of here before the kids.
Brooke
Yeah, cuz it is getting hot. Oh my gosh. Recapping we love turn turned on by himself. I really do.
Jeffrey
Not the first part, but I know a lot about fish. And if y'.
Brooke
All, I think we get it.
Jeffrey
We got it.
Brooke
Jeffrey, why did you do that?
Jeffrey
Alexis will shake her empty white claw can in your direction hoping you'll buy her a new one.
Brooke
Do you like shiny things? I haven't had the pineapple flavor today.
Josie
Today.
Brooke
Today.
Jeffrey
And Brooke, well, she's married.
Brooke
Wink. No, I am married.
Jeffrey
She is not interested whatsoever. Wink, wink, wink. And she is definitely not going to leave her hotel room unlocked. Room 307. Wink, wink, wink. Why is even the doorstop like open? So again, guys, don't DM us. Brooke is not available.
Brooke
Thank you. Jeffrey, stop it.
Jeffrey
Who is available is actually one of our listeners, Josie. And apparently she has a different strategy when it comes to meeting a guy. Josie, welcome to the show.
Josie
Hi. Thank you so much for having me.
Brooke
Are you waking right now, Josie?
Josie
Am I winking? No, no, don't.
Brooke
There's no secret codes, only leads to trouble.
Jeffrey
Yeah, Brooke would know. So tell us about the guy. Apparently you met someone when you were out recently. Who is it?
Josie
Yeah, so his name is Benjamin. And I actually, believe it or not, met him on the train.
Brooke
Oh, interesting. Like a long trip train or just like in town subway situation?
Josie
Yeah, in town subway situation. Because that's how I get to and from work.
Brooke
All right.
Jeffrey
Oh, got it. So did you pull the brook move of leaving the hotel room card like a dad on the chair?
Brooke
She's going to work.
Josie
Jeff.
Jeffrey
Train stop. F. Get out. You said. You said that you have a strategy. I'm wondering what it is.
Josie
Yes, so not quite that, but here's what I have learned, all right? I've noticed that the way that I can gauge if someone's like attracted to me is if I get as close as possible to them without actually interacting with them.
Brooke
I'm really hoping that the train that you're on is crowded, else you look
Josie
like a crazy woman.
Brooke
Just inching.
Jeffrey
There's like 40 empty seats and you're standing right next to it.
Josie
I think I'm subtle enough. I hope I'm subtle. I don't know. We'll find out.
Brooke
Okay, so, like, how does that work?
Josie
Well, okay, so I've been on the train with him a bunch of times, so.
Brooke
Oh, so you've noticed him before. Interesting. Okay.
Josie
Okay, so the first time I decided to use my strategy, I got close to him enough, but not enough where he and I could make eye contact. Right. And ignored him.
Brooke
Okay, and ignored him.
Jeffrey
I'm inching closer. Like, we're in the same corner now, but not yet.
Brooke
And why don't you say anything?
Jeffrey
Desperate people open their mouths and actually speak.
Brooke
Like, hi.
Jeffrey
Yeah.
Brooke
Okay.
Jeffrey
You gotta let the target come to you. Orbit him.
Josie
Okay, exactly. I build visibility. It's all about the visibility.
Brooke
Right? How many rides? How many rides until you got close.
Josie
So, okay, the second ride got a little bit closer than the third ride. I sat right next to him.
Brooke
Okay. Third time's a charm.
Benjamin
Oh, my.
Jeffrey
It's like those cat videos where they, like, pan away for a second and you pan back. The cat's a little bit closer and you pan away and the cat's a little bit closer.
Kalpen (Bowen Yang)
Totally.
Jeffrey
And you're, like, on his back.
Benjamin
Eventually.
Brooke
Were you sitting in his lap by this time?
Jeffrey
Where are you?
Josie
Not quite, but I'm sitting right next to him.
Jeffrey
Did he notice you then?
Josie
He noticed my jacket.
Brooke
Oh, what did. Oh, how do you know?
Josie
He complimented me on my jacket. He said, hey, nice jacket. I like that jacket.
