Brooke and Jeffrey: Second Date Update - Second Date Update: One Year Later To Rejection King

Episode Date: June 2, 2025

One of our listeners wishes she could take back what she said 11 months ago to a guy she went out with. It took her a year to realize her mistake, and now she wants another chance in a Second Date Update!See omnystudio.com/listener for privacy information.

This is an iHeart Podcast. More of you dating with intention, because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year, and find them on Bumble. Go! Amy Robach and T.J. Holmes here. Diddy's former protege, television personality, Denity King alum Aubrey O'Day joins us

to provide a unique perspective on the trial that has captivated the attention of the nation. It wasn't all bad, but I has captivated the attention of the nation. It wasn't all bad, but I don't know that any of the good was real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day, covering the Diddy Trial on the iHeart Radio app,

Apple Podcasts, or wherever you get your podcasts. I'm Andrea Gunning, host of the podcast Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife Caroline. He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific.

And quite frankly, I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeart radio app, Apple podcasts, or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them.

So during Mental Health Awareness Month, tune into the podcast, focus on your emotional wellbeing, and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify, the thing that you refuse to say, hey, this is my mountain, this is the struggle. Listen to Made for This Mountain

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover? I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover is about understanding yourself outside of sex and relationships.

It's flexible, it's customizable, and it's a personal process. Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Yes. Listen to voiceover on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

And we got a brand new second date update for you. Thanks so much for being here on the podcast. And man, and today is like a little unusual because the first date that this couple had was 11 months ago. Usually we know it's like two weeks and we're like, oh, that's kind of long. This is 11 months of not talking.

It's 11 months, and you'll find out why it's been that long. I mean, I don't know that the reason is going to make the guy feel good, but you'll hear it in just a second. But first, let's get to some of our favorite comments of the week. Alexis, what do you got? Yes, Jamil Raymond said, hi from Pakistan. Dating in the US is getting crazier to craziest. That is so true. I will say it really helps because we are a radio show

and we're syndicated in over like 50 cities. And that has like changed the game for us in order to find all these people. And not to mention dating apps. Yes. Dating apps have added a new level of crazy that never was there before. I could set my location to Pakistan right now and see who's there and cause some drama.

There you go, Jamil. Just saying. We're bringing crazy to you. Yes. All right, let's get this show started right now. Second date update. In terms of the amount of time it takes between the first date and the second date, what do you think is optimal?

Like three to four days? At least. A week? Yeah, you don't want is optimal like three to four days? Maybe two weeks is that pushing it too long? I think okay cuz for our listen last you're like out of town Yeah, it's delicate though cuz you don't lose the momentum. Yeah Well for our listener Amanda she's going on 11 months Well for our listener Amanda she's going on 11 months We need to tell her to move on at this point Well hold on cuz she says she has a good reason for that. Okay, so let's talk to her Amanda Thanks for being on with us Start at the very beginning here. Tell us who is this guy and how did you meet him? And how do you remember his name after a lot of months?

Hello Who is this guy and how did you meet him and how do you remember his name after a lot of months? Hello Who have you waited 11 months to get back together with well his name is Jordan So, you know, it reminds me of basketball so I couldn't forget him This is nuts 11 months ago you went on a date with this guy Yeah, I did. Where did you meet him? I met him on hinge. Okay She was very nice like our interactions were kind of funny. Actually, are you sure you remember in right since it was so long? Yes, because usually I won't go on a date with them unless they're funny Okay, checks nice and kind of funny.

How did you find out he was funny? Is there a moment? I mean, I wouldn't match people whose prompts are all serious. Oh, yeah. But there has to be an interesting one. That's actually true, yeah. You know, I don't want to be with someone who's boring. Okay.

Nobody does. What did you guys do for a date? So we ended up going on a coffee date. Coffee date? Yeah, that's my thing. I love that. Oh, you like to do that. Oh, that's good then. That's good. So we ended up going on a coffee date. Coffee date? Yeah, that's my thing. Oh, you like to do that. Oh, that's good then. That's good.

