Brooke and Jeffrey: Second Date Update - Awkward Tuesday: I Want To Date My Friend's Ex

Episode Date: June 10, 2025

Is it ever okay to date your friends EX? Don’t ask us, in fact, just get ‘em on the phone for an Awkward Tuesday Phone Call instead!See omnystudio.com/listener for privacy information.

This is an iHeart Podcast. Why is a soap opera western like Yellowstone so wildly successful? The American West with Dan Flores is the latest show from the MeatEater Podcast Network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the region today. Listen to The American West with Dan Flores on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

I'm Clayton English. I'm Greg Glott. And this is season two of the War on Drugs podcast. Last year, a lot of the problems of the drug war this year, a lot of the biggest names in music and sports. This is kind of star-studded a little bit, man. We met them at their homes, we met them at their recording studios.

Stories matter and it brings a face to them. It makes it real. It really does. It makes it real. Listen to new episodes of the War on Drugs podcast season two on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. Over the years of making my true crime podcast, Hell and Gone, I've learned no town is too

small for murder. I'm Catherine Townsend. I've heard from hundreds of people across the country with an unsolved murder in their community. I was calling about the murder of my husband. The murderer is still out there. Each week I investigate a new case. If there's a case we should hear about, call 678-744-6145. Listen to Hell and Gone Murderline on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. Hi-Key. Looking for your next obsession? Listen to Hi-Key, a new weekly podcast hosted by Ben O'Keefe, Ryan Mitchell, and Evie Oddly. We got a lot of things to get into. We're going to gush about the random stuff we can't stop thinking about. I am high key going to lose my mind

over all things Cowboy Carter. I know. Girl, the way she about to yank my bank account. Correct. And one thing I really love about this is that she's celebrating her daughter. Oh, I know. Listen to High Key on the iHeart radio app,

Apple podcasts, or wherever you get your podcasts. Sometimes as dads, I think we're too hard on ourselves. We get down on ourselves on not being able to, you know, we're the providers, but we also have to learn to take care of ourselves. A wrap away, you gotta pray for yourself, as well as for everybody else, but never forget yourself. Self-love made me a better dad

because I realized my worth. Never stop being a dad. That's dedication. Find out more at fatherhood.gov, brought to you by the US Department of Health and Human Services and the Ad Council. All right, it's your brand new, well, I guess it's not a second date today,

but it's your second date podcast with a brand new Awkward Tuesday. Yeah! All that matters is we're here. We're here And we got a new episode And I gotta say I surprised myself even today how quickly I changed you did you were one side to the other side She's just so convincing. Yeah, really? Real I would have given her whatever she wanted my friend I mean you're gonna understand we'd love to hear what your thoughts and comments are,

of course. Leave them in that comment section. And what are we seeing today, Alexis? Yes, I saw one from Jen590 who said, wow, I've been listening to you guys since my freshman year, and now I'm a high school graduate. Can't wait for another four years of laughs with y'all in college.

I hope you take us to so many college parties. Yeah! Please, I would like to go back to some frat parties. You know, I could skip the dining hall. We were trying to raise her right. Okay. Well, you know, we've been with her since she was like 12 or something.

Alexis is teaching her how to skip class. Yeah, we're gonna have so much fun in college together, Jen. Yeah! Hey, sit back and here's your brand new Awkward Tuesday phone call. You always hear people say, So much fun in college together Jen You always hear people say I'll do anything for my friends Yeah, but honestly would you Would you lie to a judge for them under oath Would you let them Can you cross your fingers? Maybe.

Would you let them practice tattooing on your baby's lower back? Just a cute little tramp stamp that says made in the back seat. Come on, that's adorable. No? No. Okay, so there is a limit. And one of our listeners is definitely going to push the limits today. Because she needs to ask her friend a very controversial question that could easily throw a wrench into their relationship.

But she has to try, because if she doesn't, she might regret it for the rest of her life. You're gonna hear it in your brand new Awkward Tuesday Phone Call. It's coming up next. It's Awkward. It's Tuesday. It's Tuesday. It's awkward Tuesday phone call. What are the unspoken rules of friendship? Oh.