Jeffrey
Oh, what do you say?
Josie
I said, thank you and continued to ignore him.
Brooke
And continue to ignore. Ignore him.
Josie
Ignore him. Yes.
Brooke
He's going to think you don't like him. Like, that was your opening to. Do you have headphones on? Are you just sitting there in silence facing forward?
Josie
At this point, I knew that there was interest. So then when I saw him the next time, he asked me if I wanted to get coffee. What?
Jeffrey
Hey. So it worked.
Brooke
He went. He had spoken one sentence to you prior.
Josie
And then he said a little bit like, oh, hey, it's you again. You know, like a little small.
Jeffrey
I mean, this is going to help people in real life. This is how you meet people in the real world to get, like, what happens next? At this point? Do you give in at this point?
Josie
I just prefaced by letting him know how incredibly busy I am. But I could maybe squeeze him in after work.
Jeffrey
Okay, you don't want him to know that you've been slowly, like, stalking him, getting closer and closer to him on
Brooke
the train, and that your heart's about to explode because the guy you've been crushing on finally asked you out.
Jeffrey
Playing it cool, right? Okay.
Brooke
So did you go after work?
Josie
Yes. So we met at the train station and yeah, it was a quick 15 minute situation.
Brooke
Why so quick?
Jeffrey
Probably because the train was coming.
Josie
So I noticed that, like, he's kind of, I guess, inexperienced, it seems.
Brooke
Oh, why do you say that?
Jeffrey
Oh, my God.
Josie
Because he was. He seemed a little uncomfortable, you know, like he didn't know what to do.
Jeffrey
Okay, okay, well, maybe that was confusing for him in its own right because he was so used to you being cold in before. But I'm assuming that you guys exchanged numbers after that and have stayed in touch. So what's the latest?
Josie
So we did exchange numbers, but now whenever I see him, he's acting strange. He's acting like. Like it never happened.
Jeffrey
Okay.
Brooke
Oh, interesting. But. And you're okay with the inexperienced part, it sounds like.
Josie
I kind of thought it was cute, you know, like he just doesn't look like he's been on a ton of dates. Which, you know, is actually a good thing because, like, a lot of the guys on the app seem like they've been on three a day.
Brooke
Three a day? They're doing 3A.
Benjamin
Yeah.
Jeffrey
Maybe he was just really, really nervous on that first date and had been looking forward to it just as much as you were. Yeah. So maybe he's been waiting and trying to figure out the right way to contact you. We're just going to jump in and do it for him, though. We're going to call him and try and get you your second date update right after this.
Josie
Appreciate it.
Jeffrey
Hold on.
Josie
Brooke and Jeffrey in the morning.
Brooke
Second date update.
Jeffrey
They say sometimes silence speaks louder than words.
Brooke
Yeah, never understood that, but yeah, we know you didn't.
Jeffrey
It's not just a quote. That's her entire seduction strategy.
Brooke
Believe this word.
Jeffrey
Get physically close to a guy and then just completely ignore him until he falls in love with you. Yeah, and now I understand why whenever I try to ignore Brooke at work, she just wants to talk to me. More and more and more. She's flagging me down, asking me all sorts of questions down the door to talk to you.
Brooke
I only said, how was your weekend?
Jeffrey
Oh, wow. All up in my business all over again. And that's how one of our listeners, Josie, met a guy named Benjamin on the train not too long ago over the course of several trips, she got closer and closer and closer to him till she was basically in his lap on a coffee date right before their next train. And I can feel Brooke staring at me this entire time, wanting to say something. What is it, Brooke? What do you want?
Brooke
I'm just listening to what you're saying.
Jeffrey
I'm not interested. Okay.
Brooke
So much. Just get to the point.
Jeffrey
Okay. My point has been made. That he's not calling her back.
Brooke
Yeah, that's the bad point.
Jeffrey
Yes. Yeah. Now, what would you like to say?
Brooke
I don't know. How are you feeling, Josie? No,
Jeffrey
obviously she's not feeling good. She doesn't want to talk to you. If she wants to listen, she's ignoring you.
