Brooke and Jeffrey: Second Date Update - Second Date Update: Standup Funny Guy

Episode Date: August 31, 2022

Every once in a while we have someone on the show that is so unique they're unforgettable... And today is one of those days. We are so excited for you to meet Harold!See omnystudio.com/listener for privacy information.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late-night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your mommy. Historically, men talk too much and women have quietly listened and all that stops here. If you like witty women, then this is your tribe. Listen to the Good Moms Bad Choices podcast every Wednesday on the Black Effect podcast network, the iHeartRadio app, Apple podcast, or wherever you go to find your podcast. Hey, you guys, I'm Catherine Legg. I'm a racing driver who's literally driven everything with four wheels across the planet. And I've got a new podcast.

It's called Throttle Therapy. This season, I'm competing in some of the world's most notorious racing events. Tune into my new podcast, Throttle Therapy, with Catherine Legg, an iHeart Women's Sports production in partnership with Deep Blue Sports and Entertainment. You can find us on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeart Women's Sports. Over the years, we've had people with all sorts of interesting professions call in for a second date update. Oh, yeah, for sure.

And we've had a few former pro athletes, a movie stuntman. And one time, we got a junior-level auditor at an accounting firm. I mean, that was interesting to me. Was it? Like big numbers? Well, mostly because my parents do all my taxes, so I don't know anything about that stuff. It's fascinating.

Wow. But today's phone call is pretty special because we have someone on the line who says they have one of our jobs, and that's a professional stand-up comedian, just like Jose Bolaños. Oh my god. Are you guys going to out-joke each other?

Oh my god, it's Kevin Hart? His name is Harold, so please welcome to the stage, Harold. How's it going, everybody? Hey, see how natural he is? Is that a fake accent? Is that part of your shtick, Harold?

Fake. Ain't nothing fake about me, dear, but my fingernails I got on. Okay. Okay. Is he in the game? Can we let him? No, I like this guy. All right.

This guy's going to take my job. Thanks for being with us, man. So before we get into your date date first tell us about the girl that you met what's her name oh her name is ashley okay how'd you meet her i met her through this date nap but you know that's a whole nother chick caboodle yeah you never know how boring you are until you start filling out that darn thing i tell you seriously i feel like this is a setup the whole thing for his next joke mean, but I agree with you. I'm telling you, though.

But you know what? As I was filling it out, I kid you not. I realized, hey, wait a minute. There's millions. I'm talking billions of people out here who's not dating me. What the heck is their problem? Yeah, I feel you, man. I feel that way all the time.

I'm like, how come I only have 2000 people dating me? Where are my millions? So did she hit you up? Is she the one that reached out to you on the profile? Oh, yeah. I feel that. I mean, you know, I just want to meet somebody nice and get into a relationship. Yeah, that'd be great.

A serious relationship, to me, is like freaking a marathon. It's all stupid. Huh? I thought you wanted to be in a relationship well i'm just saying i wouldn't mind being in one but for the most part you got to go through all this foolishness okay let's let can we just focus maybe a little bit i'm really enjoying your perspective on life harold but can we can we get to your date with with ashley yeah but i just figured you want to know how i came about doing all of this

that's all okay we get the idea you met her online so what exactly did you do with her i mean we went out to go eat to this restaurant carol how was the conversation between you and ashley because it's like this one yeah i may I may know why she's not calling you back. I tell you I'm gonna make her smile and laugh throughout this whole evening. Okay are you saying that you ran a comedy bit on her? Yeah well not really a comedy bit I just told her a few things that I believe in like for instance I told her i said you know what ashley she said what harold i said you know you're like a jellyfish jellyfish and i said your body's rudimentally and i'm just i'm scared to get near it what

that was a good one what they call a Harold-ism. Okay. So you're scared to get close to her body? This is where, did she laugh? She chuckled after all get out. And then I followed it up with, I said, you know what, Ashley? She said, oh, what, Harold? I said, you know, relationships are the darnest thing.

They're 90% are trying to figure out where we're going to go eat at. I'm good on the heraldism over here. I do appreciate, though, you reenacting Ashley answering your questions because I really feel like I'm there. Can we get back just to the date again? How do you think your chemistry was? Did you feel a connection there? I did. I mean, I was getting ready to walk her up to her door after we concluded a nice little dinner and walk around the lake.

