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Next Monday, our 2026 iHeart Podcast Awards are happening live at south by Southwest. This is the biggest night in podcasting. We'll honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry.
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And the winner is.
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Creativity, knowledge and passion will all be on full display.
B
Thank you so much iheartradio. Thank you to all the other nominees. You guys are awesome.
A
Watch live next Monday at 8pm Eastern, 5pm Pacific free@veeps.com or the Veeps app. Ready for a different take on Formula One? Look no further than no Grip, a
B
new podcast tackling the culture of motor
A
racing's most coveted series.
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Join me, Lily Herman, as we dive
A
into the underexplored pockets of F1, including
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the astrology of the current grid, the story of the sport's most consequential driver strike, and plenty of other mishaps, scandals
A
and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years.
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Listen to no Grip on the iHeartRadio app, Apple Podcasts or or wherever you get your podcasts.
A
Hey, I'm Jay Shetty, host of the On Purpose podcast. I'm joined by Luke Combs, award winning country 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 iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
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I'm Amanda Knox and in the new podcast 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? Evidence has been made to fit. The moment you look at the whole
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picture, the case collapsed.
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What if the truth was disguised by
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a story we chose to believe? Oh my God. I think she might be innocent. Listen to Doubt the Case of Lucy Letby, iHeartRadio app, Apple Podcasts or wherever you get your podcasts. Hi, it's Jill Winterstein, 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.
C
Just so I'm like, delusionally proud of my chart.
B
Listen to the Spirit Daughter podcast starting on February 24th on the iHeartRadio app, Apple Podcast, or wherever you listen to your podcast.
C
Hey, it's Monday after a time change. Oofta.
A
I know, right?
C
Yeah. Yeah. Hey, welcome to it. We're gonna 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.
B
I was listening to y' all during class with my earphones and it suddenly got out of power and the show
C
started blasting in the silent amphitheater.
B
Thank God my professor was a listener.
C
Now I know how to get better grades.
A
Wait, the professor was a listener too?
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I don't know. I'm scared.
C
What segment and what part was playing when it went out loud? I mean, you usually get held back for that stuff.
A
They find out you listen to us. Yeah.
C
All right. All right, dummies. Here's a brand new Sega UPD right now.
B
Brooke and Jeffrey in the morning, second date update.
A
I read an article recently where in New York City right now.
C
Yeah.
A
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. And this is where men can attend them for free. Yeah. And women have to pay $100 or more, which is crazy drastic price difference. But guys just aren't. 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, it's true. So even a free ticket just feels like a big waste of time. Totally.
C
So all the men have given up in New York City and blame the woman.
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Yeah, I love it.
C
That's what I just heard.
A
Well, it's nice that you came with such an open heart towards these guys and their feelings. I'm sure that has nothing to do with how they feel. I wonder why they'd feel weird about the women I know. No, but no one knows that better than one of our listeners stuff. Stacy, who's on the phone right now because she wingmanned her brother at one of these events. I'm not sure why he's not on the phone with us. Hold up.
C
If you're just wingman in your brother, your brother better have paid your hundred dollar entry fee.
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Oh, yeah, Stacy, welcome to the show.
B
Hey, guys. How's it going today?
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Good. We know, we ask you the questions. Brooke is right.
C
Who paid?
A
We're confused. So, yeah, I guess who paid? Did your brother pay for this?
B
My brother did pay for it.
C
Okay, good. And why did he think he wanted his sister to be there?
B
You know, he's just a really 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 gonna go with him. I want him to find happiness.
A
You're like his comfort, like, service animal. Yeah, until you. Until you find a hot guy and then he's on his own. Wait, did you participate too?
B
I did. I didn't find anybody, but he did what we thought.
C
Okay, I thought this was a second date update for you.
B
No, I am actually calling for my brother.
A
Interesting.
B
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.
A
He's not even face to face with us. Like, we're harmless. We're on the phone.
C
I know, but that's scary to be on the radio. Like, I could get that.
A
Yeah, especially when you're talking to Brooke. As a man, I would feel fear coming on.
C
I mean, your sister will air all your dirty laundry.
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Yeah.
C
The nice thing is we'll probably get the honest truth about what you think he did wrong before we call this
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girl instead of him just being oblivious to everything.
C
That's how siblings were.
A
I'm curious. How much do you know about your brother and the girl he met? Like, how much detail do you have?