Uh, pros before everybody else. Not those ones, that's a different set. You know, rules like you have to hate the same people as I do. What? Never tag me in any ugly photos Just don't post them to begin with done. You're a good friend that too and also before any night out We have to practice kissing on each other for at least 20 minutes

They're just some of the sacred rules that must never be broken. But today one of our listeners wants to violate one of the holy laws of friendship and she needs our help to do it. Her name is Monica. Monica, please tell me you're not breaking the kissing rule. It's not the kissing rule. Oh thank God. Okay.

Do we have to kiss Monica before this starts? Well we're not friends yet. Oh I thought we were okay. No, maybe by the end of this call we'll get there. We'll get a kiss, okay. But first let's try to help you out with your situation. What's going on in your life that made you email the show for help? Well, like you said, I do need to break an unspoken rule.

Ooh, I'm curious what your unspoken rule is. Uh oh, I don't like this already. Is that unflattering picture thing? Is that what it is? I have a feeling it's not. No, I want to date my friends, ex-boyfriends. Oh, God. Oh, no.

There's too many men out there. Why pick him? There's only a few good ones. He's clearly not good. Why would you want to do that? Well, OK, so they only, in my defense, they only dated for like a year. What?

That's a long time ago, you were saying like two weeks. Oh. Was it at high school they dated? That might be the only time it's like. Oh, that's a good point of his old. No. Okay. They broke up like a year ago. Oh.

Oh, man. Well, that's enough time, isn't it? No, you don't ever date your friend's It's just what you just you just don't What if it's been 40 years and you're in the retirement home together doesn't matter? I mean, you're not gonna be friend. I you're not gonna be friends anymore. Yeah But remember this is an awkward Tuesday phone call. We're here to help not to judge We're here to help not to judge That's what Monica wants to do we need to be there lifting her up I would rather talk her out of it

That's even possible Monica, so Tell us why do you want to date him? I mean, okay. So first of all, his name is Ben. And we just have like this vibe. And I don't wanna just say, okay, because he dated my friend, that we shouldn't explore this thing that we are. Keep an open mind, Brooke, whatever you're gonna say. Maybe your friend isn't that close with you. Like maybe it's like a friend, like a coworker.

I said keep an open mind. I'm sure they're friendship That's a positive to me in this situation It's not your best friend in the world. Yeah, okay? Well actually we are pretty close Okay, you're about to be even closer possibly I feel like this happens in any friend group like if you got along with your friends you tend to Friends, no It's like a family member you just put in no go Well, we're moving forward from this is there something that made you feel like

This connection was possible. Like was there a moment that stood out to you? Yeah, I mean so we were like outside hanging out or whatever And while we're talking like we had like a one of those beer ping-pong Things or whatever and it's now soft on forehead and he did the dumb thing where he like bent over and kissed The spot where it hit to make it feel better and I laugh. Oh He's got healing powers. He made the first move. I mean kinda, You know, it was just like a bob. Okay. Can I ask, before we get too far down the road, why did they break up? I mean, there are theories out there, but I don't know exactly what happened, you know.

Okay. So besides the beer pong forehead kiss that was completely medicinal for healing purposes, has anything else happened between you and the ex? I mean, we've just been texting a lot since that night Oh, you talked around the idea of us. We've been hanging out Does your friend know anything about this that this is going on She does not okay, and I mean that that's the whole thing. That's why I want to call my friend about this We haven't done anything. I kind of want to give her permission to move forward. I mean not a great move, but you're doing it in the right way Most people wouldn't even ask permission. They would just go right for it

Again if you want to keep the friendship, yeah Want to steal from Brooke, but I asked first like like hey can I take 20 bucks out of your pocket at some point today she'd probably say no but like that I asked I guess right that's an analogy we could use so do you want to give 20 bucks or no nobody's You can't have my exes though. Any of my exes if you guys want them, I will pass them out. There's enough to go around. So it's okay when you're in high school or when you're super old, but right now in middle area it's a big no. Gotcha.