But I was telling her what I thought about doing. I'm sort of glad I didn't. And she was like, well, what's that? I told her, I said, I was going to wear a parachute tonight to our date. A parachute? Hold on, just play along. was going to wear a parachute tonight to our date. What? A parachute? Hold on, just play along. Why are you wearing a parachute? You told her you'd just hear me out. Oh, I'm trying.

I don't know why I was going to wear it, but I figured it was going to start up a conversation. Wait a minute. You didn't have a punchline, right? There's no joke. Harold. Harold, you asked her. Wait, hold on.

It's a curveball now. You told her you were going to wear a parachute, and when she asked why, you didn't have an answer? Right. I showed it to her in my trunk. I said, if I got here and I didn't feel my mojo and I didn't feel like myself, I was going to strap on this here parachute

and walk in this here restaurant. Wait, there was actually a parachute there? That's what he said. He said he had an actual parachute in the back of his truck. Follow along, bro. I thought it was a figurative parachute. You never know when a good parachute joke is going to come up. So you're going to need the props ready.

No, but think about it. Somebody was going to have to ask me. She was going to need the props right now but think about it somebody was going to have to ask me she was going to have to say now harold okay why are you wearing this here parachute but she didn't say that well i didn't wear it but i'm telling you i felt good about myself and i had my mojo okay well i feel like i've gotten a pretty good idea it sounds like you guys had a lot of chemistry so maybe let's fast forward to the end of the day how did the night end with you and ashley i thought he was walking her to the door well i'd like to get to the very finish what's the last thing that happened was there a kiss was there a hug i tell you what now and i'll be very forthright with you okay

for the first time when i went there i went in for that their little kiss and i was ready embrace this you know like how they show on television just alone drawn out funny while you were wearing a pair of shoes my god there's nothing to happen i mean heck but i tell you i mean i said thank you ma'am and and i walked about four feet and i turned around and i said you know if you want you can call me cb cb cb i say yes it stands for coffee bean and then she says coffee coffee bean. And I walked another two steps to my car and I turned around and I did a thrust. I said, yes, because I grind so fine. I told her, just like Maxwell House, I'm good to the last drop.

Yeah. No drops. Well. Oh, God. Harold. That sounds like a pretty great time. I want to be you. Jeffrey.

In your mind when you look back on the date. Yeah. Don't ask. I don't think we should ask more questions. Listen. Please. You don't think I should ask if there's any moment that could have gone wrong? No.

Please. We'll be back. We'll be back. We'll be back. Okay, let's play a song. Thank you. And we'll come back, and then we'll try and get you your second date update. All right, CB? We'll try.

Good, because I got a whole plethora of assortment to tell you guys about. All right, all right. We're going to take a short intermission. We'll be back with more of Harold right after this. Second Date Update. If you're just joining us for the Second Date Update, we've been talking with one of our listeners named Harold about his first date with a woman named Ashley.

Now, Harold is a stand-up comedian, and he went into a lot of detail about their night. But here are the main points that I took away. Okay. They went to a restaurant. Uh-huh. He drove her home. Yes.

He pulled a parachute out from the trunk of his car, and he even got a short peck at her doorstep, even though he was kind of hoping for a longer, sloppier kiss. Yeah. You were missing the very end. He said, swap and spit. What is the very end? He wanted to grind on her

The CB, the coffee bean Oh, well he has a nickname, he likes to go by CB Which is short for coffee bean because he grinds so fine Yeah I feel like is a really important last ending shot of his date One thing was abundantly clear to me though And that's that he had a really nice time with Ashley And he's bummed that she's not calling him back that is true now harold about ready to make your phone call here

how you feeling i'm just so appreciative of you guys doing this here for me i mean i i went jogging the other day and man i saw this couple holding hands and i just started thinking about this little filly and i'm like oh man this makes me hopeful that one day i can find the right person that will hate that couple just as bad as me i'm just hoping it's gonna be ashley that's what i was thinking you can roast people together i hope that for you too harold harold we didn didn't hear. I mean, have you reached out to Ashley and she hasn't called you back? I sent her a couple of texts and I even called, but I got nothing. Okay. So you reached out to her a lot is what it sounds like.

