Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Proposal Sabotage

Episode Date: September 30, 2025

The guy in today’s Awkward Tuesday Phone Call has had THREE FAILED PROPOSALS. He wants out help finding out what he’s doing wrong… or if there’s another explanation…See omnystudio.com/listener for privacy information.

The murder of an 18-year-old girl in Graves County, Kentucky, went unsolved for years until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County on the Irish. Heart Radio app, Apple Podcasts, or wherever you get your podcast. And to binge the entire season, ad free, subscribe to Lava for Good Plus on Apple Podcasts. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking,

man alive, I could go for some good true crime podcast episodes, then have we got good news for you? Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really, terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club?

Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack. Available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. In early 1988, federal agents raced to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. I had 30 agents ready to go with shotguns and rifles and you name it.

Five, six white people. Push me in the car, I'm going to look back out. Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package. Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand,

and I saw the flash of light. Listen to the Chinatown Stang on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. It may look different, but Native Culture is alive. My name is Nicole Garcia, and on Burn Sage, Burn Bridges, we aim to explore that culture. Somewhere along the way, it turned into this full-fledged award-winning comic shop.

That's Dr. Lee Francis IV, who opened the first Native comic bookshop. Explore his story along with many other native stories on the show, Burn Sage, Burn Bridges. Listen to Burn Sage Burn Bridges on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Your second date podcast, and we got a brand new one for you today. It's Brooke and Jeffrey in the morning. Yes. A lot of response from the barefoot guy yesterday. Yeah.

Yeah, and that he didn't even think it was weird that he went an entire date. No. And I don't know if you read the comments, but honestly, quite a few of our listeners didn't think it was weird either. What? Yes. There's a lot of barefooters out there. Yes, we got it on the street. Yes, Sydney is too judgmental for my taste.

I don't think it's a big deal to walk without shoes. Come to Australia. We don't wear shoes here. Shoes are overrated. I feel like I'm a hybrid of this. Like, if I'm on carpet, grass, or sand, I want to feel it. with my feet. Okay.

I think that's normal. But concrete, that's crazy to me. Yeah, yeah. I don't want to walk down the road. Anywhere a car was, I don't like to be barefoot. No, you know?

I don't know. I don't know why. Oh, and then one, well, he's right. Trees have been around longer than plumbing. Because we didn't even talk about him peeing on the name of guys. Ah, it is the original toilet.

I mean, the longest living organism on the planet. Is that a fine? Okay, we're going to lose listeners, but come on. Just think trees are phenomenal. Oh, great. All right.

We got a brand new awkward Tuesday for you, And it's going to start right now. I've looked at social media once or twice. And I've learned the only thing that goes more viral than a sweet, happy marriage proposal is a messy, awkward marriage proposal gone horribly wrong. That's so true. And that's why when I saw our listener's email today, I knew we had to talk to him because he hasn't had just one failed proposal but three in a row. And he needs our help to figure out, am I doing something wrong here? Or is there another explanation?

You're going to hear it in your brand new Awkward Tuesday phone call. Next. It's awkward. It's Tuesday. It's awkward Tuesday phone call. Some people in relationships believe there's cosmic signs that show you're meant to be together. Okay. Like when you start finishing each other's sentences.

Or every time you say their name, a church bell rings. Wow. Or a pigeon lands and poops on your shoulder then flies over and poops on their car. Wow. These are positive signs from the universe saying, you belong together. But one of our listeners, apparently,

has been receiving a different kind of message from the cosmos about his relationship. Uh-oh. His name is Keith. Keith, what are the signs telling you? I mean, the signs are kind of the actions of my girlfriend recently. Oh,

all the signs aren't from the universe. Those can be determined as cosmic messages. No, I think that's just girlfriend messages, Jeff.

From the cosmos. It's her name Cosmos? Is that what we're getting at? Could be, but what is it telling you, Keith?

No, her name is Lila, but who knows? Maybe there is some cosmic energy that's affecting her because I really feel like she's trying

to sabotage my marriage proposal. Oh, I thought you were going to say my marriage. Oh, my God. I'll finish that sentence. We would be okay with either one of those things. No, we would not.

My girlfriend should have ruined my marriage. Yeah. Oh, my God. I'm sorry that had me. You're trying to propose to your girlfriend, but you feel like she's sabotaging it. Right. We are not married. We've been dating for two years. Okay.

