Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Work Friend To Boyfriend

Episode Date: July 22, 2025

One of our listeners says that a romantic spark is happening with her coworker and now she needs our help nudging this friendship with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Join iHeart Radio 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's Sports and our founding sponsors Elf Beauty capital one and Novartis just open the free I heard out and search I heard women's sports to listen now. This summer on the X-ray vision podcast we're diving deep to

the summer's biggest movies from Jurassic World rebirth to fantastic for plus we'll talk to the stars of Superman. Those are a part of the lowest lane costume that helps you feel like you were really stepping into her? It was the necklace for me. Nobody's really asked that before, so thank you. Listen to X-Ray Vision on America's number one podcast network, iHeart.

Open your free iHeart radio app, search X-Ray Vision, and listen now. So what happened at Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family.

Listen to United States of Kennedy on the iHeartRadio app, Apple podcast, or wherever you get your podcasts. 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 on a cherry tree? Were JFK and Marilyn Monroe having an affair? And, 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'm 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 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. It's Brooke 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, 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 lamb meat would be really dirty that was my whole thing It's like if it's not allowed to touch the water at all. It would be gross 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 Much plankton in this rib eye yeah, I know this woman's insane. He dodged a bullet Maybe lap me if she could eat Yeah

I thought you were talking about a pet Okay, anyways well we love your comments. Yes, 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. Because 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 their response was, you actively had to avoid them for the rest of the entire year. Yeah. Valid. Oh my God, they said yes, run! Oh God!

Awkward. Believe me. 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 coworker.

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 with a better plan when we do your Awkward Tuesday phone call. Next.

It's awkward. It's Tuesday. It's Aw 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? Oh boy. 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 aux booth. Oh! We were all thinking it. They'd be really big, though.

I mean, it's like the granny panties. I'm just saying, I like a little tummy control. Nobody asked. A little? No, you know. No, no. Jeez. You don't care about that.

We really don't like that. She uses it as a blanket. Enough about Brooke's insatiable workplace lust, as a blanket Insatiable workplace lust 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 Here love your show you don't wear granny panties do you my? I am not a granny Hey guys, so happy to be here, love your show. You don't wear granny panties, do you, Maya? Hell no.

Is that too soon for me to ask you that? I am not a granny. Okay. Tell us about the coworker 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. 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.

Oh, cute. That's exactly what Brooke was thinking about me. Oh, sorry. 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. It's 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 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 poke your head around the corner just to 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 long game. Yeah, I don't know that any guy would ever pick that up as you like in them.

Okay. So last week, we ended up finally going out with coworkers and getting drinks, right? Okay. That's a good start. Yeah. So I made sure again that I was like the last one there was Derek. Okay, this is good. Now it's a dark bar. Yeah, just the two of you.

Alcohol is involved. Uh-huh. Yes, but I made sure I just didn't drink too much and he ended up crashing at my place. Oh! Dang girl! Yeah, so I do know that he wears boxers. We did not hook up, but you know, he slept in my bed. 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 we I wore sweatpants. You know what I mean? Like we just got comfortable Did you guys cuddle we kind of did we kind of didn't like you smoked cigarettes together One cigarette back and forth Anymore, yeah, it's not like one cigarette back and forth? I don't think Jeff knows what happens when two adults lay in bed together. No one smokes cigarettes anymore. 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. Oh, interesting. That's kind of aw. Is that a romantic move? That's an interesting first kiss. Yeah, definitely for me. It's like so intimate.

Alright. Sure. But did you guys ever during the night kiss with lips? Instead of just back smooches? No. Well, his lips on her back. 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 attack.

I'm trying to figure out what base that is. Like, is that like half, half the first base? Yeah, I think it's a bunt. It's a bunt. It's a bunt. You're in the dugout. She's not even facing it. It doesn't matter. She liked it. You liked it. I mean, what happened? 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.

Yeah. With more than just back stuff. Maybe we'll move on to elbows. Back stuff? I don't know what I'm supposed to call it. And what's happened? Okay, so? I don't know what I'm supposed to 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 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

The love boat 50 year old reference We're gonna give you some advice on how to push your work relationship If you had one shot to turn a work friend into a boyfriend... After one back kiss, how would you do it? 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. Because 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 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 gonna do this. You do? We're gonna 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 gonna tell you though, my success rate, probably less than 25%. Okay, you did not do it. You shouldn't lead off with that before the advice. But listen, you gotta 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 sad. Yeah. That'd be the worst thing in here. Instead of 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? Yes! Jedi mind 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. Well I guess I have a question. Yeah. When 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? Walls in his court. Just wait for him to respond.

