Second Date Update PODCAST: Bad Boy Bobby

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. 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. Okay, it's gonna get

it's gonna get old real quick. Where'd you meet her? Where'd you meet Caroline? We met online okay, 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 online. 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. She's possibly smart. It doesn't always mean that you're smart. Sexy and semi educated. Yeah, that's

what love. 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 on 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. It 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 the interview. They were like court documents that she had printed offline. Six cases. There were my court cases. Oh wait, you got a record, a slight record. You can do a stack of papers. What were you feeling when she did that to you? I felt like I was in school, like in trouble

to teach her or something. It was weird, you know though at least she showed up like most girls would google search too probably and just never wow that show like totally 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. Who Oh my gosh, it sounds like a hot start to the day.

Were you totally honest with her? Yeah, we talked through the issues, and you just 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 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 mastered with her, and she was foking hot. I know, you want to

come off looking good to the sexy chicks. 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? I think never be your own lawyer, Jeffrey, So what do you think of your crimes? He did start to warm up, and I basically just told her I've been unlucky with the cops for pretty much my entire life. No, I'm serious. Like one of the examples is I was arrested for driving with a

deployed airbag. I had back 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 like that. How did you even see out the witch? But that's funny because now he's a criminal record because of that. He was cool with that one, but this other one she was not so cool with, which involved piece of hut rob them. But I didn't rob them for money. I got arrested while I was drunk in in college. I broke into a pizza hut

and I stole chicken wings. Okay, yeah, you didn't blame a guy for that. I mean, 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, Okay, so you guys connected. Yeah, and then she did allow us to have two cocktails, but not dinner. Okay, whoa. Okay, this girl sounds pretty uptight.

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 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, and 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. Leave. Yeah,

she left, Bobby, what'd you do? Yeah? Just tell us, just between you and me, no one else was listening. I ordered some chicken wings. Yeah, what didn't you tell her? I don't see I would. I would like to get through this without having to talk about it. I was hoping you guys work your madness. Hey, can I just ask you? Would you date you if you knew what you did? Good question? Yes, there was a hesitation there. Oh yeah, all right, Well, so have you thought about

telling her the truth? Bobby? Yeah, of course I've thought about it, but there risks this too great. Well, and I will say, I will say, I feel like you were really honest, and there's just some things that you don't have to share with everybody. It's it's not going to change who you are right now exactly. I shared with her five out of six of my court case. That should be good enough for dinner. All right, I

guess that's what we're working on. All right, Well, Bobby, you may have to tell car Line what you actually did, but we're gonna 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 second date. 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. Bobby loves driving around town with a deployed air bag and eating chicken wings that he didn't pay for and committing minor traffic violations with zero cares. He's bad Bobby. It's on the Pope for a second date update, and he recently went up with a girl named Caroline. And Caroline decided to start off their date by bringing a six page print out of Bobby's rap sheet and made him

explain every court date he's ever had. Oh my god, 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 helping 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. I just 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 would out with you. Again, 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. All right, Bobby, I believe in you. Okay, Well somebody does here. There we go, lawyer. Well, we're gonna give Caroline a call for you. Okay, I'm gonna dial the number right now. You're ready, I'm ready, Okay, let's do this. Hello, Hi, can I speak to Caroline? Please speaking this? Hi Caroline. My name's Young Jeffrey from the radio show Brook and Jubil 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. There's three of us in the studio right now. Hi, Caroline, I'm Brooke. 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. Why are you guys coming me? That's a yeah, let's get right

to it. 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 held, he told us about the rules like you're talking about. 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 day 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. Yeah, but he didn't tell me the last one. And I'm worried that she'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 just he was caught in a bad situation. So he told you guys. He didn't tell us specifically what it was, but well,

how you know it's not bad? 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. You'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, you served your time, you did the crib. You know, there's gotta be some point where society forgives you. I don't know. I don't know if we're gonna 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, Hi, Caroline. He's on the phone. Yeah, he's been on the other line listening the whole time. Carolyne. 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're gonna have to tell Caroline, but you're gonna 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? Why did he wait? Let's play a little like, Caroline, Well, how about the twenty questions like did you serve any time for it? Bobby? I was gonna take forever? Yeah, Bobby,

don't you just tell us what you did? 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, I'm Caroline. You're agreeing to go out with Bobby if he tells us no, I'm agreeing to listen and to see if i'd go out with him again. 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 tux 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 four hundred dollars on my card for no reason, and it made me angry because it was not true at all. I

didn't go 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 an uber and we took the uber to this tux 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 all right, so you took a dump in front of a tuxedo store, Caroline. Yeah, will you go to dinner with Caroline? See, 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, 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, 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 gonna say no, no, I told you everything. Yeah, and it's not horrible, but it just sounds really just 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 the fun verson you will have so much better of

a time with him. And honestly, you sound kind of like a little adle, like you showed up to the date with his rap sheets. Like you need more fun in your life, right, yeah, Caroline, think of all the businesses that you and Bobby can defecate in front of together. Well, I'd be serious, Caroline, this would be good for you. Go out with him. You can hold hands and kiss while you're doing It's it's a memory waiting to happen. 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. 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, Caroline. Listen. I'll think about it, guys, I will, but I just want to be honest. Probably it's probably going to be a no, Bobby. I'm sorry, man, it sounds like you're not going to

get a second date out of this. We all tried. Dude, what this sucks because I had to tell everybody listening when I did too. Yeah, Caroline, be careful. He sounds angry even I want to get some cameras for that doorstep look out, Caroline. Oh, Bobby, don't come to my house. We'll bring some chicken wings. It'll be fun. Moving ninety two point five