Josie
Now, I just want to know, like,
Brooke
is she nervous or does she think, like, they only spent 15 minutes together?
Jeffrey
I don't know.
Brooke
What can go so wrong in 15 minutes?
Jeffrey
Don't downplay her amazing date, Brooke.
Brooke
Oh, my God.
Jeffrey
Really? Rude.
Brooke
I'm just done with. You can talk. Call the guy.
Josie
Yes, call the guy. Call the guy.
Brooke
Thank you, Jeff.
Jeffrey
How's that feel? Well, I like to, you know, have meaningful conversations and dive into people's feelings. All right, no, we'll just get right to business and call Benjamin. I'm going to dial his number. We'll see if he answers. Here we go.
Benjamin
Hello?
Jeffrey
Hey, is this Benjamin?
Benjamin
It is. Who's this?
Jeffrey
This is a. Not just one person, A whole radio show is on the phone wanting to talk to you.
Brooke
Welcome to the show.
Benjamin
Good morning. What's going on?
Jeffrey
Well, we're doing something called a second date update because one of our listeners has been trying to get a hold of you, and apparently she wants to see you again. On a real date. Yeah, I don't know the right way
Brooke
to say this makes sense. Like, they only went. You only went to coffee for 15 minutes with her?
Jeffrey
Yeah. I wasn't sure if you would consider this a date or not. There's a girl from the train named Josie.
Benjamin
You sure it's a date? I know a girl from the train named Josie.
Jeffrey
Yeah, well, I didn't want to label it a date, but apparently you guys have hung out, seen each other a few times and had coffee together. That's the date we're referring to? Yeah.
Benjamin
I mean, we ride the same train line and. Yeah.
Jeffrey
So you're in a relationship.
Brooke
Okay, why did. Why didn't you consider the coffee meetup a date?
Benjamin
Well, I guess, like, technically, like, we made an appointment or like a time to see each other.
Jeffrey
A lot of people would See that as two people meeting up and having a drink or whatever together. That's considered a date.
Benjamin
Yeah, but I mean, like, normally there's sort of, like, I guess, date vibes, if you will.
Brooke
Oh, you didn't get any date vibes with her? Were you just being friendly?
Benjamin
Well, I just didn't even know there was supposed to be chemistry there. So the deal is, my mom's birthday is coming up, and I know this is. That's like, a weird intro, but.
Brooke
Yeah.
Jeffrey
What the heck?
Benjamin
This girl has, like. I. I don't know how to describe it other than, like, a very similar style to my mom.
Brooke
What did you just say? Josie has a similar style to your mom?
Kalpen (Bowen Yang)
I'm gonna throw up.
Brooke
I cannot think of a worse.
Jeffrey
Hold on, let's hear him out.
Benjamin
Maybe not, like, in a grow. Like, just like. I noticed she was wearing this jacket that my mom has the exact same one of.
Jeffrey
Oh, not the jacket.
Brooke
No, it's not gross. It's just insulting. Yeah, it's not gross. He's not into her. It's just insulting.
Jeffrey
Okay, Josie mentioned to us that you brought up her jacket looking really nice when you guys are on the train together. Is that what you're talking about? No.
Benjamin
Yeah, so I noticed her on the train a couple times, and I swear they must shop at the same place. And so I'm like, I don't know where to get a gift for my mom. And so I was just going to pick her brain on, like, where she shop.
Jeffrey
Oh, no, this was an information secret.
Brooke
Like, where's the Talbots so you can. Hey, maybe his mom is.
Benjamin
Oh, that might be a good place to go.
Jeffrey
Yeah. Did you tell Josie during the coffee experience that you were looking to buy a gift for your mother? Or are you just information gathering?
Benjamin
I don't know if I mentioned specifically that we talked about, like, where she shopped and, like. I mean, it was brief. Like. Okay, that's why, like, when you said date, I don't really think of it as a date.
Brooke
All right, well, man, that feels bad.
Jeffrey
Somebody who may have seen it as a little bit more than that is Josie, who, unfortunately has been listening to this entire conversation. Benjamin, she's on the other line.