Because sometimes, from a guy's perspective, if a girl says coffee date, that means I want to be very slow, I just want a quick 15, 30 minute hi and bye. I'm not sure you're... I always feel like it's I'm not sure if you're hot from your picture or not. Yeah, all of that. Let me see you in the daytime while it's sober. Well, that's the FaceTime but we've moved past that. So, okay. Um we met up and I kept thinking like honestly

like I don't know if this guy's in my league like there was something. What do you mean? Like in a good way or a bad way? Yeah. So, I know this sounds like maybe stupid but I just thought he could dress better like I didn't really like his style You know that's actually really yeah, I actually have friends And I'm sure I'm in the same boat where like you realize we don't really know how to dress But in the way we always here's the thing clothes are always fixable. That's true I know, but I made a comment about the Crocs and I'm like, I don't know about those.

Oh, you showed up in Crocs on your date? I don't know. I mean, I don't think it's nuts to show up to a coffee date wearing Crocs. You know, it's all the same. More common. Yes. Wow.

You girls are forgiving, okay. It's just, I'm a weirdo, but I guess I was being judgmental because he was so humble and nice I'm like get out of your head like the style like I can fix them, but I don't want to come in like hey We need new wardrobe Yeah, second or third date So I mean like the bond that you had with him like personality wise did you feel that?

So I don't know. I just didn't feel like the spark, you know, like the fireworks. You know, when you meet someone, you're like, oh, I thought you've been pining over this guy for the last 11 months. You didn't even like him the day you hung out with him. So here's here's like what happened. So basically at the end of the day, we gave each other a hug and he was following up with me texting me a whole bunch and I just felt like I didn't want to lead him on. Okay, that's good. That's actually really kind of you. Thank you. Well, what did you say before we start praising

you how kind you are? I just said I didn't feel the spark like we can be friends that like no romantic interest, okay And how do you take it? I think this is why I can't get him out of my head I think because he just says I think that you're a great woman and whoever ends up with you as a lucky man And his response are just so gracious. it like almost made me cry touch my heart he was nice and not mean at the end being rejected specifically that's gotta be hard for a guy to be like oh you don't like me but you know what I wish the best for you that's top three most common response when I've done it before with other guys they just react so like

immature and they honestly like try to get me harder they start texting me more this makes it weird and awkward really yeah no if it's me I'm just giving your number to one of those like scam calls and having them spam you yeah I'm not gonna fight yeah well you reject me then I'm gonna get you a million scam call She just said you weren't there was no spark it wasn't even You don't have to double down that hurts But it's nice that he was so gracious with you. That's pretty cool. It should be what's expected That happened 11 months ago, and now you're reaching out to us. Like

I don't understand what's changed. I just can't get him out of my head. He's like second man, like super glue. So I don't know. It's like kind of awkward to like reach out. I'm kind of shy now and I feel bad for rejecting him. So I really need some help because I feel like I was kind of judgmental that makes sense And I'd like to go out with him again. I mean it is gonna be hard to come back from saying there's no spark Yeah, like it means you're gonna have to put in a little extra work 11 months like do we know if you single? Well we need to call them to find out this is definitely different than what we would normally do in this segment Yeah, but remember this person?

Yeah, we'll call Jordan and be like, Amanda has decided to slum it and go down a level from where she normally would date to go out with you one more time. And have you gotten rid of those crocs? Yeah. Or improved them. Yeah. We'll see what he has to say when we do your second date update after this. Hold on.

Ugh. We're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Geminis because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you.

Someone else will too. Be more you this year and find them on Bumble. I'm Andrea Gunning, host of the podcast, Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me.

Caroline's husband was living another life behind the scenes. He betrayed his oath to his family and to his community. She said you left bruises, pulled her hair, that type of thing. No. How far would Joel go to cover up what he'd done? You're unable to keep track of all your lies, and quite frankly, I question how many other women

may bring forward allegations in the future. This season of Betrayal investigates one officer's decades of deception, lies that left those closest to him questioning everything they thought they knew. Listen to Betrayal on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Second date update.

They say the best things in life take time. That's true. Like an aged bottle of wine. I get in my mouth medium sized wheel of European she. Putting together a dresser from Ikea with just 2 of the legs missing. I don't know, but I still have extra screws and of course finding the right person to date

Not just a good one But the right person and it's taken our listener Amanda 11 months to come to the realization That that guy could have been the one in the coffee shop the day that she rejected him You know what else they also say Jeff timing is everything yes Maybe they needed a little 11 month break guys. That's true. So it's possible all the things could align, the timing could be perfect today. Yeah.