B
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. Like, my brother spent a year in Italy for a travel abroad program, and it turns out that she did too. They just seem to really, really hit it off. And like, you know, that arm touch, you just like, reach across the table when you're laughing and it means more than just touching your arm. She did that, like five times.
A
Oh, that's cute. And did he. Did he do that to her?
C
They're just touching arms.
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They're just touching arms. And maybe you touched both their arms.
B
No, no, he was very respect at the end of the date, they picked each other.
C
Okay.
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Oh, at the end of the speed dating, choose your favorite.
C
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.
A
Are you thinking about wasting money?
C
Yes.
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Yeah. Sometimes people have change of hearts. So this is the only interaction that they had. Is that the speed dating?
B
No. They did go on a follow up date.
C
Oh.
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Yeah.
B
Right after they. They went to dinner. I did not join them for that one. It is very possible he screwed it up there, but.
A
Okay.
B
He said dinner was fine, but it ended with him walking her to the car. 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.
A
Oh, that's a bad. Oh. During the walk. Most girls appreciate it. You really don't have to come.
C
Well, I mean, at night, you want somebody to.
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Anybody. I mean, guy, girl, like, friend, normally. Unless. Yeah, 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.
C
Right.
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As the sister, it's.
B
It's very possible. Ben is so sweet. Like we call him sweet Benjamin in the family. Like that is.
A
I don't know if that's a good or bad thing. Yeah, Sweet Benjamin sounds like he needs extra. Like we have our first reason why she's probably not calling him dad, so that's good.
B
It is very possible. But I also, you know, he doesn't know what's going on, and I just. I want to help because he. He walked her to the car. 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.
C
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?
B
I told him I was going to. I don't know if he believed me, but at this point, he should.
A
If this is interesting, it's gonna hit the air. He's gonna hear it.
C
Sister instinct. What do you think went wrong?
B
I feel like there was probably a misunderstanding of some kind at dinner.
C
Okay.
B
I don't know what it could be, but Vita seemed so into him that it just doesn't make sense.
C
I'm sorry, what was her name?
B
Vida. Like, don't cry for me, Argentina.
C
Okay.
A
Oh, I thought it was like the coconut water. Vida.
B
Yeah.
C
Oh, yeah. Like the coconut water.
A
All right, so she sounds a Little bit foreign. Maybe she needs, like, a spicier guy in her life. Not Sweet Ben. Well, she did go to Italy for a while. That's true.
C
If she's also a shy person, this may be really overwhelming, us calling her.
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Well, again, then we won't air it. I know. I'm. Well, I'm excited to find out. When we come back, we call Vita for on behalf of Stacy's brother. What's his name again? Ben. Sweet Ben. Oh, that's our Sweet. How can I 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.
B
Awesome.
A
Hold on.
B
Brooke and Jeffrey in the morning. Second date update.
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Behind every sweet, shy boy is a proud, well spoken sister ready to go to bat on his behalf.
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Like your sister Jeff says, our own shy boy.
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And that's why Stacy reached out to us. Cause she wingmanned her brother Ben recently at a speed dating event and watched him walk out the door with a pretty woman and watched chemistry happen.
C
Get it? Sweet Benjamin.
A
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 Stacy 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, usually. Never said thank you and just waved goodbye at him before she left. And Stacy demands answers.
C
Well, no. Stacy's trying to help out.
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Is ready to hit someone if someone doesn't explain what went on. Am I right?
C
Stacey, slow it down.
B
Oh, you are not wrong. I am ready to fight here.
C
Okay, Stacy.
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I knew it.
C
Do you know we never asked, did Vita find out that you were at the speed dating event?
B
I don't know if she did.
C
Okay. I'm just wondering.
B
But it did occur to me that could be a weird thing, right?
C
For some people, that may not sit right. Especially if they're not close with their sibling they don't understand.
A
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.
C
Yeah.
A
And that could be kind of awkward.
C
My husband often says, I married my sister. I'm like, no, you officiated the wedding, honey. Yeah, it's different.
A
I said the same. I officiated my sister's wedding. Yeah. 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.
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Hello?
A
Hey, we're looking to speak with Vita.
B
Yes, this is her.
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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.
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Hi. Thank you.
C
You sound really outgoing. Yeah, thanks.
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Brooke.
C
Not you.
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Oh, yeah. My bad.
C
Sorry.
B
Thank you, guys. What's up?
A
Yeah, we're. We're really eager to talk to you because we heard you went out with a guy that we kind of know named Benjamin. His name is Ben.
C
Yeah.
A
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.