The first time I tried to propose her, I was going to do it in a park. You know, I had the ring ready to go. And maybe she's got the sense that something. was up because I was a little nervous and like a little walk in the park is not something that we normally do as we're walking in the park she just turns to me and says

hey if you're going to do what I think you're going to do I don't want it to be like this oh damn the park is pretty public like not a lot of people like that I can't believe she just came out and said that to you like what how did you react when she told you that like don't

propose to me right now I just joked it up I was like what do you think I'm not going to propose in a park like this. It's so corny. Like, I just tried to play it cool. Yeah. You could have been like, oh, I was just going to kiss you, but not in front of these people? But I think you could take that as a positive, too.

Like, she obviously wants you to do it, and she has a vision of how it's going to happen in her mind. That means she's thinking of you. And, I mean, it sounds like she'll say yes, which is great. Yeah. Well, flash forward a little bit to a couple months ago, I tried again. we took a trip to New York City and I went like scrolling on online and I tried to find like a really fancy dinner

and she like agreed to it for a little while but then the night we were there she says she thinks she has an eye infection and she wanted to stay in the hotel that night so I was like okay you know Pink eye it'll hit you Brooke she made up an excuse that she had some eye problem I don't know if it was a fake eye infection

or if it was a coincidence. But there was one more time recently when I tried again. I like that you're not giving up. This is important. And not be asking her how she'd want it, though. I like that you know. It is a good point, Alexis, that maybe you should have said, well, what do you want? Well, she's clearly trying, he's clearly trying to, like, make it a surprise.

And she obviously knows something is coming. So he doesn't want to, like, blow it entirely. But at this rate, it's going to be like, oh, we've been married for three years. But I've been trying to propose for five. Right, yeah. So what was your idea for your third proposal? Okay, yeah, this one is where I'm really like, okay, something's up. So about two weeks ago, I had a picnic set up, and, you know, I had, like, her favorite meal and a candle and some nice wine.

Uh-oh, we're back to a park. I know. Why would you repeat the park? Is it in the park or is it, like, private? This was on the beach, not in the park. Okay. Okay. Okay.

A very private, exclusive beach. But when she came and she showed up, she, again, had that, like, nervous look on her face. And not too long after, the blanket suddenly catches on fire. What? Whoa. Because of the candle. The candle fell over, and the blanket catches on fire. So I had to put it out.

And I had my phone set up on a tree nearby because I was going to film the proposal. And I saw in the tape that she knocked the candle over, like, on purpose. I saw her do it. Oh, she started the fire? Maybe she doesn't want to marry you, man And I'm like honestly Well, that's what I'm worried about You know, like

Because we're still like everything else Otherwise is still fine Like so either she doesn't want to get married Or ready yet So what do you want to do With your awkward call though? Like are we calling her to see What she wants?

Yeah, is this proposal number four? I just need some help Navigating the conversation She doesn't know that I know She botched that last one And, you know, I don't want her to feel upset about that. I just want to know, like, what's going on. Oh, okay.

You're not proposing. Okay. So this is an information-finding mission to figure out why she keeps turning it down. Yeah, she might not even want to get married to me. And I would want to know that instead of just, like, trying and failing all these times. Yeah, is there like a return policy on these rings? What's a story there? I don't want to be negative.

But what happens if you're like, oh, we don't want to get married, then you just break up? No, you get married anyway, Jose. That's what you're married. You force the marriage and then you break up. Some couples say together, some couples break up. It just depends. You won't know until you sign that document locking you together forever. How you really feel about the marriage until you're in it.

I hope you know before you sign the document. How could you know until you're married? Exactly. You don't. We do need to focus on some advice, though. So we'll think of some to give you. We'll come back and we'll call your maybe future fiancé, depending on how this conversation goes

when we do your awkward Tuesday phone call right after this. Thank you so much. All right, man. Hold on. It's awkward. It's Tuesday. It's awkward Tuesday phone call.

How can you tell if your girlfriend is actively trying to sabotage your marriage proposals? Oh, goodness. And I say proposals, plural, because our listener Keith has attempted to pop the question three separate times to his girlfriend, One got shut down by Lila before he even really got started with them. The last one is the most incriminating because it was caught on camera while he was secretly filming. As men like to do, let us secretly film us with our girlfriends.

That is very illegal. Go to jail for a long time. Unless it's for a marriage proposal, which is totally fine. Because in the footage, he saw her purposely knock over the candle and light their picnic blanket on fire. stopping the marriage proposal before he even got to it. Have we considered she's an arsonist? Could be a possibility. He might need more flames in the next attempt.

It's just after that, Keith is wondering, is the problem actually with the proposal or does she actually even want to marry me? Yeah. Not exactly the easiest conversation to have with your significant other, so he needs advice. Brooke, what do you have to say to him?

