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Jeffrey
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Brooke
I search the Internet for answers to my cold sore problem? Now I'm stuck down a rabbit hole filled with images of alarmingly graphic source in various stages of ooze. I can clear my search history, but I can never unsee that.
Jeffrey
Don't go down the rabbit hole.
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Bowen Yang
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Brooke
Oh, I love when we get these. A check in from one of our second date couples. It's called an update. Update.
Sierra
Yes.
Brooke
Welcome to the second date podcast. And remember, okay, we are going to play the original call. You may have already heard this original call, but it's important.
Jeffrey
It's not a mistake.
Brooke
No, it's important for you to know what's up before we get this couple back on the phone. So it is part three that we're gonna hear them and get their update from them. So, yeah, stick around.
Listener/Caller
Yeah, there'll be a little ad before part three.
Brooke
Stick around. Yeah, it's worth it. Okay, here we go. What do you see in the comments?
Listener/Caller
Yeah, Jay said, I love listening to Brooke and Jeffrey so much when I'm watching hockey games. Intermission feels way too long. So I listen to these during intermission time. It always does the trick. So I can speed up the time
Jeffrey
like 15 to 20 minutes. I'm the same in between hockey intermissions.
Brooke
I'm like, what am I gonna do?
Jeffrey
Yeah, I'm like, I can go play a couple games of fortnite, man.
Brooke
All right, well, I guess turn it on. Yeah.
Listener/Caller
Hope the game's going good.
Brooke
Let's go. Your team, your second day. Update. Update starts right now.
Jeffrey
It's the classic phrase you always hear. Oh, I normally never do this on a first date.
Brooke
It always means that you always do that.
Jeffrey
Why are you so good at it? As they walk out of the exhibit at the botanical garden because the nearby porta potties broken. I swear, this never Happens to me. By the way, can I borrow a leaf real quick?
Brooke
Why do you.
Jeffrey
In today's call, we had one of those moments where somebody says, I normally never would do this. Uh, oh, but, oh, boy, did they. You're gonna find out what it was in your brand new second date update. Update. Yes, we're gonna do it next.
Sierra
Brooke and Jeffrey in the morning.
Brooke
Second date update.
Jeffrey
When your date plans change at the very last time. Second, not by your choice, but because of, like, an unforeseen obstacle with the venue.
Brooke
Okay.
Jeffrey
Like, the baseball game got rained out. Oh, yeah. You can't control that the KFC ran out of chicken. That doesn't happen. What's your move? Like, how do you respond? You could instantly give up right there and say, no, I'm not doing this. I'll FaceTime you from my bubble bath. But I don't pivot on the fly.
Brooke
Yeah. Be flexible, Jeff. Be spontaneous.
Jeffrey
That is the other option. Shake it up. Do something new. And apparently that's what one of our listeners, Sierra, had to do recently on her date, and I'm curious what that looked like. So, Sierra, welcome to the show.
Listener/Caller
Hi.
Brooke
You sound like a go with the flow type of person.
Sierra
I try sound like a baseball in
Jeffrey
the rain kind of lady.
Brooke
Yeah, that's good.
Jeffrey
Sorry to hear that your date plans crash, but tell us what happened.
Sierra
So I met this guy Ashwin on a dating app.
Brooke
Oh, he sounds fancy and rich. His name is Ashwin.
Sierra
Not gonna lie, the name intrigued me. But what I really liked the most was he was playful. Like, he was kind of saucy, but not disrespectful.
Brooke
You know what I mean?
Jeffrey
Rosy a little bit, but, like, totally joking. Yeah, it's like talking to your grandpa, but 60 years ago. No, Jeff, not at all. Everybody has a grumpy grandpa who likes to poke fun at them, right?
Listener/Caller
Not grumpy.
Brooke
Yes. He's not an old.
Jeffrey
He's playful, flirty. His name is Ashwin. He sounds like a grandpa already.
Brooke
Okay, you got us there, Jeff, but the rest of us, you lost us on.
Jeffrey
Okay, well, we all have different images of what Ashwin is, but what was the plan for the date?
Sierra
Well, you know, I'm happy to say that wasn't my first impression.
Jeffrey
That's good.
Sierra
I liked him. I liked him enough to say yes to a date with him. And I think that he was kind of trying to impress me, which obviously is fine with me. Like, he had made rooftop reservations at this, like, trendy place.
