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Thank you for supporting I Heart Women's Sports and our founding sponsors E L F Beauty, Capital One and Novartis. Just open the free iHeart app and search iHeart Women's Sports to listen now. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the answers. I am so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. The Girlfriends is back with a new season, and this time I'm telling you the story of Kelly Harnett. Kelly spent over a decade in prison for a murder she says she didn't commit. As she fought for her freedom, she taught herself the law. He goes, oh, God. Harnett, jailhouse lawyer. And became a beacon of hope for the women locked up alongside her. You're supposed to have your faith in God, but I had nothing but faith in her. I think I was put here to save souls by getting people out of prison. The girl jailhouse lawyer. Listen. On the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Spark and Jeffrey in the morning. And we've got your awkward Tuesday phone call today. But first, yes, the debate that's waging across the country, or just mostly in our comment section after yesterday's second date update is land meat versus sea meat. Yeah, yeah, yeah. Which one are you gonna touch? Dex Van Heunen commented. I still don't know. Is land meat allowed to drink water? I have so many questions. I mean, I feel like land meat would be really dirty. That was my who. It's like, if it's not allowed to touch the water at all, it would be gross. What if it rains? It's just outside and it just rains. I don't know. But then some people kind of get it. Hey, buddy said maybe she tastes algae. If we could taste pineapple or onion, I guess I kind of get it. I don't know. Gets it. There's so much plankton in this ribeye. Yeah, Yeah. I don't know. This woman's insane. He dodged a bullet. Okay. Oh, maybe lap meat she could eat. Yeah, I heard laugh. I thought you were talking about a pet that, you know, like, that just got dark. Alexis. Oh, no. Lab. Lab bug. Okay, all right. So anyways, well, we love your comments. We love your debates. Keep it going and sit back and enjoy your awkward Tuesday phone call. Man, back in grade school, it was easy to tell if someone had a crush on you. Aw. Cuz you literally just passed them a note asking them to circle yes or no. That's actually a great point. And then, no matter what the response was, you actively had to avoid them for the rest of the entire year. Yeah, valid. Oh, my God, I said y. But as adults, things get a little bit more complicated, especially if your crush is a friend at work. Oh, man. And one of our listeners says, the other night, there was A sign that maybe a romantic spark was happening with her co worker. And now she wants our help to gently nudge this friendship into more than that. Oh, man. How do we pass him a note though? We're on the radio. We have to come up with a better plan when we do your awkward Tuesday phone call next. It's awkward. It's Tuesday. It's awkward Tuesday phone call. Awkward tension between two people who work closely together. We don't know anything about that on this show. Just sitting in the middle of it every day. Brooke, by the way, if you wore underwear, you would have left it on my chair in the ox booth. We were all thinking it. They'd be really big though. I mean, it's like the granny panties. I just say I like a little tummy control. Nobody sees it as a blanket. Enough about cold in there. Enough about Brooks. Insatiable workplace lust. Cuz. One of our listeners, Maya, is looking for some romantic advice about one of her co workers. I'm hoping no undergarments are involved, but let's find out. Maya, welcome to the show. Hi guys. So happy to be here. Love your show. You don't wear granny panties, do you? Maya is too soon. Is that too soon for me to ask you that? I am not a granny. Okay, tell us about the co worker that you're having this romantic tryst with. What's their name? Ooh, we got a tryst already. Or a crush. Well, I don't know. His name is Derek. Okay. And he and I have always had a connection at work. We've been like friends. And basically I developed all these feelings for him. And every time I see him, it's just like he lights up a room. Aw, cute. That's exactly what Brooke was thinking about me. You don't have to keep throwing it my way. Brooke, I get it. You're obsessed. That new feeling of just seeing the person, that. Oh, God, it's just so good. Such a good feeling. Yeah. So here's the thing. Like about a year ago, I kind of came up with this plan where whenever he walks into a room and whenever there's a group of us, I am just going to do whatever I can to build the bond. So basically, I would always do my best to like, linger and stay there until it's just the two of us in the room. And my idea has kind of worked. So just wait it out. He's in the break room and you like, poke your head around the corner, just like, check on what he's doing? No, I think she just Stands next to him until everyone else leaves and then handcuffs him to a chair so that he can't