B
Yeah, the pity date.
C
What?
A
Oh, pity date.
C
Oh, no.
A
Why would you say that? She, like, ripped a band aid off for us.
B
Well, like, at the speed date, he was just, like, borderline crying about how he hasn't been out with a woman. Oh, no. I was like, okay, well, I guess let's just go after this.
C
Are you exaggerating a little bit? I mean, maybe he was just maybe a brook.
A
Maybe a dust in his eyes.
C
Walk us through the crying part.
B
I mean, it's not crying, but, like, 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.
A
Yeah, he's just, like, sweet. Yeah.
C
I hate that these are our boundaries as women.
A
Yeah. I feel so bad. I'll take some free dinner from this sweet, not creepy guy and then I'll ghost him forever.
C
Well, maybe she took him out. Did you pay?
B
No, he paid.
A
Okay, well, good. Like a gentleman. But, yeah.
C
When you. 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?
B
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.
A
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.
C
Remember, you had lived in Italy. He had lived in Italy.
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He had arms. You had arms. You touched your arm with his arm.
B
I remember on the speed date, I kept touching his hand because he had, like, peanut butter on it or something
C
would make me not want to touch it.
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Just eating bumps on a log. My bad.
B
So it was pretty pathetic.
A
I feel like he's adorable because he's a pathetic.
C
I mean, here's the thing. You never gave him a chance.
B
It sounds like I went to freaking dinner with him. What do you mean I didn't give him a chance?
C
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.
A
Yeah, even if he does something cool, it's hard to break out of pity. Well, did he do something cool? Like, was he. Was he at least nice and respectful during your dinner date?
B
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.
C
Okay, well, we heard he's socially awkward, so.
A
Yeah, or just maybe nervous around a really pretty woman.
B
Well, if you want to take a pretty woman out to dinner, you should at least be able to, like, order for yourself.
A
I'm taking you to the nicest place in the city. Will you read the menu for me?
B
That going to look good when he
C
finds out who's on the phone?
A
Yeah. I feel stupid. 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. His sister Stacy, however, is.
B
Are you kidding me?
A
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. Stacy,
B
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. This is so typical. He can't even, like, call the radio station himself. He has. 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? What?
C
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.
A
It was harsh.
B
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, like, literally just, like, throwing the dog a bone. Oh, my gosh.
A
Don't call him a dog. Wow. It sounds rude, but she was trying to help.
B
You were not trying to help. Are you kidding me? This wanted a free meal. You literally said it. You literally said it in the call.
C
What did she say?
B
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 gonna lose my.
C
Okay.
A
That could not have more personality.
C
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.
A
Let him break up with her.
B
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?
A
Exactly, Brooke. How dare you treat a kind man like Ben like this?
C
Your brother was, like, crying during the
B
speed I was sitting right there. He was absolutely not crying. He was engaging in the conversation.
A
Yeah, he's in touch with.
B
Yeah, a little too engaged. Just, like, a little too emotional. And then. 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. What a good sister, beta used to go out with your brother.
C
Like, oh, God.
A
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, yell
B
at her girls for my brothers.
A
Oh, hell, yeah.
C
Stacy, could you maybe see that? You guys, like, your family's maybe coddling your brother a little bit too much. Like, you're calling him, like, oh, Stacy,
A
she's doubling down, saying your brother's a wimp.
B
This isn't about my brother anymore. This is about that woman, that toxic woman and her behavior.
A
I know. Brooke is not the most pleasant person I know.
B
Not Brook, not Brooke. I'm talking about Vita. Because what she did to that sweet boy. Regardless of what, he's a grown man. Oh, Lord, that sweet boy needs to grow up. Yeah. And you need to find a soul, you harpy.
A
Oh, I don't know, 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.
B
No, I think I'm going to pass on that one.
A
So you're passing with Stacy, but not on her brother?
B
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 up.
C
Maybe a hard truth.
B
Maybe he should. But at least he won't be alone for the rest of his life.
C
Cause he'll have me. Have you? Yeah.
A
Okay. I think she meant that as a dig to Vita, but I worry that might actually happen where big sis is actually gonna end up becoming sweet Benjamin's mommy, ordering him smiley face pancakes off the IHOP menu for the rest of his life.
C
Hey, don't hate on those.
A
Oh, sorry. Love those. It's kind of sweet. You're right.
B
Brooke and Jeffrey in the morning.
A
Next Monday, our 2026 iHeart Podcast Awards are happening live at south by Southwest. This is the biggest night in will honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry.