Well, I think you do something that my husband perfected a long time ago. Oh, Brooke, we can't talk about that on there. Let's not get into the bedroom stuff. And that is play dumb. Okay? Play dumb. Go into it and just be like, okay, I didn't want to tell you, but I had a little surprise for you the other night on the beach.

So I was filming and you wouldn't believe what I saw. It looked like you tried to light the blanket on fire. Isn't that crazy? I see. So it's not like you're actively accusing her of doing it. You're just like, I saw something weird. Yeah, weird. What do you think about that, Keith?

that might work i'm pretty good at playing dumb yeah all of us sorry have that ability so okay keep that in your back pocket Jose what's your advice maybe it has nothing to do with you it could be something that she's built this up in her mind and you're not living up to this expectation that you don't even know about right

it is interesting that all of your talks about marriage those are going fine but when it comes to the actual proposal that's where everything falls off You're just not choosing the right places. All right, Alexis, where is your recommendation? Where should he propose? I don't want to get married.

She said you don't do it. Okay, there's no good place for it. All right, well, that's our advice for you, Keith. Oh, my God, she has hives just talking about it. That's so weird. The M word. We're all scared in studio. Thank God you're the person making this call.

But we will be on the other line ready to jump in if we feel like you need a little bit of help. You ready, ma'am? Yeah, I think so. All right. You got it, buddy. What's the worst that can happen? You're just asking your girlfriend if the idea of marriage disgusts her. They could break up, dude.

Oh. I was trying to ask that question in a positive way. What's the worst that could happen? I wasn't expecting everybody to jump on. All right. Oops. Sorry about that, Keith, but good luck. We'll be here if you need us.

Here we go. Hello? Babe, how's it going? Oh, hey. I'm good. How are you? What's up? Good.

I was just saying hi. You know, I'm just missing you, calling to say, hey. Want to hear your voice. Well, that's the EW. Yeah, yeah, you know. I was just thinking, too, you know, I'm sorry about the little fire accident we had a couple weeks ago. I just got bad about that. I know, I know Beach is your favorite and kind of ruined the mood there.

yeah definitely it was yeah it was a bummer to lose pizza and a blanket and all the things i know i know yeah uh i just uh i was gonna surprise you with something so i i had my phone set up so i could get your reaction and did i was like looking at the video again and i don't know i don't know why it just it looked like it looked like you um you might have set the blanket on fire on purpose but like i don't think you would do that you know I was weird, right? I don't know what happened. I mean, I didn't, I didn't meet, like, it wasn't, I don't.

Did you get the sense that I was going to have, like, a surprise for you? Maybe. Okay, yeah, yeah, I just, um, it's not a big deal, you know, I just, uh, like, we both want to get married, right? I mean, I'm just like processing all this I wasn't expecting this during my workday Is there a problem? Is there something going on? Am I like a

Like am I pick up on something here? Is everything okay? I didn't really want to talk about this But I guess I should. Oh, man. Yeah, I've just been having some second thoughts and I've been just too scared

to talk to you about it. Okay, like, what do you mean? The thing is, I'm having the thoughts and I don't know what to do about the thoughts and I don't want to, I don't want you to, I didn't want you to be hurt by this, which is why I was like, resisting yeah yeah babe i just like i don't i don't like this like i feel very nervous like i feel

like you'll be better if you just told me okay um i don't know how to say this um okay so probably about three months ago i went to pick you up at the gym and i saw that you were playing basketball outside. And for me, I've always dreamed of having athletic children. And after watching you play basketball, I don't know, I'm not sure if that's possible. What? That is not a thing. That's not it. What's going on? What are all these people? What's happening? These people that you're hearing, we're a radio show called Brooke and Jeffrey in the morning.

Oh, gosh. Yeah. So we play basketball with your future fiancé. He's really good. Yeah. He dumped on me. That doesn't matter. It could matter to her if she prioritizes that high on her list of potential partners.

I have a story that will change your mind, I promise. Oh, God. We're going to be here for 40 minutes. How much time do we have? Hold on, everybody. I just want to say something. I, like, I actually am really good at basketball. Like, I play it all through high school.

Everybody plays through high school. I know. Brooke was on the volleyball team on the C squad. Keith, I'm so sorry. I didn't know all these people were on this call. I wouldn't have said these things on the radio. Well, that's what he wanted, though. He wanted the truth out and sounded like you guys needed some help to start this conversation.

I don't know if this is overstepping, but I feel like Keith has noticed a few things over the last several months that are pointing to you not wanting to say yes. I mean, I'm just hesitant. Okay. Because you're worried that someday you're going to have babies with Keith, and there's babies aren't going to be not able to dunk. I grew up playing sports. I always imagined being at sports with my kids and doing those type of things. You can't know that.