Jeffrey
Rooftop bars are always good. Okay, so you sound like you're excited to get some rooftop drinks.
Sierra
Oh, I was so excited. I love this kind of thing. And we go up the elevator and the guy at the door said he was so sorry, but the whole place was closed for, like, some kind of a cryptocurrency event.
Brooke
Oh, God.
Jeffrey
Sorry, Brooke. Brooke isn't mad. They're closed. It's the crypto thing.
Brooke
Yeah, I know.
Sierra
I was mad.
Jeffrey
They're the only people who could afford to rent out an entire rooftop.
Brooke
I just picture bunch of dudes with receding hairlines and telling each other the same thing in puffer vests.
Jeffrey
Yeah. Careful, you're turning Alexis on too.
Listener/Caller
Even I draw the line.
Jeffrey
Oh, no, but that's. What a bummer. Your whole plan for the night just got totally ruined.
Sierra
Yeah, I mean, it was really disappointing, but I just said, screw it. Let's take a walk. I'm not wearing the greatest shoes for it, but I just really wanted to spend time with him at that point. So we walked down the street and we walked and talked for a while, and we just. Just kind of ended up at this old. It was just like a diner, like a normal, you know.
Brooke
Okay, okay.
Sierra
It wasn't like a cute, like, oh, we're trying to be retro diner. It looked like it had just been there for, like, 70 years.
Jeffrey
You went from, like, Nobu to the Waffle House.
Brooke
Yeah, the grease trap hasn't been cleaned in at least two years.
Jeffrey
But that's why the food tastes so good.
Brooke
Okay.
Jeffrey
We're putting a lot of emphasis on, like, the location of the day. But what about the bond, the connection between you and Ashwin? Did that change once you ended up at the crappy diner?
Sierra
No, I mean, it was. Honestly, it was kind of perfect. Like, we were sitting there eating cheese fries and drinking milkshakes and in our formal clothes, just talking, you know? And probably because the plans had changed and we were thrown in this situation, we ended up having just the greatest, most real conversation.
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That's awesome.
Brooke
That's such a good sign for anyone. If you can be anywhere with someone and still have a good time, that means that you actually have a real connection.
Sierra
Yes. And after our plans fell, you know, like, it just felt so good. It felt so comfortable talking to him. We talked for hours.
Brooke
Oh, my gosh. How could he not be coming?
Jeffrey
Yeah, I mean, how did this night end?
Sierra
Well, okay, so one thing led to another. He kissed me good night. And I did, of course, end up at his place.
Jeffrey
Really? Post chili cheese fries. You guys went back to his place?
Sierra
Hey, I'm telling you, I felt very comfortable with him, and I. Apparently, I didn't leave till the next morning, in fact, which is unusual for me, but.
Brooke
What did he say? Was he there when you woke up?
Sierra
Yeah. No, he was just his sweet, playful self. He gave me a little kiss on the nose, which I thought was adorable and.
Brooke
Okay, so it wasn't even awkward the next morning?
Sierra
No, not at all.
Jeffrey
It makes me wonder if it was like one of those typical guy things where it wasn't enough of a challenge and it became too easy. So the guy gets bored.
Brooke
He doesn't sound like a guy that is like that, though. Jeff. This sounds like they never.
Listener/Caller
They never do, Brooke.
Jeffrey
Yeah, they're always the prince Charming until they ghost you.
Brooke
Sounds like they were just vibing on a deeper level than that. If he just wanted to get in her pants and that's all he wanted, or he was disappointed in that. They could have gone anywhere and just gone and drank.
Jeffrey
Maybe he knew that crypto event was happening and this was all set up as, like, a little ruse. Be like, look at me. Look how spontaneous I could be. Let's go back to my place.
Brooke
You are so cynical against men right now.
Jeffrey
I'm just telling you this. I've heard guys do stuff like this and sometimes even worse.
Brooke
I know I still want to thank for the best, Jeff. I'm sorry.
Jeffrey
All right, well, you can be naive if you want, but let's call Ashwin and we'll see what he has to say.
Sierra
Thank you, guys.
Jeffrey
Your second date update right after this. Hold on.
Sierra
Brooke and Jeffrey in the morning. Second date update.
Brooke
You're in the middle of a second date update update. And we're going to find out how the couple is doing right after you hear part two.