escape. Oh, okay. So you said that's kind of working. I think it's been working. Why do you think it's been working? I mean, it's just so vague, like how so long game. Yeah, I don't know that any guy would ever pick that up as you liking them. Oh, okay. So last week we ended up finally going out with coworkers and getting drinks. Right. Okay. Okay. That's a good start. Yeah. So I made sure again that I was like, the last one there was Derek. Ok. Ok, this is good. There's a dark bar. Yeah. Just the two of you? Alcohol's involved, yes, but I made sure I just didn't drink too much and he ended up crashing at my place. Oh, hey. Hey. Dang, girl. Yeah. So I do know that he wears boxers. We did not hook up. But, you know, he slept in my bed. What? With his pants off. You didn't hook up and he was in his boxers and he's in your bed after a night out? Yeah, it was just like I wore sweatpants. You know what I mean? Like, we just got comfortable. Yeah. Sweet. Wearing bedtime attire. Did you guys cuddle? We kind of did. We kind of didn't. Like. Oh, you smoke cigarettes together. What? What? I don't. Cigarettes. Just pass the one cigarette back and forth. I don't think Jeff knows what happens when two adults lay in bed together. Cigarettes anymore. Yeah, I'm just guessing. Yeah, it's not like the 1940s movie. So what happened? Yeah, well, there was this moment in the middle of the night, and it was just so sweet and so tender. He kissed me on my back in the middle of my shoulder blade. Interesting. Is that a romantic move? I don't know. That's interesting. First kiss? Yeah, definitely. For me, it's like so intimate. All right, sure. But did you guys ever, during the night, kiss with lips instead of just back smooches? No. Well, his lips on her back? Yeah. I mean, she thinks it's really sweet. Body kisses can be very sensual. I mean, it's not a horrible thing. It's just weird that that's his first attempt. I'm trying to figure out what base that is. Like, is that like half. Half the first bit? I think it's a bunch. It's a bunch she's not even facing. Okay. It doesn't matter. She liked it. Yeah, you liked it. So. Yeah. Has that led to anything? That's kind of where I'm a little confused because, you know, we woke up, it was really sweet, but going back to work, I was hoping like he'd ask me out and maybe end up in my bed again. Right, right. More than just back stuff. Maybe we'll move on to El stuff. I don't know what I'm call it. And what's happening. Well, it kind of just like went back to the way it was and I'm just not sure how to get it back to the romantic. Have you guys not talked about it at all since that night? I didn't bring it up to him because that's kind of awkward. Like, hey, remember in the middle of the night you did this? But he sounds like an awkward guy. I mean, that's an awkward guy move, isn't it? You're definitely in this weird in between friends and maybe more than friends space. So what. What do you want to do with your awkward call here? Yeah. So basically, I guess I just want you to help me point the boat in the direction of romance. Romance. Okay, romance. The love boat. I just came up with that. That's definitely not a 50 year old reference that we're bringing. Hey, the granny panties. Full circle. Keeping it young. Here, Jeffrey. We're gonna give you some on how to push your work relationship. Row your boat down the river of romance with your awkward Tuesday phone call. Right. Blow the horn, captain. Do it right after this. Toot, toot. Okay. It's awkward. It's Tuesday. It's awkward Tuesday phone call. If you had one shot to turn a work friend into a boyfriend. Oh gosh. After one back kiss. Yeah. How would you do it? Oh man, this music is getting me pumped up. Jeffrey, tough question though. That's the question that we've been tasked with today. And I'm being honest when I say you really only have one chance to do this right. Yes. Right when the beat hit. Maya has had a crush on her coworker for a year. They ended up hanging out together at a work happy hour and were the final two left at the restaurant. He ended up crashing over at her place. And even though they down sat, spent the night in the same bed, there was no romance. No lip to lip kissing. A little tiny moment just right in the middle of the night. He kissed her back once and then went back to sleep. Now she wants them to be an item. And I know how we're going to do this. You do? We're going to have Brooke give you the best advice that you've ever heard. Brooke? She needs this Advice. What do you got? Brooke, I am a person who has told countless boys and men that I have crushes on them in my life. In my life. I'm going to tell you, though, my success rate, probably less than 25. But listen, you got to do what I shouldn't have done. Do the opposite of me, because I just always come out with it. I can't hold things in, and then it's, like, awkward. And sometimes you get a thank you. You know, that's like, the worst thing to hear. Instead of how. How you're feeling, let's talk about how he's feeling. Maybe you say that you've noticed he may have some