Brooke and Jeffrey: Second Date Update - Second Date Update PODCAST: Bad Boy Bobby

Episode Date: April 6, 2020

Bobby was shocked to learn to that his date had looked up his entire CRIMINAL RECORD, and she had some serious questions for him. There was one crime he REFUSED to tell her, but she won't date him until she knows. What did he do that was so bad?? FIND OUT in the Podcast!See omnystudio.com/listener for privacy information.

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

Hi, I'm Ed Zitron, host of the Better Offline podcast. And this January, we're going to go on the road to beautiful Las Vegas, Nevada, to cover the Consumer Electronics Show, tech's biggest conference. Better Offline CES coverage won't be the usual rundown of the hottest gadgets or biggest trends, but an unvarnished look at what the tech industry plans to sell or do to you in 2025. I'll be joined by David Roth of Defector and the writer Edward Ongueso Jr. With guest appearances from Behind the Bastards, Robert Evans, It Could Happen Here's Gare Davis, and a few surprise guests throughout the show. Listen to Better Offline on the iHeartRadio app, Apple Podcasts, or wherever else you get your podcasts from. sports and more joined by the sharp voices of the show's correspondents and contributors and with extended interviews and exclusive weekly headline roundups this podcast gives you content

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and a buttery Chardonnay. Bread and butter wines are delicious. Find bread and butter wines in your favorite store. Moving 92.5. Second date update. We got an email

into our show from one of our listeners named Bobby. Ooh, hey, Bobby. I don't know if that's how he pronounces it, but that's how I want to pronounce it. It's the only way you can say it. Hey, Bobby. Three A's and five Y's. Yeah, Bobby.

Bobby emailed us and told us he went out on a date that had two very distinctive sides to it. Okay. And I'm reading out of his email. He says, quote, one side was very uncomfortable and odd, and the other was fun and enjoyable. Okay. And I'm reading out of his email. He says, quote, one side was very uncomfortable and odd and the other was fun and enjoyable. Ooh. That pretty much describes every Craigslist meetup I've ever had.

Bobby, your email really got my attention, but before we hear about your date, tell us about the girl you went out with. What's her name? Caroline. We can't do anything with that. Caroline. Bobby. Caroline. It's going name? Caroline. We can't do anything with that. Caroline. Caroline. Okay, this is going to get old real quick. Where'd you meet her? Where'd you meet Caroline?

We met online. And what stood out about her? Well, to be completely honest with you, she was the hottest match I've had in an entire year of being on. I like that your voice goes so deep when you say that.

That's how you know it's a man thing. She was super hot. And bonus, she's a college graduate. Oh, so she's possibly smart. It doesn't always mean that you're smart. Sexy and semi-educated. That's what I'm out.

That's what men love. She's got brains. Never mind. So, Bobby, tell us. That's what men love. She's got brains. Never mind. So, Bobby, tell us a little bit about the date. Did the uncomfortable and odd part happen first, or did you start off with fun and enjoyable? It started out odd and uncomfortable. Really? Usually people don't even give it time to get through odd and uncomfortable to get to fun and enjoyable. What was so weird?

Well, we met at a restaurant, and I was the first one to arrive. I got there just a few minutes early, and when she came walking in, I recognized her immediately, and I go in just to give her a hug, and she stopped me and stepped back and said, no, thank you. Like in an aggressive way or in a I'm scared of germs type of way? It was firm but kind, I would say. Okay. You know, so I stopped and was like, I'm sorry, is there like a problem? And she says, it depends.

And then she pulled out this little stack of papers out of her purse and put them on the table. What was the papers? This is an interview? They were like court documents that she had printed offline six cases they were my court cases oh i thought you were getting served for a second wait you got a record a slight record if you can do a stack of papers there's anything slight about it what were you feeling when she did that to you i felt like like I was in school, like in trouble with a teacher or something. It was weird.

You know, though, at least she showed up. Like most girls would Google search you probably and just never show. But the records didn't actually say what I had done or what had happened because that's not available. So she asked me to explain each one. Whoa. Oh, my God. That's awkward. That sounds like a hot start to the day.

Were you totally honest with her? Yeah, we talked through the issues, and it was like, you know, traffic stops and this kind of thing. And she's very skeptical. As we are. I am right now. Yeah. And I'm feeling like I'm on trial again. Again. Yeah, I'm trying to I'm on trial again. Again.