Okay. Not answering your texts. Well, maybe we'll have better luck here because I'm ready to dial her number and we're going to try and get you your second date update. You ready to do this, ma'am? Yeah, let's go for it. Okay. Remember, I feel like I have to say this. Wait until it's your turn to talk jeffrey i'll handle it from the beginning i'll call you

in when i think you should talk to her okay i tell you guys that might be a little tough to do hell i've got a lot of heraldisms i need to get rid of okay we're trying to get you another date herald so just dampen the heraldisms on to him for a little bit, okay? Less is more. Let me try and get some answers from her, all right? All right. All righty. Okay, here we go.

I'm going to dial her number right now. Hello? Hi, I'm looking for Ashley. Who is this? Hi, Ashley. My name is Jeff from the radio show Brooke and Jeffrey in the Morning. Who did you say this was? I'm sorry.

It's okay. We're a morning radio show. Okay. We're called Brooke and Jeffrey in the Morning. And we're reaching out to you today because we heard that you love comedy. I'm sorry. What is this about, though? I'm sorry, what is this about though? I'm confused Well, we're a comedy radio show

And we have a friend of our show Who also does comedy That's your friend She knows Is this about that guy Harold? Oh girl It might be Oh no, I'm okay, thank you

Hold on, hold on I'm sorry, I am fascinated. Thank you. Hold on. Hold on. I'm sorry. I am fascinated to hear your side of the night. Yeah. He told us about your date. And what we're doing here, it's called a second date update. We're trying to help Harold understand what went wrong during your first date. Because believe it or not, he doesn't know.

Yeah. Wow. That's amazing that he doesn't. Yeah. Yeah. So. That's amazing that he doesn't. Yeah. Yeah. So we need your help. Yeah, because we all understand that Harold is a one-of-a-kind type of character.

Yeah, he sure is. You know, so is there something about him or about the date that was a problem for you? Or a few things? Well, you know, to be honest um some parts of it was fun because he's a comedian and so his jokes were even a little bit fun okay but some of them i didn't even have a punch line you know like i just i just looked at him yeah and then you know he just talks a lot yeah i'm not sure what you mean by that i mean did he ever take a second to like ask you questions no that's the thing and that's the by that. Yeah, of course you do. I mean, did he ever take a second to, like, ask you questions? No, that's the thing.

And that's the thing that made me kind of go like, yeah, this is not going to work. Because for me, the number one thing I need is a phenomenal listener. Well, I mean, sometimes people talk a lot when they're really nervous because they're out with someone that they like. Yeah, but that's okay. 70% of the time, okay, I get it. Give me a glass of water, you know? Like, take a second. I understand how you're feeling, that maybe you don't know if there's a bond there, but I don't know if Harold would necessarily agree with you on everything. You know, he probably would make a joke about it to me.

Or try to. I mean, there may not be a punchline, but he'd try. He sounds like a sweetheart in his own way. How long can you last with that a day a week no i wouldn't even give it five minutes so maybe just give it five more minutes because i need to let you know that harold is on the other line listening and he does want to talk to you right now he has not spoken an entire one word this entire time har Harold, are you there? It's been hard, I must say. But I just want to clarify something real quick. Now, Ashley, I hope you know when I talked about putting one arm around you, getting my other arm, putting it around you and squeezing you tight and just tackling you.

I'll be honest. I was talking about relationships. Then my mind went to football and I just went all out. That doesn't make any sense. Well, that's what happens when you're in love. Like things don't make sense anymore. Things start running together. Can I ask, Ashley, was there any jokes that made you laugh of Harold's? You said one about a pop-up I'm trying to forget.

I don't even want to think about that, to be honest. I don't think we heard that one. I can't discuss that one on the radio. That's a live joke. Oh, it's a live one? Okay. But I tell you, I mean, I would love to spend some more time with you so we can go over a few. That was funny.