Jeffrey
Wow, Another first date blown up by a pod of crypto bros. You have, like, this happens all the time. Every single week. We deal with this because our listener, Sierra was supposed to meet a guy named Ashwin at a rooftop bar. But of course, when they arrived, the entire venue had been rented out by a bunch of crypto nerds geeking out over yield farms and stabilizing their coin pools.
Brooke
Oh, God.
Jeffrey
Whatever they like to talk about, bro. Look at these candlesticks popping. Don't even know what that means, but it disgusts me.
Brooke
No wonder I don't enjoy any of it.
Jeffrey
Here's the thing. Sierra and Ashwin didn't let that kill their night. They actually swung it into a really fun evening at a local diner, which eventually led into a sleepover really good.
Brooke
It sounds so sweet.
Jeffrey
It did. Until Ashwin is suddenly not calling her back.
Brooke
And you've reached out to him or you haven't. You're just waiting to hear from him.
Sierra
This was what was so weird. We texted a little bit after that, but he just. I. I got the vibes that he was not. Not interested.
Jeffrey
Oh, even through texts?
Brooke
Yeah.
Sierra
Yeah.
Jeffrey
Feel that energy shift.
Ashwin
For sure.
Brooke
I hope it's one of those where he's just scared of real love.
Jeffrey
Yeah, no, that sounds stupid. But sometimes, like you had said. Oh, there's no challenge. Like, if it's too easy and everything is great.
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Right.
Jeffrey
Sometimes people don't like to be in that space. I don't know. We'll see which category Ashwin falls into if we're able to get him on the phone here. I'm gonna dial his number right now. Two perfect categories. We're praying for a Disney ending. Here we go.
Brooke
Getting her another nose kiss, Jeff. That's right.
Jeffrey
What a promise. Okay, here we go.
Ashwin
Hello?
Jeffrey
Hey, is this Ashwin?
Ashwin
Yes.
Jeffrey
Hey, man. Thanks for answering. You're on a radio show right now. It's called Brooke and Jeffrey in the Morning. Hey, good morning.
Brooke
Welcome to the show. Ashwin.
Ashwin
Hi.
Brooke
Sounds like you might be busy or something right now.
Jeffrey
Yeah, I hope you have a second to talk to us, because we're doing a segment called A Second Date Update.
Ashwin
Sure. This is weird. Okay.
Brooke
Yeah, he's nice.
Jeffrey
You give him a lot of credit. So the reason that we're calling is because you went out on a date recently with a listener to our show, a woman named Sierra.
Ashwin
Oh.
Sierra
Oh, yeah.
Brooke
You mean.
Jeffrey
Sure. So here's the thing. Sierra, we talked to her, and she told us about your hang the other night.
Brooke
The diner sounded so cute.
Jeffrey
It sounded pretty good. Despite all the obstacles that came up, you two were able to have a really good thing. Would you agree with that?
Ashwin
I mean, we did. It was probably one of the most amazing dates I've ever been on.
Jeffrey
What the heck, bro? Why aren't you calling her? We're all over here waiting to find, like, some crazy reason. Yeah.
Sierra
That's so sweet.
Jeffrey
Sorry to be so emotional about it, but it's just, like, you know, Sierra's really confused.
Ashwin
It's. It's just kind of embarrassing.
Jeffrey
For you or for Sierra?
Ashwin
For me.
Brooke
All right, well, I mean, if it's too much to share, you should do
Jeffrey
it anyway, because, yeah, we could really use the content.
Brooke
I don't want to pressure anybody, you
Jeffrey
know, And Sierra really deserves to know.
Ashwin
Wouldn't she say, yeah, yeah, no, she is. She's really awesome. This is mostly a me a me thing.
Jeffrey
Okay, well, if you're willing to open up to us just even a little bit and we could pass the message to her, I think that would go a long way.
Ashwin
We had this amazing, amazing night, and she told me that she doesn't do this a lot, where she goes to a guy's place, and that she was curious where she ranks.
Jeffrey
Oh, where she what?
Brooke
Ranks.
Jeffrey
Ranks where she ranks, like, compared to other people.
Ashwin
Yeah, I was very thrown off by that question.
Listener/Caller
Is it a joke?
Brooke
You had to do that?
Ashwin
It was not a joke because I asked her to clarify. I said, what do you mean? And she said, well, I'm sure you've been with. With X amount of people.