Because she wants us to help her get a second chance with Jordan. You know I think it's sweet. I think it shows that you have a lot of growth from 11 months ago. You know like 11 months ago you were judging somebody's clothes. Not you today, right? No, I'm not as superficial, Brooke. You're right. But I need you to help me work my magic. Like, I'm in a vulnerable state, I'm lonely, and I just miss Jordan. And I just think that you guys can help me. Okay. Okay. Well, we're willing to do that. I'm just glad that we're talking to you over the

phone so that you can't see what Brooks wearing and be able to judge it We've matured from that immature girl She can't even see you when she just knows. Because I have zebra pants on, so it's like, hey. You guys are like a zoo together. Wow. Yeah. You're so exotic, Brooke.

I wish I had zebra pants on. I love this bonding time that we're having, but we got to call Jordan here and hopefully he picks up. I'm going to dial his number right now. Here we go Hello, hey, is this Jordan Yeah, Mass is calling. Yes, you may ask just having normal conversation this is how bros conversate yeah okay well thank you for politely asking that to answer your

on yeah well if you're still there to answer your question we're a radio show called broken Jeffrey in the morning with highbrow comedy okay and what is this in regards to oh this is actually in regards to a woman who's been trying to get a hold of you you. Yes, she has. That's the usual. Not sure if you'll remember, is this a woman named Amanda? You know, there's a lot of Amandas. That's true. Right, fair. Okay, well this is a woman

that you went on a date with 11 months ago. It's like a year ago, dog. It was a coffee date. 11 months ago. Yes. Coffee date? Mm-hmm. I know, that's probably gonna be like, was it like a hinge date? Yes. Yeah. Oh, she did tell us that. OK, yeah, I think I yeah, I remember, Amanda. Yeah, we we grab coffee. Right.

OK. A long time ago. That's right. What else do you remember from your time with Amanda? There's probably wasn't much time since it was just coffee, but Honestly, I I just remember her ditching me ditching you Like when she said she didn't want to see you again. Oh Yeah, like I mean I've been turned down before so you know I'm kind of used to it Definitely wasn't expecting this. Yeah. Well, can I just tell you Jordan,

the thing that really stood out to Amanda about you was how graciously you handled her rejection over text. Okay. I know, sounds weird. I know. You said something like, you're an amazing woman, whatever guy ends up with you, he's gonna be so lucky and you like just wished her well. Oh

Yeah, you know what? I think I wrote that with AI actually It was a good it was good feedback Thing quick on my feet for Amanda it was a big moment and You know how like sometimes women aren't as emotionally mature as us men are? Yes. Historically, that's always been the case.

She has taken all this time and realized that it's possible she made a huge mistake in turning you away. Which is kind of sweet, if you want to know about it. Maybe. She said that? Yeah. Yeah. Basically, yeah.

She actually has even said she's really been thinking about you a lot Wow, I mean Honestly, I don't know what to say This is like the third time that's happened this year. What what do you mean? What happened? Yeah, you know I again I I'm used to rejection, you know I again. I I'm used to rejection You know so yeah weirdly enough a lot of these girls they reject me and don't call me back say like hey Maybe we should give another shot This isn't the first time No, are you complimented by it or is it like?

Almost kind of a backhanded compliment. You know what I mean? I'm more surprised than anything Well if you want to be the most surprised here's a shocker for you Because Amanda is on the other line right now listening to this entire conversation hoping to jump in I bet that's a surprise. Surprise. Surprise. It's me. Hi. Hey Amanda. Aloha. How are you? I don't think she talked like that before. I'm good.

Good to hear from you again. Yeah. You're excited to hear from me? I mean it's been a while. It's definitely a surprise. It's a surprise. I feel so awkward. I feel like I'm stuttering and like, I don't know. But yes, I'm very nervous to do this.

