Brooke and Jeffrey: Second Date Update - Second Date Update: Sweet Benjamin and His Big Sis

Episode Date: March 9, 2026

The guy looking to score another hangout with date isn’t even on the phone with us! Someone else is doing the call IN HIS PLACE! Find out who it is in your Second Date Update!See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember, 988, Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. Ego Woda is your host for the 2026 IHart Podcast Awards, live at South by Southwest.

Hello, is anybody there? Raised by a single mom, Ego may have a few father-related issues. Are we supposed to talk about your dad? Her podcast, Thanks Dad, is full of funny, heartfelt conversations with actors, including fellow S&L alums, comedians, musicians, and more about life and their wonderfully complicated relationships with their fathers. I think and hope that's a good thing. Get to know Ego.

Follow Thanks, Dad with Ego Wodom and start listening on the free IHeart Radio app today. Hey, I'm Jay Shetty, host of the On Purpose Podcast. I'm joined by Luke Combs, award-winning countryman. music artist and one of the most authentic voices in music today. The guy that says he's always going to be there and that will do anything to be there is the only guy that's not there. No matter what, I'm going to prioritize my wife and my children. I dread the conversation with my son.

Listen to On Purpose with Jay Shetty on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Ready for a different take on Formula One? Look no further than no grip. A new podcast tackling the culture of motor racing. most coveted series. Join me, Lily Herman, as we dive into the under-explored pockets of F-1, including the astrology of the current grid, the story of the sports most consequential driver's driver's strike, and plenty of other mishaped scandals and sagas that have made Formula One

a delightful, decadent, gumster fire for more than 75 years. Listen to no grip on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts. Hi, it's Joe Interesting, host of the Spirit Daughter podcast, where we talk about astrology, natal charts, and how to step into your most vibrant life. And today I'm talking with my dear friend, Krista Williams. It can change you in the best way possible. Dance with the change, dance with the breakdowns. The embodiment of Pisces intuition with Capricorn power moves. So I'm like delusionally proud of my chart. Listen to the Spirit Daughter podcast starting on February 24th on the IHeart Radio app, Apple Podcasts, or wherever you listen to your podcast.

Hey, it's Monday after a time change. Oofta. I know, right. Yeah. Hey, welcome to it. We're going to try to get through this all together. We do have a brand new second date for you today to kind of wake you up, keep you going. And we always love to start those with comments.

Yes. Bismingo said, hi from Romania. You guys almost got me kicked out of class. I was listening to y'all during class with my earphones. And it suddenly got out of power. And the show started blasting in the silence. Amphitheater. Thank God my professor was a listener. Now I know how to get better grades. That's awesome.

That's awesome. I don't know. That's incredible. I'm scared what segment and what part was playing when it went out loud. I mean, you usually get held back for that stuff. Yeah, that's right. All right, dummies, here's a brand new second date update right now. Brooke and Jeffrey in the morning, second date update. I read an article recently where in New York city right now. Yeah. They're holding speed dating events. Just tons of them where it's a three to one female to male ratio.

Dude, keep going. I've heard about this. Yeah. This is where men can attend them for free. Yeah. And women have to pay $100 or more. Which is a lot. Is that crazy?

Drastic price difference. But guys just aren't showing up to these like at all anymore. Oh, they're not. And the reason why is because they interviewed some of the guys and men say they feel like they're most likely going to get ignored or rejected by the women there anyway. Yeah, that's true. So even a free ticket just feels like a big waste of time. Totally.

So all the men have given up in New York City? And blame the woman? Yeah. I love it. That's what I just heard. Well, it's nice that you came with such an open heart towards these guys and their feelings. I'm sure that it's nothing to do with how they feel. I wonder where they'd feel weird about the women.

I know. But no one knows that better than one of our listeners, Stacy, who's on the phone right now, because she wingmaned her brother at one of these events. I'm not sure why he's not on the phone with us. Hold up. If you're just wingmanning your brother, your brother better have paid your $100 entry fee. Stacey, welcome to the show.

Hey, guys, how's it going today? Good. We ask you the questions. Brooke is right. Who paid? What confused? So, yeah, I guess who paid? Did your brother pay for this?