No, no, no, no. Harold, you're missing the point, dude. Are you not listening to her? I'm going to make the next thing all about her. That's what I'm trying to tell you now. How? How, Harold? How are you gonna make it all about her? I'm gonna just sit back, relax,

put my feet up, have my guitar and just sit along while she's coughing away. Wait, guitar? That's not... Give her a little background track for her to talk over. I wouldn't be able to hear the answers if you play the guitar, Harold. Yeah. I mean, because you put me on the spot that I talk so much, I'm not saying a thing.

I'm just going to listen to you. No. No. That's not what she wants either. That's exactly what she wants. She wants a man who is a very, very deep listener. You're not listening if you're playing guitar. You can do both. You can play guitar and listen.

Harold sounds like a very multi-talented person. You darn too. Tell him, Ashley. Tell him exactly what you want right now. Like, just listen to what I say. Ask me questions about me. Don't make me feel like you're testing out your joke. Okay. Do you want to give it a try

right now, Harold? Why don't you ask her a question about her that has nothing to do with you let's practice do you like whipped cream ashley i yes i do okay now Okay, now, do you like the little whips? What? Whips? Like a leather whip now? I'm just trying to find out about her, guys. Yeah, okay.

He's trying to find out about what types of foods you like. No, and whips. Like real whips. Ask her real questions, like about what she likes, what motivates her in life, what her passions are. Oh, now you guys are so picky. It's like, oh, now there's going to be specific questions? Okay, okay, let me ask you this most important question of them all. All right.

Do you like Cinemax after Dark or HBO Plus? What? Okay. I like HBO Plus. Okay, okay, now we're getting somewhere. We're not. We're not going anywhere, Kelly. now we're getting some way. We're not. We're not going anywhere, Heather. Are we getting to the end?

That's what we need to get to. I'm going to be honest with you. I'm feeling some synergy here, guys. I am too, Harold. And you know what? That's why I would love to ask Ashley, would you like to go out on one more date with Harold? We will pay for it.

Dinner's going to be free, and so are the jokes. Yeah. It's free comedy. The it. Dinner's going to be free, and so are the jokes. The dinner sounds great, but to be honest, I don't think I can stand the headache of not being listened to. That's really a big thing for me. That's not shocking. You want me to leave the guitar home? Oh my goodness.

Or I can put it in the trunk in case you change your mind on the date. With the parachute. With the parachute and the guitar together. Everything in there. Will you bring your ears today? I most certainly will. I have no problem with that. I just need to spend some more time with you.

That's really sweet, Ashley. Dude, don't take it. I mean, your jokes were funny. Some of them. Some of them. What? I mean, I'm going to be honest with you. You know, if you just eat a peanut butter sandwich, it's all good.

But there is nothing like peanut butter, jelly, and banana. And Ashley, you're that banana. Oh, boy. And you're the peanut butter and the jelly? Where's the bread? I don't think more romantic words have ever been said. Wait, are you actually changing your mind on this, Ashley? Are you actually turning? I don't think more romantic words have ever been said. Wait, are you actually changing your mind on this, Ashley? Are you actually turning?

I don't know. I mean, he is kind of cute. Oh, my God. This is working. I mean, boys and girls, do you hear that? She said it. Let some synergy up in this here air. Oh, I feel the synergy, too.

Okay. Oh, my God. Ashley, we're sending you out one more time. Even if you change your mind, you're going out on one more date with Harold. Oh, yay. Okay. Oh, my God. You have to update us on this because I need to know how the second night went.

Harold, are you feeling happy right now? I'm a little speechless. I can't even tell. Oh, that's exact. Keep with that. Keep with that. Stick with that. Go with that feeling. Brooke and Jeffrey in the morning.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show, ears edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show, ears edition, on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. The OGs of uncensored motherhood are back and badder than ever. I'm Erica. And I'm Mila. And we're the hosts of the Good Moms Bad Choices podcast, brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms. But not your mommy.

Historically, men talk too much. And women have quietly listened. And all that stops here. If you like witty women, then this is your tribe. Listen to the Good Moms Bad Choices podcast every Wednesday. On the Black Effect Podcast Network, the iHeartRadio app, Apple Podcasts, or wherever you go to find your podcast. I Heart Women's Sports