Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Numbers Don't Lie But You Should

Episode Date: May 14, 2026

Ashwin and Sierra came on our show a while back and we got SO many comments asking for more info, we HAD to bring them back for a Second Date Update UPDATE! Stay tuned to the end to hear from both of them and how their romance has gone since last time they spoke with us!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. wife is full of hurdles. So how do you keep going? On hurdle with Emily Abadi, we're talking with the most inspiring women in sports and wellness from professional athletes,

coaches, and Olympic champions about the challenges that shape them and the mindset that keeps them moving forward. At our level, at this scale, being able to fail in front of the entire world. Like, I can do anything. I can do anything. Listen to Hurdle with Emily Abadi

on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Capital One, founding partner of I Heart Women's Sports. I'm Joey Dardano, and on my new podcast, Hope From a Hypocrite, I'll be changing lives, helping people in need with thoughtful solutions. Sike, I'm a comedian. I'm not qualified to give good advice.

Join me and my comedian friends as we riff, rant, and recommend some of the most legally dubious advice known to me. This is Help from a Hypocrite, the worst advice from the dumbest people you know. Listen to Help from a Hypocrite Wednesdays on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hey, it's Edwin Castro, also known as Castro 1021. And I'm Conky, his best friend and business manager.

And we've got a new show called The 1021 Podcast. I'm taking you behind the scenes on how I became one of Twitch's most popular streamers. We also love sports. And with the World Cup right around the corner, we'll be breaking down the biggest storylines ahead of the big tournament here in the USA. Listen to the 1021 podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Why are we all so obsessed with romance? On the Radio 831 podcast, join us, Sanjana Basker and Tyler McCall, as we unpack all the trending tropes, fuzzy adaptations, book talk drama, and celebrity love stories with hot takes and sharp guests.

Each episode digs into what these stories reveal about desire, fantasy, identity, and how we love now. Listen to the Radio 831 podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Oh, I love when we get these. Check in from one of our second date couples. It's called an update update. Yes.

Who named that? That's smart. 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. It's not a mistake. No, it's important for you to know what's up before we get this couple back on phone.

Yes. It is part three that we're going to hear them and get their update for them. So stick around. Yeah, there'll be a little ad before part three. Yeah, stick around. Yeah, it's worth it. Okay, here we go. What do you see in the comments?

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. Oh, that's smart. It always does the trick so I can speed up the time. That's actually smart because they're like 15 to 20 minutes in between. I'm the same in between hockey intermissions.

I'm like, come on. What am I going to do? Yeah. I'm like, I can go play. I'm playing a couple games of Fortnite, man. All right, well, I guess turn it on. Yeah. Hope the game's going good?

Let's go your team. All right. Your second day update, update starts right now. It's the classic phrase you always hear. Oh, I normally never do this on a first date. Oh, my. It always means that you always do it. Then why are you so good at it?

As they walk out of the exhibit at the botanical garden because the nearby port-a-potty's broken. I swear this never happens. to me. By the way, can I borrow a leaf real quick? What? You? Well, in today's call, we had one of those moments where somebody says I normally never would do this. But oh boy, did they? You're going to find out what it was in your brand new. Second date update update. We're going to do it next. Brooke and Jeffrey in the morning. Second date update. When your date plans change at the very last second. Not by your choice, but because of like an unforeseen obstacle with the venue.

Okay. 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. Makes it super datable. Yeah, be flexible, Jeff. Come on. Be spontaneous. 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. Hi. Hey. You sound like a go-with-a-flow type of person. That's right. You sound like a baseball-in-the-rain kind of lady. Yeah. That's good.

Sorry to hear that your date plans crash, but tell us what happened. So I met this guy, Ashwin, on a dating app. He sounds fancy and rich. His name is Ashwin. Not going to lie, the name intrigued me, but what I really like the most was he was playful. Like he was kind of saucy, but not disrespectful. You know what I mean? Roasty a little bit, but like totally joking.

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? Not grumpy, yes. He's not an old man. This is playful flirty. His name is Ashwin. He sounds like a grandpa already.

Okay, you got us there, Jeff, but the rest of us lost us on. Okay. Well, we all have different images of what Ashwin is, but what was the plan for the date? Well, you know, I'm happy to say that wasn't my first impression. That's good. 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. Yeah, totally.

He had made rooftop bar reservations at this, like, trendy place. Oh, rooftop bars are always good. Okay. So you sound like you're excited to get some rooftop drinks. Oh, I was so excited. I love this kind of thing. Okay. 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. Oh, God. Sorry, Brooke. Brooke isn't mad their clothes. This is the crypto thing. I know. I was so mad. people who could afford to rent out an entire rooftop.