My brother did pay for it. Okay. Wow. And why did he think he wanted his sister to be there? You know, he's just a really show. shy guy. He asked if I would go with him. And of course, you know, he's my baby brother. I love him. I'm going to go with him. I want him to find happiness. You're like his comfort, like service animal. Yeah. Until you find a hot guy and then he's on his own. Most certainly. Oh, wait, did you participate too? I did. I didn't find anybody, but he did. What we thought. I thought this was a second date update for you. No, I am actually calling for my brother. Interesting. Look, I told him to call you guys.

He said he was too nervous. So I said, why don't you just email them? And he just was too embarrassed, couldn't do it. Oh, buddy. He's not even face-to-face with us. Like, we're harmless. We're on the phone. I know, but that's scary to be on the radio.

Like, I could get that. Yeah, especially when we're talking to Brooke. As a man, I would feel fear coming on to this show. I mean, your sister will air all your dirty laundry. Yeah. The nice thing is we'll probably get the honest truth about what you think he did wrong before we call this, girl. Instead of him just being oblivious to everything. That's how siblings were. I'm curious, how much

do you know about your brother and the girl he met? How much detail do you have? I mean, I have the detail in the sense that I was there, and I was kind of overhearing what they were saying, but they hit it off so well. They had so much in common. My brother

spent a year in Italy for a travel abroad program, and it turns out that she did too. They just seemed to really, really hit it off. And, you know, that arm touch, you just reach across the table when you're laughing, and it means more than just touching your arms. She did that, like, five times. Oh. Oh. That's cute. And did he, did he do that to her? They're just touching arms back and back and maybe you touched both their

arms? No, no, he was very respectful, but at the end of the date, they picked each other. Okay. Oh, that's right. At the end of the speed dating. Yeah. Choose your favorite. It's wild to, like, pick somebody, spend the money to be at the event. and then not follow through with the person that you picked. Are you just thinking about wasting money? Yes. Sometimes you don't change your hearts. So this is the only interaction that they had is at the speed dating?

No, they did go on a follow-up date. Oh. Oh, yeah. Right after they went to dinner, I did not join them for that one. It is very possible he screwed it up there. Oh. Okay. He said dinner was fine, but it ended with him walking her to the car.

Good. He was hoping to chat with her, but she was really, really quiet and just kept insisting that he didn't have to walk her back. Oh, that's a bad sign. Oh, during the walk? Most girls appreciate it. You really don't have to come. Well, I mean, at night you want somebody to do with it. Anybody.

I mean, guy, girl, like friend? Normally, unless, yeah. The server? Clearly there's something happening between the two of them where she doesn't want him around. And that's how you know he did something wrong, right? As the sister? It's very possible. Ben is so sweet.

Like, we call him sweet Benjamin in the family. Like, that is... I don't know if that's a good or bad thing. Sweet Benjamin sounds like he needs extra, like... We have her first reason why she's probably not calling him back. Yeah. That's good. It is very possible, but I also...

He doesn't know what's going on. And I just... I want to help because he walked her to the car, and apparently she didn't even say thank you. She just waved, got right in her car. Like, no opportunity to even, like, hug goodbye. Does Ben know that you're doing this for him? I know you encouraged him to do it, but does he know you took the reins?

I told him I was going to. I don't know if he believed me, but at this point, he should. If this is interesting, it's going to hit the air. He's going to hear it. Sister instinct, what do you think went wrong? I feel like there was probably a misunderstanding of some kind at dinner. Okay. I don't know what it could be, but Vita seemed so into him that it just doesn't make

sense. I'm sorry, what was her name? Vita. Like, don't cry for me, Argentina. Oh, I thought it was like the coconut water. Oh. Vita. Yeah. Oh, yeah, like the coconut water. All right, so she sounds a little bit foreign. Maybe she needs like a spicier guy in her life, not sweet then.

Well, she did go to Italy for a while. That's true. Oh, what's her to be? If she's also a shy person, this may be really overwhelming. Yes. Yeah. Well, again, then we won't air it. I know. I'm excited to find out when we come back. We call Vita for on behalf of Stacey's brother.

What's his name again? Ben. Sweet Ben. Oh, that's right, sweet Ben. I'll forget. We'll see why she was acting so awkward at the end of their day when we come back and get it with your second date update right after this. Awesome. Hold on.

