Brooke and Jeffrey: Second Date Update
Second Date Update: Sweet Benjamin and His Big Sis
09 Mar 2026
Chapter 1: Who is Sweet Benjamin and why is his sister calling in?
Salt and pepper. And invoke. Plus, Taylor Swift makes her first award show appearance this year. Also, gold medal Olympian Alyssa Liu, Neo, Nicole Scherzinger, Nikki Glaser, Sombra, Weezer, and more. Watch live on Fox Thursday, March 26th at 8, 7 central. And listen on iHeartRadio stations across America and the free iHeart app. In the middle of the night, Saskia awoke in a haze.
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The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey there, this is Josh from Stuff You Should Know with a message that could change your life. The Stuff You Should Know Think Spring podcast playlist is available now.
Whether spring has sprung in your neck of the woods yet or not, the Stuff You Should Know Think Spring playlist will make you want to get your overalls on, get outside, and get your hands in the dirt. You can get the Stuff You Should Know Think Spring playlist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 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. Bismango said, hi from Romania. You guys almost got me kicked out of class. What?
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 silent amphitheater. Thank God my professor was a listener. Now I know how to get better grades. That's awesome. Wait, the professor was a listener too? I don't know. Good. 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 if they find out you listened to us. Yeah. All 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, they're holding speed dating events. Just tons of them where it's a three to one female to male ratio.
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Chapter 2: What happened at the speed dating event involving Benjamin?
And Stacey demands answers. Well, I mean, Stacey's trying to help out. Stacey is ready to hit someone if someone doesn't explain what went on. Am I right, Stacey? Slow it down. Oh, you are not wrong. I am ready to fight here. That's a good sister. Stacey. I knew it. Do you know what we never asked? Did Vida 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 and they don't understand. Or 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. Yeah. And that could be kind of awkward. Yeah.
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 officiated 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.
Hello? Hey, we're looking to speak with Vita. Yes, this is her. Hey, Vida. Thanks for answering. We're a radio show. We're called Brooke and Jeffrey in the morning. Hi, Vida. Good morning. I like your name. Hi. Thank you. You sound really outgoing. Yeah. Thanks, Brooke. Not you. 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.
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Chapter 3: How did Stacy support her brother during the date?
Named 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? You just, like, ripped a band-aid 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.
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 he had dust in his eyes. And his mouth. Walk us through the crying part. I mean, it's not crying, but just borderline tears in his eyes. Like sulking. He wasn't creepy, so I knew he would be safe to go out with. I hate that these are our boundaries as women.
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. Like a gentleman, but yeah. 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.
I didn't seem 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 lived in Italy. Yeah. He had arms, you had arms, you touched your arm with his arm.
I remember on this V-date, I kept touching his hand because he had like peanut butter on it or something. Like a child? That would make me not want to touch it. Sorry, I was just eating bumps on a log. It was pretty pathetic. I feel like he's adorable because he's pathetic. I mean, 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 of 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, there's ick. 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're going to take a pretty woman out to dinner, you should at least be able to, like, 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. Yeah. I feel so bad.
Do we have to do this part? We do. Because here's the deal, Vida. We kind of have a surprise for you. Because Ben is not on the phone with us right now. Surprise. His sister 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 idiot.
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Chapter 4: What were the signs of chemistry between Benjamin and his date?
And I swear to God, if I hear pity date one more time, I'm going to lose my. Okay. Okay. Okay. Personality. 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 speed dating. 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, uh... And then I said to her, like, what adult cannot place their own food order? You know what, Vida? 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. Aw, what a good sister. You should go out with your brother. 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. Actually, my sister will call a girl and yell at her. I'll yell at girls for my brothers. Oh, hell yeah.
Stacey, could you maybe see that you guys, like your families may be coddling your brother a little bit too much? Like you're calling him like. Oh, Stacey, she's doubling down saying your brother's a wimp. I should. 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. Not Brooke. Not Brooke.
I'm talking about Vita. Gotcha. 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. Oh. Yeah, and you need to find a soul, you harpy. Oh, I don't know what that is. I'm not sure it hurt, though. Do we beep 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.
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Chapter 5: Why did the date take a turn after dinner?
No, I think I'm going to pass on that one. So you're passing with Stacey, but not on her brother. You're still open to Ben? On both of them. I'm good. And Stacey, I don't appreciate you calling me names. Your brother should grow the f*** up. 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 Vida. But I worry that might actually happen. Where big sis is actually going to end up becoming sweet Benjamin's mommy. Ordering him smiley face pancakes off the IHOP 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. Let's go.
Our iHeartRadio Music Awards are coming back Thursday, March 26th live on Fox. Watch as we honor the biggest stars from all genres of music that you loved listening to all year long on your favorite iHeartRadio station and the iHeartRadio app. Hosted by Ludacris. Icon Award recipient John Mellencamp. Innovator Award recipient Miley Cyrus.
Chapter 6: What were the red flags during Benjamin's follow-up date?
With performances by Alex Warren, Kehlani, Lainey Wilson, Ludacris, Ray, TLC, Salt-N-Pepa, and En Vogue. Plus, Taylor Swift makes her first award show appearance this year. Also, gold medal Olympian Alyssa Liu, Neo, Nicole Scherzinger, Nikki Glaser, Sombra, Weezer, and more. Watch live on Fox Thursday, March 26th at 8, 7 central.
And listen on iHeartRadio stations across America and the free iHeart app. I'm Bailey Taylor, and this is It Girl. You may know me from my It Girl series I've done on the streets of New York over the years. Well, I've got good news. I am bringing those interviews and many more to this podcast.
Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations, and the real work with the women shaping culture right now. As a woman in the industry, you're always underestimated. So you have to work extra hard and you have to push the narrative in a way that doesn't compromise who you are and your integrity.
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I think the negatives need to be discussed and they need to be told to people who maybe don't do this every day just so they know what's really going on. I feel like pulling the curtain back is important. Listen to It Girl with Bailey Taylor on the iHeartRadio app, Apple Podcasts, 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? Oh, wow. Excuse me. It's getting hot in here. I could use a hand. Oh, wow. It is hot. I mean, he couldn't order his own dinner. He had peanut butter all over his arm. I'm starting to see what Brooke 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, Vida actually made a good point. If he really wanted a second date with her, he should have been the one that called. Yeah. 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. Yeah. That's a real man. But look, we can help you out with your dating life or help you out with your brother or sister's dating life. Let's not. 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.
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