Brooke
Well, that's kind of a rude assumption. Yeah. But you know what? Or it's a testament to your experience that you had. You could take it as a compliment.
Jeffrey
What? Did you. I mean, did you actually rank her?
Brooke
God, no.
Ashwin
Well, I. I told her that. I'm not sure how to answer that.
Jeffrey
Yeah, that's good.
Sierra
And.
Ashwin
And eventually I said top three for sure.
Brooke
Oh, that's cute. That's a good, safe answer.
Jeffrey
Like what? Only top three.
Listener/Caller
Oh, I take top three. That's great.
Jeffrey
And you don't want, say, number one because then you're too eager and I
Listener/Caller
don't believe it if you say number one.
Jeffrey
Yeah, I've seen myself. I know. I'm not that good.
Ashwin
So then I told her, since I answered this for you, you have to reciprocate.
Brooke
Why would you do that? You don't want that.
Jeffrey
She asked it to him.
Brooke
Oh, God.
Jeffrey
What did she say?
Ashwin
She said, you're definitely in my top five.
Brooke
Okay. Okay. Not bad.
Jeffrey
She, like a little bit lower than what you ranked her, but
Ashwin
it gets worse. I asked out of how many?
Brooke
No.
Ashwin
And she said maybe five.
Jeffrey
Oh, wait, five out of five. Top five out of five. So you're in the top hundred percent.
Brooke
That changed everything for you, I assume. Because it just changed everything for me.
Ashwin
I didn't really know what to say because I already felt so vulnerable. You know, we're in my bed naked, and we've just been together.
Jeffrey
Okay.
Brooke
It's like getting a participation trophy after the fact.
Jeffrey
Well, you know, maybe. Maybe there was some sort of miscommunication or she didn't say quite what she meant. And I'll give her a chance to explain herself right here because I need to let you know Sierra is on the other line of this call listening Wanting to talk.
Ashwin
Oh, God. Oh, God.
Brooke
She's the one that should be embarrassed.
Jeffrey
Yeah.
Sierra
Ashwin, hi.
Jeffrey
Please tell us five is, like, the number one ring. Like, it's the best.
Brooke
Oh, yeah. You were going backwards.
Jeffrey
Yeah, yeah.
Brooke
She's like, I can't lie.
Jeffrey
Tried to save you.
Sierra
I feel so sad. First of all, Ashwin, I'm so, so sorry. I can't believe I made you feel that way and you've been feeling that way this whole time.
Jeffrey
Oh, that's a great apology.
Ashwin
Yeah. Thank you. Thank you.
Sierra
Is it okay if I explain a little bit?
Jeffrey
Please, yes. Go into details about why he's doing.
Brooke
You know what? Men that can take constructive criticism is not a bad.
Listener/Caller
What did one through four have that he got?
Jeffrey
There's just one thing he could do better.
Brooke
Better.
Jeffrey
Let's work on one step at a time.
Ashwin
And for. If for some reason I didn't do enough foreplay stuff, I'm open to. I'm open to feedback.
Listener/Caller
You should assume you didn't.
Jeffrey
Okay, well, you know, actually, maybe we shouldn't be asking what he could change. Maybe it's better to ask you, Sierra, why you said that to him. Yes.
Sierra
When I said, oh, you're definitely in the top five of five, I was trying to be playful. I was trying to make a joke. I was trying to be kind of
Jeffrey
kidding.
Sierra
Yes, I was kidding, and I'm so sorry.
Brooke
Why did you leave with that?
Jeffrey
It was a joke, dude.
Brooke
Don't we have a laughter sound button or something we could have hit there?
Sierra
He's definitely top four for sure. Let's just put it.
Brooke
That's a joke too, right?
Jeffrey
Yeah, I think so.
Listener/Caller
Doesn't matter. It's better.
Jeffrey
Yes. Still climbing the rang there, bud. You didn't have to do anything thing. That was great.
Sierra
Can we.
Ashwin
Can we please stop talking about what number I'm ranking?
Jeffrey
Okay. Fair. All right.
Sierra
Yes. I'm so sorry. I'm just so embarrassed. I was trying to make a joke. It didn't land.
Brooke
You definitely have said your apology.
Jeffrey
Yeah. You said that a lot. And I think Ashwin gets the idea that you didn't mean it. But we mean this when we say we'd like to send you out on another date, the two of you. Ashwin, if you're willing to give her one more chance, we would pay for it.