Brooke and Jeffrey in the morning. Second date update. Behind every sweet, shy boy is a proud, well-spoken sister. Yeah. Ready to go to bat on his behalf. Like your sister, Jeff. Says our own shy boy. And that's why Stacey reached out to us

because she wing-maned her brother, Ben, recently, at a speed dating event, and watched him walk out the door with a pretty woman. And watched chemistry happen. Get it, sweet Benjamin. He walked right out that event and took her straight to dinner where apparently things probably went wrong. He blew it.

We don't know exactly what happened there, but according to what Stacey has heard from her brother several times as he was walking her back to her car, she said to him, you know, you don't have to walk with me, which is not a good sign. Yeah. Never said thank you and just waved goodbye at him before she left. And Stacey demands answers. Well, I mean, Stacy's trying to help out of time.

Stacey is ready to hit someone if someone doesn't explain what went on. Am I right, Stacy? Oh, you are not wrong. I am ready to fight here. Okay. That's a good sister. I knew it. Do you know what we never asked?

Did Vita find out that you were at the speed dating event? I don't know if she did. Okay. I'm just wondering. But it did occur to me. That could be a weird thing. Right. For some people that may not sit, right?

Especially if they're not close with their sibling, they don't understand that. The way that Ben may have brought it up at dinner could be, you know, yeah, I took my sister to the speed dating event. And that could be kind of awkward. My husband often says, I married my sister. I'm like, no, you officiated. the wedding, honey. It's different. I said the same.

I appreciated my sister's wedding. How you say the words matters a lot. So let's find out what happened. We don't know. So the only way to find out is if Vita picks up the phone and actually comes clean with it. So let's do it. I'm going to dial the number.

Here we go. Hey, we're looking to speak with Vita. Yes, this is her. Hey, Vita. Thanks for answering. We're a radio show. We're called Brooke and Jeffrey in the morning. Hi, Vita.

Good morning. I like your name. Hi. Thank you. You sound really outgoing. Yeah. Thanks, Brooke. Not you.

Oh, my bad. Sorry. Thank you guys. What's up? Yeah, we're really eager to talk to you because we heard you went out with a guy that we kind of know. Name Benjamin. His name is Ben. Yeah, he's a friend of ours.

You guys went on a speed date. That's where you met and then went on a dinner date afterwards. Yeah, the pity date. What? Oh, pity date. Why would you say that? just like ripped a bandit off for us. Well, like, at the speed date,

he was just like borderline crying about how he hasn't been out with a woman. Oh, no. And I was like, okay, well, I guess let's just go after this. Are you exaggerating a little bit? I mean, maybe he was just, maybe. No.

Brooke? Maybe a dust in his eyes. Try you. Walk us through the crying part. I mean, it's not crying, But just like borderline, like, tears in his eyes. Like, sulking. But, you know, he wasn't creepy, so, like, I knew, like, he would be safe to go out with.

Yeah. Oh, okay. He's just, like, sweet. Yeah. I hate that these are our boundaries as women. Yeah. Oh, my feel so bad. I'll take some free dinner from this sweet, not creepy guy, and then I'll ghost him forever.

Well, maybe she took him out. Did you pay? No, he paid. Oh. Okay. Well, good. Like a gentleman, but, yeah. So, wait.

When you said yes to dinner, did you tell him, like, fine, take me out? Like, was it obvious that it was a pity date, or did he think you were actually into it? I mean, he couldn't have thought that I was too into it. Like, I didn't seem like overly enthusiastic about it. I was just like, okay, well, let's go to dinner. That's not quite the review that we heard. We were under the impression there was more chemistry between you two at the speed dating event. Remember you had lived in Italy?

He had arms, you had arms, you touched your arm, His arm. I remember on this V-date, I kept touching his hand because he had, like, peanut butter on it or something. Oh. Like a child? That would make me not want to touch it. Yeah. Sorry, he was just eating bumps on a log, my bad.

So. It was pretty pathetic. Oh. Oh, I feel like he's adorable because he's pathetic. I mean, is that a thing? Here's the thing. You never gave him a chance, it sounds like. I went to freaking dinner with him.