Like, there's no way to know, like, how your kids that don't exist right now are going to be in sports. I don't know. I saw him. Well, they'll get all the love and support I can give them. That's for sure. Like, that is such a great response. And that's what you really want to look for,

someone that'll be a great father, not someone based on their athletic ability. I never heard Lila say anything about wanting her children to be loved or supported. Not once. She didn't bring it up. But he'll be loving and supporting every time they get participation trope. I'm sorry, I'm doing it. But my best friend married one of the most unathletic people I have ever met in my life.

And her kids... Now you're slamming your friends? No, he just had heard. That's what he is. He would admit that. Yikes. And her kids. are like elite basketball players.

Well, does that make you feel better, Lila? Brooke knows somebody who has kids and they turned out to be athletic. But they're a nerd. I've just saying you don't know. Obviously, I don't want to force them to be anything, but like I would encourage sports and being athletic. And I don't know if that's possible.

Okay. We're just going to read between the lines instead of shooting more three-pointers, you go for more layups during pickup basketball. All right. Well, it's also a team sport, right? and I'm a great team player. Oh,

so much of a team player, you never shoot the ball yourself. Just keep passing it. All right. I mean, of course we can talk more about this. I'm seeing that maybe, as we're talking this out loud, that maybe there's still room for the possibility.

There's a sliver of hope for you right there. So if I was you, I would propose in the next 10 seconds and use this positive momentum to your advantage. This is not the time. Before you lose it, Keith, now or never. You don't have to propose. right now, but I am more into it.

Oh, more than you two. All right. You blew your chance. It was right there. Yeah, romance somewhere in that. Okay. Yeah. Four times a charm.

Yes. Keep us updated down the line what happens between you two and your relationship. We'll do. Thanks so much. Just remember to stay away from any beaches, parks, fancy restaurants, all of New York City. And basketball courts. And basketball courts. Brooke and Jeffrey in the morning.

All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky, went unsolved, until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy killed her. We know. A story that law enforcement used to convict six people, and that got the city. Investigator on national TV. Through sheer persistence and nerve, this Kentucky housewife helped give justice to Jessica Curran.

My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn, or any of that other stuff that y'all said. They literally made me say that I took a match and struck and threw it on her. They made me say that I took a match and struck and threw it on her. They made me say that I pour gas on her.

From Lava for Good, this is Graves County, a show about just how far our legal system will go in order to find someone to blame. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

And to binge the entire season at free, subscribe to Lava for Good Plus on Apple Podcasts. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good

true crime podcast episodes, then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. a shootout in broad daylight. People using axes in really terrible ways. Disappearances. Legendary heists. The whole nine yards. So check out the stuff you should know true crime playlist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Is anything more of a turnoff than an unathletic baby? I'm telling you, you can't judge how athletic your kids are going to be. Well, sure, but once an unathletic child comes out, say what you will, but a baby drops his rattle and immediately, I think, yikes, he's not going to the NFL. Fumble. What baby doesn't come out with a six-pack, too. Exactly. Just disappointing.

Look, I don't think we fix this relationship by any means with this phone call. I know. But at least we help them start the conversation so that they can talk about what they both really want to get out of a potential marriage. Yeah. It might not be the same things, but it's better to figure that out now than after you've got four unathletic children who can't do one pull-up. Hey, but they could be good at theater.

You know, an instrument. There you go. Chess? Okay. Look, some people want loving, trusting partners. Other people want a genetic bull who produces guaranteed NBA superstars. You're allowed to want that, Brooke. Let the women want what they want.

So weird. Okay, that's fine. If you want help with your dating life, are you approving that, Brooke? Yeah. Okay. Then you can, then you're safe to email our show. We'll help you out with an awkward Tuesday. You can check all of our content out online wherever you get your podcast.

podcast at Brook and Jeffrey. The murder of an 18-year-old girl in Graves County, Kentucky, went unsolved for years until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. And to binge the entire season ad free, subscribe to Lava for Good Plus on Apple Podcasts. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes,

then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story.

Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. In early 1988, federal agents raced to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. I had 30 agents ready to go with shotguns and rifles and you'd Five, six white people.

Pushed me in the car. Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package. Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand, and I saw the flash of light.

Listen to the Chinatown Stang on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. It may look different, but Native Culture is alive. My name is Nicole Garcia, and on Burn Sage, Burn Bridges, we aim to explore that culture. Somewhere along the way, it turned into this full-fledged award-winning comic shop. That's Dr. Lee Francis IV, who opened the first native comic bookshop. Explore his story along with many other native stories on the show, Burn Sage Burn Bridges.

Listen to Burn Sage Burn Bridges on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.