Brooke
Don't let your pride stand in the way of this one, Ashwin.
Ashwin
Yeah, no, her explanation definitely, definitely makes me feel better and embarrassed that I can't take jokes about bedtime. But, yeah, no, I. I definitely would be interested in another date.
Brooke
Oh, that's cute.
Jeffrey
All right, so congratulations. That means Sierra, you got what you came for, another date with Ashwin.
Sierra
Thank you so, so, so, so much. Oh my God.
Brooke
I feel like we just had two listeners who own their own mistakes, which was just wild on this show. Yeah, that never happens.
Jeffrey
A little bit too mature for my
Listener/Caller
this means tomorrow's going to be really bad on the show.
Brooke
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Jeffrey
months of waiting, we finally got Ashwin and Sierra back on the phone to give us an update. Update. And you know, the last time they were on, there was definitely a lot of talk about romantic rankings and room for improvement and we should just ask. First off, I mean, Ashwin's here. Are. Are you two still together? Does that still happen?
Ashwin
Yes, we are. We're still at it.
Jeffrey
Still at it. That's an interesting way to say it.
Sierra
Yes, we are. And I am very happy to tell you that I have officially bumped up his rankings.
Jeffrey
Yeah.
Sierra
Top two.
Bowen Yang
Top two.
Ashwin
She's such a kidder.
Jeffrey
She's joking.
Sierra
I mean, I'm not totally joking. Oh, my God. You know, he's still really, really good. He's like top two.
Ashwin
Well, I mean, I guess I can practice some more to make sure that I get to number one.
Sierra
Okay, baby, you got your work cut out for you. There is so much. Thank you.
Jeffrey
All right, well, sense of humor. She's kidding or not, I don't know. But at least she believes in you. Ashwin, that's. That's good. And maybe enough talk about the rankings. We're just happy that the show was able to get you two together. And it sounds like you're conn continuing with something with the possibility of a long term relationship. So that's great.
Sierra
Thank you, guys.
Ashwin
Yeah, we're happy. Thank you.
Jeffrey
One of you is. So keep us updated on your relationship and the ever changing rankings of romance. Keep up with the show. We appreciate it.
Sierra
Thank you.
Jeffrey
All right, it's Brooke and Jeffrey in the morning.
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Jeffrey
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Aired: May 14, 2026
Podcast by iHeartPodcasts
In this "Second Date Update UPDATE!" episode, hosts Brooke and Jeffrey revisit a memorable matchmaking case involving listener Sierra and her date Ashwin. After an unexpectedly romantic first date derailed by unforeseen circumstances, the two seemed to hit it off—until Ashwin’s sudden withdrawal left Sierra confused. The episode revisits their original call, details their awkward "ranking" conversation, and brings both back on air for a real-time update about where their relationship stands, combining high entertainment with some genuinely sweet moments.
| Segment | Timestamp | Key Points | |-----------------------------------|-----------|-----------------------------------------------------------------| | Update Segment Intro | 03:24 | Setting up the replay and update | | Second Date Call Begins | 05:07 | Diner date after crypto event cancels rooftop plans | | Post-Date Awkwardness | 09:22 | Sierra stays over, feels good, but gets ghosted | | The Ranking Conversation | 14:49 | Sierra and Ashwin swap "rankings" post-hookup; Ashwin deflated | | Sierra's Apology & Clarity | 17:22 | Joke gone wrong, honest discussion, reconciliation | | Agreement to Second Date | 19:23 | Both agree to another date, thanks to the hosts | | Final Relationship Update | 22:23 | Couple confirms they're still together, with playful banter |
This episode of Brooke and Jeffrey's "Second Date Update Update" offers an entertaining and heart-warming look at modern dating mishaps, the importance of communication, and how a little humor (and humility) can create a real connection. Despite an awkward misstep around "rankings," Sierra and Ashwin emerge as a promising couple, leaving listeners with one of the show’s rare double-ownership happy endings.
For listeners who missed the episode:
You'll find a fun, relatable, and cringe-tastic story of a first-date disaster that turns into a memorable, genuine connection, nearly derailed by a playful but misunderstood question about "performance rankings." With both parties coming clean and communicating openly, hope for romance wins—no matter what the numbers supposedly say.