Yeah. I mean, you could just even say, am I reading that right? Oh, am I reading that right? Oh. Remember, though, Brooke is 25% success rate. Whether you go with Jose or Brooke's advice, we're all really invested. We're all rooting for you. I'm going to dial your coworker, Derek Derek right now and hopefully convince him to fall in love with you let's do this.

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? Uh, 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. Fantastic. You. Yeah, I had a great time. And, um, 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? Uh, 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, you, you, you actually kissed me between my shoulder blades. Oh, what? It wasn't, I mean, it's not that big a deal, right? Get the out of here. Are you serious? No. Yeah.

Yeah. Yeah. Is this a, no. Yeah. Yeah. Yeah. Is this a no. I'm sorry. I do not remember that at all. And I am. Oh, guys. I probably shouldn't have even spent the night there because yeah,

I was I was just so out of it. So I'm I'm really sorry if you were offended. Actually, I wasn't offended at all. I kind of, 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 going to say it. Um, I had so much fun the do you, what do you mean by that? Okay. I'm just gonna say it. Um, 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. Uh, okay. I, that's not what I expected at all. I thought you were gonna call me

because you just needed help with your spreadsheets. No, actually I want you back in my real sheets. That was a good one. That was amazing. Smooth. Who's got games? What's happening? Oh my god!

He doesn't know yet! What's up, Derek? Oh, Derek! Hey! You're on the radio with Brooke and Jeffrey in the morning. Oh, f***! That's something you can't say on the radio, but that's okay. We'll give you a pass.

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.

We couldn't tell based on the things you were saying today. Oh, that's sweet. Well, the back kiss made her feel like you were trying to cross into a more than a co-workership. So? Is there any possibility that might be true? Oh, wow. Not to put you on the spot or anything like that, but... No, no.

Exactly to put you on the spot. No, no, just, you know, on the radio and stuff. Yeah. No, no, just on the radio and stuff. I, look, I legitimately, a lot of the other night is very hazy. Okay, so you don't remember that back kiss at all? Oh God, oh God. I don't know, but hold on, hold on. If I'm being honest, even though things were hazy

the other night, I Probably have feelings, too I got nervous Because I think I might have feelings Okay, sorry continue Sorry, continue. Oh my God, Maya. I can't believe this is on the radio. This is like two besties I've ever, this is like two besties I could have expected.

Oh. Yeah, 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, doubly dangerous and so it's like. Oh, doubly fun is what I heard. Don't get Brooklyn rolled up again. She's less than 25% percent.

Yeah. Well, you know, I was just thinking that, you know, if you wanted to ask me out. Oh. Oh. Getting it back into his life is. It would be the perfect moment. Wait, right now? Yes, exactly.

On the show? Yes. Yeah, Derek. It's just great. Everyone's listening. Yeah. Yo, that's a good point. No one is listening.

No one's listening. He said everyone's listening. Maya, you are so good at this. OK, Derek. Derek, this is your chance. OK, Maya, on the radio. Are we forcing him? Okay, Maya on the radio. Do you want to go get Subway with me at lunch? Oh, kind of.

Yes, I do. I thought you said you liked her. I do. I do. It's just, you know, I'm sorry this has never happened to me before where somebody's asked me to ask them out on the radio Don't let broke get in your head all right, I think subways 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? She's chill yeah, thank you guys so much you guys go to subway together, and who knows maybe that turns into something else Maybe we could end up going to red lobster for a night time

Little cheddar biscuit action with a back kiss on top. Count me in. Oh, that was cute. 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, you know, could have been a bad Subway experience. You know, 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 at work now. We were different places Do we have another comment to know someone, someone said Subway Red Lobster.

This guy loves his chain restaurant. Yes, he does. I mean, we do too, right? Yeah, you can't blame him. Show me those cheddar biscuits. Yeah. 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 don't forget to subscribe. It's Brooke and Jeffery in the morning. by passion. Podcasts that amplify the voices of women in sports. Thank you for supporting I Heart Women's Sports and our founding sponsors, Elf Beauty, Capital One, and Novartis. Just open the free I Heart app and search I Heart Women's Sports to listen now. This summer on the X-Ray Vision podcast, we're diving deep into the summer's biggest movies from Jurassic World Rebirth to Fantastic Four. Plus, we'll talk to the stars of Superman.

Is there a part of the Lois Lane costume that helped you feel like you were really stepping into her? It was the necklace for me. Nobody's really asked that before, so thank you. Listen to X-Ray Vision on America's number one podcast network, iHeart. Open your free iHeart radio app, search X-Ray Vision, and listen now. So what happened to Chappaquiddick? Well, search X-ray vision and listen now. So what happened to Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond.

And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy's on the iHeartRadio app, Apple podcast, or wherever you get your podcasts.

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'm 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 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 iHeart Radio app, Apple Podcasts, or wherever you get your podcasts.