Benjamin
I mean, hello. She never seemed interested.
Jeffrey
That's Josie. Say hi. Because she wasn't playing hard to get.
Josie
That's, like, so offensive. And my mom's cool.
Benjamin
No, no, no, no, no.
Josie
Your mom is cool.
Jeffrey
It's possible maybe his mom is some sort of model.
Josie
Why didn't you just ask me where I got the jacket when you complimented me on it.
Benjamin
And because she already has that jacket, you don't need.
Jeffrey
Oh, okay. It's kind of funny. He was probably taking your feelings into consideration by not bringing that up.
Brooke
I bet his mom was a really, like, maybe a teenager when she had him, so she's very young.
Jeffrey
I'm sure he's the product of a teenage pregnancy.
Brooke
I don't know.
Benjamin
That's not true.
Jeffrey
Okay.
Benjamin
It's like, bohemian style. I don't know what you would call it.
Brooke
Okay, that's okay. That's not bad. At no point, though, three people.
Jeffrey
You know what Josie probably wants to hear from you, Benjamin, is an apology of some sort.
Benjamin
Why am I. What did I do?
Jeffrey
Well, you said that she has the style of your mom.
Benjamin
Would you rather my. My mom has your style? I don't know.
Jeffrey
Nobody. You should not remind each other of either.
Josie
Okay, can we get off the whole I dress like his mom thing? Okay? I think that's been established. I was genuinely, like, interested. You seemed like a really nice guy, and you just seem like you were a little bit experienced. Inexperienced, rather. So now I just feel like an idiot.
Benjamin
How?
Brooke
Well, I think he is inexperienced. I mean, buying gifts for his mom.
Benjamin
I don't think I'm inexperienced. Like, you didn't give off any signs of, like, hey, let's go have a date.
Josie
Why did you think I wanted to have coffee with you?
Jeffrey
Yeah, she was playing hard to get with you, Benjamin.
Benjamin
She didn't even want to have coffee with me. It was like pulling teeth. She's like, maybe I can fit you in. I was like, well, perfect. I just need, like.
Jeffrey
Yeah,
Benjamin
read between the lines.
Jeffrey
That means she likes you.
Josie
Telling you that I'm gonna make time for you should be indicative of interest.
Brooke
No, you need to be real clear.
Benjamin
I don't have that Dakota rig. I thought you were just, like, literally busy.
Brooke
I mean, she obviously, you know now that she likes you, right? Like, it's very clear.
Jeffrey
Yeah. So put all the mom stuff aside. Do you see her, like, as a potential romantic interest for you?
Benjamin
I haven't really even thought about it. Like, all I can do is just, like, picture my mom's clothes.
Jeffrey
That could be sexy in some circles. It could be.
Benjamin
No, it's not like that.
Jeffrey
Okay, well, I'm doing more damage than I am helping.
Brooke
Can you, like, donate the jacket and then maybe get something?
Josie
I'm not changing my wardrobe because of.
Benjamin
No, you. You shouldn't change it. I mean, you look amazing at it. I. I was serious when I complimented you.
Brooke
Dude, she's never gonna be able to wear that jacket again. Just so you know, she'll find something
Jeffrey
out even hotter to wear on your first official date that we. We're gonna send you on it and pay for the day if you want to do this. Benjamin, what do you think?
Josie
Can we just not. Don't even ask him. I. I don't know.
Jeffrey
You're right. We should probably ask his mom for permission first. Make sure it's okay before he's allowed to go out with. She's crazy.
Brooke
I think. I think she's gonna go home.
Jeffrey
Oh, you're done with it?
Brooke
Her clothes?
Josie
Yeah. I don't know if there's coming back from this.
Brooke
Yeah, I would agree with that.
Benjamin
Hey, Josie, I. I'm sorry. I. I really didn't see it as what you were shooting for, so I apologize. And like, I just don't want it to be awkward when we see each other on the train again. So, like, I really am sorry.
Josie
Oh, no, it won't be. I'm probably gonna start taking the bus.