So why did you reach out to our show for help? What are you looking to get from us? Well, I'm terrible at confrontation. I would rather just avoid it, but I'm really hoping it doesn't come to any confrontation I hope that I come up with some valid points. You guys help me and she's just like sure go for it Okay, you know what? If she was like disgusted with him, I can see it be like oh that guy's awful girl Go ahead. You're gonna find out real quick. Like I could see a yes

I mean because of that the vibe from her is important how does she feel about her ex do you know we haven't talked about him in a while I honestly don't know where she is with that I was gonna say usually they don't talk about it makes you think they're really seeing that I have a feeling the total opposite is gonna happen and she's not only gonna okay it she's gonna be a hundred percent supportive When we come back and call your friend Erin and ask permission to date her ex-boyfriend We're gonna do it with your awkward Tuesday phone call right after this phone call right after this. It's awkward.

It's Tuesday. It's awkward Tuesday phone call. Cool people let their friends date their exes. And we're about to find out if Monica's friend is cool. I mean I know that's not the popular opinion

in the room right now. But you know what? We voiced what we needed to say that some of us aren't 100% okay with this question being asked. All of us were not cool with it, Jay. We voiced that. I'm on the fence, but now we're moving on to the help portion of this call.

That's our jobs, where we give our advice on what Monica should do here. So Brooke, what's your advice? She's doing it the right way. I will say that if you're gonna do it. Now listen, Monica's your advice? We are required to do that. She's doing it the right way. I will say that if you're going to do it. Now listen, Monica, this is what I think you need to do is you need to talk your friend up. Does that make sense?

Okay, how? So you need to maybe speak on how easy it is for her to get a man and how charismatic and beautiful she is and how maybe it's not quite as easy for you. Oh. Oh, boy. Listen to me. This is strategy. and beautiful she is and how maybe it's not quite as easy for you it's kind of almost a sympathy card you're playing yeah and that you have this really great option but there's one kind of hurdle with it and you need her support her with the pathetic brush I mean I have no option okay can you make yourself seem pathetic Monica I'll see my bed okay that's good Jose what's your advice and this is his

distraction actually works best so there's another guy that she's interested in yeah her focused on that person right That way she's thinking happy thoughts about someone new. I feel like Jose is talking to himself because he's easily distracted. He's like, what would I do if I was the friend? It's like a little magic act illusion, like, oh, look over here, you won't see what's going on over there while I'm hooking up with your ex.

What do you think about that, Monica? That works for me, I can do that. Okay, so we've got a little bit of compliments, some self-deprecation, and some distraction thrown in too. Butter them up as much as you can. What's your friend's name, by the way, Monica? Her name is Erin. Erin.

And if Erin doesn't give her blessing on this, will you still go through and date her ex? That's the question. I really don't think that I could. I just hope that she sees it from my perspective and gets her blessing, you know? You're a good friend. Yeah.

Yes. She's a good friend. She's trying. And if she says no, we will come after her hard on your behalf. OK, Monica? That's Brooke's promise. So let's dial this girl's number right now. You're the bad friend here.

Wow. There we go. I'm dialing it right now. Good luck. Thank you. Hello. Hey. Hey, wait, who is this? It's Monica. Hey, wait, so what phone are you calling from? I'm so confused. Work? Work? Why are you calling from your work phone?

I'm at work. Girl, that is so weird. Just call them yourself on next time. Oh, my bad. I mean, there's a lot on my mind. OK, like what? So I can talk through it. You're so sweet. You're such a good friend. I know. But tell me, OK, I don't have long. Just tell me what's up.

Well, you remember Dilla's party the other week, right? I mean, yeah, barely, but yeah, I guess, yeah. Oh, well, I noticed you were talking to that like really tall guy. Yeah, a little, why? Oh, nothing, I mean, I saw you two go outside. Anything happened? Oh. Oh my God, no, no, nothing. I mean, I saw you two go outside. Did anything happen? Oh, my God. No, no, no.

We just like we made out a little bit, but nothing happened. That's more. Okay. I mean, he was cute. Yeah, it's whatever though. I just feel like, you know, I always see you hanging out with guys and you're the pretty one. You're the popular one. And I want to have fun and meet someone, too. I guess I just. Yeah, you totally should. Like you deserve whoever you want in this world. Well, thank you for that.