feelings for you. You leave it real general. I'll put it on him and then maybe say, maybe that's something we should talk about. Wait, like, say that I've noticed he has some feelings for me? Yeah, trick him. He kissed you on the back. He's got something going on. Jose, what do you think? Well, here's what would work on me. Tell him that you had so much fun with him the other night and you want to do it all over again. But only you two this time. No co workers involved. Okay, so just ask him out, is what you're saying. Asking him out on a date. Well, I guess I have a question. Yeah? You said to say, oh, I've noticed that maybe you have some feelings for me. Yeah. Like, what's the next step? Then what would you say? Falls in his court? Wait for him to respond. Yeah, I mean, you could just even say, am I reading that right? Right? Oh, am I reading that right? Oh. Remember, though, Brook is 25% success rate. Whether you go with Jose or Brook's advice. We're all really invested. We're all rooting for you. I'm going to dial your coworker Derek right now and hopefully convince him to fall in love with you. Let's do this. A date. I don't know about the L word, but. Hello? Hey, Derek, it's Maya. Hey, what's going on? Hey. So I had a lot of fun last week when we all went out with everybody from the office. What did you think? Wasn't that fun? From what I can remember, it was fantastic. I can't believe some of the things that Nick said, but, yeah, it was a good time. It was a really good time. Yeah, it was fantastic. You? Yeah, I had a great time. And do you, like, remember in the middle of the night that anything happened? Wait, I didn't. I didn't pee on anything. Did I. No, no, it was really sweet. You know, you kissed me. But, I mean, not on the lips you just kissed. I mean, not there either. You just kissed me. You actually kissed me between my shoulder blades. What? It wasn't. I mean, it's not that big a deal, right? Get the out of here. Are you serious? No. Are you serious? Yeah. Yeah. Is this a. No. I do not remember that at all. And I apologize. I probably shouldn't have even spent the night there because. Yeah, I was just so out of it. So I'm really sorry if you were offended. Actually, I wasn't offended at all. I kind of noticed that maybe you have some feelings for me. And, I mean, am I reading it right? What do you mean, am I reading it right? What do you. What do you mean by that? Okay, I'm just gonna say it. I had so much fun the other night, but I was hoping we can do it again. And this time maybe just the two of us. What do you think? Wow. Okay. That's not what I expected at all. I thought you were gonna call because you just needed, like, help with your spreadsheets, like. No, actually, I want you back in my real sheets. That was a good one. Wow, that was amazing. Smooth. Took both our guys. What's happening? Yeah, what's up, Derek? Derek. Hey. You're on the radio with Brooke and Jeffrey in the morning. Oh, that's something you can't say on the radio, but that's okay. We'll give you a pass. I'm sorry. I'm sorry. We're doing something right now called an awkward Tuesday phone call. Trying to help out Maya. Sort out what happened between you two at her place the other night. I think you know exactly what Maya wants now. Yeah, they've been giving me some advice because I really just have had a crush on you lately and we couldn't tell based on the things you were saying to them. That's sweet. Well, the back kiss made her feel like you were trying to cross into a. More than a co. Worker ship. So is there any possibility that might be true? Oh, wow. Not to put you on the spot or anything like that. No, no, exactly. To put you on the spot. No, no, just, you know, on the radio and stuff. Yeah, I. Look, I legitimately, a lot of the other night is very hazy. Okay, so you don't remember the back kiss at all? Oh, God. Oh, God. But hold on, hold on. If I'm being honest, even though things were hazy the other night, I probably have feelings too. Really? Oh, my God. Wait, why do we hit record again? That's so cute. I don't know. I just. I got nervous. You weren't expecting that answer? Because I think I might have feelings, too. Stop it, Jeffrey. Don't fulfill it. Let them have it. Okay, sorry, sorry. Continue. Oh, my God, Maya. I can't believe this is on the radio. This is, like, the best news I've ever. This is, like, the best news I could have expected. Yeah, but. But I'm sorry. Like. But honestly, I'm a little bit worried about ruining our friendship, Maya. And, like, the fact that it's at work is. I don't know, it's doubly dangerous. And so it's like, ooh, doubly fun is what I don't get. Brooke. All right. Less than 25%. Well, you know, I was just thinking that, you know, if you wanted to ask me out. Oh. Oh. Putting it back in his. It would be the perfect moment. Wait, right. Right now on the show? Yes. Yeah. Everyone's listening, yo. That's a good point. No one is listening. He said everyone's listening. Maya, you are so good at this. Okay, Derek, Derek, this is your chance. Okay, Maya on the radio. Do you want to