What do you mean I didn't give him a chance? I know, but you'd already written in your mind that it was a pity date, you know? Like, once you pity someone, you can't. Like, there's no respect there. Yeah, even if he does something cool, it's hard to break out a pity. Well, did he do something cool? Like, was he at least nice and respectful during your dinner date? He was fine, but just like anything, like, once you get the ick with somebody, like,

and you know what? Like, he couldn't even order his own dinner. Like, I had to pick his meal for him, like, mother. Like, I'm surprised he didn't ask me to cut up his food. Okay, that is a little childish. Well, we heard he's socially awkward. So. Or just maybe nervous around a really.

pretty woman. Well, if you take a pretty woman out to dinner, you should at least be able to order for yourself. I'm taking you

to the nicest place in the city. Will you read the menu for me? It's not going to look good when he finds out who's on the phone. Yes. I feel so bad.

Do we have to do this part? We do. Because here's the deal, Vita. We kind of have a surprise for you. Because Ben is not on the phone

with us right now. Surprise. His sister's Stacy, however, is. Are you kidding me? I'm not. She was the one who reached out looking to get answers on Ben's behalf, so she wants to talk to you, I think. Stacey? How dare you?

You are an absolute monster of a human, and I am so grateful, so grateful that my brother is not going on a second date with you. And I cannot. I cannot be. You're like, this is so typical. He can't even, like, call the radio station himself. He has his sister. He can't call the radio station himself because he's so used to women like you, causing these kinds of problems. How dare you?

Stacey. No. What? Let's take a deep breath. Like, she didn't know you were listening. She didn't know. Like, she wasn't trying to hurt anybody's feelings. I understand it was probably hard to hear.

It was harsh. It was harsh. But you know what? If she didn't like him, why'd she pick him for the date? Why was he the one? You have to pick a person. I didn't want him to bust out trying. I was literally just like throwing the dog a bone.

Oh, my gosh. Don't call him a dog. It sounds rude, but she was trying to help. You were not trying to help. Are you kidding me? This bitch wanted a free deal. You literally said it. You literally said it in the call.

What did she say? She said she was not interested and that she went out with him anyway. She called it a pity date and I swear to God, If I hear pity date one more time, I'm going to lose my... Okay, okay. Okay. You know, I agree Vita is saying some not nice things. But Stacey, maybe, like, even though it's a pity date, maybe your brother doesn't have to know.

You know, it's like getting a job when you already have a job is easier. Like going on another date when you know you've been on one, maybe it's a boost of confidence he needs. Let him break up with her. Y'all are spinning this in a way that you're trying to get her off the hook. And how dare you treat a kind man like that? Exactly, Brooke. How dare you? Treat a kind man like Ben like this.

Your brother was like crying during the speedy. I was sitting right there. He was absolutely not crying. He was engaging in the conversation. Yeah, he's in touch with his emotions. Yeah, a little too engaged, just like a little too emotional. And then at dinner, like, what adult cannot place their own food order? You know what, Vita, I've heard enough.

You've already said all of these things. And you have absolutely made the worst decision of your life. You would be lucky to date someone like my brother. Oh, what a good sister. You should go out with your brother. No, no, no, no. Oh, God. I like this segment.

Okay, but listen. I know. We should do more brother-sister second date updates because this is awesome. My sister will call a girl yell at her. So all yell at girls for my brothers. Oh, hell, yeah. Stacy, could you maybe see that you guys, like your family's maybe coddling your brother a little? little bit too much. Like, you're calling them like...

Oh, Stacey, she's doubling down saying your brother's a wimp. I just... This isn't about my brother anymore. This is about that woman, that toxic woman and her behavior. I know Brooke is not the most pleasant person. I know. Not Brooke. Not Brooke. I'm talking about Vita.

Because what she did to that sweet boy, regardless of what... He's a grown man. He's like 40 or something. Oh, Lord. That sweet boy needs to grow up. Yeah, and you need to find a soul, you harpy. Oh, I don't know that is. I'm not sure it hurt, though.

Do we beat that? You know, it's at this point in the call where we always offer to send the couple out on another date and we would pay for it. So at this point, Vita, I feel like there's a chance that we could have all three of you meet up one more time to work out your differences and all order food for each other. No, I think I'm going to pass on that one. Oh, thank God. Passing with Stacy, but not on her brother. You're still open to Ben? On both of them, I'm good.

And Stacy, I don't appreciate you calling me names. Your brother should grow the fuck up. Oh, okay. Maybe a hard truth. Maybe he should, but at least he won't be alone for the rest of his life. Because he'll have her. Okay, I think she meant that as a dig to Vita. Yeah.