Like I said, you're such a good friend and I kind of am hanging out with someone. Wait, stop. No way. You're seeing someone who? Well, I'm not exactly seeing someone. I mean, not yet. It's kind of complicated. What do you mean complicated? Like, have you looked up with him? But no, definitely not. I've only sent him to accept it. Oh, my God. No, I mean, yeah, just once in a while. Actually, Ben used to always ask me to send him pics.

Like, even when I was at work and stuff, such a frigging perv. Well, Aaron has that's the thing. It is Ben. Wait, what is Ben? What do you mean? So the guy that I'm kind of talking to is your ex Ben. Wait, I'm just no, you called me from your work phone to tell me that you are talking to someone who is my ex boyfriend.

I mean, I respect you. That's why I called you to kind of tell you that we were catching feelings from one another. And how, how can you like Ben, you know, he literally cheated on me, right? Oh, wait. Come on, girl. That's a theory. Like, Ben and I talked about it, and he doesn't think that. Oh. Okay, no. Please, please, please tell me

that you're not defending my ex-boyfriend right now. Oh, I get that you guys had history, and I would never do anything unless I got your permission. I'm asking you if you'd be okay with it and that's where I'm gonna leave it. No. Wow. That's crazy considering that I gave you a break after you kissed my brother. Wait, no. He was in the hospital.

That doesn't count at all. What? What? I never heard that rule. I didn't know the hospital doesn't count. Wait, who? Kiss anybody there apparently. Oh, that's fun.

I'll be going to the hospital. I know. We need to have an emergency right now. Who are these people? Why are they on the phone? Hey, Erin. Hey. You're on the radio right now with a show called Broken Jeffrey in the Morning. Why? Why are they on the phone? Hey? You're on the radio right now with a show called broken Jeffrey in the morning

Why why am I on the radio? There's a lot of drama going on between you and your friend Monica drama that we didn't know about honestly I'm shocked that you didn't give her your blessing you're sure what are you guys like I mean I wouldn't give it he's a gross dude like you don't care about he said that's a theory he doesn't believe that remember that you know what whatever if Monica wants to date Ben and be cheated on and have a miserable life, then go ahead. I don't even care.

No, that's not the blessing we were looking for. That sounds nice. I think that's the best she's gonna get. It's a half blessing, so... It's like a sarcastic one. Look, the whole reason that Monica reached out to a radio show for this is because she understands that it breaks some rules of friendship and she's gonna be crossing some boundaries. She didn't wanna do that without like going through it

the right way and asking your permission. I think you need a pick. I think you just need to pick me or him. No, no, no. No, that's not what I'm gonna do. Don't do that, Aaron. Did you hear her like, listen, you have every guy is willing to make out with you,

it sounds like, which is great, good on you, Erin. Monica needs somebody. And maybe, maybe just cause this guy cheated on you, that doesn't mean that he's gonna be, have a bad relationship with Monica. Yeah, it's been less than a year. Yeah, it's probably. It's funny that Brooke's so on board now with this.

Well, it's like- We're fighting to date the ex. Monica's doing the right thing. This is the last time that I'm gonna ask, like our friendship is more important than any dad, but I'm asking you one last time. Think about you kissing her brother in that hospital bed too.

The hospital part I have a lot of questions about. Yeah, I kind of do. But I don't know that we have time. I don't think we have time to really break it down. But Erin, what do you say? Are you willing to give your blessing to Monica to date your ex? A lot right now. I will think about it It's fair but at least she's willing to mull it over and come back with a decision like that's better than we could have It's gonna be texting the other friends in a group message

decision like that's better than we could have expected. I think it's gonna be texting the other friends in a group message without asking and then going back. Girls you will not believe what Monica asked me to do. Oh my god, Aaron, please don't do that. Just tell me yes't hit. That was so close. Really, really good effort there, Brooke. Brooke and Jeffrey in the morning. The American West with Dan Flores is the latest show from the MeatEater Podcast Network, hosted by me, writer and historian Dan Flores, and brought to you by Velvet Buck. This podcast looks at a West available nowhere else. Each episode I'll be diving into some of the lesser known histories of the West. I'll then be joined in conversation by guests such as Western historian, Dr. Randall Williams and bestselling author and meat eater founder, Stephen Rinella. I'll correct my kids now and then where they'll say when cave people were here.