go get Subway with me at lunch? Oh, kind of spot. Yes, I do. I thought you said you liked her. I do. I do. It's just, you know, I. I'm sorry. This has never happened to me before where somebody's asked me to ask them out on the radio who I want. You're welcome, man. Don't let Brooke get in your head. All right? I think Subway's great. It's top 50 most romantic fast food chains in the country. You got a very, like. What's the word? Unneedy person to go out with right now. Maya's just happy to be here. She's chill. Yeah. Thank you guys so much. You guys go to Subway together, and who knows? Maybe that turned into something else. Maybe turns Baskin Robbins afterwards, and maybe we could end up going to Red Lobster for a nighttime date. I love the cheddar biscuits. Little cheddar biscuit action with a back kiss on top. Count me in. Brooke and Jeffrey in the morning. Oh, that was cute. Yeah. I want them to write us and give us an update. I know. I need to know what happened. Either that or they went to Subway and it was a total, like, fail, and that's why they're not. Could have been a bad Subway experience. Yeah, you know. You know that. That was awesome. I love that people are writing in the comments about shipping them or being excited about them together. Yeah. One person commented, said, my husband and I met at work, too. We've been together 27 years and married for 21. I feel like the best place to meet someone is at work. I never knew that. We said it one time on the show, like the number one place, whatever. And after that day, almost everyone I talked to, I swear, it's like, oh, yeah, well, we originally made it work. Now we work different places. But we. And I'm like, what the heck? Am I supposed to marry Jeff? Yeah, maybe, maybe. I mean, you could perform those first. I'm looking, that's for sure. I think it's right under my nose. I love it. I love it. And do we have another comment, too? No. Someone said, Subway, Red Lobster. This guy loves his chain restaurant. Yes, he does. I mean, we do too, right? Yes. Can't blame him. Show me those cheddar biscuits. All right, well, thank you so much for being here on our second date podcast. And I hope you love the Awkward Tuesday. It happens once a week and it'll be back here next Tuesday. So. Yeah, don't forget to subscribe. It's Brooke and Jeffrey in the morning. Join iHeartRadio and Sarah Spain in celebrating the one year anniversary of iHeart Women's Sports. With powerful interviews and insider analysis. Our shows have connected fans with the heart of women's Sports. In just one year, the network has launched 15 shows and built a community united by passion podcasts that amplify the voices of women in sports. Thank you for supporting iHeart Women and our founding sponsors, E L F Beauty, Capital One and Novartis. Just open the free iHeart app and search iHeart Women's Sports to listen now. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the answers. I am so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. The Girlfriends is back with a new season, and this time I'm telling you the story of Kelly Harnett. Kelly spent over a decade in prison for a murder she says she didn't commit. As she fought for her freedom, she taught herself the law. He goes, oh, God. Harnett, jailhouse lawyer. And became a beacon of hope for the women locked up alongside her. You're supposed to have your faith in God, but I had nothing but faith in her. I think I was put here to save souls by getting people out of prison. The Girlfriends Jailhouse Lawyer listen on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. My Uncle Chris was a real character, a garbage truck driver from South Carolina who is now buried in Panama City alongside the founding families of Panama. He also happens to be responsible for the craziest night of my life. Wild stories about adventure, romance, crime, history and war intertwine as I share the tall tales and hard truths that have helped me understand Uncle Chris. Listen now to Uncle Chris on Will Ferrell's Big Money Players Network on the iHeartRadio app, Apple Podcasts or wherever you listen to podcasts. I knew I wanted to obey and submit, but I didn't fully grasp for the rest of my life what that for my heart. Podcasts and Rococo Punch this is the Turning River Road. In the woods of Minnesota, a cult leader married himself to 10 girls and forced them into a secret life of abuse. But in 2014, the youngest escaped. Listen to the Turning river road on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Podcast Summary: Brooke and Jeffrey: Second Date Update
Episode: Awkward Tuesday: Work Friend To Boyfriend
Release Date: July 22, 2025
Host/Authors: Brooke and Jeffrey
Platform: iHeartPodcasts
In the episode titled "Awkward Tuesday: Work Friend To Boyfriend," hosts Brooke and Jeffrey dive into the complexities of transitioning a work friendship into a romantic relationship. The episode centers around listener Maya's experience with her coworker Derek, exploring the nuances of workplace romance and providing actionable advice to navigate such tricky waters.