B
And the winner is.
A
Creativity, knowledge and passion will all be on full display.
B
Thank you so much, iheartradio. Thank you to all the other nominees. You guys are awesome.
A
Watch live next Monday at 8pm Eastern, 5pm Pacific free@veeps.com or the Veeps app.
B
Hi, this is Jill Winterstein, host of the Spirit Daughter podcast where we talk about astrology and natal charts and how to step into your most vibrant life. And I just sat down with a mini driver.
A
The Irish traveler said when I was 16.
B
You're going to have a terrible time with men. Actor, storyteller and unapologetic Aquarian visionary. Aquarius is all about freedom, loving and different perspectives. And I find a lot of people with strong placements in Aquarius like are misunderstood a sun and Venus in Aquarius in her seventh house spark her unconventional approach to partnership. He really has taught me to embrace people sleeping in different rooms, on different houses, in different places, but just an embracing of the isness of it all. If you're navigating your own transformation or just want a chart side view into how a leading artist Integrates astrology, creativity, and real life. This episode is a must. Listen. Listen to the Spirit Daughter podcast starting on February 24th on the iHeartRadio app, Apple Podcast, or wherever you listen to your podcast.
A
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.
C
Oh, God.
A
Sweet Ben shyly raises his hand and asks the woman to help him put on his prophylactic. Excuse me, 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 arms. I'm starting to see what broke Brooks saw during their conversation.
C
I did not see that. Nobody pictured that. Only you were there.
A
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.
C
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.
A
Yeah. Are you practicing the speech to give to your son? Like, a few years?
C
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.
A
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.
C
Let's not offer that again.
A
I mean, I thought it was fun, 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. Next Monday, our 2026 iHeart Podcast Awards are happening live at south by Southwest. This is the biggest night in podcasting. We'll honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry.
B
And the winner is.
A
Creativity, knowledge and passion will all be on full display.
B
Thank you so much, iheartradio. Thank you to all the other nominees. You guys are awesome.
A
Watch live next Monday at 8pm Eastern, 5pm Pacific free@veeps.com or the Veeps app. Hey, I'm Jay Shetty, host of the On Purpose podcast. I'm joined by Luke Combs, award winning country 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 iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
C
Ready for a different take on Formula One?
A
Look no further than no Grip, a
B
new podcast tackling the culture of motor
A
racing's most coveted series.
C
Join me, Lily Herman, as we dive
A
into the underexplored pockets of F1, including
B
the astrology of the current grid, the story of the sport's most consequential driver strike, and plenty of other mishaps, scandals
A
and sagas that have made Formula One a delightful decadent dumpster fire for more than 75 years.
B
Listen to no Grip on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. Hi, it's Jill Winterstein, 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.
C
So I'm like delusionally proud of my chart.
B
Listen to the Spirit Daughter podcast starting on February 24th on the iHeartRadio app, Apple podcast or wherever you listen to your podcast. I'm Amanda Knox and in the new podcast 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? Evidence has been made to fit. The moment you look at the whole
A
picture of the case collapsed.
C
What if the truth was disguised by
B
a story we chose to believe? Oh my God, I think she might be innocent.
C
Listen to Doubt the Case of Lucy
B
Letby on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Podcast Summary
Podcast: Brooke and Jeffrey: Second Date Update
Episode: Second Date Update: Sweet Benjamin and His Big Sis
Date: March 9, 2026
This episode dives into a unique Second Date scenario where a listener, Stacy, steps in on behalf of her shy brother Ben, who has been ghosted after a speed dating and dinner event. The episode is a wild ride through sibling dynamics, social awkwardness, modern dating woes, and the unpredictability of "pity dates," all served up with Brooke and Jeffrey’s irreverent, playful humor.
Stacy’s reaction when hearing this live: She erupts in defense of her brother, directly confronting Vita.
Vita’s unapologetic honesty:
Hosts struggle to find a positive spin:
This episode is a classic rollercoaster Second Date Update—a sibling fights fiercely for her shy brother after a disastrous pity date, only for the truth to be harsher (and funnier) than anyone expected. The conversation covers real issues of social anxiety, modern dating exhaustion, "ick" factor, and how family support can both help and hinder. In the end, everyone agrees Ben needs to fend for himself, and the hosts (and listeners) are left with equal parts laughter, cringe, and empathy.
Perfect for fans of awkward dating stories, family drama, and sharp, unsparing humor.