And I'm glad that AI was able to help you out. But there's no AI now. You like that you used AI? Yeah. I mean, you know, thinking about his words before speaking. So it's not like me Like I just kind of was impulsive and was superficial but I hope that we can maybe see each other again. I'm not sure Are you like asking me out or is this is this what this is I mean I needed their help

Yeah, it might be like a little crazy. It's been like almost a year, right? And maybe you can have amnesia and dementia about what happened in the past That was a lot Jordan I know that she kind of dumped on you there But um, you know anything that you would like to say back to Amanda or ask your AI what to say back? To be honest, Amanda, it's been a while since I've seen you or seen your picture. Yeah.

One way that really jogs my memory is, do you still have that nice butt? No, what? Wait. You didn't swap it out? Oh. Well, so I was just telling them about these zebra pants that I'm wearing, and I could potentially send you a selfie if you'd like.

How is that that easy? Amanda, maybe work for it a little bit. Do zebra pants make it look bigger? I bet it will. Just the stripes. It's like an optical illusion. ask you for a friend yeah, I you know I messed up So I'm trying to like you know clean point here I come Clean slate includes picks

Jordan yeah Jordan she's apologetic for how she treated you she still got the same features and all the things that you liked from the first Time you met up so at this point We'd like to offer to send you and Amanda out on another date and we would pay for it at this point I feel like we're interrupting a date on the phone But Jordan it's up to you I Mean she's cool with me seeing the other two girls. They rejected me and her being the third. I'm open to that. Okay. It's a harem of rejection. Amanda, now balls in your court. Heavens no. You know, this was nice, but no, I cannot handle that. I'm too

jealous. No way. I want you to make a little competition for you. You know no way Jose I'm not that desperate are you ditching him now twice in one year? I was just hoping that we could be just one-on-one monogamous not you know a trio Okay Goodbye to her and she'll probably call you Six leftovers, I guess I'll type one up and I'll send it to you later, Amanda. Check your text messages. Yay.

Oh my God, he's like the rejection king. I hope you have a nice life and a nice day. Oh, wow. That's what gets him. You're melting hearts right now, Jordan. Hang up so we can all call him back. Oh. No.

Brooke and Jeffrey in the morning. I think the lesson that we all learned from that is you can let a nice butt in zebra print walk away and still be gracious about it. That's right. Yeah. It was a good lesson. It is shocking that she was so surprised. Yeah

Like I'm worried about her choice in people to go out with It was snap. Yeah, totally, but it would be funny if she does text him though in like a couple of weeks or Couple of minutes after that call ended. Yeah, just to like give him a third chance Well, I mean she's gonna go on one more date with a guy that's a jerk and then a third chance. Well, I mean, she's gonna go on one more date with a guy that's a jerk and then she'll come again. But also, the way they were flirting on the phone for a minute, I thought for sure they were gonna go out with each other. I thought it was a yes before we even asked.

I know. Maybe we should have stayed out of it. Maybe that's the problem. It was a yes. He just said add to the team. She said no. She said no. I know.

But that's the thing about love. It's weird and unpredictable Sometimes and you can find lots of weird love by listening to our podcast on YouTube on tik-tok Spotify The weird the better. That's right. All of our episodes of second-aid update are there at Brooke and Jeffrey designed for your ocular pleasure I'm Andrea gunning, host of the podcast Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives.

You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeart radio app, Apple podcasts, or wherever you get your podcasts.

Amy Robach and TJ Holmes here. Diddy's former protege, television personality, Danity King alum Aubrey O'Day joins us to provide a unique perspective on the trial that has captivated the attention of the nation. It wasn't all bad, but I don't know that any of the good was real. I went through things there.

Listen to Amy and TJ presents Aubrey O'Day, covering the Diddy trial on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional well-being, and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify.

The thing that you refuse to say, hey, this is my mountain. This is the struggle. Listen to Made for This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover? I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy,

but to me, voiceover is about understanding yourself outside of sex and relationships. It's flexible, it's customizable, and it's a personal process. Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Listen to VoiceOver on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I've seen a lot of stuff over 30 years, you know, some very despicable crime and things

that are kind of tough to wrap your head around. And this ranks right up there in the pantheon of Rhode Island fraudsters. I've always been told I'm a really good listener, right? And I maximized that while I was lying. Listen to Deep Cover, The Truth About Sarah on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. This is an iHeart podcast.