The episode kicks off with Maya reaching out for help regarding her budding feelings for a coworker named Derek. Maya shares her journey of developing feelings over the past year, culminating in a company happy hour where they became the last two remaining guests. After the event, Derek stayed over at Maya's place, leading to an intimate but platonic night.
Key Points:
Brooke and Jeffrey dissect Maya's situation, offering contrasting yet complementary advice to help her move forward.
Brooke's Approach: Subtlety and Emotional Insight
"[00:30] Brooke: 'You got to do what I shouldn't have done. Do the opposite of me, because I just always come out with it... Instead of how you're feeling, let's talk about how he's feeling.'
Brooke suggests that Maya should refrain from directly expressing her feelings. Instead, she recommends observing Derek's behavior and creating opportunities to strengthen their bond without making immediate declarations. This approach aims to create a natural progression from friendship to something more.
Jeffrey's Approach: Directness and Clarity
"[05:15] Jeffrey: 'Tell him that you had so much fun the other night, but I was hoping we can do it again. And this time maybe just the two of us. What do you think?'"
Contrasting Brooke's subtlety, Jeffrey advocates for a straightforward approach. He advises Maya to communicate her interest openly, suggesting a one-on-one outing to gauge Derek's feelings and intentions clearly.
Embracing the episode's interactive format, Brooke and Jeffrey take Maya's plea for help to the airwaves by initiating an "awkward Tuesday phone call." Jeffrey dials Derek live on the radio to address the situation directly.
Highlights of the Call:
Initial Hesitation:
Addressing the Past Night:
Derek's Realization and Admission:
Final Resolution:
Following the successful phone call, Brooke and Jeffrey express their excitement and anticipation for Maya and Derek's budding relationship.
Listener Interactions:
"[05:15] Jeffrey: 'Tell him that you had so much fun the other night, but I was hoping we can do it again. And this time maybe just the two of us.'"
Jeffrey emphasizes the importance of clear communication in pursuing romantic interests.
"[14:20] Maya: 'You know, you kissed me between my shoulder blades...'"
Maya confronts Derek about their ambiguous intimacy, seeking emotional clarity.
"[18:30] Derek: 'Even though things were hazy the other night, I probably have feelings too.'"
Derek reveals his own feelings, indicating mutual interest with Maya.
Awkward Tuesday: Work Friend To Boyfriend offers a heartfelt exploration of workplace relationships, blending listener experiences with expert advice. Brooke and Jeffrey adeptly navigate the conversation, providing both subtle and direct strategies for Maya to pursue her feelings without jeopardizing her professional rapport with Derek. The live phone call serves as a climactic and encouraging moment, demonstrating the podcast's commitment to engaging and resolving real listener dilemmas.
Listeners are left eagerly anticipating updates on Maya and Derek's relationship, while also feeling equipped with valuable insights to handle their own romantic pursuits in the workplace.
Connect with the Hosts:
Stay tuned for the next episode of Brooke and Jeffrey in the Morning for more engaging discussions and listener stories.