Brooke
Oh,
Jeffrey
but that's like ignoring him. And when she ignores someone, it means that she likes him.
Brooke
Don't read.
Josie
I'm throwing that strategy out from now on. I'm never using that again. Brooke and Jeffrey in the morning.
Brooke
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Jeffrey
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Josie
Yeah, terrible.
Jeffrey
Why is that terrible?
Brooke
Oh, you know, no one wants to be compared to their mother.
Jeffrey
Excuse me, I would like to ask that we destigmatize the idea that moms aren't sexy. Okay, I don't like this narrative that you guys are painting that moms can't be hot.
Brooke
Jeffrey, you cannot be attracted to someone who looks like your own mother. It doesn't matter if your own mother is Heidi Klum. It is gross.
Jeffrey
Okay, that's your opinion. This. If you're a hot mom, text into 78592. Especially if you're single.
Brooke
Are you just trying to get hot bobs to text in?
Jeffrey
We need all the hot moms.
Brooke
That is not what this is about.
Jeffrey
Solidarity in numbers. And if we can't agree on that, at least we can agree on this. We'll help you with your dating life.
Brooke
Yeah.
Jeffrey
No matter who your mom is, no matter what they look like.
Brooke
All right, Heidi Clum's daughter, give us a call.
Jeffrey
That's right, email the show. We'll call that person who's not calling you back. And go check out all of our second dates wherever you get your podcast. Brooke and Jeffrey, this is Bowen Yang from Lost Culture Research with Matt Rogers and Bowen Yang. We all know the feeling when life gets really busy. Taking care of yourself can feel impossible. That's why Premier protein shakes are my go to. They have 30 grams of protein, 160 calories, no added sugar, and they taste amazing. So they're a healthy choice you'll actually want to make. It's not just for fitness. It's for getting after life. Premier protein powers me to say yes to more. Find your favorite flavor@premier protein.com. that's P R E M I E R protein.com.
Kalpen (Bowen Yang)
hey, everyone, it's Kelpen. I'm inviting you to join the best sounding book club you've ever heard with my podcast, Hearsay the Audible and Iheart Audiobook. Club. Every episode, I nerd out with amazing guests and dive into the best new audiobooks available on Audible. It's the book club for your ears. Listen to earsay, the Audible and iheart Audiobook Club on the iheartradio app or wherever you get your podcasts.
Jeffrey
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Kalpen (Bowen Yang)
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Jeffrey
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Josie
What?
Jeffrey
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Episode Date: May 22, 2026
Podcast: Brooke and Jeffrey: Second Date Update
Main Theme:
Exploring why Josie hasn't heard back from Benjamin after their brief coffee follow-up to a series of flirty encounters on a train. The episode unpacks miscommunications, awkwardness, and the perils of romantic signaling.
Brooke, Jeffrey, and the morning crew address another listener's dating quandary: Josie, who met and slowly courted Benjamin on her daily train ride but is now being ignored after their first (and only) "date." The hosts investigate by calling Benjamin, uncovering a hilariously cringeworthy case of mistaken intentions and, unfortunately, mom-style jackets.
Josie’s strategy, editorialized by Brooke:
"I'm really hoping that the train that you're on is crowded, else you look like a crazy woman. Just inching..." (Brooke, 05:27)
Jeffrey paints the scene:
"It's like those cat videos where they, like, pan away for a second and you pan back. The cat's a little bit closer and you pan away and the cat's a little bit closer." (Jeffrey, 06:33)
Benjamin, summing up the awkwardness:
"All I can do is just, like, picture my mom’s clothes." (Benjamin, 17:31)
Josie on her failed approach:
"I'm throwing that strategy out from now on. I'm never using that again." (Josie, 19:00)
This “Second Date Update” episode delivers a classic comedic misunderstanding: Josie orchestrates a slow-burn train flirtation, only for her crush to be interested in her jacket—because it could be the perfect gift for his mom. The result? Rather than sparks, both leave red-faced—and viewers leave with a reminder to be just a bit more direct with their romantic interest... and maybe to pick a jacket that doesn’t say “motherly.”