Yeah, I'm trying to put myself in your shoes. Like, you just must have been so nervous. I was very nervous because I wanted things to work out. Like, I had matched with her and she was smoking hot. I know. You want to come off looking good to the sexy chick. So was she impressed with what you said? Or not impressed, but was she okay with the things that you crimed up?

How do you say it? Crimed up? I like it. I think never be your own lawyer, Jeffrey, just so you know. So what did you think of your crimes? She did start to warm up, and I basically just told her I've been unlucky with the cops for pretty much my entire life. That's what they all say. Yeah, they're out to get me.

No, I'm serious. Like one of the examples is I was arrested for driving with a deployed airbag. I had backed into something and it went off and I still had to get to work. I had to get to where I was going so I just kept going.

That's funny. That's amazing. went off and I still had to get to work. I had to get to where I was going. So I just kept going. Like, that's amazing. How could you even see out the witch? But it's funny because now he has a criminal record because of that. He was cool with that one. But this other one, she was not so cool with, which involved pizza hut.

What'd you do? Rob them? Well, I didn't rob them for money. I got arrested while I was drunk in college. I broke into a pizza hut and I stole chicken wings. Okay. Yeah, you can't

blame a guy for that. Was there a turning point in the night? I mean, because it's pretty impressive if you were able to actually get her on your side. At one point, she did open up and that was the fun and enjoyable part. Okay, good. So you guys connected. Yeah, and then

she did allow us to have two cocktails, but not dinner. Okay. Whoa, okay. Man, this girl sounds pretty uptight. She's strict. But I have an idea about why she didn't want to have dinner with me, and it's because I didn't want to tell her about my last

court case. There was one left, and it was just super embarrassing, and I didn't want to tell her about my last court case. There was one left and it's just super embarrassing and I didn't want to talk about it. So you spilled on the other ones, but that last one you said, nope, not going to happen. Yeah, she said that she was going to get up and leave unless I told her and I wouldn't do it. Oh, no. Did she leave?

Yeah, she left. Oh! Bobby, what'd you do? Yeah, just tell us. Just between you and me. No one else is listening. I ordered some chicken wings. No, come on.

Bobby, what'd you do? That was so embarrassing. Yeah, what didn't you tell her? See, I would like to get through this without having to talk about it. I was hoping you guys would work your madness. Oh, no. Okay. Can I just ask you, would you date you if you knew what you did?

Good question. Yes. There was a hesitation there. I'd date me. Alright, well, so have you thought about telling her the truth, Bobby? Yeah, of course I've thought about it, but the risk is just too great. Well, and I will say, I feel like you were really honest,

and there's just some things you don't have to share with everybody. It's not going to change who you are right now. Exactly. I shared with her five out of six of my court cases. That should be good enough for dinner. All right. I guess that's what we're working on. Yeah.

Is that the rule? All right. Well, Bobby, you may have to tell Caroline what you actually did, but we're going to play a song first, come back, and get your second date update right after this, okay? All right. Thank you so much. All right.

Hold on. 92.5. Second date update. We're right in the middle of a second date update, but before we go any further, all the women listening right now better watch out because we have a certified bad boy on the phone his name is bobby aren't they all named bobby bobby loves driving around town with a deployed airbag and eating chicken wings that he didn't pay for in committing minor traffic violations with zero cares.

He's bad. Bobby is on the phone for his second date update, and he recently went out with a girl named Caroline, and Caroline decided to start off their date by bringing a six-page printout of Bobby's rap sheet and made him explain every court date he's ever had. So he told her about five out of the six charges, but was too embarrassed to share his sixth offense, and that's when Caroline decided to cut the date short.

Now he's hoping for a second chance. Bobby, you bad boy, you. What do you say? You guys, I really don't want to have to tell her about this last case. Can you please just try so that I can go on another date with her without having to divulge this? You know, I'm usually all for honesty in a date, but I also think that there's some things you should be allowed to keep private. But can I ask before we do this? You promise that that last one isn't something that, like, I don't know, where she'd be putting her life in danger if she went out with you again?

Yeah, it's not scary, is it? I promise she would not be in any danger with me. It's just one of those things I haven't told many people. Only a few of my closest friends know about it. She'd be in danger of being too turned on because he's bad. Bad boy Bobby. All right, Bobby. I believe in you, okay?