And I'll say, it seems like the ice age people that were here didn't have a real affinity for caves. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the region today. Listen to The American West with Dan Flores on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when we come face to face with death? My truck was blown up by a 20-pound anti-tank mine.

My parachute did not deploy. I was kidnapped by a drug cartel. I just remember everything getting dark. I'm dying. We step beyond the edge of what we know. To open our consciousness to something more than just what's in that Western box. And return.

I clinically died. The heart stopped beating, which I was dead for 11.5 minutes. My name is Dan Bush. My mission is simple, to find, explore, and share these stories. I'm dead for 11.5 minutes. My name is Dan Bush. My mission is simple, to find, explore, and share these stories. I'm not a victim, I'm a survivor. You're strongest when you're the most vulnerable. To remind us what it means to be alive.

Not just that I was the guy that cut his arm off, but I'm the guy who is smiling when he cut his arm off. Alive Again, a podcast about the fragility of life, the strength of the human spirit, and what it means to truly live. Listen to Alive Again on the i about the fragility of life, the strength of the human spirit, and what it means to truly live. Listen to Alive Again on the iHeartRadio app, Apple podcasts, or wherever you listen to your favorite shows.

We need to try to get an update from these two and find out if Erin ever gives Monica her blessing. Dude, yeah. Because our producer has reached out to try and figure out if there's been any update, no response yet So could still be mulling things over or Monica may have already run off to Thailand with the X Person we needed to have contacted Ben

Obviously the reliable X who said he didn't cheat Erin has every right to say no, I don't feel comfortable with you doing that, it's too weird for me. But if she says yes and this relationship actually works out, just think of the material she'll have for the maid of honor speech. Oh man, let me show you how they met and then she plays our audio. There's so much potential, but we'll try and keep you updated on what happens there. But if you ever need help with anything going on in your life, any awkward situation, reach out to us. We'll give you a little bit of advice.

Yeah. Not necessarily great advice, but. And just a little. But if you listen to this show long enough, you'll know that it's not good. That's right. But go check out all of our Awkward Tuesdays and all of our content. They're up wherever you get your podcasts at Brooke and Jeffrey. Why is a soap opera western like Yellowstone so wildly successful?

The American West with Dan Flores is the latest show from the Meat Eater podcast network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the region today. Listen to The American West with Dan Flores on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Clayton English. I'm Greg Glott. And this is season two of the War on Drugs podcast. Last year, a lot of the problems of the drug war this year, a lot of the biggest names in music and sports.

This is kind of star-studded a little bit, man. We met them at their homes. We met them at their recording studios. Stories matter and it brings a face to them. It makes it real. It really does. It makes it real. Listen to new episodes of the War on Drugs Podcast, Season 2, on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Over the years of making my true crime podcast, Hell and Gone,

I've learned no town is too small for murder. I'm Catherine Townsend. I've heard from hundreds of people across the country with an unsolved murder in their community. I was calling about the murder of my husband. The murderer is still out there. Each week, I investigate a new case. If there is a case we should hear about, call 678-744-6145.

Listen to Hell and Gone Murderline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. High Key. Looking for your next obsession? Listen to High Key, a new weekly podcast hosted by Ben O'Keefe, Ryan Mitchell, and Evie Oddly. We got a lot of things to get into.

We're gonna gush about the random stuff we can't stop thinking about. I am high key going to lose my mind over all things Cowboy Carter. I know. Girl, the way she about to yank my bank account. Correct. And one thing I really love about this is that she's celebrating her daughter. Oh, I know. Listen to High Key on the iHeart radio app, Apple podcasts, or wherever you get your podcasts.

Here's the deal. We gotta set ourselves up. See, retirement is the long game. We gotta make moves and make them early. Set up goals. Don't worry about a setback. Just save up and stack up to reach them. Let's put ourselves in the right position, pregame to greater

things. Start building your retirement plan at thisispretirement.org, brought to you by AARP and the Ad Council. This is an iHeart Podcast.