But I worry that might actually happen, where Big Sis is actually going to end up becoming sweet Benjamin's mommy, ordering him smiley-faced pancakes off the I-Hop menu for the rest of his life. Hey, don't hate on those. Oh, sorry. It's kind of sweet. You're right. Brooke and Jeffrey in the morning.

Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember 988, Canada's suicide crisis hubline. It's good to know just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada.

Hey, I'm Jay Chetty, host of the On Purpose podcast. My latest episode is with Hillary Duff, singer, actress and multi-platinum artist. Hillary opens up about complicated family dynamics, motherhood, and releasing our first record in over 10 years. We talk about what it's taken to grow up in the entertainment industry and stay ground. through every chapter. It's a raw and honest conversation about identity, evolution, and building a life that truly matters. You desire in family like this picture, and that's not reality a lot of the times for people. My sister and I don't speak. It's definitely a very painful part of my life, and I hope it's not forever, but it's for right now. Listen to On Purpose with Jay Chetty on the Iheart Radio app,

podcast or wherever you get your podcasts. I don't know why during the call, I just, I had this weird image in my mind. But do you think that during intimacy, sweet Ben shyly raises his hand and asks the woman to help him put on his prophylactic? No. Excuse me. It's getting hot of here. Oh, wow.

It is hot. I mean, he couldn't order his own dinner. He had peanut butter all over his arms. I'm starting to see what Brooks saw during their conversation. I did not see that. Nobody pictured that. Only you were there. Oh, I was jumping straight to the end.

Imagine just going in for a kiss. I can't imagine any of it. I mean, I hate to admit, Vita actually made a good point. If he really wanted a second date with her, he should have been the one that called. Yeah. I mean, that's kind of all the dates. That's the problem. It's like, I understand it can be probably really hard if you're socially anxious.

But also, you can't have somebody hold your hand the whole time either. Yeah. Are you practicing the speech to give to your son in like a few years? Dude, I already tell my kids. I'm like, listen, Mommy's not going to be around to cut your meat when you're on a date someday. That's going to be real embarrassing. So learn to ask your date.

That's a real man. We can help you out with your dating life or help you out with your brother or sister's dating life. Let's not offer that again. I mean, I thought it was fine. But if you need help, reach out to the show. And we can call that person who's not calling you back. Go check out all of our second date updates.

They're online wherever you get your podcast at Brooke and Jeffrey. WOTA is your host for the 2026 IHart Podcast Awards, live at South by Southwest. Hello, is anybody there? Raised by a single mom, Ego may have a few father-related issues. Are we supposed to talk about your dad? Her podcast, Thanks, Dad, is full of funny, heartfelt conversations with actors,

including fellow S&L alums, comedians, musicians, and more about life and their wonderfully complicated relationships with their fathers. I think and hope that's a good thing. Get to know Ego. Follow Thanks, Dad, with Ego Wodom, and start listening on the free IHeart Radio app today. Ready for a different take on Formula One? Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series.

Join me, Lily Herman, as we dive into the under-explored pockets of F1, including the astrology of the current grid, the story of the sports most consequential driver strike and plenty of other mishaps, scandals, and sagas that have made Formula One a delightful, decadent, dumpster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hey, I'm Jay Chetty, host of the On Purpose podcast. My latest episode is with Hillary Duff, singer, actress, and multi-platinum artist. You desire in family like this picture, and that's not reality. My sister and I don't speak. It's definitely a very painful part of my life. And I hope it's not forever, but it's for right now. Listen to On Purpose with Jay Chetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hi, it's Joe Interesting, host of the Spirit Daughter podcast where we talk about astrology, natal charts, and how to step into your most vibrant life. And today I'm talking with my dear friend, Krista Williams. It can change you in the best way possible. Dance with the change. Dance with the breakdowns. The embodiment of Pisces intuition with Capricorn power moves. So I'm like delusionally proud of my chart. Listen to the Spirit Daughter podcast starting on February 24th on the IHeart Radio app, Apple Podcasts, or wherever you listen to your podcast. I'm Amanda Knox, and in the new podcast, Doubt, the case of Lucy Letby, we unpack the story of an unimaginable tragedy that gripped the UK in 2023.

But what if we didn't get the whole story? I've just been made to fit. The moment you look at the whole picture, the case collapsed. What if the truth was disguised by a story we chose to believe? Oh my God, I think she might be innocent. Listen to Doubt, the case of Lucy Lettby on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.