Well, I'm glad somebody does here. There we go. You're catching your lawyer. All right, Bobby. I believe in you, okay? Well, I'm glad somebody does here. There we go. You're a lawyer. All right. Well, we're going to give Caroline a call for you, okay? I'm going to dial the number right now. You ready? I'm ready.

Okay, let's do this. Hello? Hi, could I speak to Caroline, please? Speaking, who's this? Hi, could I speak to Caroline, please? Speaking, who's this? Hi, Caroline. My name's Young Jeffrey from the radio show Brooke and Jubal in the Morning. I'm sorry, who is this?

It's Young Jeffrey. I'm a radio host. Hi, Caroline. You're not familiar with Young Jeffrey? That's actually not that shocking, Caroline. I'm sorry, how many people are on the phone right now? Oh, that's confusing. There's three of us in the studio right now. Hi, Caroline. I'm sorry. How many people are on the phone right now? Oh, that's confusing. There's three of us in the studio right now.

Hi. Hi, Caroline. I'm Brooke. I'm Jose. We're a radio show. You said that part already. Okay. We're a repetitive radio show.

Yes. And did you know that we broadcast our show on the radio? Oh, God. Jeff, stop. Sorry for annoying you. Why are you guys calling me? Yeah, let's get right to it. Let's annoying you. Why are you guys calling me? Yeah, let's get right to it.

Let's do that. We're doing something called the second date update. Basically, that's where if one of our listeners has gone out on a date recently but isn't getting a call back, we can call that person for them and figure out the reason why. So you recently went out with a guy named Bobby. Bobby wanted you guys to call me? Right. Bobby had a great time on his night out with you, and he's just wanting to know the reason why you're not getting back in touch with him.

You know, I think I made it pretty clear to him when I saw him last week, and if he doesn't want to follow my rules, then I don't want to go back out with him. Well, Caroline, he told us about the rules. Like you're talking about that you showed up with the rap sheet and all of his criminal convictions, and he wouldn't tell you the last one. So you guys know all about the date? Well, I mean, some of it. From his perspective. We don't know it from your perspective.

And kudos to you for being very thorough on background checking him. I think that's a good call on your part. I mean, honestly, I just want to feel safe, and I feel like every woman should do, you know, a little bit of digging and make sure they know who they're going out with. Totally. But they all seemed like pretty silly offenses, nothing crazy. He told us about the Pizza Hut one where he stole the chicken wings when he was drunk, driving with a deployed airbag. I mean, that if he's so ashamed or if it's so horrible, then that's simply not going to make me feel safe or comfortable enough to see him again.

Well, I can understand that emotion, but he assured us that it was nothing bad, nothing terrible. He's a good guy, and he was caught in a bad situation. So he told you guys? He didn't tell us specifically what it was. So how do you know it's not bad? Because all the other ones are so... I guess, okay, here's the thing. There's a certain level of trust at some point in any dating, right, that you have to be able to give.

And because the other five were pretty harmless and because this guy seems pretty cool, like, why not give him another chance? You don't have to know everything about someone before you go out with them.'re right i don't have to know everything but i should know if he has six offenses what the heck the last one is but he's not locked up so it can't be too bad i mean is that a bad standard for me to have i don't know it's like so many felons you served your time you did the crime you know there's got to be some point where society forgives you. I don't know if we're going to agree with Brooke on that sentiment, but maybe there's a chance that Bobby will tell you what he did. If he told you right now, would you be willing to hear him out?

Well, yeah. He absolutely has to tell me, otherwise I'll never go out with him again. All right. Bobby, tell us what you did. Hi, Caroline. He's on the phone. Yeah, he's been on the other line listening the whole time. Caroline, you just need to trust me.

It's just a super embarrassing thing. If you come to dinner with me, I'll tell you there. No, I'm not going to dinner with you. You already have that chance. You could have told me last dinner. See, I feel like Bobby really screwed up on this one because it sounds like if you want a date not only are you going to have to tell Caroline but you're going to have to tell everybody.

But he says it's not that bad so maybe it's not that bad. I didn't say was it bad you asked if it was life threatening. What? Okay wait let's play a little like Caroline how about some 20 questions like did you serve any time for it, Bobby? I was going to take forever. Yeah. Bobby, why don't you just tell us what you did?