I just picture a bunch of dudes with receding hairlines and telling each other the same things. In puffer vests. Yeah. Careful, you're turning a Lexus on too much of your description. Even I draw the line in crypto. Oh, no, but what a bummer. Your whole plan for the night just got totally ruined. 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 kind of ended up at this old it was just like a diner like a normal you know oh okay 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 yeah you went from like no boo to the waffle house yeah the grease trap hasn't been cleaned in

at least two years but that's why the food tastes so good yeah okay we're putting a lot of emphasis on like the location of the day but what about the bond the connection between you and Did that change once you ended up at the crappy diner? 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. That's awesome.

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. Yes, and after our plans fell through, you know, like it just felt so good. It felt so comfortable talking to him. We've talked for hours. Oh, my gosh. How could he not be calling you?

Yeah, I mean, how did this night end? Well, okay, so one thing led to another. He kissed me good night and I did, of course, end up at his place. Really? Post-chilly cheese fries, you guys went back to his point. 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... What did he say? Was he there when you woke up?

Yeah, no, he was just his sweet, playful selfie. He gave me a little kiss on the nose, which I thought was adorable. Okay. So it wasn't even awkward

the next morning. Yeah. No, not at all. 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. He doesn't sound like a guy that is like that though, Jeff. This sounds like they They never do, Brooke. Yeah. They're always the Prince Charming until they goes to me. No, but it 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. 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. You are so cynical against men right now. Brooke, I'm just telling you. I'm just telling you this. I've heard guys do stuff like this and sometimes even worse. I know. I still want to think for the best, Jeff. I'm sorry. All right. Well, you can be naive if you want, but let's call Ashwin and we'll see what he has to say. Thank you guys. With your second date update right after this. Hold on.

Brooke and Jeffrey in the morning. Second date update. You're in the middle of a second date update and we're going to find out how the couple is doing right after you hear, part two. Wow. Another first date blown up by a pod of crypto bros. I knew I think 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. Geekin out over yield farms and stabilizing their coin pools or whatever they like to talk about.

Look at these candlesticks popping. Don't even know what that means, but it disgusts me. No wonder I don't enjoy any of it. 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. Aw, really good.

It sounds so sweet. It did until Ashwin is suddenly not calling her back. And you've reached out to him or you haven't. You're just waiting to hear from him. This was what was so weird. We texted a little bit after that. Oh, you did. I got the vibes that he was not interested.

Oh, even through text. Yeah. Yeah. You can feel that energy shift for sure. I hope it's one of those where he's just scared of real love. Yeah, no, no, that sounds stupid, but sometimes like you had said, oh, there's a real challenge. Like, if it's too easy and everything is great, 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 going to dial his number right now. To perfect category. Yes, yes. We're praying for a Disney ending. Here we go. Getting her another nose kiss. kiss, Jeff. Through the phone.

That's right. What a promise. Okay. Here we go. Hey, is this Ashwin? Yes. Hey, man. Thanks for answering.

You're on a radio show right now. It's called Brooke and Jeffrey in the morning. Hey, hi. Good morning. Welcome to the show, Ashwin. Hi. Sounds like you might be busy or something right now. Yeah, I hope you have a second to talk to us because we're doing a segment called a

second date update. sure this is weird okay yeah 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 oh yeah I mean oh sure

so here's the thing Sierra we talked to her and she told us about your hang the other night the diner sounded so cute 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? I mean, we did.

It was probably one of the most amazing dates I've ever been on. What the heck, bro? Why aren't you called? We're all over here waiting to find, like, the crazy reason. That's so sweet. Sorry to be so emotional about it, but it's just that, you know, Sierra's really confused. It's just kind of embarrassing. For you or for Sierra?

For me. I mean, if it's too much to share. You should do it anyway because we could really use the content. I don't want to pressure anybody, you know? And Sierra really deserves to know, wouldn't she say? Yeah. Yeah, no, she is. She's really awesome.

This is mostly a me, a me thing. 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. 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 where she what ranks? Ranks? Where she ranks like compared to other people? Yeah I was I was very thrown off by that question That's a weird question.

Is it a joke? You had to do that. If it's a joke, it's actually funny. 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 X amount of people. Wow. Wow. That's kind of a rude assumption. Yeah. Okay. But you know what? Or it's a testament to your experience that you had. Yeah. I guess. So that's... You could take it as a compliment. What did you say? Did you actually rank her? God, no. Well, I told her that I'm not sure how to answer that. Yeah, that's good. And eventually, I said top.

Three for sure. Oh. See, that's cute. That's a good safe answer. I don't like, what? Only top three. I take top three. That's great.

And you don't want to say number one because then you're too eager. And I don't believe it if you say number one. Yeah. I've seen myself. I'll find out I'm not that good. But then I told her since I answered this for you, you have to reciprocate. Why would you do that? You don't want that.

She asked it to him. Oh, God. What did she say? She said you're definitely in my top. five. Okay. Okay. Not bad. She liked a little bit lower than what you ranked her, but yeah, it gets worse. I asked her out of how many. No. And she said maybe five. Oh, five out of five. So you're in the top hundred percent. That changed everything for you. Okay. assume because it just changed everything for me.