I have a short attention span. I know. The minutes on our station's phone plan doesn't have that much in it, so just get right to it. Okay, okay, I'll tell you, but I can't believe I'm saying this. All right. And Caroline, you're agreeing to go out with Bobby if he tells us? No, I'm agreeing to listen and to Bobby if he tells us? No, I'm agreeing to listen and to see if I'd go out with him again. Oh, come on. We're peer pressuring this

guy. Okay. What'd you do, Bobby? Okay. A few years ago, I was in a wedding and I rented a tux. And when I returned it, the owner of the tuck's rental place said that I had ruined it. Like I had spilled some stuff on it, which I didn't. And then he charged me $400 on my card for no reason. And it made me angry because it was not true at all. I didn't spill anything on it. So a little while later, one night, I get drunk with those same guys from the Pizza Hut thing. And we hopped in an Uber, and we took the Uber to this Tuck's place.

And I defecated in front of the front door. And I didn't realize that there were cameras out front, like security cameras. And I got arrested two days later. Oh, my gosh. All right. So you took a dump in front of a tuxedo store. Caroline. Yeah.

Will you go to dinner with me? Wow. Hold on, Bobby. Caroline, see? I like him. Your life's not in jeopardy. Maybe your ball gowns are, but. That's pretty crazy, Bobby.

It's silly. I mean, what are you feeling right now, Caroline? I don't know. This is so weird. And it's just more weird every time I talk to him. Come on. Caroline, I told you all six of my court cases. Like, the least you could do is just have dinner with me.

I'm not asking for anything more. Yeah, Caroline, he's really gone out on a limb, like, revealing his entire criminal history on the radio now. Seriously. I mean, can you give him another chance? I mean, we'll pay to send you guys out on a date. Well, I mean, Bobby, I don't think you're a bad guy, but I'm going to say no. What? No, that's not fair.

Caroline. I told you everything on the radio. Yeah, and it's not horrible, but it just sounds really dumb. No, Caroline, listen to me. This guy is fun, okay? Yeah, sometimes it gets out of control, but that's what fun does when you're with a fun person. You will have so much better of a time with him. Honestly, you sound kind of like a little anal, like you showed up to the date with his rap sheets.

Like you need more fun in your life. Yeah, Caroline, think of all the businesses that you and Bobby can defecate in front of together. I'm being serious. Caroline, this would be good for you. Go out with him. You can hold hands and kiss while you're doing it. It's a memory waiting to happen. I'm with Jeff.

You guys aren't helping me. I disagree. I think this is working. Caroline. Come on, Caroline. You need a good story in your life. Go out with Bobby. Yeah.

I just can't see myself with someone who makes these kind of really stupid decisions. Oh, come on. That's the only people I could ever see myself with someone who makes these kind of really stupid decisions. Oh, come on. That's the only people I could ever see myself with. That's why you work with us. Caroline. Listen, I'll think about it, guys. I will, but I just want to be honest. It's probably

going to be a no. Oh, come on. Bobby, I'm sorry, man. It sounds like you're not going to get a second date out of this. We all tried, dude. It sounds like you're not going to get a second date out of this. We all tried, dude. But this sucks because I had to tell everybody listening what I did, too. Caroline, be careful. He sounds angry. You may want to get some cameras for that doorstep.

I know. Look out, Caroline. Bobby, don't come to my house. Come on, we'll bring some chicken wings. It'll be fun. Moving 92.5. Ugh, we're so done with new year, new you. This year, it's more you on Bumble.

More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention is because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you.

Someone else will too. Be more you this year and find them on Bumble. Hi, I'm Ed Zitron, host of the Better Offline podcast. And this January, we're going to go on the road to beautiful Las Vegas, Nevada

to cover the Consumer Electronics Show, tech's biggest conference. Better Offline's CES coverage won't be the usual rundown of the hottest gadgets or biggest trends, but an unvarnished look at what the tech industry plans to sell or do to you in 2025. I'll be joined by David Roth of Defector and the writer Edward Ongueso Jr., with guest appearances from Behind the Bastards' Robert Evans, It Could Happen Here's Gare Davis, and a few surprise guests throughout the show. Listen to Better Offline on the iHeartRadio app,

Apple Podcasts, or wherever else you get your podcasts from. Jon Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into john's unique take on the biggest topics in politics entertainment sports and more joined by the sharp voices of the show's correspondents and contributors and with extended interviews and exclusive weekly headline roundups this podcast gives you content you won't find anywhere else ready to laugh and stay informed

listen on the iheart radio apps, or wherever you get your podcasts.