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. Oh, God. Okay. It's like getting a participation trophy after the fact. Well, you know, 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 to. What?

Oh, God. Oh, God. She's the one that should be embarrassed. Ashwin, hi. Please tell us five is like the number one rank. Like it's the best. Oh, yeah, you're going backwards. Yeah.

Yeah. She's like, I can't lie. You're trying to save you. I feel so bad. 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. That's a great apology.

Yeah, thank you. Thank you. Is it okay if I, if I explain a little bit? Please. Yes, go into details about why he's going to. You know what? Men that can take constructive criticism is not a bad thing. Once it's one through four have that he did.

Just one thing he could do better. Let's work on one step at a time. And for some reason, I didn't do enough for play stuff. I'm open to, I'm open to feedback. You should assume you didn't. Wow. 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. 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 funny and slurdy. You were kidding? Yes, I was kidding. It was a joke. Dude, don't you know a laughter sound button or something we could have hit there?

he's definitely top four for sure let's just put it up that's a joke too right doesn't matter it's better yeah you're still climbing the rain you have to do anything

that was great can we can we please stop talking about what number I'm ranking okay fair all right

yes I'm so sorry I'm just so embarrassed I was trying to make a joke it didn't land you definitely have said your apology 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. Don't let your pride stand in the way of this one, Ashwin. Yeah, no, her explanation definitely makes me feel better and embarrassed that I can't take jokes about bedtime. Bed time. Yeah, no, I definitely would be interested in another date. Oh, that's cute. All right. So congratulations.

That means Sierra, you got what you came for. Another date with Ashwin. Thank you so, so, so much. Oh, my God. I feel like we just had two listeners who own their own mistakes, which was just wild on this show. Yeah. It never happens.

It's a little bit too mature for my life. This means tomorrow's going to be really bad on the show. Brooke and Jeffrey in the morning. Experience Harry Styles live in London, England, at Wembley Stadium. This is Harry Styles. Iheart Radio wants to send you and a mate across the pond

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Very excited to see you at the show. Kiss all the time, disco occasionally, available now. Another podcast from some SNL late-night comedy guy, 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, 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. After 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, Sierra, are you two still together? Is that still happening?

Yes, we are. We're still at it. Hey. Awesome. Still added. That's an interesting way to say. Yes, we are. And I I am very happy to tell you that I have officially bumped up his rankings. Oh. Now, top.

Yeah? Top two. Top two. She's such a kidder. She's joking. I mean, I'm not totally joking. Oh, my God. But, you know, he's still really, really good.

He's like, top two. Well, I mean, I guess I can practice some more. to make sure that I get to number one. Okay. No, baby, you got your work cut out for you. There is so much. Thank you. I have to my idea.

All right. I get the sense of humor. She's kidding or no. I don't know. But at least she believes in you, Ashwin. 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 continuing with something with the possibility of a long-term relationship. So that's great. Thank you, guys. Yeah. Yeah, we're happy. Thank you. Okay. End it there.

Yeah. At least 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. Thank you. All right. It's Brooke and Jeffrey in the morning.

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. Life is full of hurdles. So how do you keep going? On Hurtle with Emily Abadi, we're talking with the most inspiring women in sports

and wellness from professional athletes, coaches, and Olympic champions, about the challenges that shape them and the mindset that keeps them moving forward. At our level, at this scale, being able to fail in front of the entire world. Like, I can do anything. I can do anything.

Listen to Hurtle with Emily Abadi on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Capital One, founding partner of IHart Women's Sports. The story I told myself can then shape my behavior and that can lead me to sabotage

the possibility of connection. This Mental Health Awareness Month, Tune into the podcast Deeply Well with Debbie Brown. If you've been searching for a soft place to land while doing the work to become whole, this podcast is for you to hear more. Listen to Deeply Well with Debbie Brown from the Black Effect Podcast Network on the Iheart Radio app, Apple Podcasts, or wherever you get your podcast. Why are we all so obsessed with romance? On the Radio 831 podcast, join us, Sanjana Basker and Tyler McCall.

as we unpack all the trending tropes, fuzzy adaptations, book talk drama, and celebrity love stories with hot takes and sharp guests. Each episode digs into what these stories reveal about desire, fantasy, identity, and how we love now. Listen to the Radio 831 podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Joey Dardano, and on my new podcast, Hope from a Hypocrite, I'll be changing lives, helping people in need with thoughtful solutions. Sike, I'm a comedian. I'm not qualified to give good advice. Join me and my comedian friends as we riff, rant, recommend some of the most legally dubious advice known to me.

This is Help from a Hypocrite, the worst advice from the dumbest people you know. Listen to Help from a Hypocrite Wednesdays on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.